Reframing Imposter Syndrome

For about year when I worked at a 50-person startup, the most common thought that I had was “I have no idea what I’m doing.”

What should we build next? How should we set up a good process for performance reviews? How do we get more people to want to buy our product? Are we shipping too many bugs? Are we overly conservative and shipping too few? Almost every day involved at least one strategic decision that I didn’t feel that I had the qualifications to make.

These moments could be unsettling, and in retrospect I had a classic, low-grade case of imposter syndrome. I felt like I was playing in a band and improvising while everyone else knew the music. With the benefit of hindsight and substantially more experience, I wanted to write up a few thoughts on scaling companies to reframe this imposter syndrome in a more realistic light.

Everybody is Improvising

As that same company grew to over 500 people, I kept waiting for the magic moment where I (or others) suddenly knew how to handle the decisions that came our way. As a 50-person company we figured things out as we went along, or made the best call we could with imperfect processes, data, and first-principles thinking. After growing over 10x larger, the problems changed, the processes and data improved, but the approach didn’t.

In retrospect this should have been obvious. Every company and team is different, and there is no sheet music to play from.

Even startups that are widely considered to be successful still need to figure stuff out the old-fashioned way:

  • People at all levels of the organization, including the highest-level executives, often reason from first principles. There are techniques that one can learn to be more effective; there is no manual for how to respond to any arbitrary new situation.
  • Most decisions are made with imperfect or incomplete information.
  • Company leadership does not have all the answers, and very smart people make both brilliant decisions and damaging strategic errors.
  • Experienced leaders are also capable of being irrational, reacting in an emotionally driven way, or surrendering to groupthink of various forms. People struggle, question decisions that they’ve made, and generally stress out.

Simply put, if you’re feeling like a fraud for needing to figure things out from first principles, know that almost everyone else is doing the same at least from time-to-time (although experienced people do tend to have a more zen attitude and realize that it’s just a part of the process). All startups are messy, and things get done by smart people making the best decisions they can with the data and resources that they have. There is no secret cabal of “grownups” who know the secret to scaling companies.

But Experts Are Actually Better In Some Ways

Of course, experience is extremely beneficial. I find that there are generally two major areas in which experience matters. Neither of them should make you feel like an imposter, and neither will give you definitive answers on how you should operate your company.

The first important dimension is that experts have a really wide portfolio of operating techniques. To extend the music analogy, these techniques are like chords or guitar licks that you can learn and later use to improvise. It might take a while to build a repertoire, but most startup techniques are straightforward and can be learned through reading, advice, or practice. These are technical skills, not God-given talents.

The other area where experience is critical, is giving you reps in challenging situations. Examples include:

  • How do you know if you’re wasting time on something unimportant? How do you know what to half-ass vs. whole-ass?
  • How do you handle stress over long periods of time? How do you strike a balance between optimism and realism with your team? How do you stay calm in the face of pressure? How do you know when you or someone on your team is burning out?
  • How do you handle difficult situations? What do you do the first time someone has a personal tragedy on your team, when you have to fire someone on your team?
  • How do you know if a struggling team member’s performance is salvageable, or if they’re unlikely to be able to turn things around?

For these skills, the fact of the matter is you just need to live through a lot of situations to build strength at identifying patterns and preparing your mind for future situations. In the musical performance of a startup, these skills are like practicing until your fingers are strong and you can easily play whatever comes your way.


Decision-making from first principles is the default at most companies, even successful ones. There is no sheet music for running your team or business.

Experience can give you more operating techniques and build the muscle required to be a good manager or leader. We try to write about these transferable techniques and perspectives. But there is no playbook that will teach you how to make the right decisions.