Through coaching, T-Groups and more casual interactions with founder friends, I’ve encountered dozens of startup founders who battle with impostor syndrome.

Impostor syndrome is not a mental illness, but rather a psychological phenomenon in which someone struggles to internalize their own accomplishments. It sabotages confidence and can create high levels of anxiety and stress. It generates feelings of being an incompetent and fraudulent outsider, even when objectively you are a competent insider with real accomplishments. And while the term was first coined by psychologists studying professional working women back in 1978, I’ve seen impostor syndrome affect modern-day male and female founders alike.

My suspicion is that impostor syndrome among entrepreneurs is a symptom of the fast-growth environment; a side effect of achieving external success (relatively) quickly; and then further exacerbated by the real need many founders face to “fake it until they make it.”

It starts with the basic premise of being a founder—because it’s a requirement for them to have the audacity to think they can do something better than everyone else—even if (or perhaps because) they have less experience in a field/industry. Then, you layer on the need for some fakery (or at least naïve exaggeration) in the very beginning. Let’s take the first time they landed a customer who was actually going to pay them money for their fledgling product. It was a time of joy and excitement, but maybe also fear. And the first symptoms of inaccurate thinking set in. A founder might think: “Whoa, why me? Do these people know how much I don’t have my sh*t together? If they had any clue, they wouldn’t want to buy this product.” They fail to understand what they did and how they enabled that first customer to happen. This isn’t humility—it’s a failure to internalize an accomplishment. And so it begins.

Then a founder starts to hire people and they’re floored to see how many real, talented people want to come work for them. And they don’t understand how that happened. And then somehow they’re able to charm some reasonably smart people into investing hundreds of thousands (and sometimes millions) of dollars in their idea and their team.

At this point, founders might be serving up lofty quotes to Techcrunch or other startup press, but in the back of their minds they can’t turn off this message. “We got lucky. We fooled all these investors. It’s all just smoke and mirrors and a great story. What if I can’t pull this off next time?”  And, again, they fail to internalize the accomplishment of what they did to put themselves in a position to get lucky. They don’t build their own sense of self-efficacy as a founder who can raise money.

And all of this happens over a 9 or 12-month period when they’re 26-ish (+/- 4 years) and they’ve never run companies before much less super-fast-growing ones. Who wouldn’t feel like an impostor at some moment along the way?

Some founders are savvy to this struggle. They even know the syndrome by name and talk about it with a coach or a trusted founder friend who has also done battle with this particular demon. But they still work hard to keep up a front that is solid, confident and consistent with the image portrayed in media, trumpeted by investors, and revered by their teammates.

But privately, there is a cost to all that hard work. It can be crushing at times.


Does This Sound Like A Founder You Know? Maybe You?


As a coach, I have privileged access to what many founders really think and feel—but if you are someone who advises, invests in, or works with/for a startup founder, you’re unlikely to ever hear about impostor syndrome directly.

(This is particularly heart-breaking when founders get together and collude in not talking about their struggles with each other. How tired are you of hearing how so-and-so is “crushing it” with an uncomfortable smile plastered on his or her face? And yet you still just nod your head and respond back with how you’re “crushing it” too. And so the cycle continues.)

Here’s how to help the founder in your life who might be struggling with impostor syndrome (even, or especially, if that founder is you):

1) Make room for emotional ambivalence at what you’re assuming should be unequivocally positive milestones.

So, instead of asking “Are you feeling excited about the expansion to X?” ask “How are you feeling about the expansion to X?” Or if a founder just closed a seed round, you might hold off on saying congratulations and just ask them how they’re feeling about it all. You will find that you just might get more honest answers when you don’t expect them to feel a certain way. We can all do more to help normalize ambivalence and give ourselves permission to feel lots of different ways about things that are supposed to be good.

2) Encourage everyone on the startup team (especially the founder) to debrief the good stuff and even dwell on a it for a bit.

It’s easy and even instinctual for founders to debrief and problem-solve when things aren’t going well. As humans, we have a negativity bias wired into our brains and founders are no different. But something important gets lost when all we do is talk about what’s not going well. We start to take what is going well for granted. We fail to learn from success. And we risk institutionalizing impostor syndrome across the whole startup team if we never stop to practice how we internalize accomplishments. So, make sure you take a few extra minutes to ask: What is going well? What’s enabling that to happen? How are we doing that? How do we keep that going or replicate it in other areas of the company? That’s how you build self-efficacy in yourself and others, and that’s how you stop impostor syndrome from running rampant across your team.

3) Assume other founders have struggled with this at times—and find a safe environment to talk with them about it. 

Impostor syndrome can become particularly pernicious when founders start comparing themselves to other founders and resolve they’re the only one struggling in this way. Researchers believe that up to 70% of people have suffered from it at some point—so chances are more founders have struggled with it than you might think—even if you’re never hearing about it. It can be deeply validating or reassuring just to know that you’re not the only one. I wish I could name names here—but since I can’t, all I will tell you is I’ve met several objectively badass founders who have struggled at times with impostor syndrome. It’s real. It’s common. And it’s surmountable–if you start with some of the steps listed here.

And lastly—if you can—try to find a safe environment where you can talk with other startup founders about struggles like impostor syndrome. This could be a T-Group, a founders-only support group, a discussion group at a startup conference that prizes vulnerability and authenticity like Failcon, or just a real conversation with a trusted founder friend. Not only is it validating to realize you’re not the only one going through this—talking about it in a small-group setting can also speed up the process of challenging flawed thinking and starting to internalize your accomplishments in a more accurate way.