Vision or delusion? (Part 1)

Why ambitious builders need self-trust

At some point in the startup journey, every ambitious founder wrestles with the question: am I one of the visionaries? Or am I just deluding myself?

Popular wisdom tells us it’s basically a tossup. All founders must delude themselves into a false sense of certainty, we’re told; the ones we later call “visionaries” are the ones who happened to get lucky. 

But this popular wisdom grossly misrepresents the reality of founding. The kind of thinking that produces genuinely visionary insight—like Alexander Graham Bell’s vision for the telephone, or the Wright brothers’ vision for air travel, or Oprah Winfrey’s vision for a new kind of talk show, or Jeff Bezos’ vision for the future of e-commerce when he quit his comfortable finance job in 1994—looks and feels starkly different from the kind of “thinking” that props up a wanna-be founder’s delusions of grandeur.  

The difference lies, fundamentally, in a person’s relationship with the truth. 

Contrary to the widespread assumption that “all founders self-deceive,” a close examination of the thinking habits that distinguish the world’s most ambitious entrepreneurs reveals that they are, if anything, obsessively truth-oriented. For instance, one of the most oft-cited differentiators of today’s most successful builders—like Jeff Bezos, Paul Graham, and Peter Thiel—is “first principles” thinking, characterized by an active questioning and checking of all assumptions by reference to what one directly and independently knows to be true. And a close second is “bias for action,” which amounts to maintaining a tight, efficient feedback loop between one’s judgments and reality. True visionary insights do not come from nowhere; they are forged in the crucible of many smaller judgments faithfully tested in reality, with each new result getting thoughtfully incorporated into your evolving model of the world.

Crucially, this truth-orientation extends to unpleasant truths as much as pleasant ones: as venture capitalist Ben Horowitz puts it, “Almost all CEOs know where the problems are, but only the truly elite ones run towards the fear.” In other words, the truly great founders treat unpleasant emotions as cues to attend more vigilantly to reality, rather than to avoid or rationalize away the unpleasantness. 

The vigilant truth-orientation of great founders is especially manifest in their approach to risk and uncertainty. For instance, as Julia Galef documents in her book Scout Mindset, founders like Musk and Bezos did not delude themselves about the odds that their most ambitious ventures would succeed. When 30-year-old Bezos quit his finance job to start Amazon, he reportedly put his odds of succeeding at about 30%. Reflecting back on his reasoning at the time, he recalled, “If it failed, fine. I would be very proud of the fact when I’m 80 that I tried.” Crucially, even though he did not know for certain whether his specific e-bookstore venture would succeed, he had a deeper certainty—rooted in careful observation and “first principles” thinking about how fast the web was growing, what new modes of human interaction it made possible, and what fundamental facts about his customers could be relied on over time—that the Internet was going to change the world. So even if his first 10 online business ventures failed, he had good reason to believe that the experience and expertise he gained from each iteration would get him closer to eventual success. 

Likewise, Musk put the odds of success for both Tesla and SpaceX at about 10% at the time of their founding. In reflecting on his founding decisions, he said, “If you just accept the probabilities, then that diminishes fear. So in starting SpaceX, I thought the odds of success were less than 10 percent, and I just accepted that probably I would lose everything.” 

Why bet most of his fortune on such a low-probability outcome? Because, as he explained in a 60 Minutes interview (quoted in chapter 8 of Scout Mindset), “If something’s important enough you should try. Even if the probable outcome is failure.” The possibility of sending humans to Mars was, in Musk’s estimation, a bet worth making, even at just 10% odds. And again, he did not regard the potential failure scenario as a net loss: “If we could just move the ball forward, even if we died, maybe some other company would pick up the baton and keep moving it forward, so that we’d still do some good,” he explained.

Betting on your cognitive integrity

Notice that all the reasoning and decision-making strategies described in these examples rest on the precondition that you can be honest with yourself about what you do and do not know, and with what degree of certainty. Do you actually believe this has a 10% chance of success, or are you just telling yourself that because you know you couldn’t justify the risk at 1%? Are you actually doing all these customer discovery calls because you believe it’s the fastest way to check your assumptions about the market (a la “bias for action”), or are you really just avoiding the harder but more important step of building out your product? Or, for that matter, are you actually pouring time and energy into building out your product because you believe it’s the best way to test the plausibility of your vision, or are you really just avoiding the scarier but more urgent step of making customer discovery calls? In other words: are you actually trying to bring your vision into reality, or are you just trying to get yourself to feel as if you are?

The more innovative and complex a vision you pursue, the harder it is to actually know what your work is adding up to, and the easier (at least in the short-term) to BS yourself into feeling as if you know. The biggest bet you make as a founder is on your ability and willingness to tell the difference, even when there is no answer key and no one else to keep you accountable. 

What fundamentally distinguishes the genuine visionaries from the wanna-be’s, I contend, is that they have earned their own trust through a track record of cognitive integrity.  As such, they can count on themselves to keep their judgments tethered to reality, even when it’s hard to do so and there’s no one checking their work. In other words, they have established self-trust. 

What does self-trust look like?

Self-trust is not the same as self-worth or self-confidence, though it’s intimately connected to both. Self-trust refers specifically to the internalized conviction that your judgment is credible—not because it’s always right, but because you’re always (or nearly always) genuinely striving to get it right. Emotionally, this amounts to the feeling that you have your own back; that you’re not going to blind yourself to uncomfortable truths or otherwise sabotage your progress in reality for the sake of a comforting fiction. 

If you’re not sure what this looks like “from the inside,” it may help to consider first what it looks like from the outside: just think about the visionaries you find most credible and inspiring, be they teachers, coaches, supervisors, colleagues, friends, or public figures. Think of the people you’d be willing to follow into battle, or whose startup you’d seriously consider joining, for that matter. What is it about them that inspires such trust in you? And in particular, what have you observed about their relationship with the truth? I would wager, for example, that they’re more interested than threatened by information that seems to challenge their assumptions; that they run toward rather than away from their fear; that they are measured in the assumptions they form, and in the level of certainty they express; that they’re more often right than wrong, and first to acknowledge when they’re wrong; that they do not make promises lightly, and are serious about keeping the promises they do make; that they have fresh, thoughtful, often unconventional takes on the issues that concern them most, and reserve judgment on issues they have not thought much about; that they ask a lot of questions, and generally seem more interested in learning and building than in proving themselves; that they double down on checking facts and testing assumptions as the stakes get higher, rather than relax their scrutiny.

By contrast, think about the most toxic and uninspiring leaders you’ve encountered. What was their apparent relationship with the truth? And how did this affect the productivity and ambitiousness of those under their leadership?

So it is that we also build or undermine trust in our own self-leadership over time. Do we habitually observe ourselves running toward the fear or rationalizing it away? Do we generally keep our commitments to ourselves, or do we find that our self-talk is cheap? Do we really try to get the facts straight, even when they lead to uncomfortable conclusions, or do we just “tell ourselves what we want to hear”?

Most of us at least occasionally find ourselves opting for the latter path. But every time we do, we undercut our self-trust ever so slightly—and make it that much harder for ourselves to distinguish visionary insight from self-delusion. 

The way to tell apart vision from delusion, then, is to check our level of self-trust with respect to the venture at hand. The greater our track record of cognitive integrity, the higher and farther we can generally trust ourselves to set our sights without falling off the rails. 

Even in making this assessment, of course, we can choose to exercise cognitive integrity—by being honest with ourselves about the extent to which we trust our own credibility at this level of ambition and complexity—or we can try to BS ourselves into feeling as if we do. But in making this choice, let’s recall what’s on the line: our chance at whatever actual ambition we might actually be able to achieve in this world.

The good news is that cognitive integrity, like any character trait, can be practiced and cultivated over time, with growing self-trust as its natural reward.

Even if you can’t yet trust yourself enough to bet on your most ambitious vision, you can bet on your ability to earn that trust.

Continue to Part 2 for more on why this matters and how to do it in practice.