Vision or delusion? (Part 2)

Why ambitious builders need self-trust—and how to build it

Read Part 1 of this post here.

How self-deception undermines ambition

Self-trust matters in direct proportion to the ambitiousness of what you’re trying to build. 

Building something truly new, be it a product or service or organization or methodology or scientific insight, means betting on the soundness of your independent judgment—unchecked by anything but its inexorable effects in reality. Building a startup, for example, means staking your time, energy, and reputation on your ability to see something that others haven’t seen, such as a fundamental human problem that needs solving, or the promise of a new technology for solving that problem. 

The work of forming such judgments may involve tracking a thicket of if-then contingencies and margins of uncertainty at multiple levels of abstraction. For instance, you may be fully confident that some form of machine learning technology will ultimately solve the problem you’ve identified, while knowing there’s a fairly low chance that this (or any) particular machine learning technology will solve it. And you need to make judgments about what sorts of evidence you would need to gather over what time horizon in order to validate or invalidate a given solution, since this can inform the relative costs and benefits of pursuing one solution over another. 

Being a founder, or a trailblazer of any sort, means taking ultimate responsibility for the accuracy and resolution of your roadmap. Even when consulting with fellow trailblazers who’ve successfully charted other, similar frontiers—and consult them you should!—you’re the ultimate judge of whether and how their experience maps onto your terrain. Do you heed the advisors who tell you “this way be dragons”? The ones who say “that way be unicorns”? You have only your judgment of each path’s relative downside and upside—grounded in whatever observations and inferences you’ve assimilated into your model to date—to help you decide. 

At every point in this model-building work, there are self-deceptive shortcuts you can take—and will often be tempted to take—to feel as if you have done that work.

For instance, you might tell yourself you’ve spoken to enough potential customers to validate that there is a market for what you want to build, when you know on some level that you have selectively chosen the easy targets and avoided the tougher ones.

Or you might talk yourself into believing you’ve sufficiently invalidated your really ambitious idea after some painful customer feedback, when you’re really just afraid of the further hurt and rejection you might face if you put it to a fuller test.

Or you might deliberately choose to focus on a solution that takes longer to build, telling yourself it’s because you’re “focused on the long-game,” when you’re really just putting off the moment when you might find out you’re wrong. 

Or you might defer to a big-name investor’s advice on a decision that’s mission-critical for your company, telling yourself it’s because you’re “being responsive to feedback” when you’re really just avoiding the responsibility of having to think it through for yourself.

Or, on the flip-side, you might choose to ignore an investor’s guidance on the excuse that “they don’t really get my vision,” when in fact you’re just afraid to follow that guidance through to its logical conclusions. 

Only you have sufficient context to determine, in each case, whether you’re forming an honest best judgment or merely putting on a show of one. But every time you put on a show, you feed fraudulent data into your mental model—and some part of you knows it. This, in turn, diminishes your trust in your own judgments and decisions, making you increasingly more anxious and more likely to defer to convention or to let others decide what and how you should be building. And the less visibility and ownership you have over your own ventures, the more threatening and unknowable they become—making it all the more tempting to distort your awareness of them through further self-deception. 

In this way, the self-deceptive pretense at ambition corrodes whatever genuine ambition you may have started with. 

(Re)building self-trust

So how do you break out of this vicious cycle and (re)build the self-trust to match your highest ambitions?

In addition to the journaling process I recommend here, it might also help to think back to whatever especially inspiring and effective leaders came to mind for you in last week’s post—and to focus on doing them proud in those moments when you know you’re at highest risk of self-deceiving.  

How might you recognize when you’re facing one of those moments? 

To get you started, here’s a partial inventory of some of the most common decisional contexts in which I’ve observed founders and other ambitious builders (including myself!) succumb to self-deception, along with some suggestions for catching and pushing past it:

Deciding whether or not to have a difficult conversation, usually involving some form of critical feedback, disagreement, or other “bad news.” 

Because this has come up again and again in my coaching of founders, and has been among the costliest mistakes I’ve seen founders make at various points in their startup journey, I have quite a bit to say about it—much of which should generalize to other decisional contexts that commonly trigger self-deception. 

There are often legitimate reasons to put off a difficult conversation. For instance, you might hold back on disciplining a new employee because you want to give them room to grow and make their own mistakes; or you may need time to gather your thoughts and formulate some actionable solutions before you offload your worries on the rest of your team; or you may decide that a relationship is too damaged to be worth fighting for. Such judgments may or may not turn out to be the best ones in a given circumstance, but as long as you’ve formed them in good faith, you can trust yourself to check and update them continuously in light of new data. For instance, if you observe that the new employee does not seem to be noticing or correcting their mistakes over time, or that your worries don’t seem to be getting any clearer without input from the team, or that you miss the person you broke ties with much more than you expected, you can count on yourself to adjust your approach accordingly.   

By contrast, the way to know if you’re self-deceiving is if you’re telling yourself you’re putting off the conversation for the above sorts of reasons, when some part of you knows these are just rationalizations for whatever real reasons you don’t want to name (often for fear that you wouldn’t endorse them by your own lights). One clue that this may be happening is if you keep finding new “reasons” (e.g., “ok, he still doesn’t seem to be improving, but now’s not the right time to confront him because…”), or if you feel immediately defensive when someone (yourself included!) tries to ask you about it. This is not so unlike the experience of getting manipulated into acting against your own best interest—only the person manipulating you is you.

If you suspect some of this might be going on, try to muster the courage to push through and name the unstated reasons for your continued hesitation. Ask yourself, “What am I actually afraid of?” Looking past your own rationalizations in this way is the emotional equivalent of ripping off a bandaid: whatever the initial sting of admitting the unadmitted, there almost always follows a sense of relief at being able to see it and deal with it. The very act of naming it allows you to reason with it openly, and to scrutinize it in light of everything else you know. In some cases you might quickly see that the fear was unwarranted (e.g., “I’m afraid it’ll be extremely uncomfortable for both of us”—ok, but for how long? Haven’t we both tolerated worse discomfort before? Isn’t it going to get more uncomfortable the longer we don’t have this talk?). 

Other times it may be harder to tell what’s an honest judgment and what’s a well-rehearsed self-deception. In such cases, it can be helpful to structure your thought process by asking yourself, “What are actually the worst and best case scenarios here??” Make sure you pose this question for both of the scenarios you’re considering: the one where you have the conversation, but also the one where you don’t. 

Deciding whether to pursue a relatively more or less mainstream career path. 

As with every complex decision, there are genuine and counterfeit versions of the reasoning on both sides of this one. On the one hand, it’s easy to get caught up in chasing the social trappings of ambition—status, popularity, prestige—as cheap substitutes for the work of forming and pursuing your own unconventional path and evaluating yourself accordingly. This is one form of what I have come to call “pretend ambition.” For instance, I still sometimes catch myself rationalizing why I should prioritize the conventional standards of academia (e.g., “I’ll have more freedom to pursue my real interests once I’m tenured!”) instead of doing the harder work to figure out how to build the kind of career I actually want (as I mused about here) more-or-less from scratch. As I often have to remind myself, an unconventional mission requires unconventional progress metrics, and I only lose time—and erode self-trust—by pretending otherwise. On the other hand, as Don Watkins excellently argues here, it can also be tempting to use “rejection of the mainstream” as a self-congratulatory excuse for lowering one’s standards and avoiding objective scrutiny altogether. 

Deciding how to manage your impostor syndrome.

Feeling like an impostor doesn’t necessarily mean you’re self-deceiving; just that you’re judging yourself against an overly conventional standard that’s detached from the reality of what ambitious, innovative work looks like! But if you aren’t able to put this feeling in perspective, it can easily push you to pretend to yourself and others that you know more than you do (instead of just asking the questions and pursuing the information you need)—or, on the flip-side, to use self-deprecation as a defense mechanism.

Deciding how to manage your perfectionism.

I think it’s crucial to distinguish the genuine quest for perfection—in the sense of building your chosen masterpiece—from the “perfectionism” that is its counterfeit. The former is about holding yourself to the highest bar of intentionality and unwavering purpose in pursuit of your ambitious vision; the latter is about making yourself feel as if you are engaged in such a pursuit, usually at a cost to the pursuit itself. One way to tell which of these modes you’re in is to ask yourself whether and how the outcome you’re currently aiming at will actually get you closer to your desired masterpiece, as compared to whatever else you might be doing with this time instead. For instance, how much will refining the graphic layout of your pitch deck improve your chances of getting your project funded, as compared to the work you could be doing to improve the pitch itself? Or, how much will an extra 3 points on this licensing exam affect your competence as a practitioner, as compared to the extra initiative you could be taking at your internship instead? If the answer is “not much,” then you may be going through the motions of “seeking perfection” rather than seeking it for real. In such moments it may help to channel your quest for perfection into the often scarier, messier, and more purposeful work that you honestly believe will move you closer to your aim—and to realize that this is a raising of your bar, not a lowering.

Deciding whether to call it “quits” on a given venture. 

Because the particular judgments involved are so highly contextual and person-specific, there is no universal prescription I can give you for when to quit and when to keep trying—except to use the framework and tools I’ve described here to distinguish your honest best judgment from its counterfeits. As with every other complex decision, the counterfeit (i.e., self-deceptive) judgments can cut both ways: on the one hand, you might cling to a venture or ambition primarily out of fear, guilt, or shame (often triggered by some form of sunk cost fallacy), despite knowing—or at least suspecting—that it’s no longer the best path for you. On the other hand, you might find yourself seeking excuses for why you “can’t” succeed at this venture, despite knowing on some level that you’re just afraid of the work. 

Stay tuned for future posts that dive deeper into each of these variants and more, discussing how you can gain real perspective and coach yourself out of self-deceiving in each circumstance. For now, I hope this will serve as an invitation to start earning your own trust in more of the moments of your life—that you may pursue your most audacious vision for real, not merely for pretend.