Because building ambitious things is hard, ambitious builders naturally gravitate toward anything that makes it seem easier.

One way this manifests, especially in Silicon Valley, is in the cult-like attraction to the latest therapy and self-help fads: from Landmark and Tony Robbins, to CBT and mindfulness, to psychedelics and biohacking, to the parts-based/experiential/somatic frameworks, most notably Internal Family Systems (IFS), that have become ascendant.

Each framework makes big promises, offering its own well-charted path to whatever lies on the other side of all the anxiety, burnout, emotional numbing, and other psychological ills that afflict the ambitious.

In reality, none of these paths is as well-charted or universally applicable as its acolytes seem to imply and as we, in any case, wish to believe. What’s worse, as I’ve argued elsewhere, each framework smuggles in philosophical baggage from systems of thought that range from suspicious to outright scornful of the builder’s ambition. And yet there are also troves of valuable insight and tooling buried amid the baggage, if you know where to dig.

This is the ambitious builder’s dilemma: we need all the tools we can get to keep our psychological software up-to-date with our ambition; and yet, if we’re not careful, the therapies dispensing these tools can undermine the very ambition we entrusted them to serve.

So how do we mine these therapies for value without succumbing to their costs? The best way I can answer is by example, so let’s consider the case of IFS: the "hot new therapy” of Silicon Valley.

Internal Family Systems (IFS) through a builder’s lens

Mining the value

If you aren’t already familiar with IFS, it is a therapeutic orientation (originally developed by Richard Schwartz in the 1980s) that analyzes human psychology in terms of interacting subpersonalities or “parts.” Given its popularity among the kinds of psychologically-minded Silicon Valley founders I work with, I’ve seen ample evidence of its value as well as its costs. By and large, the clients who’ve done a lot of IFS show a more differentiated awareness of their emotional states, and they have a richer vocabulary for identifying and distinguishing between the mindsets often encoded in those states—such as the “inner critic” and the “taskmaster” (loosely mapping to what I call the “drill sergeant”), the helpless “inner child” and the “firefighter” who rushes in to protect it via numbing and avoidance strategies (not so unlike my “Zen master”), and so on. And they already have tools for dialoguing with and gaining some healthy distance from these “parts,” enough to be able to work out what their authentic Self wants and believes.

If you struggle either to feel and connect with your emotions in the first place, or to stay grounded and rational in their presence, the tools of IFS (like those of meditation, or somatic experiencing, or DBT, or mindfulness-based CBT, or emotion-focused therapy, or a range of other modalities, as best suited to your style and personality) can help. Specifically, these therapies can:

• orient you toward the kinds of physiological signals you might not otherwise attend to, and help you trace those signals to the emotions that are generating them

• give you evocative images and metaphors for better understanding your emotional states and capturing them in words

• help you understand and develop empathy for even your most “irrational” emotional states by tracing them to their developmental origins (e.g., how your excess anger at your team members today stems from an unmet need for care and support when you were 10)

• give you practice and skills for connecting with another human being (the therapist) on an authentic emotional level while still maintaining healthy adult boundaries

IFS particularly excels at evocative metaphors, tried-and-tested hacks for heating or cooling your emotional states, and tricks for catching and disrupting old thinking habits without self-flagellation. So long as you recognize these as the metaphors, hacks, and tricks they are, you can get tons of leverage by adapting and repurposing them to your needs.

Mitigating the costs

Unfortunately, the IFS framework takes its own metaphors very literally. Beyond treating the “parts” as useful heuristics to check for in their mental lives, I often notice my IFS-experienced clients reifying the “parts” to a degree that interferes with building a more accurate, updated, and holistic self-view. And they tend to resign themselves to the permanent presence of these disparate parts in their “system.” Despite IFS’s formal claim that the parts can be “unburdened” through therapy, these clients tend to assume they will always periodically “dissociate” or “people please” on account of their protector parts, and will need to spend hours unblending from, befriending, and witnessing those parts on each occasion. Compared to those who’ve never done any parts-based therapy, the IFS-experienced clients are more surprised and skeptical when I suggest, for instance, that they can largely shed their overanxious “protector” parts by taking some calculated risks (as I’ve seen many others, including myself, do successfully). Whether this points to a fault in IFS, or a misconstrual by some of its practitioners, or a preexisting bias among those drawn to IFS or other therapies of its kind, it’s a common failure mode worth attending to.

Relatedly, many of my IFS-experienced clients have formed rigid assumptions about the forms of “self-care” they require, given the ostensible needs of their various parts. The idea of skipping their morning workout or afternoon meditation session for a day to make an important deadline feels anathema, as if they fear their inner child might be too fragile to handle it.

If I were to refer someone for IFS, I’d first want to make sure they know that they need not resign themselves to a fractured and compartmentalized existence; rather they can nourish and integrate their healthy parts and marginalize the outdated or destructive ones until they experience themselves, not as a multitude of bickering parts, but as one harmonious, uninhibited, fully-flourishing self.

Finally, let us reckon with a cost that’s especially pronounced in IFS but by no means unique to it: the assumption of moral neutrality. According to the “No Bad Parts” doctrine of IFS, all of our parts have good intentions for us, even if they are burdened with false assumptions about how best to serve those intentions. But this is importantly untrue of the parts of ourselves that have habitually succumbed to self-deception, or of the internalized voices of former caregivers or authority figures who in fact did not have our best interests in mind. If we suspect this of some part of ourselves, it behooves us to identify its motives (e.g., is this part of me looking to get a quick fix of pseudo-validation or an illusion of control by tearing me, or others, down? Is it more interested in shielding me from discomfort than actually fostering my growth?). And if we don’t endorse those motives, we can choose to withdraw our energy and support from them—to starve our worst parts for the sake of our best.

In my own work with clients, I often analogize such bad-faith inner voices to online trolls: the shitpoasters who always come back with new objections and “yeah, buts” as long as we keep engaging with them, since their interest is not in the truth but in keeping us talking. The same goes for our inner “trolls”—like the ones that doggedly cling to the narrative that we are helpless and weak, or that the world is hostile and cruel, to distract us from taking action. The healthy response to such trolls is not to spend energy dialoguing with them; it’s to call them out, calmly and succinctly (e.g., “these aren’t real reasons, they’re just excuses”) and speak to the honest fear underneath (e.g., “I know it’s scary to put ourselves out there, but we’ve got this”), then get on with our life.

Instead, IFS counsels empathizing with such parts and attempting to meet their needs. But the “needs” of a self-deceptive narrative are not legitimate, reality-based needs: e.g., the “need” of our “helpless and weak” troll isn’t really “safety” or “control”, but evasion of responsibility. So any attempt to dialogue with the trolls in good faith only emboldens them to keep lying to us (insofar as we seem to be “buying it”). Perhaps this is why the “unburdening” of one’s parts never seems to last very long.

The intent of such moral neutrality, common to every mainstream therapeutic approach, is to honor your agency and provide a safe space for you to work out your own values and choices. But in practice it often has the opposite effect. By pretending away your agency over the ill-motivated, even downright immoral parts of yourself, they 1) also deny you responsibility for your virtues, 2) stigmatize the acknowledgement of real moral fault, and 3) rob you of the chance to own and improve those moral faults in therapy: that is, to be morally ambitious. If you notice a practitioner promoting acceptance or tolerance of internal narratives you yourself are not proud of, you can push back on this: let the practitioner know that you don’t need all that validation to feel like they’re on your side, and that you’d actually feel more supported if they empathized with your remorse and took seriously your desire to improve.

The upshot: build your therapy

Perhaps the biggest takeaway of the IFS example is that we must notice and resist the urge to treat any given framework as gospel, even if it (implicitly or explicitly) tells us to. Try on the frameworks and tools that resonate, ideally more than one so you have some basis for comparison, and approach them as the mixed bags that they are. Use or adapt what serves your self-determined aims, and toss the rest. If you outsource your agency and judgment to a framework, you’ll eventually pay for it in rigidity, self-excusing narratives, and rituals that start consuming the very time and ambition you set out to protect.

Incidentally, this is why my builder’s mindset framework (which you should subject to as much scrutiny as any other!) doesn’t prescribe any one standardized path or regimen for “becoming a builder,” much as I’ve been asked—and in some cases tempted with big rewards—to provide one. Instead, I apply a broad set of principles to my coaching and therapy, and co-create my clients’ individual “regimen” with them accordingly. Of course I also use plenty of procedures and exercises in the process, many adapted from existing therapies like IFS. But none of them fit every client’s path nor look the same from one client to the next.

Perhaps science will one day advance to a point where we can reliably prescribe the right therapeutic “regimen” to anyone based on some known set of variables, just as athletic trainers prescribe exercise regimens to athletes and physicians prescribe insulin regimens to diabetic patients. Alternatively, we may discover that the very mechanics of psychological growth preclude such exact prescriptions, given the kind of agency a person must exercise over her own mindsets and motivations in order for any change to really stick. My experience aligns more with this latter possibility: the more actively and extensively my clients shape whatever “regimen” we develop together, the faster and farther they tend to grow. And speaking for myself and every decent practitioner I’ve met, regardless of their framework: never are we more alive than in the meeting of minds and souls wherein we get to lend our creativity to the custom design of an unscalable growth regimen suited to the N=1 ambitious individual in front of us.

In my “Fantastic Builder” spotlight of John Gill, the math professor who invented the sport of bouldering in his spare time, we see that Gill designed his career in much the same way he designed a new category of sport: from first principles.

In Silicon Valley, the phrase “first principles” has become so commonplace as to devolve into a buzzword, thrown around to signal “depth” and “originality” without requiring much of either: just another shortcut, ironically enough, for the actual work of thinking from first principles.

And yet there could be no Silicon Valley, and no transformative human progress of any kind, without the actual work of thinking from first principles. So let’s now apply that work to the concept itself, and take seriously the question of what a “first principle” is and what it means to think from (to? through?) it: the first principle of first principles thinking, as it were. 

Whence “first principles thinking”? 

As best I can tell, the term “first principles” originated as a translation of the ancient Greek term “archē,” literally meaning “first-thing” or “beginning,” used by Aristotle to refer to the fundamental truths within a discipline: the truths that cannot be deduced from any prior truths within that discipline, and that cause or explain most of the other truths within it. This principles-focused approach to science featured prominently in Enlightenment thought and in the Scientific Revolution, as epitomized by Newton’s aptly named Principia. 

The person who seems to have played the largest role in popularizing this term in Silicon Valley (again somewhat ironically, given how far his social media persona has deviated from his own epistemic ideal) was Elon Musk, who defined it similarly: “first principles is a kind of a physics way of looking at the world. You boil things down to the most fundamental truths and say, ‘What are we sure is true?’… and then reason up from there.”

Asking the right questions

If you search the internet for examples of “first principles in entrepreneurship,” what you’ll mostly find are examples of the deep and penetrating questions that first-principles thinkers ask themselves. 

For instance, LinkedIn founder Reid Hoffman describes it this way: “Instead of blindly following directions or sticking to a process, a first-principle thinker will constantly ask, ‘What’s best for the company?’ and, ‘Couldn’t we do it this other way instead?’” Likewise, this Medium article suggests three questions for entrepreneurs to ask themselves when looking for potential product opportunities: What is the customer’s fundamental problem? Is the market big enough? What would a 10x solution look like? 

That said, we can learn a lot by examining the kinds of answers that first-principles thinkers actually generate in response to such questions, and how these answers guide their decisions about what and how to build.

First principles thinking in action

Customer obsession drives business success

Jeff Bezos famously built Amazon around the value of “customer obsession”—a shorthand for the first principle above. How did he arrive at this principle? According to his own account, he got there by asking himself: “What will remain true over the long-term?” This question led him to the following insights: 

“In our retail business, we know that customers want low prices, and I know that's going to be true 10 years from now. They want fast delivery; they want vast selection. It's impossible to imagine a future 10 years from now where a customer comes up and says, ‘Jeff, I love Amazon; I just wish the prices were a little higher.’ ‘I love Amazon; I just wish you'd deliver a little more slowly.’ Impossible. When you have something that you know is true over the long term, you can afford to put a lot of energy into it."

In other words, the value of good customer service (or the “need [for] happy customers,” as another company puts this principle) is a “fundamental truth” because it can be counted on to stand the test of time, and to be widely applicable across many different situations and decisional contexts that Amazon and its employees might encounter. Indeed, so fundamental is this principle that it might seem obvious: of course a company whose survival depends on attracting and retaining customers needs to prioritize its customers! And yet we can plainly see that most consumer-facing companies don’t consistently uphold or “think from” this principle. Part of the reason, I suspect, is that the long-term business consequences of treating customers badly are harder to see, and to keep fresh in one’s mind, than the shorter-term considerations that might get prioritized instead. After all, a company like United Airlines, to take one notorious example, could get away with treating customers quite badly and still remain in business for a long time, even if a closer analysis would reveal how these practices are injuring its reputation and profitability over the long-term. Keeping the inexorable but complex effects of customer experience in mind as a constant guide to one’s decision-making takes an effort of imagination and deep causal reasoning. Invoking the principle that “customer obsession drives success” doesn’t obviate the need for this work, but it guides and accelerates it by focusing one’s mind on the essential variables at play.

Incredibly, United Airlines seems to have made a dramatic turnaround in recent years under the leadership of new CEO Scott Kirby, and I have reason to believe he achieved this transformation precisely by reasserting first principles: every decision-maker in the company, I’ve heard it rumored, now knows to begin every internal conversation or staff meeting with “If we are to be the best airline in the history of aviation, then…” Can you imagine skimping on snacks or droning into the PA system about one flight delay after another if that is the cause you are daily called to serve?

What rockets are made of

Musk illustrated “first principles thinking” with reference to his thought process when first inquiring into the cost of a rocket, and being quoted prices in the ballpark of $65 million. Most people would have taken these prices as a given, perhaps after some attempts to negotiate or tweak particular specifications, and would thus have abandoned the idea of privately-funded space flight as unaffordable. Instead, Musk described breaking down the problem thus:

“What is a rocket made of? Aerospace-grade aluminum alloys, plus some titanium, copper, and carbon fiber. And then I asked, what is the value of those materials on the commodity market? It turned out that the materials cost of a rocket was around 2 percent of the typical price—which is a crazy ratio for a large mechanical product." 

Let’s break down what Musk actually did here. First, he recast his problem not in terms of the concrete goal of “purchasing a rocket,” but in terms of the more fundamental goal of acquiring one. Then, instead of taking the current price of rockets as set by the aerospace industry as an irreducible starting point for his decision-making, he identified the fundamental causal determinants of the cost of any large mechanical object. In so doing, he brought to bear his general knowledge about the inherent nature of such objects, including the fact that their physical materials necessarily make up a large proportion of their cost.  Thus he could estimate the cost of building one’s own spacecraft in-house—which turned out to be about 1/10th of the going price. His in-house solution was SpaceX: the first private enterprise to send humans successfully into space.

The first principle behind “first principles”

Across these various questions and examples, the fundamental principle that emerges is: go as deep as you can go. Thinking in first principles about a given field or endeavor means working to identify the most general, fundamental forces at play—be that the core problem that causes and explains many of the particular symptoms you’ve observed, or the core customer need on which your long-term success as a company depends, or the inherent nature and composition of a rocket in virtue of its being a large mechanical object—and then bringing them to bear on every decision you make, rather than letting superficial, short-term, or incidental considerations drive your decision-making.

Getting down to the fundamentals of a domain or discipline is really hard. Normally we think in “formulas” or “proxies”: ideas or frameworks in which we have reasonable confidence, and which we thus take as starting points for further decision-making. For instance, if we want to buy a certain kind of vehicle, we do our research on the relative costs and fuel efficiencies of different models, but we don’t usually consider deconstructing the vehicle into its basic constituents and taking it upon ourselves to build it from scratch. This is not a functional way to go about most of our day-to-day decisions, nor would it leverage the benefits of living in an advanced division-of-labor society. But it is the kind of thinking we need to do within our chosen domain if we want to conceive and create something qualitatively new. 

If this is something you want, then the most important thing you can be doing is constantly seeking to articulate and bring to bear the deepest underlying causes of everything you know and observe within the relevant domain. This assumes, of course, that you’ve gathered your own observations and built your own knowledge from the ground up, and that you’ve done so in good faith—with the genuine intent to identify and understand what’s true. So building and maintaining a good deal of self-trust will be mission-critical.

First-principles thinking is the difference between making small tweaks to an existing recipe, and developing an entirely new sort of dish from scratch—taking nothing but your knowledge of the tastes and interactive chemical properties of different ingredients as your starting point. 

This way of thinking is much harder work (as anyone knows who has ever tried developing an original recipe from scratch) and often higher risk (at least you won’t accidentally poison someone if you follow the existing recipe!). It means putting a lot more responsibility on your own shoulders. But, in helping you arrive at important, non-consensus truths, it sets the limit on the greatness and novelty of what you can build.

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As a coach and therapist, I’ve worked with clients who have both committed and been the victims of some serious wrongs (from physical and emotional abuse, to cheating and deception, to professional and financial malfeasance). This has given me a close-up view of how people deal, or fail to deal, with the worst in themselves and those around them.

And I have seen some things.

I have tried, in quiet desperation, to catch and reverse the barely-perceptible spread of evil within a soul, only to realize I was already too late.

I have reckoned with my own culpability for missing early warning signs I was too afraid to see, partly because they reminded me of things I’d noticed in myself.

Then again, I have also been privileged to witness some spectacular redemption arcs.

What follows is my attempt to document what these experiences have taught me about the psychology of evil, and about what it takes to really fight for the good.

When we encounter evil behavior, it can seem to us bewildering and incomprehensible: as a form of senseless, wanton destruction. This apparent senselessness makes evil hard to comprehend. If we could manage to inhabit the other side’s point of view, either seeing it as correct or as understandably mistaken, perhaps their actions would become more intelligible to us, and we would shed some of our moral outrage.

This more clinical, empathetic perspective may seem more mature, more enlightened, but most of us have the sense that something important is lost when we adopt it—some important insight that is needed to understand and combat evil.

My friend , in a talk on “The Nature of Evil” (from which I’ll quote at length later, since it has helped put words to my own understanding), speaks of the “dual nature of evil” which makes it “appear as both alien and familiar”: “it possesses something akin to human motivation and is yet alien from it. That is what is both so perplexing and so monstrous about it.”

We need a way to make evil comprehensible to us without trivializing it. To do this, we first need to relate it to experiences and motivations we can readily understand, while taking care to differentiate these more routine cases from the truly evil ones.

A natural starting point is to consider what happens in more familiar instances of destructive behavior.

Destructive vs. Constructive Responses to Threat

We’ve all met someone who let their anger and hurt overtake significant portions of their lives: the embittered exes—or disgruntled employees or disaffected community members—who spend their time and energy rehashing their grievances rather than moving on. Perhaps we’ve even been such a person ourselves, even if only for a stretch.

What’s wrong in these cases isn’t that the person is angry, or even hostile or aggressive. Some acts of hostile or aggressive behavior are appropriate and healthy—like standing up to a bully, or filing charges against an abuser. In these examples, you encounter a threat to something or someone you value, and you respond in a manner aimed at protecting or restoring that value.

In such cases, you act to destroy the threat, but as part of an overall constructive pattern of value pursuit. This presupposes you are a person focused on building yourself a life and finding solutions to your problems, including any threats that need neutralizing or injustices that need redressing in that context.

Even then, fashioning an appropriately measured response to threat or injustice is no small feat. For an admirable example of a good person’s struggle to thread that needle, I recommend reading and listening to everything Patrick McKenzie (better known as “patio11”) has written and said about his experience running VaccinateCA: the project he and some tech friends spun up on Discord in January 2021 to solve the COVID-19 vaccine distribution crisis that California’s government was dismally (and, in Patrick’s view, more-or-less deliberately) failing to solve. When I sat down with him last week to discuss that experience, I could not help but notice his still-lingering shock and horror at what he witnessed behind the scenes of the government’s botched vaccine distribution effort: not the simple incompetence he might have expected, but the self-righteous incompetence of many people in positions of authority who were so fixated on their “equity” agenda, particularly in the wake of George Floyd’s death and the January 6th insurrection, that they systematically prioritized it over saving lives. Still, rather than vent his grievances on social media or elsewhere, Patrick responded by doing what he does best: rallying his fellow tech builders to solve the problem in front of them, with “getting shots in arms” as their constant North Star. And though the evils he encountered clearly continue to haunt him to this day, he also clearly has not let them overtake the rest of his life and mind.

This does not mean he brushed the many ills he observed under the rug—indeed, he has devoted significant time and energy in recent years to making sure his story gets told. But nor does it mean letting his preoccupation with those ills eclipse his other writing, advising, and investing projects, nor letting himself indulge in bitterness without reflecting on constructive solutions in the same breath.

This constructive way of dealing with injustice is an achievement; it is not any of our default response to feeling angry and hurt. By default, we over- or under-react, we lose perspective, we lash out blindly or throw ourselves under the bus. All of us have at some point kept stewing in anger or ruminating on someone’s mistreatment of us past the point where it served our life in any way. All of us have, in other words, gotten caught up in destructive spirals of anger and hurt, letting our emotional reactions come untethered from whatever actual values were at stake. Calibrating our responses to grievance so that they serve our values is, like all forms of constructive self-direction, something we need to do and to learn to do. And it can be particularly hard to marshal such constructive long-term thinking when our fight-or-flight system is activated.

The choice to double down

Of course, getting carried away with hurt and anger is not inherently evil, as any clinical psychologist would rightly tell you. To account for actual evil, we need to challenge an idea that’s too common among psychologists: the view that basically everyone “means well” and is doing their best, however misguidedly (as exemplified by the Internal Family Systems [IFS] mantra that there are “no bad parts”). On this view, all behavior is understood as an attempt to fulfill some legitimate need, given whatever (often inadequate) resources one has on hand. For instance, those who commit violent crimes are viewed as trying to establish the sense of safety or control they lacked in their traumatic childhood environment.1

While it is in some sense true that all behavior is motivated by “unmet needs,” the conventional psychologist’s view neglects to distinguish between two fundamentally different ways of dealing with those needs: honestly dealing with them, and merely pretending to ourselves that we are dealing with them.

The key decision that either puts the destructively spiraling person on a trajectory toward evil or restores them to their senses is: what do they do at the first glimmer of awareness that they might be destructively spiraling? Do they look toward this awareness, examine it honestly, work to understand where and how it originated, ask themselves what evidence they might be selectively ignoring or over-interpreting, and then deliberately reorient toward living their life and pursuing their values (including whatever redress of grievances is warranted)? Or do they look away, actively fabricating a defensive narrative that allows them to continue in their stewing while telling themselves they are fighting for the good?

This is a decision we make not once, not twice, but in nearly every waking hour: do we marshal our energy and resources toward the honest pursuit of real values that sustain and enhance our life? Or do we expend those resources instead on the pretense at that pursuit, aimed at covering up our discomfort at failing to pursue it for real?

The pursuit of values is a sustained project that requires active effort, and everyone slips into passive autopilot sometimes. This is especially easy to do in the face of strong emotions like anger, hurt, or fear. But sooner or later we get some kind of signal from the world—candid feedback from our therapist, or a friend losing patience with us, or a missed deadline on a valued project because we had been too busy fuming and scheming against our perceived enemy—and we face a choice: either reckon honestly with the signal and adjust our approach accordingly, or come up with a rationalization (e.g., “he made me miss that deadline by stressing me out so much”) to justify our continued stewing.

The fact that getting carried away and losing perspective is the default, does not excuse the willful indulgence of that default. Rather it puts a responsibility on us to figure out how to do better. Every time we actively take up that responsibility, we feed and strengthen our better angels, and learn from whatever honest mistakes we make along the way. Every time we actively resist and evade that responsibility, we let a dash of evil into our souls.

Most of us have engaged in at least some of this active resistance and evasion at least some of the time. I know I have. And the most important advice I’m going to give in this post is that you run a scan for any issues or contexts in which you might be doing it too. Because the more you conceal this vice from yourself, the bigger a part of you it becomes.

To illustrate, imagine two ways an employee might deal with lacking the support and even basic respect she needs from her supervisor.

In the first case, she might first stand up to the supervisor directly and express what she needs from him (e.g., “I need more guidance than I’m getting” and “it doesn’t work for me when you hang up the call while I’m still speaking”). She might also solicit the supervisor’s feedback on where she can improve and how she might elicit support more effectively. Then if that doesn’t lead to her desired changes, she might speak with HR and discreetly request a transfer to another department, or look for another job, or simply get the support she needs elsewhere so she can continue to learn and grow in this job while minimizing unpleasant interactions with the supervisor.

In the second case, she might say nothing to the supervisor but meanwhile spend much of her workday venting to coworkers about her rude, incompetent boss, perhaps continuing to vent to her partner and friends when she gets home. Whenever she misses a deadline or makes a mistake, she blames it on her rude and unhelpful supervisor, leading the supervisor to disrespect her even more. Other employees also start to tire of her constant venting, which leads her to feel (correctly) that her coworkers have now cooled to her and are no longer meeting her needs for camaraderie and collaboration. Sooner or later she gets fired or quits in a huff, despite not having another job lined up (since she spent all of her time raging against the boss rather than thinking about what she wants out of her career). With all the time she now has to stew in anger and resentment, she starts to spread vicious rumors about her former colleagues online, and pours her savings into a nuisance lawsuit against the company. Instead of asking herself why she now feels even less valued and supported than when she started this crusade, and how her own externalizing of responsibility for those needs might have contributed, she doubles down on her victim narrative, finding new enemies—like “the sexist political regime” or “my soulless friends”—to blame for her continued misery. Soon her resentment spreads to anyone who seems happy in their work or relationships, despite her efforts to reassure herself that they are just “gaming the system.” Eventually she gets recruited by a fringe activist group dedicated to “dismantling late-stage capitalism” by vandalizing office buildings, and next thing she knows she is throwing broken glass through windows and hoping it will hit someone.

Evil is what lies at the extreme end of this descent. The further we descend, the harder it gets to own up to it and change course, given the accumulation of lies and self-inflicted harms we have to reckon with. At the end of the road is a life entirely consumed, not by the pursuit of real, life-giving values, but by the tearing down of anything or anyone who might remind us that we have opted out of that pursuit. Protecting whatever lies we have erected to avoid facing this fact about ourselves becomes our greatest need, above whatever legitimate needs might have motivated our anger (or perhaps our fear, which we promptly disguised to ourselves as anger) at the start.

Evil is thus the metastasis of a common vice with which we are all familiar: the vice of self-deception. All of us have succumbed to it at least on occasion or in moments; evil is the result of doubling down on our self-deceptions and letting their harms compound, until they overtake everything (or nearly everything) that is better about our personality.

Quoting Greg’s talk again:

Think about a tumor. A tumor is a collection of a person’s cells that are multiplying out of control in a way that might kill the organism. What does it mean to say they’re multiplying out of control? It means that they’re malignant, that they’re a threat to the organism’s life. It means that the metabolic processes going on in these cells are no longer aimed (as most metabolic processes going on in most cells are) at supporting the life of the organism. Cell mitosis is good for organisms, but only, to paraphrase Aristotle, at the right time and in the right way. There are certain conditions under which it’s good, and there is a system within the organism that directs its various processes, such that they happen at some times and not at other times. But there are some diseases that amount to the turning off of that regulatory system in some part of the organism. That’s what cancer is: the thing that’s meant to regulate cell division is just not there, and so the cell division no longer happens in a way that is in any sense aimed at benefiting the organism.

In a human being, the thing that directs our other systems—that integrates our many activities into a self-sustaining life for us is reason. And when reason’s not running the show, your other systems are no longer directed at life, at happiness, at anything positive. Reason is what would so direct them, and it’s absent; the master is gone. Emotions work for us (and are only even trying to work for us) to satisfy our needs, in a context where they’re directed by reason. Absent that, they’re like the cancer cells: out of control, not serving us, not aimed in any way at serving us. That’s when fear and hatred come to rule the day; and that’s true of immorality generally, not just evil (which I take to mean severe and full immorality or irrationality).”

The psychological defaults I often speak about are what happens in the absence of rational self-direction. And the point that Greg is making here is that in this default state, our felt needs do not actually serve us. They can be self-destructive fixations, which become increasingly self-destructive if we act on them uncritically, evading the evidence that they’re destructive to our values.

Like a tumor, the spread of such “anti-values” is progressive. There are people who operate in this unhinged, dishonest way in one area of their life or under certain stressors or conditions, while still retaining their rationality and value-orientation in other contexts. For instance, Elon Musk is a stark example of someone who exemplifies principled, reality-oriented thinking in the realm of hardware innovation, but has no compunctions about bending the truth to slight his political enemies or broadcasting widely debunked conspiracy theories to his millions of followers on social media.

The fact is we all have the capacity to lie to ourselves and paper over our own missteps, and we will sometimes opt for this tempting alternative to the harder work of thinking and building in reality. Depending on our circumstances and the cultural climate, it may not take much for our self-deceptions to get out of hand and lead to serious, even devastating consequences. The more ambitiously we live our lives, the more influence and capital we are likely to wield, and thus the more damage our self-deceptions can do. The solution is neither to truncate our ambition nor double down on our B.S., but precisely the opposite: it is to raise our moral ambitiousness, starting with the courageous practice of self-honesty.

How to recognize—and reverse—the descent into evil

As we have seen, evil is often downstream of misprocessing one’s own response to (real or imagined) wrongdoing in a way that untethers one’s anger and resentment from real values. The result is often that one gradually turns into the very thing one hates or fears.

Some symptoms that you or someone else may be caught in this descent include:

• A preoccupation with negatives absent any constructive solutions or credible paths to resolution. Quoting Greg’s talk again:

That is what the immoral kind of motivation by fear is: the dislodging of an aversive motivation away from the values that would justify it and the reasoning that supports those values. It becomes untethered emotionalism; you find that you just fear and hate things. And maybe you have something to say, some story to tell, about why you fear and hate them; but that story is not really what’s motivating you.

• Finding that you get energy or excitement primarily from seeing your “enemies” get punished or knocked down a peg, rather than from the positive advancement of whatever values you think they are threatening. Quoting Greg again:

There are people like this—people who are motivated by negative things. And maybe this happens in people who aren’t altogether awful; maybe even in people who are pretty good. But in some issue you notice that they get excited by someone’s downfall. Maybe they get really excited when they hear something bad about Trump or about Biden, or get to put a dig in at one of them. Now, I think Trump and Biden are very bad people; and Trump, in particular, I think of as essentially morally like [the main villain of Atlas Shrugged]. Nevertheless, we all know people who get really fired up by putting the screws into Trump: ‘Now I can really hate on him,’ that kind of attitude. Maybe it’s you that’s like that. And maybe, at the same time, you don’t get excited by things that are actually good in this same realm. That should make you suspicious. Maybe in general, or in some particular realm of life, your fears, your anger, your frustrations have come unmoored from the positives. When you ask yourself, why do I hate or fear this thing or this person, does the answer you give yourself really account for the intensity of the emotion? Or is there some residual, some extra left over, unexplained and unjustified by the ways in which they are actually bad? Where is that extra coming from? Maybe you should de-prioritize that thing a little bit, until the amount in which you’re acting on it is commensurate with the reasons you have for acting. Maybe you should think about the positives. If I’m so upset at this thing or this person and my reason is that it threatens this other thing, all right. But am I doing the things to promote that other thing? Or do I only get interested in this when I can tear down the thing that’s a threat? For example, if I tell myself that I’m really for free speech, and that’s why I hate so-and-so who’s against free speech, or a threat to it in some way, then besides doing something against so-and-so, am I doing anything for free speech? If I’m not doing anything for free speech, and not motivated by anything in this realm other than when it’s against this other person, then maybe what’s driving me isn’t a love of free speech, or not all the way down, and maybe I should do more to promote my values.

• A tendency to view yourself as a victim lacking in agency. From Greg again:

  If you really are a victim of something, it’s important to know it, acknowledge it, and not to sanction your victimization…. But people sometimes fall into the mode of thinking of themselves as essentially victims, as if their victimhood is something deep and important about them. And they navigate life on the premise that everything is someone else’s fault and nothing is their own—everything is “the patriarchy,” or “white privilege,” or “the liberal media,” and so on. Some of these things are real and some of them are imaginary; but I’m talking about the kind of person who adopts the mentality that whatever is wrong with their life, someone else is to blame for it, someone else is victimizing them. And because they think this way, they’re not doing anything to change it. They’re miserable, and they can tell you why everyone else is at fault and not them. Maybe they’re interested in politics and all they can tell you is about what’s wrong with politics, and how there’s no chance for improvement, and everything’s just bad. And it’s because of some other group, and if only those guys were out of the way… But there’s no positive alternative being offered. This kind of resentment, victim mindset is, I think, characteristic of passive thinking… of not focusing on your values. And I think everyone experiences this sometimes. Everyone sometimes needs to give themselves a little kick to get out of this mindset, to remind themselves that there are things we can do about our problems, about our victimization, about our values, about our lives.”

The case of ICE

If you’re reading this in late January of 2026, you might be feeling like there’s a giant elephant in the room: how can we talk about “facing evil” without talking about ICE’s ongoing activities in Minneapolis, and particularly the recent killings of Renee Good and Alex Pretti? And, indeed, when an administration and its agents become so fixated on eliminating the alleged threat posed by a perceived enemy (in this case, illegal immigrants and those allegedly aiming to disrupt the process of large-scale deportations) as to dispense with such values as due process and the rule of law, this is a clear sign of the moral metastasis I have described. As my husband Matt recently tweeted, “A minimally decent, extremely obvious initial response for those in power would be to open independent inquiries”—which ICE officials and the entire Trump administration have aggressively resisted, doubling down instead on slandering the dead to excuse their agents’ misdeeds.

This is essentially the same malignant fixation which the BLM rioters displayed in 2020 when they burned down cities under the pretense of protesting racism, and which the MAGA mob displayed in 2021 when it stormed the Capitol on the basis of a conspiratorial delusion. It is what drove the KKK, and the Nazis, and the KGB, and Hamas, and every evil movement in history. No one political party or ideological camp has a monopoly on evil.

And while the leaders of these movements are, in my view, unambiguously evil, there is a great deal more ambiguity to reckon with when considering the many overall decent people who are drawn to aspects of these movements for various reasons and in various degrees—often in reaction to whatever they find legitimately abhorrent in the “enemy” movement.

So what should we do with these observations, now that we have also seen how evil can take root in any of us insofar as we indulge our grievances?

The fundamental antidote to evil, whether you find it in yourself or others, is to reorient toward the values at stake:

A lot of us have that feeling some of the time about something, but if we focus on positive values and we think about why they’re valuable, those things that might count as evil if you consider them in isolation—this was an evil thought, that an evil motive—aren’t the whole picture. They’re not who we are; they’re out of character thoughts and feelings. And they atrophy in us and disappear, to the extent that we double down on what we want that’s good, and on our reasons for wanting it that we know are good reasons, and on our reasons for opposing the bad insofar as it’s a threat to the good. Sometimes you need to work explicitly on improving your psychology, but not necessarily. All of that could happen even without any explicit work on improving yourself.

The same basic approach applies when dealing with some delimited amount of evil in people who also have a lot of good in them:

It doesn’t mean that I’ll ostracize or castigate anyone who I’ve ever seen any of this in. But it is not what I’m in this life for; it’s not what I’m in this relationship for; it’s not what I’m going to promote, praise, or deal with in people. I’ll deal with what I see as good in them. I’ll deal with them around their values, not around their fears of disvalues. And in my own life, I’ll focus on what matters to me—on why it matters to me, on how I can achieve it, including how I can remove or avoid whatever obstacles there may be to my achieving it. I won’t be driven by fury and terror at the bad in the world. I know what evil is; I can avoid it insofar as it’s possible; and there’s a lot of room to make for myself a fantastic life.

Of note, orienting toward the values at stake absolutely includes judging and taking seriously the wrong that has been done to those values, including its scale. If you are the offending party, then you should expect to feel a corresponding dose of guilt and shame; if you are the aggrieved party, then it is healthy and appropriate to feel anger or even outrage in proportion to the injustice committed. But rather than stew in those feelings and lose all sense of context or proportion, you need to calibrate your feelings to the facts, and then think about what it would look like to move forward in light of all the facts, including that these wrongs have been done.

All of this is easier if you view morality, not as a code of compliance by which some higher authority legislates your basic worth, but as a guide to building a full and flourishing life. On this latter perspective, you have nothing to lose and everything to gain by diagnosing and correcting any vices that have derailed you from this project ASAP.

What might this look like specifically with respect to currently unfolding political events in Minnesota? The appropriate response will vary widely depending on who you are and what role US politics plays in your life, of course. For instance:

• If it has no short-term impact on your life other than to upset you and make you ruminate, the immediate response might simply be to limit your news intake and get on with your life, perhaps taking extra care to extend kindness and goodwill to friends or colleagues who might be affected (e.g., because they are awaiting green card approval, or they work in politics, or they have loved ones in Minneapolis). Over time, however, you do need to care about these events enough to form your own understanding of what they mean for your country (especially if you are a US citizen), and how you want to be voting or otherwise participating in the civic process in light of them.

• If you find yourself getting a rise out of the blatant inadequacies and hysterical backtracking of people whose political views you oppose, you might reflect on what could actually be driving those people, and what it might look like for you to succumb to similar forms of groupthink or hysteria, and how to catch and reorient yourself if/when you do.

• If some aspect of the situation connects to your valued projects and interests, you might offer your insights specifically on that aspect (as I am attempting to do in this post, or as my friend has done by sharing his own experiences and perspective as an immigrant from Iran, or as my friend has done by providing a highly accessible primer on the nature and function of sanctuary cities).

• If you have publicly voiced support for ICE’s activities or the broader Trump administration in the past but have now grown concerned or disillusioned, you could take inspiration from people like , who voted for Trump in 2024 and has since modeled an honest and reflective approach to rethinking his position. Even if you’ve gone so far as to stake your social media identity on being a diehard Trump and ICE supporter, you could follow the example of those who, after jumping on the “Alex Pretti was a domestic terrorist” bandwagon, owned up to being wrong after seeing the videos of his killing (like in this, this, and this tweet).

• Regardless, if you choose to make public or private comments, the key is to think about 1) what audience you are addressing, 2) what constructive insight or perspective you are expecting them to gain from your comment, and, most important, 3) what value(s) of yours you intend it to serve.

Build something better

As I have often said, death is the default: by default we do not take action to solve our problems, we do not articulate our own values or mobilize in pursuit of them, we do not see our life as adding up to an integrated whole. It is up to us to take those actions, to conceptualize those values, to engineer that integrated whole. Life calls upon us to actively go beyond the default; evil is what becomes of us when we actively resist the call, doubling down on death and destruction instead.

When we fail to take active responsibility for our life, we tend to feel helpless, which breeds resentment of others—especially those who seem to be doing better than us and to be looking down on us. A passive person is easily hurt and so fixates on, exaggerates, or manufactures grievances. This then creates a felt need to expend energy on destroying perceived threats instead of creating and defending genuine values. This felt need takes the form of an unadmitted motivation that’s possible to all of us, and that we’ve all experienced in moments, but which is fundamentally different from the rational pursuit of values, and which can come to dominate and pervert a soul: the motivation to destroy.

When we see signs of it in our selves, our neighbors, or our nation, we can and need to recognize it for what it is, to isolate and disempower it—and to turn our attention toward building something better.

Two years ago today, I published “A New Year’s dialogue with myself”, wherein I shushed my inner drill sergeants long enough to talk myself through what New Year’s really means to me (spoiler: it’s about taking your own happiness seriously). At that time I was just starting to experiment with AI as a self-reflection tool, and I mused that “perhaps [ChatGPT] will even be able to conduct this interview itself by the end of 2024.”

Ok, so I’m a year late, but the timing is actually perfect: just a couple weeks ago I started vibe coding an AI-augmented coaching app (with the urging and inspiration of ), and now I’m completely hooked. So what more fitting way to realize the promise of that original post than to put my own app to the test?1

With that, I bring you: key snippets from my 24-page “year in review” dialogue with “GenaGPT” [placeholder name, real one coming soon]. This AI coaching assistant is trained on my builder’s mindset framework and has been compiling and updating a cumulative psychological profile based on our conversations. It also offers specific guided exercises adapted from my coaching toolkit (like my Life Vision and Values Clarification worksheet), though I opted for a more freeform conversation this time.

Note: In the interest of full disclosure, I’ve marked the places where I skip over the first 3-4 lines of the AI’s response to spare you its effusive praise (which is benign but slightly embarrassing) and its summary reflections (which were useful to me at the time but would likely bore you as a reader).

Snippet 1: Illusions of scarcity

AI: Let me start where you started two years ago: What internal pressure are you feeling as 2026 approaches? What does your inner drill sergeant sound like right now—and beneath that noise, what genuine longing can you detect?

Me: With the holidays approaching, my drill sergeant is pestering me with his usual mantras about needing to maintain momentum and grow my audience by posting regularly, particularly around occasions that “call for it”, such as New Year’s. There’s also a new flavor of urgency and anticipation to his pestering, now that I’m 40, working on a book with a proper publisher (but can’t yet see a publication date in sight), and trying to take bigger swings with my coaching business despite having just poured a bunch of my savings into a house.

AI: I hear the familiar drill sergeant, but with new stakes this time—the urgency of 40, the reality of a publishing contract without a finish line yet visible, the financial commitment of the house creating pressure around the coaching business.

What’s the genuine longing beneath all that pestering?

When you tune out the drill sergeant’s anxious urgency about momentum and audience growth and “occasions that call for it”—what does the quieter voice actually want to say or mark or celebrate as this year ends?

Me: Yeah, good question; there’s definitely a longing to reach and connect with more of the kinds of ultra-ambitious founders/builders/thought leaders who stretch me intellectually and spiritually, to gain still sharper clarity into the ideas I’m pulling together, to experience the effortless flow of words on a page again when I’m writing (not in rare snatches but as a regular and abundant luxury)… and a lot of genuine questions about whether I’m approaching my projects in the right way to facilitate all those things.

AI: That’s a rich and honest answer. There’s a real hunger there—for the right kinds of connections, for intellectual clarity, for that flow state in writing to become abundant rather than scarce.

Let’s stay with those “genuine questions about whether I’m approaching my projects in the right way.” What specifically are you questioning?

What doubts or uncertainties have been surfacing about your approach—to the book, to the coaching business, to how you’re spending your time and energy?

Me: One stack of questions has to do with how entrepreneurially and “strategically” (if that’s even the right word) I should be approaching my practice: for instance, should I be actively advertising or doing outbound recruitment to attract more of my ideal clients, should I be more aggressively asking for referrals or testimonials from current and former clients, should I be charging more or have different price tiers, etc.

AI: I hear that stack of questions—the tactical ones about advertising, outbound recruitment, pricing, testimonials. These are real questions with real implications for the sustainability and growth of your practice.

Before we go deeper into those, I’m curious: does that feel like the core question, or is there something underneath it?

You mentioned you have “a lot of genuine questions about whether I’m approaching my projects in the right way.” The entrepreneurial/strategic stack is one set of questions. Are there others? What else are you genuinely questioning about your approach?

Me: Yes, I also have questions around how I’m approaching the work on my second book draft: for instance, what would it take to reactivate the kind of fluent generation of prose that I miss and long for so much? Is it a function of how much uninterrupted time I allot per writing session? (I thought it might be, but my experiments with two “1-week writing sabbaticals” last year suggested it’s probably not the full fix.) Or is it getting even clearer on the high-level structure and conceptual architecture of the book, so I can focus on adding the meat without ever losing sight of the skeleton? Is it that I need to start certain chapters from scratch instead of trying to tinker with what’s already on the page?

AI: Now we’re getting to something that feels deeply important. The longing for that fluent generation of prose—that “effortless flow of words on a page”—isn’t just about productivity. It sounds like it’s connected to something more fundamental about how you experience your own thinking and creativity.

You’ve tried the time variable (two one-week sabbaticals), and it didn’t deliver the full fix. You’re wondering about structural clarity, about starting fresh versus tinkering.

Here’s what I’m curious about: When you have experienced that flow state in your writing—whether recently or in the past—what were the conditions? Not just the external logistics, but the internal state. What were you writing? How were you approaching it? What did it feel like in your body and mind?

And conversely, when you’re in the “tinkering” mode that feels stuck—what’s happening internally? What does that experience feel like?

Me: Yeah, I’ve thought about all that a lot, and it’s still not entirely clear to me. One obvious variable is that I went to grad school and got steeped in the norms and unnatural contortions of academic writing, which I feel like I’m still not fully recovered from. Another, more local variable is that I’ve been able to get into the flow more when I’m telling a personal story or reflecting on my own internal experience, which I guess is both obvious and somewhat limited in its scope… but I wonder if there’s a broader phenomenon I could tap into here, which is that I’m not second-guessing my own expertise or the accuracy and precision of my words as I go. In principle there’s no reason I must second-guess myself as I write even if I’m writing about something I might get wrong, since that’s what editing is for…. But this is where my scarcity mindset about my own time and cognitive resources does me in, because it pushes me to operate on a premise of “I’d better get this more-or-less right the first time, or I’ll have wasted my time / or I never will.” This rhymes with the scarcity mindset that used to kick in for me (and, ok, still sometimes does) when I meet new people I respect and admire: the feeling of “I need to make a good first impression / ‘seal the deal’ on the friendship now because the opportunity is fleeting and may never come again.” This came up when I was at the Progress Conference and then at Satori (an exclusive retreat with incredibly impressive people from across industries) this year. And I suppose it also makes me overly stingy and risk-averse with money (which I always jokingly blame on my immigrant upbringing, but I’m pretty sure the statute of limitations has expired on that one now that I’m 40!); so yeah, it’s pretty pervasive.

AI: This is a profound connection you’re making—and I want to make sure we don’t lose the thread of it. You’ve just identified what sounds like a core pattern that shows up across multiple domains of your life:

In writing: “I’d better get this right the first time, or I’ll have wasted my time/never will”

In relationships: “I need to seal the deal now because the opportunity is fleeting”

With money: Overly stingy and risk-averse

All of these seem rooted in the same scarcity mindset—a fundamental belief about the non-renewable nature of your resources: time, opportunities, money, cognitive capacity. This connects directly to your builder’s mindset framework. Builders operate from a fundamental conviction in their capability and value. Scarcity thinking undermines both—it makes you question whether you can aim higher and whether you should invest in what matters most.

So here’s what I want to ask: What would it look like to approach your book—and your coaching business, and those high-stakes connections—from a premise of abundance rather than scarcity?

Not in some woo-woo “manifest abundance” way, but concretely: What if your time, your opportunities, your cognitive resources actually were renewable? How would you approach the book differently? The business? Those relationships at Progress Conference and Satori?

Me: Yeah, for one thing I think they’re not only “renewable” but endlessly self-generative and compounding - as in, the more of these resources I “spend” (assuming I spend them on valued pursuits that constitute and sustain my chosen life), the more and better I produce.

As to what it would look like: with the book, it would mean leaning into the fact that this is a long-term project aimed at generational impact, and letting myself guiltlessly dive into research that interests me, free-write extensively without prior expectation of how much will make it into the book, throw out whole chapters and start fresh if the current versions don’t inspire me, etc.

With my coaching business, it would mean taking big swings that are likely to fail but would have extremely high upside if they succeeded (e.g., putting money into more aggressive experiments with this app; doubling or tripling my rates; spending a week in SF every month or 2; cold emailing the high-profile billionaire founders I most want to work with, and communicating my value unapologetically; etc). And with my own family, paradoxically, it would mean valuing my time with them more fully and disconnecting more guiltlessly when I’m with them, as my time with them - particularly with my kids qua kids - is my one truly non-renewable resource.

Snippet 2: The need for tighter feedback loops

AI: You’ve got concrete examples on both sides [of “abundance” and “scarcity” moments from 2025], and I notice something interesting: many of your abundance-minded moves happened in the relational/professional domain (asserting terms at [a conference], reaching out to impressive thinkers, holding clients accountable), while the scarcity mindset has been most stubborn in your writing process and in your presence with your kids.

Notice the pattern: Where abundance won, you trusted in your agency—the third core conviction of the builder’s mindset. You recognized that achieving what you wanted required chosen, deliberate work, but you trusted yourself to do that work.

Where scarcity won, you were operating from protection mode rather than building mode. You were trying to avoid loss (wasted pages, wasted time, lost revenue) instead of actively creating value.

What made abundance thinking easier or harder in different contexts?

What internal conditions or mindsets allowed you to access that confident, expansive energy? What thoughts or emotions were present for you in those moments that you didn’t experience in the more scarcity-driven ones, especially while working on your book or engaging with your kids?

Me: I think the main difference is that these moves come with quick, clear feedback loops: either I get a dm or email back within hours to days or I don’t; either the person is willing to talk to me or they’re not. Whereas the book has an extremely slow, delayed feedback loop, and it’s much harder to tell whether I’m on the right track, or to even keep the whole project in mind at any given point in time.

As to time with the kids, the feedback loop is immediate but it’s subtler and more ongoing, so the cost of any given moment spent distracted on Twitter doesn’t hit me as hard as a moment spent lost in thought during a conversation with Scott Alexander, say. That’s at least a large part of it, I think.

AI: [skipping gratuitous praise + summary] So here’s what I want to explore: What would make it possible for you to trust yourself in those slow-feedback, high-ambiguity domains the way you trust yourself in the quick-feedback ones? How do you create your own feedback loops when the natural ones are too distant?

This is actually core to your framework—builders don’t just respond to external feedback, they actively construct the conditions that allow them to build well. What would that look like here?

Me: I think what it would take is finding ways to keep the ultimate meaning and value of these activities—and the fact of their self-generating abundance— “on tap” for myself, even if it’s harder to see on short time horizons. For instance, when I sit down to write, I can conjure up the image of Kati Kariko working away in obscurity at U Penn for decades while delighting in each new mRNA-related discovery, or James Dyson eagerly iterating toward a commercially viable model of his bagless vacuum cleaner for something like 8 years without external recognition (because he understood that it would revolutionize the industry once he got it right). And I can explicitly identify what I’ve learned from each writing session (even if it’s just “that example is less compelling than I thought,” or “this point is going to stretch across several chapters instead of just one”), and see the fundamental likeliness between my process and theirs.

AI: [skipping fluffy praise] You’re describing a way to create your own feedback loop—not by waiting for external validation, but by actively recognizing the value generated in each session.

Let me ask: Have you been doing this consistently? Or is this more of an aspiration—something you know would work but haven’t yet turned into a regular practice?

And if it’s the latter: What would it take to make this your default mode when you sit down to write? What’s the barrier?

Me: I have not! And I’m excited to start. The barrier was simply that I hadn’t asked myself these questions explicitly yet (so thank you!). As to what it will take, I’m going to select a few key quotes and a self-prompt for myself, and I’m either going to print them and attach them to my monitor, or put them in a daily reminder that goes off every time I sit down to write (or both). As to remembering to be more present for my kids, I need to come up with a good mantra or mental image with which to really zap myself into awareness on this point (will think on this a bit), but I’m confident I can think of something.

Snippet #3: “Remembering what I know”

AI: [So] what feels like the core insight or shift you want to capture?

What’s the throughline that connects all of this?

Me: One clear throughline is that I need (and want!) to double down on my own mantra of “remembering what I know”, with all that it implies: I know I’m saying something new and important enough in this book to be worth another 1-2 years of effort and 1-2 million discarded draft pages to get right; I know my kids will only be this young and adorable once; I know, as Matt pointedly reminded me in his “happy 40th birthday” letter, that I’ve “already—in literally every important respect, and in ways that are, if not quite unprecedented, at the very least novel and rare—completely, totally, and irrevocably won at life.” And I know I have many decades left in which to relish and further compound those winnings.

I know these things, not on faith or as some sort of cope, but as hard-won wisdom, chiseled over years of iterative study and action and painstaking self-correction and philosophical-psychological synthesis. But though that wisdom is hard-won, it is not yet fully hardened: it takes work to feel and embody it on demand, and to protect it from the deforming influence of older, more scarcity-shaped narratives.

What kind of work? Some of it falls under the heading of “explicit psychological hacks,” like conjuring up images of people like Kariko and Dyson, naming what I’ve learned in each writing session, or using tools like the “life map” [now available as online tool built by Karel Vuong] to envision my life over longer timeframes than is my default.

But most of it is “building myself by building”: e.g., by learning and retelling the stories of wide-ranging builders whose lives exemplified this wisdom (as I’m already doing on Substack and for the book); by helping others accrue the same wisdom in the context of their particular lives (as I’m already doing for my therapy/coaching clients and my kids); by acting opposite to my own scarcity-driven fears, long enough and often enough for the fear-disconfirming evidence to sink in (as I’m already doing when I hold my clients accountable, free-write drafts I will likely discard, or put away work to be with my kids).

So I guess the through-line is: I’m already living as a builder, now let me really remember and own (and relish!) that fact.

Happy New Year, dear readers, and may you savor all the abundance already within your reach as you look ahead to 2026.

When I tell my clients, most of whom are entrepreneurs running multimillion dollar businesses, that I think they are an “underserved population,” I get an interestingly intense reaction: a mix of surprise at hearing me say it, and equally strong surprise at how much it resonates.

Why do I think they’re underserved? Because they’re striving to do something more innovative, uncertain, and psychologically demanding than most of us ever try to do—with potentially larger impacts on all of us—and yet their distinct psychological needs have gone largely unstudied and unaddressed by the mental health field.

Why are they so surprised to hear me say this? After all, they are all keenly aware of the unsparing mental and emotional marathon they’re running every day. And many have come across the headlines signaling a “mental health crisis in startups,” with several high-profile suicides calling attention to the generally high prevalence of mental health issues among entrepreneurs. Yet most founders I speak with take a somewhat stoically dismissive attitude toward their own struggles, to the effect of “this is my chosen burden” and “I’m so privileged, what do I really have to complain about?”

This attitude isn’t coming from nowhere. When mental health advocates speak of “underserved populations,” they usually mean those with socioeconomic or health-related disadvantages that make it harder for them to access or afford care. To say that entrepreneurs are underserved—not in virtue of being women, or entrepreneurs of color, or members of some other disadvantaged group, but simply in virtue of choosing to work on something really hard and new—would probably raise some eyebrows among my fellow mental health professionals.

Besides, many of the high-performing founders I work with are, in fact, in pretty good mental health already. According to a conventional narrative within my field, these founders would fall squarely under the heading of the “worried well.” The tacit assumption is that they would be basically fine with or without my psychological help, because most of their needs have already been met. They’ve got access to at least adequate financial and social supports; they’ve developed at least the interpersonal skills needed to convince investors to give them money (and family members to give them at least some degree of patience); they’re able to manage their anxiety and maintain their motivation at least well enough to have gotten a lot of work done in a relatively unstructured environment where they are the ultimate responsible party when anything goes wrong. They also tend to be scrappy and resourceful, which means many of them are already familiar with the tools conferred by the gold-standard psychotherapy and positive psychology approaches by the time they come to see me.

So what’s left for me to do, really, other than redirect them to those tools and encourage them to make some time for self-care? If I wanted a real challenge, wouldn’t I be taking on clients who are struggling to stay alive and make ends meet, never mind figuring out how to scale their venture-backed startup?

The psychological needs of the ambitious

My experience has been the polar opposite: one of the main reasons I love working with founders (and other equivalently ambitious, formidable creators) is that they challenge me in ways no one else does. I don’t mean because they struggle with more than their fair share of mental health issues (though they do); I mean because their ambitions demand levels of psychological competency beyond what the current gold-standard psychotherapy and self-help tools are even aiming at.

Take, for example, the ambition to “scale your venture-backed startup.” Any idea what it takes to develop, market, and distribute a product or service that’s never existed before, in a form that’s valuable and accessible enough for people to want to pay for it, and then getting exponentially more people to use it and pay for it every month, all without running out of capital or selling your (or your company’s) soul?

If you’ve never tried to do this, you probably under-appreciate just how psychologically demanding a task it is: in particular, how much fresh and unfettered thinking, authentic conviction, earned self-trust, intellectual ambitiousness, disciplined focus, win-win relationship building, and emotional self-management it requires.

If you’re among the few who have, then you have some idea of what it took—and you may be facing the next-level challenge of maintaining a strong company culture at scale; or trying to get yourself, your cofounder(s), and your board aligned on a decision about whether and how to exit the company, while taking care not to undo everything you’ve done; or grappling with the existential question of what to do next, now that you’ve gotten a taste of what’s possible (but also how damn hard it is).

If you’re like a significant subset of my clients, you may also be dealing with one or more of the distinct (or at least distinct-looking) psychological problems that can afflict the ultra-ambitious, such as a “visionary martyr” complex, or an over-reliance on gut hunches in contexts where they may be miscalibrated, or a mix of cynicism and insecurity about your ability to “get through” to others, for example. Steve Jobs is a great example of an epically ambitious builder who, by all accounts, seemed to grapple with all three problems at certain points in his life. As I’ve elsewhere described his “cynicism about others” problem:

In the Becoming Jobs biography, for example, we see multiple instances in which the young Jobs gets frustrated with his team members’ performance and responds by shortchanging them the very resources and support they would need to improve their performance, thus further fueling his frustration and perpetuating the cycle. The underlying mindset, if I had to speculate based on similar patterns I’ve observed in my clients, might have amounted to something like “people either get it or they don’t”—a kind of fixed mindset applied to the talents and capabilities of others. 

Even if you don’t struggle with these or other “pathologies of the ambitious,” you’ll need to blaze new psychological trails to the extent of whatever technological or cultural or scientific or artistic trails you’re blazing. New heights of human endeavor require new tools for managing every aspect of the endeavor, including the psychological. For instance, here are some of the distinct psychological needs I’ve observed in my most ambitious clients, as I wrote about here:

• Beyond “setting more realistic goals”, my clients sometimes need help setting wildly ambitious goals, while being ruthlessly honest with themselves about the low probability of success.

• Beyond “reappraising their catastrophic thoughts”, they need help recognizing when their “reappraisal” is just rationalization of what is in fact a looming catastrophe that needs to be faced and problem-solved.

• Beyond “taking other people’s perspectives”, they sometimes need help disconnecting from other people’s perspectives long enough to work out their own.

• Beyond “asserting themselves”, they need help seeking out relationships and communities that offer them closeness without assimilation.

• Beyond “learning meditation to manage their stress”, they need help recognizing when they're using meditation to procrastinate on the more important but uncomfortable tasks they are avoiding.

• Beyond “scheduling self-care”, they sometimes need help powering through a week without rest for the sake of a valued endeavor.

• Beyond identifying some generic values to guide their choices, they need help articulating an idiosyncratic personal life vision that captures the full novelty of their aspirations, while allowing appropriate flexibility in execution.

• And, beyond all of these particular skills, they may need help determining which skills they need when—and developing the self-awareness and self-honesty to check their motives for deploying a given skill at a given time.

The more ambitious and innovative your life projects, in sum, the more formidable your psychological needs—and the fewer the psychological resources that have been developed for navigating those needs. But this doesn’t mean you either have to settle for misery and burnout or lower your ambitions. Rather, it means you need to be that much more vocal in articulating and advocating for your needs, and that much more entrepreneurial (or, as Paul Graham would put it, relentlessly resourceful) about hunting down the best available resources and boostrapping them to suit your specific psychological purposes. Therapists and executive coaches can help accelerate this process for you, particularly if their approach sits at the intersection of both (as is the case with my founder coaching practice).

A difference in emphasis: raising the floor versus raising the ceiling

Matt Clifford has written about how building a world-changing technology company has never been easier than it is today, particularly with the advent of startup accelerators and platforms (like his own organization, Entrepreneur First) to make the collected wisdom of prior founders more accessible. But for all the technical and commercial and industry-specific knowledge that founders can readily access today, the psychological knowledge lags behind. (In fact, Matt hired me to coach and consult EF’s founders largely in recognition of this fact, as we discuss together here.) Perhaps this is why the number of tech founders remains small, and the number who actually get some traction—much less turn a profit—is far smaller still.

Why, then, are more researchers and practitioners not jumping to address the distinct psychological needs of the ambitious?

One reason, I suspect, comes down to a difference in the kinds of problems regarded as important and urgent to solve. Most of my field (along with most of our social and ethical systems and institutions, so I’m told) is focused on “raising the floor” of human functioning: lifting more people out of depression, anxiety, trauma, etc., and up to the mean level of wellbeing, resilience, self-efficacy, or whatever outcomes we’re trying to optimize. The methods and metrics used by the vast majority of psychology research reflect this focus, as I’ve written about elsewhere.

Such problems definitely need solving, and I want to see them solved as much as anyone. But I believe “ceiling-raising” problems are at least as important, far more likely to be neglected, and potentially the more fundamental of the two.

As I have learned through years of studying, treating, and coaching hundreds of ultra-ambitious builders, they need (and deserve!) as much psychological support as anyone. And we all have plenty to learn from their struggles and triumphs, insofar as we want to raise the ceiling on our own flourishing.

Specifically, here are some of my biggest learnings from working with ultra-ambitious and impressive people:

First, that they do not “have their act together” any more than the rest of us; in fact they struggle with more than their fair share of self-doubt, conflict avoidance, burnout, analysis paralysis, anxiety, depression, post-traumatic stress, you name it—and these issues often hit them even harder given the higher stakes, pressure, and sheer volume of work to be done.

Second, and more notably, that they have been able to pull off staggeringly impressive, genuinely awe-inspiring feats of greatness even without having their act together.

This latter observation has been one of the biggest surprises of my career. Some of the clients I’ve worked with have conceived, built, and scaled technology products that are now part of all of our daily lives; and they did it all while not knowing how to find a dentist, or leave their vaguely abusive spouse, or talk about their feelings. Witnessing what these clients have been able to achieve, even amid the chaos and dysfunction in which they found themselves (and, in some cases, created for themselves), has radically transformed my understanding of human achievement. I have come to see that the presence of a single overriding factor—namely, wholehearted engagement in meaningful, self-chosen work—is disproportionately more load-bearing for our success and happiness than all of our deficits and dysfunctions combined.

That said, I’ve also learned that even these ultra-ambitious people are experiencing only a fraction of the achievement—and reaping an even smaller fraction of the joy—that could be theirs if armed with the right moral-psychological resources.

Why we should care

This matters, first and foremost, because they deserve better. If you are a highly ambitious but less-than-deeply-happy person reading this post, you deserve better. Not because of the good you’ve done for the rest of us, though I don’t doubt you have; but simply because you have built yourself into someone capable of pursuing great, ambitious ends, and reaping deep joy from your life is the greatest end of all. To quote from my favorite novel, Rand’s The Fountainhead: “Don’t work for my happiness, my brothers—show me yours—show me that it is possible—show me your achievement—and the knowledge will give me courage for mine.”

A secondary reason why the psychological health of highly ambitious people matters—to me, anyway, though perhaps you can also relate—is that I want to live in a certain kind of world, and for my kids to live in a certain kind of world; and the psychologies of the most ambitious people will tend to have the most outsize impact on that world.

Imagine: how much more, better, more widely and cheaply available technology—including mental health, education, and wellbeing-enhancing technology—would we all be enjoying today, if more people were equipped with the psychological wherewithal to conceive and execute on big, ambitious ideas? If they were equipped, moreover, to do so with a spirit of joyful, forward-thinking benevolence, rather than myopic one-upmanship, and to grow progressively happier and wiser and more skillful at doing so throughout their lives?

For that matter, how much more uplifting would our news cycles and social media feeds be if the world’s most influential builders—like Elon Musk, Peter Thiel, and Mark Zuckerberg—had the tools and insights they needed to up their psychological game?

These are the kinds of problems I’m most excited to solve. They are the kinds of problems almost no one is publicly talking about; in fact they haven’t even been formally identified as problems yet, because they’re beyond our current conceptions of how good a human life can be.

Some of my clients are already living that life or something close to it, as I wrote about in my “psychological perfection” post. But even they don’t fully know what they’re doing differently or how they got there, so it’s not something they can reliably pass on or consistently maintain even within themselves. I thrive on helping such clients understand what they’re already doing right and how to do it more and better, even as they navigate uncharted waters or take on unfathomably complex execution challenges.

Other clients aren’t quite living that life yet, but it is within readier reach than they realize (often because they’ve internalized a cultural narrative on which it is impossible, as in the case of “Jack”). I equally thrive on helping such clients glimpse the heights within their reach and architect their ascent.

The growth I have witnessed in both sets of people has raised the ceiling on my own ambition: now that I know it’s possible to inspire and empower new heights of human thriving in my individual clients, I want to figure out how to do it at scale. This newsletter and my forthcoming book are efforts in this direction, though of course I’m just getting started.

To the most ambitious builders and innovators reading this: know that your psychological needs are formidable and real, not in spite of your awesomeness but (at least largely) because of it. You deserve more and better support than you’re likely getting, which is all the more reason to go and seek it out.

Meanwhile, let’s not be too quick to deride or dismiss the most ambitious builders of our day, even (perhaps especially) when they act out or appear to be going off the rails. Instead let’s thank them for the rails they’re laying down, however unevenly, and recall that their endeavors raise the ceiling for our own.

If you’re a venture-scale founder who resonates with this piece and wants ceiling-raising support, book a coaching session now. Everyone else: feel free to leave a comment below, or become a paid subscriber and claim your complementary 1:1 Zoom chat, or subscribe for free and stay tuned for more content like this:

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Updated from a 2023 post by the same name.

In this follow-up to our first Substack Live conversation, further inspired by this Notes thread regarding the therapies (IFS, meditation, etc) favored by Silicon Valley, we did our best to surface and explore the substantive differences in how we think about:

• the role of the judging, evaluative self in mental health

• the methods and aims of therapy / coaching / meditation

• the relationship between our conscious and subconscious selves (more like “rider” and “elephant”, or more like “sculptor” and “clay”?)

• the extent to which we can change our personalities (and when it is worth doing so)

• the nature and origins of spiritual experience

• ….and more!

Listen above if you missed it, and tell me which topics you’d like me to expand into long-form posts (as I feel like there are at least a few waiting to be written).

Get more from Dr. Gena Gorlin in the Substack app

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Some features of the modern world are so ubiquitous, so commonplace, that it is particularly surprising and illustrative to realize what creativity and ingenuity went into bringing them about.

If you’ve ever been to a rock climbing gym even casually in the last 30 years, you will have encountered a category of climbing called bouldering. For climbers today, bouldering is like hallways. It’s obvious and it’s always been there. It is the most common and popular form of climbing. It’s all the technique and athleticism of rock climbing, but low enough to the ground that it’s safe to fall on pads; no ropes, harnesses, or other special gear is required. It’s the sport of choice for many of my ambitious tech founder clients, and no wonder: what better, faster way to nourish your builder’s mindset than to concentrate all your creative and physical powers on solving a short, intensely challenging “boulder problem”?

And yet: 60 years ago, bouldering did not exist. The entire sport of rock climbing was barely even a sport. Some people engaged in it, but they conceptualized it as something akin to “extreme hiking.” Just as with hallways, a small number of people, in this case one person in particular, had to rethink the sport; had to notice latent possibilities and think about them afresh, by analogy to things other than hiking; then had to work out the details, developing a new form of the activity.

This came into clearer focus for me as I listened to episode 4 of the Climbing Gold podcast co-hosted by Alex Honnold (whose legendary climbing feats you may recall from the movie Free Solo) and Fitz Cahall:

“Bouldering has become the most popular, the most accessible, the most athletic, the most pervasive form of climbing today. The essence of the sport gets distilled down into a few moves typically no higher than a single story building. It’s an incredible path into the sport because there’s no technical rope skills required… If you were to walk up to one of these [bouldering] areas on a busy weekend, you’d find people working out sequences of moves until perfection, dipping their hands into buckets of chalk, lunging dynamically for holds, cheering for each other with each tiny summit reached. It all seems so intuitive when you look at it. The dynamic movement, the chalk, the ‘practice makes perfect’ mentality.

Sometimes it’s easy to forget that somebody actually invented all of that [emphasis added]. And the light bulb went off, not in Yosemite, but in an Intro to Gymnastics class in the 1950s, while a young freshman was fulfilling a PE requirement.”

That young freshman was John Gill, whom Alex and Fitz proceed to interview in the episode. Now 88 years old, Gill pioneered the art of bouldering back in the 50s by reconceptualizing rock climbing as an extension of gymnastics rather than hiking. He developed his then-radical approach to climbing while getting his undergraduate and advanced degrees in math, serving as a meteorologist for the U.S. Air Force, and spending the brunt of his career as a math professor.

Intrigued by his story and the transformative influence he has had on climbing, I reached out for an interview. He replied within hours, offering to answer my questions by email. Here is our (lightly redacted and annotated) exchange, followed by some reflections on what Gill’s story crystalizes about the builder’s mindset:

Me: In the decades before bouldering became mainstream, I understand you were viewed as somewhat of an anomaly in the climbing world. How did you relate to this fact, and how did you view your own role? Did you consciously view yourself as pioneering something important and new that ought to be adopted by other climbers, or did you view it more as a personal project, or something else?

Gill: I got used to being described as a “mere boulderer” and much later in life made a T-shirt with that written on it. I was introduced to climbing as a junior in high school in 1953 by a classmate who had learned the bare essentials at Cheley Camp in Estes Park the previous summer. There were no books or magazines on the subject available to me so I learned the sport pretty much on my own, scrambling around various rocks in Georgia. Then, after graduation, a friend and I drove to Colorado in August of 1954 and I scrambled solo up the east face of Longs Peak (you can hear me describe this on Alex Honnold’s Climbing Gold podcast episode 4). Thus, I was following a path common to neophyte climbers at the time. But that Fall I enrolled in a gymnastics class at Georgia Tech and my perception of climbing began to change. I no longer imagined the sport as an outgrowth of hiking, but began seeing it as an extension of gymnastics, and where better to exercise this perception than on boulders and small outcrops.

There seemed to be a huge disparity in pure strength between climbers and gymnasts, with rock climbers doing a few pushups while gymnasts were holding inverted crosses on the still rings. In a couple of years I put on 25 pounds of muscle and began doing moves on boulders that exceeded existing levels of difficulty, and doing them smoothly, like a gymnastic routine. I sensed I was fortunate to be at a formative stage in the evolution of climbing in America, and I clearly saw into a future in which bouldering’s growth was inevitable. At the same time I imagined the ultimate form of rock climbing as “free solo exploration”, and experimented with that approach to longer climbs until reaching my limits on the Thimble in 1961. [Gill famously climbed the Thimble, a steep 30-foot granite spire in the Needles of South Dakota, from the ground up and without a rope: a feat no one would be able to repeat for another 20 years. See “Reflections” below for some insight into how and why he did it.] A friend and executive director of the American Alpine Club, Jim McCarthy, encouraged me to write an article for the AAC Journal describing my vision of bouldering.

As an aside, I used to “boulder” on the campus of the U of Texas [where Gill noticed I am currently a faculty member] in 1948-49 where my dad was getting his PhD…. Also, during 1958-59, Mihaly Csikszentmihalyi, Father of Flow, was a member of the small U of Chicago mountaineering club that drove to Devils Lake to climb. Flow during a bouldering “performance” was very important to me at the time, although this aspect of my vision failed to take root.

Me: You introduced things (chalk, dynamics, an early grading system) that were controversial or novel at the time. Did the controversy or pushback affect you? If so, how, and how did you deal with it?

Gill: Chalk was by far the most controversial. I bouldered with [Patagonia founder] Yvon Chouinard in the Tetons during the late 1950s – he coined the expression for bouldering, “Instant Suffering “ - and he chose not to use it, but he wasn’t particularly upset by its use. Others were more disturbed by it and must have let their strongest feelings out when I was not around. I don’t recall anyone confronting me about its use. So, I didn’t have to deal with it.

Me: Do you see yourself equally as a “mathematician” and a “climber”? Does one feel more fundamental than the other? Is the former your job and the latter your hobby, or how do you conceptualize it? How has this evolved across different stages of your life?

Gill: I was an only child and we moved about every two years or so. In high school I grew to over six feet, but weighed only 145 lbs. and was no athlete. Glee club and ROTC. This bothered me, but when I began climbing in 1953 I saw a path I could follow and build my personality and, hopefully, my physique. I didn’t see myself as a mathematician until leaving the Service and enrolling in grad school. I became a mathematician when I did original research and got my PhD in 1971. Thereafter, I was a math professor who had the avocation of climbing.

Me: Do you mention being an only child and moving every couple of years because these factors made it harder to build a stable personality / set of friends and interests, which you then saw a path to doing through climbing? Or am I misunderstanding the relevance of these early influences? Also: was there anything or anyone in particular that shaped your view of physical strength / fitness / “being an athlete” as positive traits to strive for? Was this a general cultural norm at the time, and/or did it partly have to do with romantic/dating goals, and/or were there particular athletes you admired, etc?

Gill: I think moving every couple of years made me more introverted and singular in my activities, so climbing seemed very attractive and had an exploratory element that appealed. The one person I really admired after learning about the sport was the Armenian gymnast Albert Azaryan. His performances on the still rings were inspiring. As for climbers, none come to mind, although I respected a number, including Royal Robbins. I was a year younger than my classmates and was envious of their physiques and burgeoning maturity. I needed a more muscular body, but wasn’t sure how to accomplish that. At first I thought climbing would do the trick, but when I saw how gymnastics developed the musculature I was entranced. At that time being tall was not an impediment. John Becker, the American champion, was six feet. These days one must be shorter for moves that are more difficult than before.

Me: How would you describe your dominant motivations for climbing, for doing your academic work, and for any other activities that have occupied significant portions of your life? What needs did each activity fulfill for you? Are there any needs you feel haven’t gotten fully met in your life, or not until later on?

Gill: Where is the overlap between mathematics and climbing? Exploration. I never enjoyed repeating something someone else had done first. I trudged through grad school, working on problems at the end of the chapter, but I didn’t come alive until I began exploring the unknown. As for bouldering, it gave a purpose to my life: advocating its acceptance as a legitimate sport. As a novice climber I was obsessed with what I saw as an ultimate form of the sport, Free Solo Exploration; and after finding my limits along that path I reduced the risk factor considerably, but continued the practice until a revelatory moment in the early 2000s that convinced me to retire from the sport.

Me: Anything you’d be willing to share about the specific nature of the “revelatory moment”? Did this have to do with your reflections in the “Climbing Gold” podcast episode about the injuries and spinal damage you accrued due to bouldering?

Gill: After 1987 I only did modest bouldering and moderate free solos. Exploratory rambles. There were several granite formations in Hardscrabble Canyon, not far from Pueblo, that I climbed over and over again for the pure exercise and flow. One was a pinnacle that stood high above the highway through the canyon and caught your eye when you drove. I had free soloed a highly exposed but modest route up its face years before, then occasionally returned. This time when I reached a very exposed point on the nearly vertical face where one has to balance over to a refrigerator sized detached block, leaving all handholds for a moment, as I gently shifted weight onto my left foot – in the calm and quiet of the day – the block began to shift. This was a paralyzing moment, but I quickly decided to continue the move, reaching up for a handhold in the process. I stood and pulled off the block – which remained attached to the wall – glancing down the 900 feet to the canyon road. I was in my mid 60s and had free solo explored perhaps 50 miles of rock over the years – and I interpreted this as a message, fatal if ignored.

Me: I know you’ve often described climbing as a spiritual, aesthetic, almost “metaphysical” experience. To what extent did your aspirations for the future (whether short- or long-term) play a part in how you approached and experienced climbing, vs to what extent was it really a present-focused, meditative activity?

Gill: The aspect of climbing that could be described as meditative is the sense of flow. I mentioned Mihaly C. who devoted his career to this subject, in all its settings. As I learned gymnastics I experienced flow upon polishing a short routine on the rings or a fast climb on the rope. Also, I felt it to be an important part of climbing, although I was virtually alone in this regard. Once the Verm (John Sherman) introduced his V-grading system the numbers race began. I had been using a grade system designed to discourage number chasing, but I clearly had misunderstood human nature.

Me: Looking back on your life and career, is there anything you would do differently, if you had a do-over?

Gill: “What ifs...” have never interested me. [Touché! Probably the best response anyone could give to this question, honestly.]

Me: Your origin story includes some important early inflection points: the high school trip with your friend, the gymnastics class to fulfill your university’s PE requirement (if I understand correctly), etc. Do you think your life would have gone very differently if not for these serendipitous events, or do you think you would have found your way to bouldering or another movement-based art no matter what?

Gill: Alternate histories are fun sci fi reads. What might interest you is that, while a young USAF officer stationed at a distant air base in the early 1960s, I read Sartre’s Being and Nothingness, and became a practicing existentialist. I believe we create our own destinies when conditions allow, and we generate meaning within our lives.

[This concluded the substantive portion of our email conversation, after which I thanked him profusely and he asked for a copy of whatever I end up saying about him in my book.]

Reflections: A study in the builder’s mindset

In pioneering a new category of sport, Gill created not only his own destiny, but a new set of conditions that did not exist before. And, like the consummate builder he was, he applied this same level of fresh thinking and intentionality not just to the sport of bouldering, but to the design of his life as a whole. With every chosen pursuit, he laid down another building block in the nested hierarchy of valued pursuits that together both enabled and constituted his singular form of fully-lived life. He took up climbing, partly as a means to develop the strong physique he admired in his older classmates, and partly because it afforded him opportunities for the solitary exploration he loved. Then he discovered that he could build up his physique better and faster through gymnastics, and that he could get the combined value of both sports by integrating them. In time he realized this new form of climbing he had developed could shape the future of a young and rapidly evolving sport and community he had come to value, and that his role in advocating for its acceptance could give “purpose to [his] life.”

As testament to his builder’s knack for integrated life design, here is Gill’s recollection of why he decided to climb the Thimble (from an interview he gave at age 39 for the book Master of Rock):

“I suppose it was a psychological point in my climbing career, and I felt as though I had to really produce, really do something substantial…. I felt as though I had to do something with an element of risk in it, something difficult.”

Note how strategically Gill approached his risk calculus, welcoming greater risk at certain important inflection points in his life and prioritizing safety more highly at other times.

As to how he prepared for his historic ascent of the Thimble:

“…I looked it over very carefully, scrambled halfway up the route on the left and looked at the holds. I saw what sorts of moves I would be responsible for, if I were willing to commit myself to the climb… I went back to the base and started to devise ways, around the gym, in which to train for some of the difficult moves that I would have to do on the Thimble. I did all sorts of peculiar things that made a lot of people working out in the gym hysterical… I did squeeze-type exercises, because I noticed that there were some little nubbins up there that I would have to squeeze when the horizontal holds ran out… I trained for a period of one winter. The Thimble was on my mind during that whole time.”

This was the kind of effortful preparation and long-term planning by which Gill earned himself the flow states he so dearly valued as a climber. As he reflects elsewhere in the same interview: “Applying your intellect to problems, thinking about them, is actually an intermediate step in the development of technique in climbing. You want to reach a point where it fits together in your subconscious, and then you climb it instinctively.”

Gill equally exemplified the builder’s mindset in his math career, and in how he integrated these two major life projects. Quoting again from the Master of Rock interview:

“At the end of three years [as a university math instructor with a Master’s degree], I really felt that if I wanted to progress professionally I’d have to acquire a PhD. So I looked around and tried to find a school which was reasonably good at the doctoral level of mathematics. It didn’t have to be Yale or Harvard, but a reasonably good school that was near a very nice area with good boulders, hiking, swimming, fishing, and all the rest.”

This is what it sounds like to design one’s own success criteria from first principles, with the laws of nature and the requirements of one’s fully-lived life as the only constraints.

This is a more ambitious design process than our conventional views of “ambition” permit. It does not optimize for metrics like prestige or wealth as ends-in-themselves. But nor does it eschew “prosaic” considerations, such as the need to make a living.

By the same token, Gill did not develop his bouldering approach so he could secure a legacy and transform the sport for future generations (an ambition he did not form until much later). He developed it so he could get the kind of exercise and explore the kind of terrain that interested him.

This is exactly the sort of private, personal motivation that drove many of the creative and ingenious solutions we now take for granted. And it’s the sort that will drive whatever solutions we might build today, aided perhaps by the physical and spiritual uplift of our latest trip to the climbing gym.

• Excitement, because it is my birthday and I frankly enjoy being showered in affection and subjected to the high-variance hijinks of my little brood.

• Restless impatience, because there is so much I want to do and haven’t done, and my mom died at 62 and my cholesterol is high and who knows how much time I even have left…

• Then terror, because… 40?? The age Sally freaks out about “someday” approaching in When Harry Met Sally? The age at which one is officially considered “middle-aged”? The age that so many of history’s great talents, like MLK Jr and Michelle Trachtenberg and Frederick Chopin and George Gershwin, never even reached?

And then I told my husband Matt of my grand plan to write a post that catalogues what various great builders had and hadn’t accomplished yet by the time they were 40, and he twisted his eyebrows in scorn. “You’re thinking about this so completely wrong,” he said. And when I rushed in to mount some sort of half-hearted defense he immobilized me with: “You are one of the richest and happiest people who ever lived.”

So then I sat there and tearfully took it in, surrendering to the fact that it was true. Once again, I had slipped into measuring my life against a drill sergeant’s checklist, myopically focusing on discrete “attainments” absent any elevated view of what I am building: the dense web of beloved projects and people and places and prized possessions and peak experiences I have soldered together into a singular, joyfully abundant life.

From that elevation, the impatience and terror faded to light wisps of worry, mostly in smiling tribute to my inner drill sergeants and their well-meaning neuroticism. In their place, two new feelings emerged: in looking back, a flood of gratitude—to whom? to myself, to Matt, to my kids, to my friends and colleagues and clients and every human who has ever touched my life, to the fact of existence itself—and, in looking ahead, a kind of trepidatious resolve: a sense of the vast space of possibility for reaping still further joy and abundance from these remaining 40 years, and a kind of inward nudge toward navigating it wisely, lest I forget that joy and abundance are not the default.

Given Matt’s preternaturally healthy relationship with aging and mortality, it is no wonder he came up with the perfect exercise to do on the occasion of turning 40 himself 3 years ago: after mapping the first half of his life on a timeline from 0 to 40, he then mapped the projected second half on a timeline from 40 to 80. (The whole thread is well worth reading, and gives a more explicit account of the perspective I’m only briefly gesturing at here.) I’ve been recommending this “life mapping” exercise to clients and friends ever since, but only today am I coming to understand its function more fully: it is a retrospective and a roadmap, not for one isolated project, but for the most complex mega-project you will ever build.

So without further ado, I present to you: my retrospective and my roadmap. Elsewhere I have and will continue to elaborate on many of the episodes and aspirations represented here, but for now I prefer to let it speak for itself.

(You can now do this life mapping exercise for yourself at lifemap.cc . Thanks, !!)

Some of my immediate takeaways from this exercise:

• A decade is way longer than I tend to assume. Seeing how much I’ve managed to do and how much my life has changed in the decade from 30 to 40, despite almost never feeling like I’m moving “fast enough,” gives me a wholly different perspective on what I can expect from each of the decades ahead.

• I am only going to be actively parenting for about 16 more years (which, ok, duh, but this is not something I naturally think about or factor into my life design!). Seeing that fact visualized 1) makes every moment of the next 16 years feel uniquely precious and scarce, and 2) makes salient the prospect of nearly 3 decades in which I will have dramatically more free time and flexibility than I have today, with all the wealth and wisdom I will have gained in the meantime.

• Getting old is actually kind of awesome. (Damnit, Matt, one of these days you WILL be wrong about something! Good thing I have 4 more decades to prove it…)

In my own work with cofounders, couples, and anyone looking to improve their relationships, I present this modified version instead: 

The basic insight here is that no one ultimately benefits from a relationship in which someone’s needs are being steamrolled over.

This is easiest to see by thinking back to the relationships, whether personal or professional, where you were the one on the allegedly “winning” side of one of these “win-lose” scenarios: e.g., when you were being an aggressive jerk to someone you loved, or when someone else was deferring to you at their own expense. Maybe they were feeling done with the relationship but were staying in it for your benefit; or maybe you kept airing your frustrations without pausing to listen to theirs; or maybe you were underperforming, but they didn’t want to hurt your feelings by telling you.

Who actually “wins” in these scenarios? How do they play out? Sooner or later the other person’s frustration and unhappiness start to show; you feel less and less appreciated, or like you’re somehow a burden, combined with a sense of helplessness to do anything about it. Maybe you start doubting your own worth and capabilities, which then makes you defensive in ways that only breed further distrust and resentment in them. Worse still, you waste time stagnating when you could have been growing, whether through this relationship (if you’d been getting regular input and feedback about what’s not working), or through whatever other relationships or growth opportunities you might have pursued instead. And if you do manage to get comfortable with someone else martyring themselves for your sake, you do so at the cost of significant damage to your own character—by turning yourself into someone who is at ease with exploitation.

In this light, it might seem like a no-brainer that “winning” at the expense of those we love and care about isn’t really “winning,” in the long run. But this is not how most people—or, I daresay, even most psychologists and relationship coaches—usually think about it.

The “zero-sum” approach

This idea that “either everyone’s winning or no one is” runs counter to a deeply ingrained narrative within our culture: one that regards relationships—and human interactions generally—as zero-sum. Love is about “give-and-take,” we’re told, meaning that someone is always giving and someone is always taking. Our only choice is about how best to balance the giving and taking so that everyone gets their fair share of the relationship pie. With this comes the corollary assumption that the more we care about a person, the more we should want to give up for their sake: as Olaf the snowman cutely pontificates in Frozen, love is about “putting someone else’s needs before yours”—implying that your needs and theirs must inevitably conflict, at least often enough for you to be able to prove your love. 

Ironically, I’ve seen this approach kill the love between more couples, friends, and cofounders than probably any other factor, at least when practiced in earnest. 

Part of what’s damaging about the “zero-sum” model is that it leads us to equate valuing someone else’s need fulfillment as a multiplier of our own with what is in fact its opposite: the surrender of our own need fulfillment as a kind of sacrificial offering.

For instance, suppose you and your spouse live and work in City A, but your spouse gets an amazing new job opportunity in City B. Here are two very different scenarios where you might agree to leave your current job and move to City B “for your spouse’s sake”: 1) Upon reflection, you realize that the joy and inspiration of seeing your partner succeed would be worth more to you than your current job, which is easily replaceable; plus the prospect of a fresh start is actually energizing to you. You also do some research on City B and realize that, while you would have otherwise preferred to stay in City A, City B is also a place where you can thrive. Furthermore, you and your spouse have established a mutual precedent of taking each other’s needs and preferences seriously and factoring them into your joint decision-making, so you’re confident that your willingness to compromise in this instance will not perpetuate an unhealthy pattern of deferring to your spouse’s wishes. 2) You love your job and have deep roots in City A, but you feel it would be selfish to put these considerations ahead of your partner’s needs. So you agree to the move, perhaps secretly hoping your partner will regret it after seeing how unhappy you are in City B. (I’m deliberately steering clear of the potential gender dynamics here, though suffice it to say that the “zero-sum” narrative fits very neatly with stereotypical gender roles.) 

Or suppose you’ve got a friend who’s struggling through a rough period and is asking for a lot of emotional support.  Here are two very different scenarios where you might devote time and energy to supporting them: 1) You’re genuinely interested in the thoughtful way your friend is processing her challenges, and genuinely want to be a part of that process. Besides, you want her happy, confident self back in your life, and you value the deeper connection and intimacy borne of sharing in her struggle. 2) You find it incredibly draining to listen to your friend vent about her struggles for hours on end, but you feel guilty for feeling this way, so you continue to spend significant time with her despite the lost opportunity to fulfill your needs for deeper connection and intimacy elsewhere.

Or suppose you’re withholding negative performance feedback from an employee, even though this means needing to pick up some of their slack. Here are two very different sets of reasons why you might be doing this: 1) Because you want to see if they’ll rise to the occasion by identifying and addressing their own performance issues, at which point you could entrust them with a more senior leadership role. 2) Because you feel they “need the job,” and you know you might not be able to justify keeping them on once their performance issues come to light. Or you simply dread hurting their feelings, or are doubting your own capacity to give feedback, or worry that their weak performance might actually be your fault, and are using their “needs” as an excuse to avoid an honest conversation.

In each “version 1” scenario above, you’ve created net value for all concerned; whereas in version 2, by assuming your loss will be their gain, you’ve actually incurred a net cost for all concerned. In each latter case there’s a festering misalignment in goals or priorities that never gets addressed, so that no one is quite getting what they want out of the relationship. 

Relationships are either “win-win” or “lose-lose”; they are never zero-sum. 

What builders need from relationships

Traditional communication frameworks like the “assertive-passive-aggressive” triad offer some strategies for increasing the value and mitigate some of the costs associated with these scenarios, but they fail to challenge the fundamental assumption that relationships are “zero-sum.” By putting all three approaches on a single “win-lose” continuum, they imply that there’s a certain static amount of total need satisfaction to go around, and the “assertive” approach is one where neither party wins quite as much as the “winning” party would win in the other two.

This leaves people with no principled guidance on what and how much they should be compromising for each other’s sakes—nor on when to say that the relationship is just not working. It offers no way of differentiating between a relationship where no one is too fulfilled and no one is too miserable—a relationship of mutual stasis, if you will—and a relationship where each person’s growth and fulfillment is a catalyst for the other’s. To understand the difference more fully, we need a further modification of the framework: 

A builder’s need fulfillment is not zero-sum; it is as limitless as her capacity to think, work, and create. What she fundamentally needs from other people (at least as a fully functioning adult) are not static, depletable resources, but dynamics that fuel her ongoing work of building her own best life. Everything she needs from other human beings—like knowledge, inspiration, understanding, competent collaboration, coaching, thought partnership—requires the active and willing engagement of both parties. Human beings need to build; and the only way to engage with each other as builders is through mutual value creation and exchange, not through freeloading or free labor. 

As expressed by a young aspiring builder in my favorite novel, Rand’s The Fountainhead, which set me on my own builder’s journey when I first read it at age 16:

Don't work for my happiness, my brothers—show me yours—show me that it is possible—show me your achievement—and the knowledge will give me courage for mine.

What this means in practice

This modified framework gives us a powerful metric for evaluating and improving the health of our relationships. Instead of trying to weigh our needs against theirs in some sort of delicate balancing act, we can simply ask: are we energizing each other to build and grow? If yes, then we’ve got “win-win”; if no, then this is the first problem we need to communicate and resolve together, whether by changing the relationship or ending it. Tools like this reflective listening exercise I sometimes use to facilitate constructive cofounder/couple conversations are a good starting point.

Remembering that the only real alternative to “win-win” is “lose-lose” should also give us the moral courage to say “no” to whatever aspects of the relationship aren’t serving our needs, even when this means facing a lot of hard conversations and hurt feelings. When we’ve searching for the words to tell someone we don’t want to move cities with them, or they’re not performing up to par, or we’re not enjoying the friendship anymore (at least pending some new boundaries), we can keep in mind that love is not about “putting their needs before our own”: it’s about valuing, respecting, and empowering the fellow builder within them, and expecting no less in return.

This is a preview of the much more detailed win-win communication and relationship-building guidance included in my forthcoming Penguin book. Subscribe below for book updates and release details:

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Note: This is a re-print of an older post titled “A builder’s approach to relationships.”

Dear readers,

At long last, the update I’ve fantasized about sending you for the better part of a year: I have now submitted a full book draft to my editor at Penguin. Here is how it felt:

At the urging of my editor (and everyone else who’s had to deal with me in recent months), I’m stepping away from the manuscript for a while, so I can approach it with fresh eyes when it hits my desk again.

Meanwhile, I thought I’d indulge in some general reflection on what my book is really about, and what writing it has taught me about ambition and about my own psychology.

A more fundamental sense of “ambition”

You might think, given I’m writing a book on the “psychology of ambition,” that I’d have long since nailed down a definition of “ambition.” But as I was fielding questions on the topic at a speaking event just last week, I realized I had been semi-deliberately toggling between two meanings of the term.

The first meaning is the one you’re more likely familiar with: “ambition” as in the desire to achieve outsize outcomes with respect to a given (usually professional) endeavor. This is much broader than the term’s original meaning, derived from the Latin “ambire” (to “go around”), which had a negative valence and referred to the obnoxious practice of walking around the city courting votes or political favors. But it still retains that underlying connotation of hustling to maximize whatever metric is conventionally used to measure attainment within one’s field or social circle (be it votes won, or dollars earned, or lives saved, or honors awarded).

On this definition, you are more “ambitious” if you want to become a doctor versus a nurse, for example, or a tenured professor versus a low-paid lab technician, or a company founder versus a hired manager versus an independent contributor (IC).

But this definition breaks down when you try to apply it to the lives of particular people: for instance, did Tony Fadell become “less ambitious” when he went from running his own startup (Fuse) to taking a product manager job at Apple? Not by his own account: he had founded Fuse because he wanted to create a consumer electronics device that “would hook up to the internet, but wouldn’t look or feel like a computer.” Working as a product manager at Apple allowed him to realize this ambition far more fully, first by leading the creation of the iPod and later the iPhone. Apple was, in his words, “the place where I finally grew up. I wasn’t just managing a team anymore. I was leading hundreds, thousands of people. It was a profound shift in my career and in who I was.”

Or was Kati Kariko being “less ambitious” when she chose to pursue an unpopular research topic (mRNA) that kept her at the bottom of the academic ladder for decades, rather than pursuing something more “fundable” and rapidly rising in status and salary?

For these and many other ambitious builders, eschewing the conventional metrics of “ambition” within their field was precisely the ambitious thing to do, given what their self-defined projects required.

This brings us to the second, more fundamental meaning of “ambition,” which I believe underlies the legitimate appeal of the first, and which is the real subject of my book: the desire and will to live one’s best life. The project of building a life for ourselves is, after all, our ultimate endeavor, of which all our more particular endeavors are part. And the more agency we exercise over the particular endeavors we pursue and the metrics by which we measure them, the better our lives will tend to go.

I’ve met startup founders who are living their best lives, and I’ve met startup founders who are far from it. I’ve also met plumbers who are living their best lives, and those who are far from it. Some plumbers I’ve met are living fuller, better lives than some of the most “successful” startup founders.

So then, you might ask, why do I bias so heavily toward startup founders when writing about ambition?

This is a question I’ve always had an intuitive answer to, but choosing what stories and examples to include in my book, and seeing the high proportion of founder stories, has forced me to grapple with it more explicitly.

The main reason my book features a lot of founders is because I’ve spent much of the past 5 years working with them. But more interesting, perhaps, are my reasons for choosing to work with them:

1. Because their chosen endeavor requires them to exercise agency over large swaths of their life (like how, where, and with whom they spend their time, what they prioritize, whether and how much they get paid, etc), thus naturally selecting for people who want to be ambitious in the more fundamental sense.

2. Because I’ve realized I can offer them a ton of value just by helping them reframe their understanding of “ambition” from the more concrete to the more fundamental sense.

3. Because their situation makes more starkly visible the facts and conditions of reality to which all of our lives are subject (like that death is the default, and that we are all making it up as we go), which in turn ought to motivate all of us toward greater ambition.

4. Because I personally love them. The founders in my life have consistently elevated and inspired me, and my life is better and fuller when I get to spend significant portions of my time with them.

Ambition begets ambition

When I ask repeat founders why they keep founding startups, the first (tongue-in-cheek) answer is often that they are “gluttons for punishment.” But what they actually mean, on further prompting, is that they are gluttons for growth. They’re never fully stimulated or satisfied unless they are pushing their own personal frontier in some way (akin to Lin Manuel Miranda’s portrayal of Hamilton, who “will never be satisfied”). For some of them this means finding new industries to master, or problems to solve, or leadership and management skills to develop as they scale. But whatever the particular dimensions along which they want to grow, their psychology necessarily comes along for the ride.

Some of them start caring about their psychology only once it becomes a rate limiter on the worldly ambition they want to achieve (e.g., they can’t scale their product any further unless they develop some people management and emotion regulation skills); others seek out the worldly ambitions primarily as outlets and forcing functions for the psychological growth they crave. But whatever their primary motivator, neither the worldly outcomes nor the psychological growth can function as “mere means” to the other; to achieve and sustain either, you need to care about both. Just look at what happens to lottery winnings or inherited fortunes when placed in the hands of someone who lacks the character traits to figure out what to do with them. If you want to be materially ambitious, you need to be psychologically ambitious, and vice versa. We build ourselves by building, and we can’t build except by building ourselves.

Likewise, in writing this book, I’ve needed to push my own psychological frontier forward in ways I couldn’t have previously imagined. As just one example, I’ve had to experiment with a hundred ways of triggering my mind to spit out creative and fluent prose “on demand,” which had been hard enough to effect even when I wasn’t operating within the confines of a pre-established book structure and a writing schedule tightly regimented to fit within the interstices between work and parenting. And I had to fight the frequent urge to get resentful of those constraints, forgetting why I had chosen to work within them and how beautifully they solved for everything else I want and value in my life. And I had to muster unprecedented levels of self-trust to get out of my own way of generating the sheer volume of text I needed to generate, absent any definitive feedback, while counting on myself to impose some kind of order on it afterward.

Once the book is published, I already know I’ll be up against another frontier, which is my long-endured but never-fully-tamed public speaking anxiety. Even as I type these words, I feel that familiar mix of sinking sensations and butterflies that have preceded so many of my worthiest projects; the telltale signs of “growing pains” ahead.

Whatever lies on your personal frontier, there are psychological hills you’ll need to scale as you venture into them. My book is about the framework and tools, not only for scaling those hills, but for choosing the frontiers and charting the paths most eminently worth scaling.

Or at least I think it is…. will let you know for sure when I re-read it some weeks/months from now! :D

Seventeen years later, I credit Adderall with enabling me to build a 10x happier, healthier, more virtuous version of myself (to the chagrin of the countless Twitter trolls decrying my “meth addiction” in reply to this recent viral post). Here is my story.

Coming out of college, I thought ADHD was a made-up diagnosis designed to give lazy, weak-willed kids an excuse to demand extra time on their school assignments. After all, I’d been the laziest and weakest-willed among them, and still managed to get through an insanely demanding curriculum with highest honors, no “extra time” required.

Never mind the torturesome all-nighters spent zoning in and out of panicked procrastination and finally vomiting out a 20-page paper in the final hours before (or sometimes after) it was due; the days spent chasing lost phones and wallets and backpacks; the missed flights; the constant talking and interrupting that wore out the very sorts of friends I most wanted to keep; the apartment that had to be rush-cleaned into some semblance of a more ordinary “mess” on the rare occasions when I let anyone see it. As far as my inner drill sergeants and I were concerned, these were all shameful moral failings that I “should” have been able to fix by now, if only I were less lazy and weak-willed. If I could write a solid paper the morning it was due, then I should be able to write one anytime. And indeed, I could pretty much always muster enough focus and discipline when I wanted something badly enough to try.

Until I couldn’t.

A month into my job as a research assistant at Massachusetts General Hospital, I got my second warning: if I kept zoning out during trainings and making too many careless errors on study protocols, I might lose the job.

This feedback hit me on a new level: this time I wasn’t just risking my grade in a class, but the integrity of real patient data that I was being paid and entrusted to collect. My chance at graduate school, my nascent reputation in the field, my financial independence, everything I cared about was on the line.

So I stepped up my efforts 10-fold: 9pm bedtime, gallons of coffee, color-coded highlights and sticky notes, extra practice sessions. And still I’d zone out mid-training; and still I’d skip an item or forget to start the timer when administering study protocols.

When research became mesearch

As luck would have it, two of the protocols I was struggling so much to administer were for adult ADHD studies. So even as I came face to face with my own limits, I interviewed dozens of study participants about symptoms that described me more perfectly than any of them. Meanwhile I heard the faculty present research on the thinner and slower-maturing prefrontal cortices, task- and context-specific cognitive performance deficits, and genetic heritabilities of people who share those symptoms.

Slowly, reluctantly, I started re-thinking what was and wasn’t “made up” about ADHD.

One night I Googled my way to a page describing undiagnosed adult ADHD, and I broke down in sobs. “Maybe you’ve been told you are morally weak, and you carry a lot of shame…”

The next day, I casually asked my supervisor for a referral. One evaluation later, I had a diagnosis, a prescription for Adderall XR, and a pill bottle waiting on my nightstand.

The first dose

At first, nothing seemed especially different.

It was a Saturday, so I decided to experiment with outlining a short story I’d been stuck on for years.

Five glorious, uninterrupted hours later, it was done.

The “Tinges” and the Gear Shift

The next morning, I noticed an anxious unease (the “tinges,” I came to call it) about 30 minutes after taking Adderall. My psychiatrist cycled me through Focalin, Dexedrine, Vyvanse. Same dreaded “tinges,” same or smaller benefits. We circled back to Adderall. I took up mindfulness practice, which turned the tinges from a ruminative spiral into a barely noticeable blip.

What Adderall didn’t do: give me a high or erase my bad habits overnight.

What it did: turn my fleeting bursts of focus into something I could summon and sustain on demand. As a result, my efforts to change or override my habits went much further than they ever had before. If I put my phone away and set the intention of “listening and taking notes during this 2-hour training session,” that intention stayed with me for the entire 2 hours. Not only did I have more energy available (as would have been the case if I had guzzled coffee), but I could aim that energy more precisely and enduringly toward my chosen, values-aligned goal.

It was like I had gained access to a purer, more stable, and more malleable form of the raw material that powers my agency. What I did with that raw material was and is, as ever, up to me.

Imagine a car whose gear shift jerks unpredictably between Drive, Reverse, and Park unless you keep your hand on it, and sometimes gets stuck entirely. That’s how I experience my attention off Adderall. On Adderall, the gears click into place and stay until I decide to shift.

Compounding Returns

Since that first dose, Adderall has multiplied the intentionality and loving care I am able to bring to my work, my marriage (just ask ), my kids, my home. It has allowed me to become more fully me, in every area of my life.

Of course, your mileage may vary. There are real risks and downside cases, real problems with misdiagnosis, real potential for abuse and addiction (which I’ve treated more than once in my own practice), real ways these medications get coopted into a medicalizing narrative of what are in fact deficits of the educational system rather than the kid.

But as for me, I’m eternally grateful for this genuinely miraculous medical technology and the fully-lived life it has unlocked for me. As Matt put it, largely based on his observations of Adderall’s impact on me:

I’ve also added plenty of other tools, from the above-mentioned mindfulness practice, to David Allen’s GTD system, to keeping an honesty log, to developing my own builder’s mindset. But given all the stigma and misinformation surrounding it, I want to be very clear that Adderall has been the most transformative intervention by far.

The Small Print (That’s Actually Big)

If there’s a unifying thread among the various symptoms of ADHD, it’s a weakness of executive function: the ability to aim and sustain mental energy toward your goals in context. For instance, if you tell yourself “I’m going to work on my book for the next hour,” to what extent do your cognitive resources get mobilized in service of that goal? Does your attention stay fixed on material related to the book, while filtering out irrelevant stimuli that would distract you (like email notifications or thoughts of what’s for dinner)? Are you able to keep secondary intentions like “keep track of the time so you can stop in an hour” on the periphery of your mind without either losing sight of them or being derailed by them? If and when you do notice the time is up, are you able to pry your attention away from the book and shift it to your next intended task, or else reassess your goals and priorities based on the context?

Your executive function isn’t static: it’s better when you’re rested, worse when you’re hungover, better when you care about the task and relate to it as a builder, worse when you self-deceive about your reasons for engaging in it. Biology also matters, with the latest heritability estimates putting it at 60–80%.

Executive function exists on a continuum. Diagnosis cutoffs are arbitrary. People with weaker executive function tend to benefit more from stimulants, but you don’t need to meet a diagnostic threshold to get value. In my ideal world, adults could weigh the upsides and tradeoffs without leaning on a formal diagnosis as a crutch.

Even absent this legal autonomy over what we ingest into our own bodies, we can still choose what and how much meaning we personally imbue in a diagnosis. When it comes to ADHD, I still prefer the framing of “My executive function is weak and benefits hugely from interventions like Adderall and GTD” over “I have ADHD,” which is too easily placed in service of an agency-undermining “disease victim” narrative.

Agency Above All

Executive function is one critical ingredient in human agency. You can exercise agency over it, in turn, by a bunch of different methods, stimulants like Adderall being foremost among them. You can work on strengthening your executive functions, or you can leverage your existing strengths in a way that largely lets you work around them. The point is: you get to decide. Just make sure it’s your life, not the false clarity of a diagnostic label or the Luddite preaching of internet trolls, that is your ultimate yardstick.

Stay tuned for “part 2” next Thursday, when we’ll be challenging each other with some real (anonymized / lightly fictionalized) client case examples. We’ll also be taking audience questions, so feel free to send yours in advance!

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Hot take: our attachment styles actually say more about how we relate to the world as a whole than how we relate to other people, per se.

No, really, hear me out:

The common view is that attachment styles reflect our internal working models of what to expect in major relationships, largely based on our earliest relationships with caregivers. Let's call this the "generalized-caregiver-model" (GCM) view. Here are some problems with the GCM:

1) Even the most secure child-caregiver relationship is too weird and unique to serve as a good model for adult relationships. A healthy adult relationship (including with our former caregivers) presupposes 2 independent agents who no longer require "caregiving".

Indeed, part of being a "securely attached" adult is not wanting or needing to be mothered by your friends/partners/colleagues; if you do, this generally reflects an unmet developmental need. The best caregivers are those who make themselves obsolete (qua caregivers, at least).

2) The best evidence we have for distinct childhood attachment styles that have enduring effects in adulthood comes from Ainsworth's famous "strange situation". Note the key differences in how children react to this situation:

True, some kids get more visibly distressed at mom's leaving and more readily comforted by her return than others; but the key differentiator between the "secure" and “insecure" kids is how much interest they show in the rest of their environment throughout the experiment.

The anxiously preoccupied kids cling to mom upon her return, whereas the avoidant kids pay her little heed. But, crucially, neither type of kid shows as much independent interest and initiative in exploring the rest of the room as the securely attached kid.

This difference, I submit, has way bigger implications for adulthood, and for what we should be doing as caregivers, than any of the things we tend to focus on when we think about attachment styles.

3) All the functions of "responsive parenting", the best studied approach for fostering secure attachment, are functions we should ideally be able to perform for ourselves as adults: accurately identifying our own needs, responding to them consistently and appropriately, etc.

What distinguishes the best responsive parents from overprotective or permissive ones is that they set up the child's world in a way that equips her to identify and fulfill her own needs, rather than always swooping in to do it for her:

For an infant this can mean offering a breast when she's hungry, or putting her on her tummy when she wants to move; for a toddler it often means helping her put words to her feelings, or giving her access to developmentally appropriate problem-solving tools.

(Like when my then-2-year-old refused to nap in her room because "the sun was up," but eagerly relocated all her naptime paraphernalia and took the most glorious nap after I suggested she try sleeping in the slightly darker guest room. Or when my now-2-year-old clings to the breakfast table and cries “I don’t wanna go to school!”, until I offer to put his plum in a plastic bag for him to eat as a snack in the classroom, at which point he lights up and says “I wanna go to school!”.)

If I put words to the "internal working model" I was trying to build for them in those moments, and in all my better parenting moments, it would roughly amount to: "the world is a place where I can thrive, and it's up to me to do it." This is the “generalized-world-model” (GWM) most closely corresponding to secure attachment.

In fact, this model only becomes fully and literally true as we approach adulthood—once we no longer need to rely on unchosen caregivers to chaperone our relationship with the world. We still need love and inspiration and visibility and connection from other humans, of course, but these needs are on a par with other needs, like health and meaningful work and financial resilience, which we ideally have the capacity to fulfill by our own chosen efforts and on our own terms. We are at home in the world, and can trust ourselves to get from it what we need.

We're free to love and connect with others, partly because we aren't paralyzed by the fear of losing them; we know our ability to function in the world does not fundamentally depend on them.

This is my hope for both of my kids. If all goes well for them developmentally, they will have the needed mental and physical capacities to choose and manage all their life projects independently, through their own direct causal agency—brooking no unchosen intermediaries between themselves and their world.

But to internalize this model of the relationship in which they stand to their world, they need to experience relating to their world in this unmediated way from early on, even before it’s strictly true. And this is where responsive caregiving comes in.

The best way I can give them the experience of exerting direct causal impact on the world is by "filling in the developmental gaps," so to speak; by lending my own agential powers to their cause until they are ready to sub in their own. The clearest example, for me, is when our then-2-year-old Alice (and now-2-year-old Adam) would instruct me or their dad on what to draw, and we would lend our (only slightly, in my case) more developed fine motor skills to their artistic vision. Some form of this is also happening when I curate their food and clothing selections to fit with their evolving preferences, while also explaining, in cause-effect terms they can understand and relate to their own needs, why I'm not honoring certain preferences (e.g., because "this type of drink would make you sick" or "you're not quite big enough to fit into that sweater yet").

All of this basically squares with the recommendations of "responsive parenting," paired with Montessori's recommendations for preparing the child's environment so she's always equipped to fulfill her own needs through the materials provided her.

But contra the explicit aims of attachment-based parenting, my primary goal is not to get them securely attached to me; it's to get them in direct, joyful and capable contact with their world, whilst making myself as peripheral and unintrusive a player in that relationship as possible.

Conversely, the failure modes I'm trying to steer clear of are ones where their path to impacting the world is through my arbitrary whims and preferences—making me, not the logic of reality, the final arbiter of whether and how they get their needs met.

This failure mode isn't reserved for cruel or unthinking parents; I've fallen into it simply by going back on previously set limits (e.g., "we brush our teeth before bed") because I'm too tired to insist, or letting my reflexive "hurray" become my toddler’s main reward for using the potty.

A few isolated instances like this aren't likely to do lasting harm (I hope!). But the more we let our own moods intervene between a kid's causal reasoning and reality, the more we message that their need-fulfillment is not fundamentally up to them. This naturally leads them either to 1) feel tethered to others' good favors as a prerequisite to their own need-fulfillment (hence becoming “anxiously attached”), and/or 2) suppressing their needs altogether so they don’t have to be so tethered (hence becoming “avoidantly attached”).

Personally I've found it quite clarifying to reinterpret the findings of attachment research through this lens. Instead of worrying about whether my kids have a secure enough relationship with me, I'm instead focused on curating their relationship with the world: a world filled with chosen delights they can pursue by their own thoughtful efforts, but not through tantrums or coercion; where their actions have real, discernible consequences; where knowledge gives them power; where there are no artificial limits on what they can envision and build.

[This post is a lightly edited version of this 2022 Twitter thread, which I’m reposting here by popular demand]

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Specific areas of exploration included:

• how to reconcile Sasha’s reported experience of letting go of his personal will with his being a person who exemplifies and is even co-authoring a book on agency

• self-honesty vs self-dissolution as correctives for defensive identity?

• the danger of severing our feedback loops with reality (as manifested in everything from Jiu Jitsu to corrupt guru scandals)

• healthy (“habituating to openness”) vs unhealthy (“spiritual bypassing”) approaches to meditation

• Interpreting Stoicism as “low-budget equanimity” versus “high-budget equanimity” (and the difference it makes)

• what it looks like to go through “annihilatory grief” with grace

• a bunch of other stuff like that

Tune in above if you missed it, and tell us what you think!

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As my book draft deadline to Penguin approaches, I’m getting a lot of questions about how it’s going. The short answer is: it’s going fine, thanks. “Fine” spans a wide range of potential scenarios, though; as this is my first book, I’m trying to stay open to the full spectrum of ways it could plausibly play out, from “it’s in pretty good shape by June” to “it’ll need several massive re-writes that take another year or 2.”

That said, my sense of (largely false) urgency and impatience are not so easily quelled, as you can probably surmise from the journal excerpt I’m sharing with you below. My goal in sharing it is to offer you a kind of meta-preview of the book via this glimpse into a messy and emotionally fraught moment in my writing process, which itself instances (to an almost comical degree) some of the book’s core frameworks.

Warn…

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First off, you’ll be pleased to know I’m high-minded enough to forgive you for showering Matt’s cringe-inducing puff piece about me with the most “likes” and views of any Psychology of Ambition post to date. It’s ok, two can play this game: just wait ‘till you read the dedication in my forthcoming book.

Second, a heads-up that I’ll be in SF from April 16-24, so reach out if you’re in the Bay Area and want to grab coffee. And if you’re a founder, VC, or founder-adjacent person, I invite you to join my fireside chat on founder psychology with two seasoned founder/VCs on Thursday, April 17.

Lastly, while I stumble through the dense, overgrown thickets of verbiage that somehow need to get shaped into a complete book draft by June 1, I hope you’ll enjoy this story of a fellow Penguin author (hah!) who did his own share of stumbling before his first manuscript took shape. You may recognize this spotlight from the inaugural installment of the Fantastic Builders series, where it was originally featured.

Builder spotlight: David Allen

Principle on display: Building yourself by building; why builders need self-trust (and how to build it)

Many people have positively shaped my life, but there’s only a handful—maybe 3 or 4 among those still living—whose ideas have fundamentally transformed my life for the better. David Allen, the creator of the Getting Things Done (GTD) system I was lucky enough to discover back in college, is among that handful. Beyond the many well-documented wellbeing and productivity benefits of GTD, its most personally meaningful benefit was its role in helping me build and maintain self-trust. By providing a reliable method for capturing and tracking our intentions and choosing whether, when, and how we want to act on them, GTD makes it both harder and less necessary to BS ourselves about what we intend to do.

And so you can imagine my barely-containable delight when I got to spend 30 minutes picking David’s brain in a 1:1 Zoom call the other day. (Thanks for making the intro, !)

David spoke, and listened, with the easy manner of someone who’s living his best life and knows it, and so feels no need to prove anything to anyone. You’d never guess from his mental spryness and casual demeanor that he’s either a day over 60 (he’s 78) nor the legendary author whose work has transformed how millions of people and organizations around the world relate to their work.

Here are some tidbits he shared about his backstory and how he went from being penniless and hospitalized for heroin addiction (a story you can read more about in this Wired piece) to becoming the world’s most sought-after productivity expert and executive coach:

For all the immense success David has enjoyed as a result of Getting Things Done, he never actually set out with any sort of “grand plan” of transforming how people work or achieving any sort of large-scale influence. “I’ve never been that entrepreneurial,” he said; rather he’s always experienced himself as “just putting one foot in front of the other.” For instance, after the “self-exploration” journey that led him to drop out of his UC Berkeley PhD program, take up heroin, and eventually hit rock bottom, David needed to pay the bills somehow. So he started taking odd jobs wherever he could find them. One of his first jobs, he recalled, was driving a delivery truck for a company making small industrial tools for some of the first “startups” in what eventually became Silicon Valley.

Some of David’s friends at the time were starting their own small businesses, and they needed help “managing their systems”—i.e., getting themselves organized. David was always “Mr. Lazy” (his words) and liked the idea of making things more efficient. So he’d spend some time helping one friend get organized, then he’d “get bored, move on, and find another job,” and so on. At some point he learned that the types of jobs he was doing were called “consulting” (not a category he’d ever encountered growing up in Louisiana), and that he could get hired to do more of them. Then “some corporate guy saw” what David was doing for these small business executives and said “we need this for our whole team,” so he asked David to do a training for his company, which then got picked up by other companies, including Lockheed, where it became “one of their most popular trainings.”

“Who’d have thought I’d end up in the corporate world?”, David mused. Consulting eventually turned into coaching for top executives, who would hire him to come to their office, sit desk-side with them, and help them implement the system he had come up with. It was 20 years later that someone said to him, “David, you’ve gotta write the book.” And it was another 4 years before he’d gotten the book written and “out of his head,” with little expectation as to how it would sell.

The rest, as they say, is history.

If you need a free and easy GTD start guide, by the way, Tyler DeVries has written a good one.

Despite my highly contagious, overtly diseased visage, Gena deigned to stay in the other bed. We stayed up all night talking—about work, about people we both knew, about psychology and philosophy. A few months later we were dating, and a year and change later we were married.

This March marks our sixth wedding anniversary. Our marriage not infrequently leaks onto Twitter. We both “Work in Public”, and also Parent in Public—we have two small children. Marriage in Public happens as a matter of course. Here follows a more considered, essay length treatment On Being Married to Gena, a circumstance as wonderful as it is rare.

There’s “good with people”, and then there’s Gena

In that all-night conversation, what most struck me were Gena’s deep insights about people. That initial impression has endured. I am often quite opinionated about people; I consider myself an astute judge of human character, motivations, and needs. Gena not infrequently disagrees with me on these fronts. She is almost always correct.

She’s in a league of her own. It’s not just that she has good judgment, though she does. It’s not just that she has great diagnostic and interventive instincts, though she does—she’s a stellar therapist. It’s not just that she genuinely loves people, though she absolutely does.

On top of all of that, Gena is attuned to the human condition, in the manner of a novelist. She is specially attuned to the elements of the human condition that bear on happiness, on greatness, on lust for life, on ambition. This attunement is the result of a mixture of lifelong interest, extensive and diverse formal education and clinical experience, and a generous splash of romantic folly that she was seemingly doused with in the womb.

Gena developed her tremendous empathy over decades while always centered on the grand, on ambition. That combination—a master therapist’s skill and interest in the subtleties of people, and a romantic’s captivation by human ambition—makes her insights unique, and uniquely accurate. It turns out that human grandeur in the spirit of the 19^th century isn’t merely awesome, but also probative.

Gena is profoundly interested in the challenges that people face in living up to their most exciting life quests, up to and including skepticism, confusion, or demoralization about those quests. Whether it’s literal war trauma, run-of-the-mill anti-patterns, or insufficient social skills to kickstart one’s love life—whether it’s imperceptible traces of self-doubt or raging metastatic self-doubt—Gena can see it, understand it, articulate it, and find real paths forward. The paths she sees are always aesthetically rich, blessed by her unwavering belief in adventure, in redemption so swashbuckling that the need for redemption is obviated. These paths are real, and not easy for others to see, even when she is pointing right at them.

This is all obvious in the context of amelioration of various woes, but it’s ever-present in all social contexts. Gena is preternaturally good at understanding and connecting with people generally. Imagine you were instantly 10x better at evaluating a teacher or babysitter for your children. Or imagine you were 10x better at sowing and reaping social value at parties. Or imagine you were 10x better at hanging out with your friends. Being married to Gena is having a live-in social multiplier.

Contrary to the adage “great minds discuss ideas, average minds discuss events, small minds discuss people”, great minds discuss—and consider and interact with—all these things, especially people. Marriage is a social affair; two people’s interpersonal relationships are interpolated. You jointly share many friendships and communities, jointly attend social occasions, jointly help people and are jointly helped by people. It is a superpower to be married to a person who is more right about and better with people than you are.

A marriage of ambition

When we started dating, Gena was at the very tail end of a very long course of education and training in clinical psychology. She had worked with postpartum mothers, veterans, couples, teenagers, and more. She took a tenure-track research position. Gena loved this work and was great at it, but she was boxed in by the typical career container and orthodox clinical approaches. The proper scope of psychology was, for her, more ethical, more characterological, and more agential than could be captured with standard methods of research and approaches to therapy.

She started seeking out clients who were struggling to be more ambitious, or with the challenges of ambition. Many of these were startup founders or founder-adjacent types. Working with these clients has more resonance for Gena. They have more resonance, not because they are exceptionally untroubled (they aren’t) or elite or accomplished (sometimes they are, sometimes they aren’t), but because their ambitiousness represents what Gena sees as the universal human condition.

Being married to Gena has meant the gift of watching her blossom even further as this career transition unfolded. Ambition is in fact at the heart of moral psychology, and I feel like I am married to the one person who sees this. Who really, fully sees it. Who has spent her life practicing seeing it, in every aspect of every life she encounters: in people in the wider world, in her clients, in her friends, in her family, even in fictional characters.

Her special insight is at the heart of our marriage. Not just in the sense of being a power couple with increasingly successful careers or increasingly more influence. It may sometimes look that way! But the main career ambition Gena encourages in both of us is to be less standard, to be ambitious, not primarily in the direction of more success or impact or influence, but in the direction of being more creative and principled about work and life projects. E.g.: Gena left her tenure-track job and swapped social science research with philosophical writing on the internet. I left my startup to write a book. Gena romanticized both leaps; both involved significant changes for both of us; they are now part of the story of our marriage.

But career encouragement isn’t even the paradigmatic case of how she brings ambition into our marriage. It’s more like: We critique each other’s parenting, sharply, but always on the exciting premise of raising the ceiling for our children. Or, almost without thinking about it—just as a matter of course in interaction and conversation—Gena spiritualizes our life together energetically and creatively. She competes over shows of affection, over writing poetry, over enjoying our children together fully and in the present. Thanks to Gena, these are fundamentally solved problems; the question is now how high we can raise the ceiling.

Our marriage itself is an object of ambition, and at least one participant in the marriage is ridiculously, unfairly expert at the psychic architecture of ambition.

Aesthetometry

If you’re a novelist or a filmmaker, Gena is your ideal audience. She will immediately and completely suspend her disbelief, fully invest herself in the characters’ motivations and struggles, and intensely feel every emotional beat in the story arc.

She is unsullied by acclimation to convention or genre savvy; if the literature is competently executed, she will experience each trope, no matter how predictable, as if for the first time. Gena is devastated when the teacher in October Sky gets cancer; Gena is shocked when Schwarzenegger’s Terminator is, the second time around, the good guy; Gena is overjoyed when Hatteberg hits a home run.

On our honeymoon in France and Italy, I teased Gena for running up to every sculpture she saw in the manner that a friendly dog runs up to other potentially friendly dogs. Gena actually does treat figural sculptures as potential friends: they are ensouled, and it is always worth investigating souls for possible affinity. Years ago, we happened upon a set of small bronze sculptures for sale. It was a series of figures, portraying a woman’s progress from hunkered misery to expansive serenity. Bronze sculptures cost tens of thousands of dollars. We had no money. Gena, who is disposed to extreme frugality: “We should buy them.”

Gena is hungry for art. She is starving to surrender herself to a small exhibit of paintings in a museum or an hour of a serial on her living room TV. She is too good of an aesthetometer to, in moments of aesthetic appreciation, descend to analysis or other modes of cerebration. She simply experiences the metaphysical emotions, raw and unfiltered.

Her capacity in this regard extends beyond art. She is ecstatic when the lights on the Empire State Building dance on the hour; she is wrenched when hearing about new calamities, be they personal or world-historical; when someone announces an engagement or shuts down their company or shares a cute experience of their toddler, I suspect Gena often experiences it more acutely than her interlocutor.

When we first started dating, I had mixed feelings about these patterns. They were cute, but I felt they had a detached, manic pixie dream girl vibe. But I quickly came to see that the connection was superficial, or, even inverted: that the manic pixie dream girl vibe was a fuzzy simulacrum of what people like Gena have, an aesthetic enthusiasm that is in fact grounded, by an infinite aesthetic sensitivity.

Now, seven years in, I actually think of Gena as an aesthetometer, as (amongst other things) an instrument. I am loath to watch films without her, to go to museums without her, even, as mentioned, to hang out with friends without her. If you had a high-quality aesthetometer—a gauge exquisitely sensitive to, and adept at displaying, the meanings of things—why would you leave it at home? Imagine creating a home and raising children with such a person. My baseline experience of family life is that the deepest significance of pretty much everything is continuously distilled into a clear emotional signal.

Marry your best frenemy

Gena and I have a marriage centered around talking, and it is almost always in at least a mildly adversarial mode. We riff, we debate, we bicker, we rib, we retort. (One reason to write and publish this essay, on her Substack no less, is to generate in her an amusing mixture of affirmation and discomfort. Happy anniversary babe.)

I didn’t know, before I got together with Gena, that I wanted a relationship dynamic that had the flavor of an episode of Frasier. But now it’s the salt of my life. Benefits:

1. It’s constant flirtation, a constant escalation of romantic tension.

2. Amongst the things we rib are our insecurities; we habitually emphasize our security and tremendous confidence in the relationship. We don’t tiptoe around our issues, we laugh at them, together.

3. Comedy turns out to be a great way to develop insights about ordinary things, which are replete in married life.

4. Both of us have predominantly intellectual interests, which get natural uptake, and then sharpening, in an adversarial mode.

5. It requires, and naturally brings about, fresh material from both of us; boredom and stagnation are utterly alien to our marriage.

Before Gena, my mental model of healthy relationships was that they needed to be basically agreeable. With hindsight, this was, for me at least, a relationship killer. Now I operate on the opposite model: Gena and I do agree on most things, but its preferable that we agree in a disagreeable way.

I’m not completely clear on how this dynamic developed, but I do know that it is not incidental to Gena’s person. She’s a dancer. That’s literally true, she’s a phenomenal Lindy dancer. But I mean more metaphorically. She, more than anyone else I know, is perpetually putting herself out there: her insecurities, her confusions, her struggles, her half-baked hypotheses. I don’t like the term “vulnerable”, especially not for her—these behaviors are precisely what make her invulnerable—but what that term is gesturing at is characteristic of Gena. She’s never holding back, and her intent and hope in never holding back is to be always engaging. She yearns in all things for the back and forth; she has no notion that there might be something to “protect” from a back and forth.

I am not naturally like this, at least not nearly to this extent. Being married to Gena brings it out of me, especially regarding the marriage itself. I don’t know how legible our marriage is to outsiders, but within the marriage, it’s maximally legible. Not in a boring, analytic, direct way, but in a fun, roundabout, romantically combative way. There’s constant back and forth. Through (deliberately manufactured) adversity, strength.

Typical, really

Gena is an exceptional person. Our marriage is, I not-so-humbly believe, exceptionally good. But, as a concluding thought: our relationship is in many ways almost comically normal.

Gena and I are opposites in a standard “opposites attract” sort of way. She’s outgoing, loud, and enthusiastic; I’m introverted, quiet, and grumpy. (This is true in a stereotypical enough manner that one of our wedding toasters roasted us for it.) She’s the warmer parent; I’m the firmer parent. (Our children roast us for this.) She’s mildly anxious; I’m mildly avoidant. (On such matters, we, as implied above, roast each other.)

One of the keys to happiness that I did not learn until too late in life, and have learned primarily by being married to Gena, is that greatness can come from intentionally leaning way into a conventional pattern. Ambition is more obvious when it’s breaking dramatically with the status quo, but it’s no less real when it’s according with it.

One of the best things I can say about being married to Gena is just that it’s a marriage. We spend a lot of time together, we love each other, we share chores and finances and friends, we have children. Our joint life together is more than the sum of its separate parts. The unique idiosyncrasies of our marriage matter tremendously to me, but it also matters tremendously that the generalities of marriage are perfectly accurate.

Hopefully, with good fortune and health, we can, over the coming decades, continue to pattern-match on all the clichéd stereotypes of a long, happy romance.

Builder spotlight: Celine Halioua

Principles on display: Your life as the yardstick; finding person-life fit

, the 30-year-old firebrand founder and CEO of Loyal, is one of the purest examples of practical idealism that I’ve ever had the pleasure to encounter. Her long-term ambition is to increase the human lifespan through anti-aging drugs. This is notoriously hard for a million different reasons, some of them regulatory (the FDA doesn’t like approving experimental drugs for non-disease targets), some economic and structural (e.g., it takes 20-30 years to see if a human anti-aging drug is working). But instead of giving up or getting cynical, Celine found an ingenious path forward: start by extending the lifespan of dogs, and establish a precedent for the human use case from there. 

Whenever I hear Celine speak, her boundless energy and optimism belie the enormous complexity and multi-decade time horizon of the mission she’s taken on. How does she do it? And how does she stay so cheerfully patient through all the regulatory and bureaucratic hurdles that have forced her onto this circuitous path to begin with? 

The simple answer is that this path has been anything but “forced” on her; she chose it. Indeed, she custom-crafted it, based on the sum total of her values and proclivities. During the talk she mentioned that she happens to be a dog lover, and afterward I asked her whether she would’ve been able to sustain the same excitement about this path if she hadn’t been. “No,” she said, after a moment’s reflection. “I’ve actually come to love dogs and dog owners even more since I started this,” she continued, smiling with delight as she described her conversations with prospective customers and the lengths to which they’re willing to go for the chance of a few extra years with their beloved pet. 

This is the big secret behind Celine’s seemingly infinite reservoir of energy and enthusiasm: she has charted a path that she can love, with her own life as the ultimate yardstick.

Builder’s Spotlight: Henrik Karlsson

Principles on display: Raising your psychological ceiling, Your life as the yardstick, build yourself by building, Worrying on schedule

When I stumbled into Escaping Flatland author ’s note about how he “decided to be more ambitious” with his writing and parenting—and his subsequent note thanking himself for that decision a year later—I had half a mind to just republish that original note verbatim, so emblematic is it of the kind of story I like to spotlight in this series. But then I realized it would be way more fun to get to talk to him about it, so I reached out for a conversation.

And what a conversation! Of all the many impressive people I’ve interviewed for this type of spotlight, Henrik left the most lasting epistemic imprint, so to speak: almost 2 weeks later, I can still hear certain fragments echoing in my head and shaping how I talk myself through writer’s block, how I think about life design for myself and my clients, what I give myself time to explore and digest (including of Henrik’s own essays!) even if I don’t yet have a tangible outcome in mind.

Below are some of those fragments, together with some exposition to put them in biographical and psychological context (with thanks to Matt for extracting an orderly narrative from the meandering chaos of the original transcript).

Henrik’s narrative of his career as a writer is roughly as follows:

• A period of significant conventional success in his youth that he ultimately did not like

• “Seven years in a desert”, where he did miscellaneous things to make ends meet, and, most importantly, where he wrote strictly and only for himself

• The present, where he is making a living writing weird (and wonderful) essays

There are also as-yet unwritten future phases, in which he envisions being ever-weirder and more ambitious—books, large scale artistic collaborations, operas, films.

Seven years in a desert

Henrik had an unusual amount of early success as a young writer. But it was a success that that had hard limits. He increasingly felt himself encountering groupthink, and pushing into writing territory to which his audience and publishers reacted negatively. “It made it hard for me to stay connected to my curiosity,” he told me.

So he quit.

The story of my life is a lot of these very hard decisions. The decision of, like, I had a book deal, and I did a guest lecture at Harvard which was very alluring to my ego at the time. I had a very good career for a 23-year-old-poet, yeah? The decision was: blow that up because of principles. And doing that again and again.

For seven years, he did other things. He worked as a programmer, he ran an art gallery, he had children. But through it all, he was, privately and intentionally, developing himself as a writer.

“I got so sick of the publishing world, I thought I would never publish anything, so I was just writing for myself,” Henrik told me.

But it wasn’t out of general misanthropy; he was missing something.

He calls this seven-year period his “years in the desert.”

I think the years in the desert were super important, of just doing stuff for myself without compromise for seven years. You see that in the stories of a lot of people who do creative work, that they have years in the desert where they learn to trust themselves, to keep going to amuse themselves.

There is a very peculiar thing that happens when there is no expectation. You’re not even trying to get published. You're just writing things for yourself. And if you do that for years, the writing starts to change. You’re starting to develop some kind of taste that is totally unaffected by expectations of what is fundable—or anything at all.

And that also takes a long time. It’s running the kind of loss function of your mind until you figure out what it is you’re doing. I just needed a long time to figure things out, to unlearn all the things about how writing should look, and what is doable and not doable. And also building up skill, because—I was quite skilled, I could do the established things, but I had this feeling for another thing I wanted to do, but I didn't have the tools to do it.

It was a question of both: figuring out what is this other thing, and that I could only do by running hundreds and hundreds of experiments, and also gradually building up the tools to do that thing.

He had many interests in this time, most especially in education. The writing was coextensive with thinking about his parenting. In discussion with his wife, Johanna, he concluded from first principles that homeschooling was best for their children, but in Sweden, where he had lived his entire life, homeschooling is illegal. (He also had to deprogram himself from the cultural default he had internalized, that homeschooling is child abuse.) This thinking led him to another excruciatingly hard decision: that he and his family needed to leave Sweden and build an entirely new life on “a small island in the Baltic sea.”

Shortly thereafter, perhaps emboldened by the experiences of navigating and even thriving in the wake of these prior “hard decisions,” Henrik began to experiment with posting some of his writing online.

“There was also that longing for a community and belonging somewhere. But I thought that was totally impossible, because the weird combination of the things I wanted to do didn’t fit anywhere.”

At first he had “no signal whatsoever” from any audience except for his wife. And he even “deeply internalized that no one’s ever going to care about this. I had plenty of time to build up those habits of thought.”

When you’re doing something strange, there's no signal until there’s signal. If you're going into a pre-existing scene or pre-existing genre or something, there’s going to be signal. There’s going to be systems in place to move you along. But if you’re trying to stitch together like some kind of genre that will hold your voice, there will be no signal of whether you are making progress or not.

Finding signal

But Henrik did start to get glimmers of signal. His social graph was changing, and he was meeting people online who saw talent in Henrik and encouraged him to be vastly more ambitious. He started dipping his toes in the water more—he started a blog, he posted on LessWrong, he followed and engaged with interesting people on Reddit.

From there, I got in contact with some people who directed me to subreddits and so on. So I started to get some people who would see some potential in what I was doing and who were guiding me. They’re like, “Oh, you’re almost where you should be, but you should go over there.”

The internet proved connective. He found other young writers who gave him community, and others who effectively functioned as talent scouts for him.

A surprising number of these very unknown people became quite successful later. For example, Tracing Woodgrains. I think I met him very, very early on, when he was just writing comments on Reddit. There was him and there were a few others who were just totally unknown at the time, and have gone on and done things in parallel.

I remember at one point there was an early reader who I started talking to, and he explained to me how to write cold emails to people. And I was like, “Can you send me exactly what you wrote?” I used that to write to José Luis Ricón Fernández de la Puente, who writes Nintil, and he put one of my essays on his link list, and so on so. So there were people like José who helped to accelerate things, put me on the map a little bit.

It was still like a very slow first year there. But there was a process of some people coming in, and these people who have very exceptional taste and are extremely online. There were some people like that who I guess in some sense are scouting. These are VC type people. Some of them are actual VCs, but some of them are more like VCs for culture, but they are looking for new talent and giving them nudges and so on.

Importantly, the signal that he kept getting was: be weird. Be more yourself. Do more of the things that are off script.

I realized, I think that I’m good and disciplined enough that I can do this weird other thing and actually still pull it off. I’m getting some signal from that, from people I trust. I’m assuming they’re ahead of the curve. And if I just put in the hours and do the work, I could actually do that thing.

The belief that he could do it came partly from the fact that Henrik was getting signal from people he admired. And it also helped that the kind of people he admired and interacted with, the kind of people who responded to his writing, tended to be in the orbit of San Francisco culture. A core part of that culture: be more ambitious. Don’t underestimate yourself. You can do way more than you think you can.

And there’s a very different mentality than the small island life where I live. You get a lot of this very nice American thing where it’s like: you totally underestimate what you could do. To have people who have really good judgment tell you that—it’s just like, oh, yeah. Then I’m like, I trust your judgment more than mine.

Growth was slow in the first year. Henrik had 30 subscribers to his Substack when he wrote The Learning System. It didn’t explode, in Henrik’s words, but “that’s when the weird internet nerds found me—very high signal on the people who found me on that post.”

Henrik shifted his lifestyle to be able to write more. As he developed competencies and had material success in his non-writing work, he would “spend” that capital, both the literal monetary capital and his increased credibility with his employer, on working less and writing more. (More on that in Henrik’s essay: 6 lessons I learned working at an art gallery.)

What I did concretely was that I gradually lowered the amount of hours I worked. For the last two years, I’ve worked 20 hours a week whenever I wanted to write. That was my deal. Like, I traded all of my increased income toward just having more and more ridiculous demands on my employer. By being more agentic, I became so valuable to them that I could have these ridiculous demands, and that meant I could write.

Now—as of a few months ago, and two years after finding his first glimmer of signal—he can support himself and his family solely with his writing.

Ambition in all things

Since I’m writing a book on the psychology of ambition, I asked Henrik about whether his ambition in writing—his gradually changing belief that more no-compromise success was possible to him in writing—affected other areas of his life. His answer was an unambiguous “yes”.

Wait a minute, if my understanding of what is possible in writing and what I can do is so flawed, and it’s actually like 100x bigger what I can do, then that is probably true of parenting, too, and it’s probably true of all of the aspects of the things I care about.

Parenting was one obvious major domain. But it really was everything that mattered to him. “It was my exercise and my diet. And having a better diet makes me a better father. All these things are connected.”

I'm in this flywheel right now where I'm, like, getting better at things, and I'm using those resources to help me do better things. Concretely: I was able to stop working three months ago, and then I could channel that extra time into better diet and more exercise—so I can have more stamina writing. Hopefully that means I earn more money now. There’s this flywheel of getting more resources to spend more, be more ambitious around the things I care about.

It’s also notable that the form of Henrik’s ambitions is incredibly unique. He draws from the general sense of ambition in San Francisco while rejecting, at least for himself, its most common specific manifestations—e.g. growing his user base (audience) by 100x, or turning that into capital.

I have this sense in my head that I want to make something really big, much bigger than I had thought. Previously I thought that maybe I could one day publish a book, and now I’m thinking on a much grander scale than that.

That I got from the San Francisco people, in a way. But to me, it’s even more ambitious. I’m going to do that with both of my hands behind my back. I’m going to do it the hard way. I’m not going to compromise on the super weird things that I want to do, but I’m going to figure out the way of doing it at the scale that they’re talking about. To me, that’s, like, doubly ambitious.

Henrik also had unorthodox advice for people who haven’t yet built their own flywheel on their creative projects: consider separating into two phases the (1) tackling and refining your interior world and (2) development of competencies to deal with the external world.

You have to have two maps. You have to have a map of your interiority, and you have to have a map of the external world. And both of those are going to be terribly wrong by the time you’re 20, and I think trying to do both at the same time, for me, it’s just not going to work. I think it’s much easier, if you should just make a dividing line.

So—if you want to be more ambitious, right? So during the years in the desert, I was starting companies, and I’ve been running an art gallery, and I’ve been agentic there, and I’ve all the skills I’ve learned there. I was only trying to pay my bills, but I was gradually becoming better and better at doing that. I leveled up my skills at doing ambitious projects by understanding the external world kind of separately.

And [meanwhile] I was just trying to indulge myself and trying to figure out the internal map. Doing those two things separately, to sharpen both of those knives.

You need to have both an extremely deep connection to yourself and also be just like, “Okay, I've moved to Thailand, and I need to figure out the tax code, and I need to do it in two days, and I can do that, and I need to find the best helicopter pilot in Bangkok today.” You need to be able to do those things. But you can practice those things separately.

And whatever you learn there you can use over here. I was just reading the biography of Philip Glass, or his memoirs. He’s starting companies all the time when he’s young, like he’s starting a plumbing company, he’s starting a moving company, he’s doing taxi work. That is super useful for him when he’s making operas later.

Once, he becomes a famous composer, like he’s really good at negotiating, he owns all of the rights himself and runs his own publishing company. Because he’s already had four companies, and he knows how to negotiate. So once he gets to operas, he’s like, “Yeah, I’m not going to do the normal contracts, I want better pay and I keep the rights.” Because he’s done that at plumbing companies.

4 days to do whatever you want, 3 days to be “evil to yourself”

Towards the end of our conversation, I selfishly asked Henrik about his writing process.

How much of his writing makes it through to publication? He ballparked it at 10%. “90% of what I write, no one ever sees.” It’s mostly exploration, free-writing, pre-draft of any specific essay. Henrik still writes a great deal that is, in effect, for no one but himself. What about once he starts putting together material to form a specific essay? “Even when I get to a first draft, only like 50% of that gets published.”

Henrik divides his seven day week in half: 4 days and 3 days.

I do four days of the week which are total self-indulgence. My only job during those four days is to get up, get to work early in the morning, and to sit down and I ask myself: what is going on in my mind right now? What am I excited about? And my only job is to think about that. I do that for four days in a row.

Usually what happens at the end of that is that I have three half essays. That just totally unblocks me, because then I just be like, “Today, I just want to learn about grammar.” It’s just totally random things.

This is, not incidentally, his cure for writer’s block.

I try to not censor myself at all. The reason I get blocked is because I'm thinking, “Oh, this. The people aren’t going to like this a lot.” You have to separate those two things. So, yeah, I need to have a phase where I'm just totally crazy. I just trust my intuition 100% percent…

The other three days go towards sifting through the raw material generated during the first four days, and crafting essays designed to be read by an audience.

I have three days a week where I'm like, “Okay, I need to pay the bills. What in this mess could I present in a way that is meaningful to other people?” And then I take the thing that I can workshop into something that I can ship.

The fact that he gives the part of himself that is worried about money three days a week is also psychologically important to his creative process. Designating a stretch of time for that part of himself allows him to ignore it when he needs to be more freeform and exploratory.

The parts of me that are worried, they know that there will be three days where they are allowed to be totally evil toward me if they need to get work done. “Right now, I might just be following my curiosity, but you’re going to be allowed to be as evil toward yourself as you want you on Monday. There’s three days when you can just spank me all day long.” And then that part of me says, “Okay. I’ll sharpen my knives until Monday then.”

And there you have it, friends: a cutting metaphor for the very essence of the builder’s mindset, as applied to the intentional management of one’s own psychology. Thanks again, Henrik—my wanting-to-get-lost-in-cool-people’s-biographies part and my needing-to-meet-a-book-deadline part both really needed that.