Unmask Imposter Syndrome
Or why a startup founder's greatest critic lives rent-free in their head
The Next Founder helps founders build great startups. We offer advice on managing your mental health and productivity, hiring and managing great people, building a strong culture, and keeping people aligned and working on the right things. See the series overview at Welcome to The Next Founder and find out more about me at My Story.
In “Unmask Imposter Syndrome,” we’ll talk about what founders can do to manage imposter syndrome which, although common in startup founders, can hurt your company and make you miserable.
“Among the vicissitudes incident to life, no event could have filled me with greater anxieties than that of which the notification transmitted by your order and received on the 14th day of the present month.”
— George Washington (upon learning he was to become President of the United States)
“Each time I write a book, every time I face that yellow pad, the challenge is so great. I have written eleven books, but each time I think, ‘Uh oh, they’re going to find out now. I’ve run a game on everybody, and they’re going to find me out.”
— Maya Angelou
"It doesn't go away, that feeling that you shouldn't take me that seriously. What do I know? I share that with you because we all have doubts in our abilities, about our power, and what that power is.
— Michele Obama
"Jacked guy wearing suit must have it all figured out.”
— A Headline from The Onion
You’ve got that frauding feeling
Your Senior Director of Design started four months ago. This week, you gave him some harsh performance feedback that you don’t think he has come up to speed on your startup’s product, customers, and design principles. You tell him the work he delivers is not aligned with your market or your brand, and you spend too much time asking him to redo it.
He gets defensive and turns the criticism back at you. He says your design principles were flawed when he arrived, and he’s trying to nudge your startup in a better direction. He claims his two decades of design experience give him insight that you lack. He keeps the conversation professional, but the message is clear, “You hired me for a reason. I know what I’m doing. Butt out.”
After the meeting, you try to decompress. You wonder, “How do I know he’s not right? I don’t know for sure that our design principles are correct. I’ve never run a design team. What right do I have to criticize someone who has?”
This line of inquiry triggers you, and you start spiraling. You think, “I’ve also never run a Sales, Marketing, or Finance team, not to mention an entire company. Do I have the right to boss people around when I’ve never done the job they are doing? My team must have noticed by now that I’m in over my head. Maybe I never shouldn’t have founded a startup!”
You take a deep breath and try to calm yourself, remembering that other founders you know have shared some of the same feelings with you. And yes, these feelings are normal, but they can still do real damage. To succeed and not be miserable while doing it, you need to Unmask Imposter Syndrome.
The imposter syndrome syndrome
The typical characterization of a startup founder is of a visionary who sees a future no one else does and boldly leads her team to create that future. She assembles an incredible team, sets ambitious goals, and pushes her team to hit them like clockwork, leading to fame and fortune.
Does this describe a typical founder? Excuse me, but LOL.
Sure, the best founders have these characteristics in their best moments, but it’s far more typical for founders to stay awake at night haunted by thoughts about their:
Experience — “I’ve never run a startup before and don’t know what I’m doing. Why do I deserve to do this?”
Leadership — “I convinced some awesome people to quit their jobs and join me. Their careers are in my hands. What if we fail? What happens when they discover I don’t know what I’m doing?”
Investors — “I convinced investors to give me $3 million that could have gone to a better startup, AAPL stock, or feeding the hungry. What happens if I lose every penny? Will I ever work in this town again?”
Competition — “Why do I think we can take on Salesforce, Microsoft, and SAP with 15 employees and a few million in funding? Those companies have trillions of dollars of market cap and luxury boxes at the Chase Center. Am I delusional?”
Of course, we are talking about imposter syndrome1, which is a mix of feelings that you don’t deserve to have the position you have and are bad at your job. Your co-workers will realize this at any moment and probably react by abandoning you.
Imposter syndrome is not unique to startups: many people with demanding jobs have it, and awareness is growing, which is why you’ve probably heard the term before. It’s especially prevalent in people from underrepresented groups who don’t have many role models or success stories from people from similar backgrounds.2 Anyone can suffer from it, though, and almost everyone does at some point.
Founders can get a bad case of imposter syndrome
As a startup founder, you are especially susceptible to imposter syndrome for a few reasons:
The stakes are high
At a big company job, the cost of poor performance is contained. No, you don’t want to lose a deal or slip a deadline, but unless you are in a very senior role, your failure won’t put the company out of business. It might barely register. Maybe you don’t get the raise or the promotion, but you are unlikely to crash the stock price. The worst case is that you get fired, in which case you get another job and try to do better next time.
At a startup, the upside is much higher, and the downside seems much lower. If you succeed, you achieve fame and fortune, and you bring your team along for the ride. If you fail, an entire corporation goes out of business and ceases to exist, leaving a million-dollar crater.
You probably are in over your head
If you’ve ever soothed a friend suffering from imposter syndrome at their corporate job, you probably reassured him by saying, “Don’t worry, they hired you for a reason! You are good at your job! You got this!” Not only were you being a good friend, you were probably right.
But when startup founders feel like they don’t know what they are doing, they might actually be right. Many founders have little management experience, or their experience was at larger companies. They may have never managed people or planned and operated an entire corporation. They don’t have a team of people who have expertise in all of the functions that need to be covered. And they certainly haven’t sold this product to this market, since no one has.
You are asking people to take a leap of faith
The people you recruit for your startup aren’t joining because of what you have accomplished, since you haven’t accomplished much. They join because of what you will accomplish.
So every time you recruit someone to the cause, whether an investor, board member, or an early customer, you are doubling and tripling down on the commitment to make the journey worthwhile. It’s like twisting friends’ arms to show up for a party you promise will be amazing. It’s a highwire act, where you raise the stakes every time you convince someone to come along for the ride.
You have little margin for error
Most startups fail, so it’s rational to lose sleep that yours will. Even if you succeed, you’ll go through long periods where you’ll feel like you are failing. Investors reject you. Customers leave you. Competitors launch scary-looking alternatives. Your bank account runs dangerously low.
Getting beat up daily and reminded that you might not live to fight another day isn’t exactly a confidence-building exercise. The constant negative feedback naturally triggers imposter syndrome.
You don’t have a boss
We all love to complain about the boss, especially if you’ve been unlucky enough to have had a bad one, but bosses serve a valuable function you take for granted: they provide guardrails that give imposter syndrome some natural limits.
A boss can give you feedback about your performance, which can rein in your overactive imagination. Even negative feedback can keep you from imagining something even worse, in the way that getting a C on a test means you at least didn’t fail.
The boss can also jump in and help if you are floundering, or they can help you get more resources. And that boss is ultimately responsible for your deliverables. They have every incentive to keep you from failing.
At a startup, you’re the boss. You get little feedback on your performance, no encouragement, and you can’t kick problems upstairs to the boss. The boss is you.
The job keeps getting harder
In theory, your imposter syndrome would subside after you experienced a bit of success, like closing your first customer. It would be evidence you can succeed, and it would build your team’s confidence in you.
This might happen at a larger, more static company where you might get a few months or years to enjoy mastery over your new skills, but startups don’t work like that. Success just gives you permission to take on the next set of challenges, like leveling up in a video game or progressing to the next bracket in a tournament.
After you land your first customer, you need to learn how to keep them. Once you raise money, you have to learn how to spend it and manage investors. After you learn how to manage a few individual contributors, you have to learn to manage a team of managers. Imposter syndrome often follows you on the journey.
At this point, your imposter syndrome is probably worse than when you first started reading, but hang in there, I promise we are going somewhere.
Imposter syndrome can damage your startup
Imposter syndrome isn’t helpful no matter what your job is, but it can be especially damaging for startup founders for a few reasons:
Imposter syndrome slows down decisions
A founder’s job is to make decisions. You decide who to hire and who to fire. You decide what customers to target and what channels, messages, and features will attract them. You decide how aggressively to grow and what operating plan will get you there.
Slow decision-making makes everything worse, and slow decision-making is almost always rooted in a lack of confidence. A founder who isn’t confident in themselves will delay decisions until they get more data, even if no new data is coming. A founder who fears being found out by his team might not ask for input on decisions or be willing to debate them. A founder who fears they are in over their head will be less likely to admit a bad decision and pivot.
Imposter syndrome lowers your team’s confidence
If a founder fears they are bad at their job and that their team might find that out, they might do unnatural acts to keep that from happening. Some founders might be reluctant to share information out of fear of having their decisions scrutinized. Some might get defensive or angry when challenged by their team.
This will keep you from accomplishing your most important job as a founder: attracting a great team. No one wants to work at a startup where the founders are skittish, don’t share information, and don’t want to discuss and debate the right things to work on.
In the most extreme cases, imposter syndrome can lead to a toxic corporate culture. You probably have stories about politics and conflict from previous jobs. Toxic conflict seldom happens between people who are confident in their abilities and open to debate and feedback. It happens between people who are insecure and brittle.
Imposter syndrome keeps you in your comfort zone
Human nature is to stay in our comfort zone. Think about how much more fun it is to play a sport where you excel than a sport where you are floundering. Think about how much more fun it is to hang out with close friends than to walk into a room full of strangers.
A founder suffering from imposter syndrome is more likely to want to work in the areas of the business where they are most comfortable instead of where they are needed. Founders who enjoy building products will gravitate to coding when they should be talking to customers. Founders who doubt their ability to manage senior people won’t hire any.
But success at a startup almost always lies on the other side of extreme discomfort, like hiring people who challenge you or spending time selling when you’d rather be coding. Imposter syndrome makes you less likely to jump into areas where you are in over your head.
You’ll burn out
Even the most successful startups founded by the most competent founders can be stressful and painful.3 Imposter syndrome makes a startup even harder. Feeling like you are bad at your job causes you to spend your days criticizing yourself. Fear that someone will find out causes anxiety and hyper-vigilance. This can lead to depression or anxiety.
No one can withstand this for long, so a founder will eventually be tempted to pursue the only thing they feel can relieve the anxiety: leaving their startup or shutting it down.
Your reaction to this litany of fail might be, “Sure, I may have a bit of imposter syndrome, but I’d never do any of this!” and on a good day, you probably won’t. But startups have a lot of bad days, where you might have to accept that an important project has failed or that you need to fire a key staff member. Those are the moments when it’s most important to make good decisions, and they are the exact moments when imposter syndrome is most likely to rear its ugly head.
So if imposter syndrome is a constant threat, what can you do about it?
Wear imposter syndrome as a badge of honor
There is one surefire way to banish imposter syndrome: don’t try anything hard. Take a boring job that doesn’t challenge you and spend your days staring at the clock until you can go home and burn down your Netflix queue. You’ll have plenty of problems, but imposter syndrome won’t be one of them.
Of course, if you are reading this, that’s not the life you want. You know that a fulfilling life means taking on challenges and risks. If a bit of imposter syndrome is the price you pay to have that kind of life, that’s a trade worth making.4
Imposter syndrome also means you’re a self-aware and conscientious person. Sure, some people never suffer a moment of doubt about themselves and their capabilities: they are called sociopaths. You aren’t one, and it wouldn’t help you if you were. You’re self-aware and care about others.
So when you feel some imposter syndrome coming on, consider it the price you pay to have an extraordinary career and a fulfilling life. It might not ward off imposter syndrome, but it might help you reframe it and give you a different starting point from which to attack it.
Accept that imposter syndrome is normal
Imagine a successful business leader, and you’ll probably come up with a caricature of “important and successful business-ish person” out of a Netflix series: the decisive leader with good posture who charges into a conference room to rally his team around obviously-correct decisions that he made on his own.
You probably don’t picture him sitting alone at a bar after work, wracked with self-doubt and fighting back tears. You might assume that good leaders both act effective and feel effective, but not all of them do, at least not all of the time.
This is why imposter syndrome can be so insidious: when you feel like you’re doing a bad job, you assume that you must be doing a bad job since someone doing a good job surely wouldn’t feel like they are doing a bad one. That self-doubt might lead to you actually doing a bad job, leading you to think, “See, I was right: I’m bad at this.”
If it was exhausting just reading that, well, that’s the point. Imposter syndrome can suck your energy by triggering loops in your brain, where you put your energy into wondering if you can do the work instead of just doing the work.
Remember that most people have imposter syndrome at some point, especially startup founders taking on one of the most demanding challenges in the business world. Don’t assume you’re an imposter just because you feel like one. Instead, think of it as a nuisance, like a crosswind during a long bike ride. It’s an annoyance to manage, but not a reason to pull over and take the bus.
Stop comparing
We all compare ourselves to our peers, especially in a community as hyper-connected and communicative as the startup world. Although following and connecting with peers can be a source of information and inspiration, it can also trigger imposter syndrome if you compare yourself to them.
Most founders employ a bit of “fake it until you make it,” which is rational when trying to attract customers, investors, and new hires. “I don’t know what I’m doing” isn’t exactly a great way to rally support. You then end up comparing an unrealistically positive version of someone else to the worst version of yourself.
Judge yourself by absolute standards, not relative ones. Develop milestones for your business and work to meet them. Don’t spend time wondering whether someone could do your job better. Sure, someone out there probably can, but they aren’t here right now. You are.
Like most advice, the converse is true, too. Some founders take comfort in looking at other flailing startups and thinking, “Well, at least I’m doing better than them!” This can make you complacent. Customers don’t buy from you, and investors don’t invest in you just because you were the least hapless founder on your accelerator’s demo day. They judge you on absolute, not relative, measures.
Relish the wins
These tips help put imposter syndrome into perspective, but the most satisfying solution to imposter syndrome is to stab it in the heart. Prove to yourself that you are good at your job by getting good at it.
No, you’ll never excel at everything you need to do, but you can get laser-focused on the short list of items you have to nail at a given time, like getting product/market fit or raising a seed round. Learn everything you can and relentlessly work on them until you succeed. This is, of course, what you should be doing anyway.
Once you’ve had a bit of success, take some time to let it sink in, celebrate a bit, and use it as a launchpad to build some confidence. Don’t just relish in the skills you have learned, but celebrate that you’ve learned how to build new skills. If you can learn one part of your job, you can learn others.
This kind of mental fortitude is essential if you are going to successfully do what we’ll talk about next: Gaze Into the Abyss.
Imposter syndrome seems to be everywhere right now. This Psychology Today article is a good starting point.
We’ve made it this far without sharing Theodore Roosevelt’s Man in the Arena quote, but it’s so good that, even if you’ve heard it before, take a moment to internalize it.
This is exactly what I needed to read. Thanks