Raising humanity's psychological ceiling

Why I think ambitious builders are underserved, and why I've devoted my life to serving them

Updated from a 2023 post by the same name.

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 make their venture-backed startup profitable?

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 “make your venture-backed startup profitable”. 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 large numbers of people to want to pay you for it over and over again, in sufficient quantity that your revenue consistently exceeds your costs?

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, win-win relationship building, emotional self-management, authentic conviction, earned self-trust, intellectual ambitiousness, and disciplined focus 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 deciding whether and how to hand over the reins so you can move on without undoing 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 mindfulness skills to manage their stress”, they need help recognizing when they're using these skills as procrastination tools.

• 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 maximum 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 gain 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.