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Imposter Syndrome

Jason Freedman's Avatar
By Jason Freedman



In May 2009, I walked into Y Combinator. My company, FlightCaster, had just gotten accepted and this was our intro session to the group. And kind of like the Dean of Admissions on the first day of freshman orientation, Jessica got up and recounted a bunch of stats about how cool our summer 2009 batch of Y Combinator was.

this company is taking on Google Analytics…(MixPanel)

and this company already has 1 million downloads…(Bump)

and this company will change banking forever…(WePay)

and on and on…

As she went through the list, I could feel this pit in my stomach growing, realizing that everyone else deserved to be here but us. Somewhere towards the end, she mentioned, “And this company wants to forever change the way flight delays are forecasted.”

I looked up to see if there as any reaction.

Not a one.


Our bold vision of revolutionizing the travel industry had barely registered on the scale. To make matters worse, I now understood that not only did our vision not seem world changing enough, but we were also way behind everyone else in terms of just about everything: lines of code written, users, revenue, investor interest. It was like I showed up to freshman orientation and realized that everyone else was going into their sophomore year.

It was the worst case of imposter syndrome I’ve ever felt.




One more quick story to tell you before we jump into the meat of this post. This goes back to high school. Math was my favorite subject all throughout growing up. And in my senior year, I took linear algebra and differential calculus with some other math-oriented students.

For the first couple of months I held my own. But as we started to get into some of the more advanced concepts, I noticed that my friends in class were starting to pull ahead of me. Some quite easily. They seemed to be devouring the new material while I had to dig in just to keep up. This had never happened to me in any class. Especially not in math.

After a few short weeks of this, I kind of just gave up.

It wasn’t some epiphany. I just let my supply of motivation run low. By the time we got to the half-way point of the year, I had missed so many of the fundamentals that I was just lost in class.

I had just become okay with the idea of giving up.

I will leave the critique of classroom-style learning and our educational system for another time. I can say with honesty that this professor was really good and my school gave me every opportunity I needed to be successful at learning this material. The problem was related to me and me alone.

I had gotten intimidated and I didn’t know how to deal with it.

When I went to college the next fall, I didn’t take a single math class and my academic pursuit in math came to an end – pretty sad.




Everyone has times when they feel intimidated.

They are these inflection points when you get to decide whether to give up or whether to fight. The only way to actually give up is to look away. That’s what I did in my high school math class. I just hid out of sight and became smaller.

And it has forever changed me. I never took math in college, I ignored most of the sciences, and simply lost an entire piece of myself that could have existedhad I shown a little grit. Even just a little bit of determination, and I could have powered through.

trophy room cartoon


By the way, this is a now well documented problem with gifted and talented programs. Kids that are consistently told how “special” they are, fail to show any determination when the subject matter gets tougher.  Psychologist Carol Dweck studied the effect of praise on students in a dozen New York schools. “When we praise children for their intelligence,” Dweck wrote in her study, “we tell them that this is the name of the game: Look smart, don’t risk making mistakes.” Dweck discovered that those who think that innate intelligence is the key to success begin to discount the importance of effort. You can read more here.

Some people respond to intimidation differently. In that moment of flight or fight, they choose to fight. That self doubt in some strange way seems to spur them on like the cyclist who gets out of her saddle to bike harder when she first feels fatigue in her legs. Some people have it – this store of resilience.

Resilience is a learned trait, perhaps one of the most important character traits one can possibly have.




Back to startups.

When I started in Y Combinator in 2009, I powered through. I’m not really sure why. Maybe it was that the stakes were too high or the social component of not wanting to let down my co-founders, or simply that the Y Combinator partners are already aware of this issue and eager to mentor us through it.

But regardless, we did fight and in 12 weeks, with a literally a day to spare before demo day, we launched our website, iPhone app, Blackberry app and did our Techcrunch debut. While we were never the top of our class, FlightCaster wasn’t in the bottom half either.  By the way, the eventual winner of our batch had nothing to show on demo day. And really not much for a year after that. They were still little group of late bloomers building some awkwardly named company called ‘dev/finance’—you probably know them by the name Stripe.

Anyways, we went on to raise money, build our company and while we ultimately didn’t make it as an independent company, we found a soft landing exit and now live to fight another day.

The wonderful thing about resilience is that grit begets grit.

In the course of building our little office space startup, 42Floors, my cofounders and I have felt intimidated dozens of times. But now we have this weird, delusional self-confidence; we know we can do anything no matter how unlikely the odds. And I say delusional because we are often wrong, and we have failed far more times that we have succeeded in this company. But our grit is unmistakable and we have never failed for lack of trying. Now that the startup is doing fairly well, it may look from the outside to be one of those easy-to-come-by runaway successes. I know for certain that it wasn’t.




I wrote this post not actually thinking of how a founder feels but thinking of how employees within a startup feel. I’ve had a number of conversations recently with people working in startups, both on my own team and friends in other startups. They’ve expressed that they feel intimidated by all the other smart people. While everyone else on the team seemed so smart, they were in over their heads or didn’t have enough startup experience or had tried a product idea and it had failed or whatever. While trying to be understanding and appreciative of this intimate revelation, I usually also let out a bit of a laugh and say, “Welcome to the club.”

The reality is the vast majority of us are in unchartered waters. That’s what makes it so fun.

Trying to be a tad more helpful though, here are a few suggestions for you. I’ll openly admit a lot of this shit sounds trite. But hopefully you’ll find a few good nuggets in there…



How to Learn Resilience


Talk to others.

The easiest way to give into intimidation is to not let anyone know. I suffered in silence during my senior year in math class and skipped that final exam out of embarrassment. I did all of that quietly. The reality is that if someone had called me out on it, I probably would have responded better.

When people on my own team have talked about feeling intimidated with me, it’s always been a massive relief to get it off their chest. And because this is something that affects so many people, it’s also comforting to know you’re not alone. While you may have a best friend or roommate or whatever that is your confidant for these sort of internal fears, that’s not quite good enough. It’s a thousand times better to share how you’re really feeling with the people you work with because those are the people who will then be in a position to push you harder and help you get over the hump.


Turn stress into a tradition

It’s obviously trite to say that whatever doesn’t kill you makes you stronger, but trite comments are usually true as well. Now whenever I feel out of my element (which is often) I try to find an ounce of perspective and remind myself that this is what I wanted. This is what it means to feel alive. And the overwhelming feeling I would have if I was never pushed beyond my comfort zone would be that of boredom. While it’s easier to gain that type of perspective after the tough moments, push yourself to learn how to relish them during the stressful times.

I actually have this little tradition I do personally when I’m most stressed out and my body feels weak – I have this strange craving for McDonald’s. It happens every time. And I don’t really eat McDonald’s any other time in my life except for when I’m really feeling stressed. So now I have this thing whenever I’m really feeling pushed a bit too hard, I head straight to McDonald’s and have my little ceremony with my hamburger, chicken mcnuggets and fries. And I think back to all the times I have sat in this exact same seat, eating this exact same thing, feeling this exact same way. It helps me, in the moment, gain that temporal perspective that allows me to remember that this too shall pass.


Don’t avoid failure by settling for small wins

This one is a bit counterintuitive, but stick with me. One of the ways you shy away from intimidation is by making the challenge small. You reduce the danger it poses in your life. But really, you want to be doubling down on yourself. Because you have a lot to gain no matter what the outcome.

If you double down on yourself when times are tough and you make it, you will be forever changed.

And if you double down on yourself and fail, you’ll realize that failure itself wasn’t nearly as scary as you thought it was because it’s actually fear of failure that is at the root of intimidation, just as the fear of pain is worse than pain itself. Once you actually fail, you make it back just fine and realize now that your fears had been out of proportion.

That’s what happened to me when I failed my first startup. The final months were so miserable that when we finally shut the doors, it wasn’t nearly as bad as I thought it would be. The whole experience left me with both a chip on my shoulder to do better the next time and a sense of confidence that I could rebound from anything.


Get everything else in your life stablized

If you’re in over your head at work make sure your personal life is really stable. The only time I see people really fall flat and not get back up is when they’re fighting a multi-front battle. If where you live, your relationship with a significant other, your family life, personal finances, whatever, are all in shambles then your store of energy to power through in your startup is going to suffer.

I find this especially true with my weight. My health, as noted by my McDonald’s example, often goes to shit when I’m stressed at work. It’s unfortunate. I wish it didn’t happen, but it does. In fact, you can see every crisis of 42Floors reflected in the graph of my weight over time. Each stressful moment represents a sharp spike.

So now that I know this pattern, I actively work to get in the best shape possible right before I start a stressful period so at least I start from a strong position.


Write it down.  Preferably publicly.

The act of writing helps your brain work in different ways. At the very least, keep a journal. It’s funny, when I go through my journals from high school, college and afterwards, they all seem to be a recounting of crappy times. I sometimes wish I had spent more time writing to myself when things were good so I could remember those as well, but the reality is I didn’t need it then so I didn’t do it.

Since I started blogging a few years ago, I’ve realized that writing in a social context is far more powerful. I’ve written about humility and depression several times and I’ve worked hard to force myself to do it in real time. Like last April when things at 42Floors weren’t nearly as good as they are today.

When you put yourself out there publicly, you’ll find that the whole world conspires to support you and, your opportunity to let yourself give up goes away completely.


Don’t lie to yourself

Too many people try to paint a prettier picture of what’s going on. At first, you say it to other people just to avoid the conversation, and then you start saying it to yourself to make yourself feel better. And what occurs inside is this gap between reality and how you are perceived. That gap creates all sorts of isolation and stress that is not helpful at all. Instead, just be real.

The easiest way to ensure that your rosy colored glasses are fully off is to let metrics tell the story. Force yourself to sum up your progress in only 3 metrics. Everything else is noise. When I see entrepreneurs writing investor updates that are eleven paragraphs long I know that things are actually not going well. But it will be impossible to find out why.





Here’s one last footnote, if you’re feeling like you might be the imposter and everyone else deserves to be here but you, I would just say, maybe accept it as true.   And let that be the motivation that gets your engine going. Go prove everyone wrong, including yourself.


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