Hot Seat

Chapter 28. Impostor

You’re doing the CEO job and doing it well. You’re focused on the things you’re good at, and have found wonderful people to do the things you stink at. The company’s going well, yet still you feel like a failure.

This is not helped by the amazing degree to which entrepreneurs are “killing it,” “crushing it,” and various other permutations of enthusiastically doing well. The press is full of these stories, and in casual confirmations you hear more of the same—everyone’s best features are on display.

But if you burrow down to a level of honesty and trust with a startup founder, you sometimes hear a different story. Actually, not just sometimes. Always.

One truth you hear is that things aren’t all roses. Perhaps funds are running low. Cofounders are at each others’ throats. The valuation was low. Investors are talking about replacing management.

That’s not what I’m talking about.

The truth I’m talking about is this: most entrepreneurs feel like impostors–impersonators, unable to do their jobs, struggling not to be called out for their incompetence.

The first time I had someone confess this to me it was a revelation. I think the exact form of the revelation was me rapidly replacing my beverage on the table and shouting “Me too!” at a volume inappropriate to the venue in which we were seated.

We were both reasonably successful entrepreneurs at that point; we knew what we were doing. Yet we still felt like impostors.

While there’s no formal research on entrepreneurs, ...