Back to home

The Fool: I'm Never Really Ready, and I Try and Do It Anyway

Matt Holztrager
Matt Holztrager
May 18, 2026
The Fool: I'm Never Really Ready, and I Try and Do It Anyway

I listened to a speech from a Stanford graduate on entrepreneurship today, as I've been toying with the idea of attempting admission into a fancy business school lately and wanted to hear some retrospectives.

At one point, the speaker shared his perspective, paraphrased, that once he actually made it into those exclusive cadres he was aiming for (Stanford, for example), the mystique was somewhat dispelled, and that on the other side, he found that the expected transformation in his sense of self hadn't occurred. Why didn't he feel like a legitimate entrepreneurial candidate despite studying at one of the best business programs for it in the world (and eventually creating a business worth tens of millions)?

I think most of us would label this imposter syndrome, which I'd colloquially define as the state of actually being something but not feeling like it.

Just look to physicians for an example of this. The AMA says that ~60% of physicians in a large sample showed anywhere from moderate to intense levels of feeling like an imposter, despite the fact that these physicians necessarily received extensive education, lengthy on-the-job training after graduation, and are highly intelligent on average. Older, more experienced physicians had a slightly lesser degree of this, but it was not entirely absent even in that population.

That is a puzzling thing. If so many highly trained, intelligent, and even experienced physicians feel like imposters, then what hope is there for the aspiring business operator who didn't make it to Stanford GSB and has no real credentials to boot?

I've experienced this before multiple times (getting started in basically every new job position or business endeavor I've undertaken), and I found that it was through just taking the next sensible action (again and again) that caused a shifting of personal identity over time in line with those actions. Credentials can certainly help kickstart the psychological shift, but ultimately, it remains a question of identity, and identity is really wrapped up in action.

I'm not much into tarot cards for psychic readings, but consider one interpretation of the tarot archetype of the fool. The fool is almost always depicted as one walking off a cliff, head in the clouds. In the suit of cards, it is assigned the number zero, and I would propose that one possible interpretation for this placement and symbolism is that the archetype of the fool is present in all our beginnings— and we all necessarily walk off a metaphorical cliff in our ignorance as we embark on any new journey.

As I write this, it occurs to me Peterson is likely the one who first exposed me to this concept nearly a decade ago, so I'll pass you to him if you want a more eloquently articulated presentation of the idea.

So, we all begin as fools, and we have to step from security (our current sense of self and qualification) into the unknown in order to succeed and grow.

Now, nuance holds, and you shouldn't do a surgery without a medical license. That said, some disciplines like entrepreneurship (or meditation and athletic performances, to name others) are arguably trials by fire, and no amount of intellectual preparation or academic certification can substitute for just making that step over the edge despite not feeling ready.

And the reality is that in some sense, we're never really ready for that step, and it's only in taking it anyway that we eventually become the thing we're aiming for.

In my experience, there just comes a point where identity finally falls in line with that repeated action, and that can definitely make the sailing a little smoother from there.

Even still, we're always still the fool in one way or another, starting from zero and stepping off a new cliff, ignorant of what lies beneath and before us.

That's all a long-winded, poetic way of stating that I've found that when I want to be something new, I take that first step, and take another, and let my sense of self expand to absorb that new pattern of behavior. Then, one day I find I am the object of my endeavor, and ready (ironically), to become a fool again.

Read next

The Runway is Not Infinite: Don't Forget About Today
Reflections · April 30, 2026

The Runway is Not Infinite: Don't Forget About Today

Matt HolztragerMatt Holztrager
Anthropic's Managed Agents: An Easy Sandbox Foundation for the Next Generation of Web Agencies
Technology · April 11, 2026

Anthropic's Managed Agents: An Easy Sandbox Foundation for the Next Generation of Web Agencies

Matt HolztragerMatt Holztrager