Startup CEO Imposter

First time startup CEOs are rarely qualified for their jobs. How could they be? There’s really no other role that can properly prepare you for managing every department, a board of directors, fundraising, mergers and acquisitions, and bankruptcy to boot. “Fake it until you make it” is essentially the only viable option.

But at some point, imitation gives way to competence. 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.

So why do you feel like a failure?

The matter is not helped by the amazing degree to which entrepreneurs are “killing it,” “crushing it,” and various other phrases normally attributed to insect exterminators. 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 even more deeply buried 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 both felt like we were faking it.

Even more strangely, as I get to live out my science fiction dreams developing a 3D laser printer at Glowforge, my fourth startup, I am finally, objectively well qualified for my job. Yet I've never shaken the feeling that I’m madly improvising, the wrong person for the role.

While there’s no formal research on entrepreneurs, the symptoms we were experiencing are far from unique. They were first described in 1978 by Dr. Pauline Rose Clance — under circumstances not too dissimilar to mine.

In an attempt to get to the bottom of this, I had the pleasure of talking to Dr. Rose Clance at her home in Georgia. Thirty-five years after her groundbreaking paper on the Imposter Phenomenon[1] (often referred to as Imposter Syndrome), she’s still the foremost thinker in the field.

Dr. Rose Clance grew up in rural Appalachia. She was a model student and got an undergraduate liberal arts degree at Lynchburg College. Throughout high school and college she experienced bouts of self-doubt, as any of us might when faced with a dramatically new and challenging environment. But when she was accepted to the graduate program at the University of Kentucky, it was different.

The psychology program at the University of Kentucky was rigorous and strict. Twenty-five students were admitted, and most of them would wash out before being awarded their PhD.

Every two weeks, a faculty member would lecture on a subject of his or her expertise. Every two weeks, there was a test. And every two weeks, someone was at risk of being sent home.

The pressure was brutal. Everyone felt it. As exams finished, students would thump their books down and escape to a local watering hole to debrief and decompress.

Pauline felt it more than most. Every two weeks, she’d collapse on a stool and confide in her friends. She didn't think she had what it took to make it through the program. Every missed question glared at her in retrospect. Every concept she failed to fully grasp, every lecture she didn't quite understand, every theory she didn't perfectly commit to memory loomed large.

And even more than this, she truly believed that she shouldn't be there in the first place. Pauline grew up in rural Appalachia. She didn't have the educational background of many of her peers. She was proud of her education and her history, but she told herself that — if she was being honest — she just wasn't prepared for the program. Fortunately, she had a group of three close friends she could confide in.

Until they told her to shut up about it.

You see, Pauline was, for lack of a better description, crushing it. She was nailing every test. She was outperforming many of her friends and peers. The data was not matching the hypothesis. She was, in fact, fully qualified, and was on a trajectory to graduate with outstanding marks.

Imposter Phenomenon affects different people differently. Some are crippled by it; some are motivated by it. Pauline had the presence of mind to listen to her friends when they set her straight, and the perspective to be able to analyze what they were telling her objectively. She realized that her fears, while real-seeming, were ultimately unfounded. She finished her program and got her degree.

Her experience made it hard not to notice, several years later as a professor and working psychotherapist herself at Oberlin, when a stream of highly qualified students came to her with secret confessions.

“I think I’m going to fail.”

“Maybe I got in by mistake.”

“Maybe I’m just here because my dad knew someone.”

Three decades later, in her lilting, Georgia-inflected voice, Dr. Pauline Rose Clance described her breakthrough moment thusly: “Maybe I wasn't just a hillbilly imposter after all!”

The young doctor realized that there was a common undercurrent to the students seeking her advice. She wrote a paper — the first published work on the subject — where she hypothesized that the Imposter Phenomenon selectively affected women early in their careers, based on her clinical observations and interviews with both male and female students. She also developed, and over the years studied and refined, the first test to assess the degree to which people suffer from IP. You can take it yourself at her website.

But it was only after years of research and administering the test to thousands of subjects anonymously that she discovered that IP was not restricted to either women or people who were early in their careers. In fact, men suffered from IP just as frequently as women. And while it is normal to experience uncertainty and self-doubt when faced with a new challenge, severe cases of IP would persist throughout a career, in the face of mountains of evidence that would belie it.

So it wasn't just women and youths who suffered, as she had first thought. It was simply that, until she started making her surveys anonymous, men and career professionals refused to admit to it.

I talked to Dr. Rose Clance about my experiences with startup CEOs and asked her if she thought it was plausible that there was a high rate of IP to be found in that population.

Her answer surprised me.

She explained to me that IP wasn’t, in fact, a singular diagnosis of an abnormal condition. It’s not listed in DSM-V, the psychiatrists’ bible of disorders — because it’s not a disorder. It’s not always a negative experience; it can, in fact, be quite positive. That is, incidentally, why she prefers to call it a “phenomenon” instead of a “syndrome.”

IP, she said, can do great things.

Some individuals with IP use it to propel themselves to tremendous heights. Common symptoms of IP include perfectionism, a tendency to “overwork” — spending long hours at the office to the exclusion of personal obligations — and a habit of pushing themselves to consistently outperform previous benchmarks. IP sufferers are often found in senior jobs, leadership roles, and positions of high prestige.

Of course, it’s not all happiness and light. Some IP sufferers are prone to self-sabotage. They may turn down opportunities due to self-doubt. They may procrastinate out of a fear of failure. They may fail to delegate, out of concern of letting their superiors down. Even those who accomplish great things may do so at the expense of social and family relationships. And IP sufferers are prone to anxiety and depression.

Startups, in short, are great places to look for the Impostor Phenomenon. As Liquid Planner CEO Liz Pearce puts it, “If you’re not making mistakes that are painful, you’re probably not trying hard enough.”

Fortunately, there’s quite a bit that can be done to make things better.

First off, there are many people who experience the phenomenon without serious problems. For these folks, the worst curse is the feeling of aloneness and nagging doubt that dogs their successes. Just knowing that these feelings of inadequacy and self-doubt are not abnormal or unusual can be a tremendous relief. Sympathy and camaraderie, for these sufferers, can be good medicine.

For those who suffer more — experiencing stress or depression, for example — improvement starts by understanding the root of their problem. IP can start naturally when someone is worried about her odds of success, and then achieves her goal. If this repeats over time, a negative pattern can form: worrying about success seems like it must be a natural prerequisite to being successful. Like a gambling addiction, the habit loop locks in: worry, attempt, succeed. Worry, attempt, succeed. With every success, the worries deepen.

For those so affected, counseling can be a tremendous boon. Therapy for IP can include breaking the habits of worry, self-examination, priority setting… pretty straightforward stuff, where the therapist may be able to make a difference quickly. Electroconvulsive treatments are rarely required.[2]

I’ve talked about this with a number of startup luminaries, and one of my Glowforge investors, Chris DiBona, put it best. He’s been watching technologists and entrepreneurs ascend and implode since his early days as an editor of Slashdot, as cofounder of Damage Studios, and as a part of the mergers and acquisitions due diligence team for Google.

“I don’t trust someone who doesn't have a little bit of that faker feeling. If there’s a spectrum from ‘I’m a fuckup’ to ‘I’m perfect,’ I don’t want to see them on either extreme.”

Chris told me that he doesn't bet on CEOs who wear their insecurities on their sleeve.

“I want it farther from the surface. I want someone who’s just humble enough to get help, not someone who’s either so confident or so insecure that they never ask questions.[3] I see too many founders gloss over fundamental details of their business — stock table, board composition, etc. I’m only going to bet on someone who’s just nervous enough to do their homework.”

And that’s the last, crucial misconception that needs dispelling. Perhaps, freed by the knowledge that you are not alone, you will be inspired to shout the truth from on high and/or in your next shareholder update, “I think I’m an imposter! I’m pretty sure my success is due only to luck! I don’t think I’m a very good CEO for my company!”

This is probably a mistake. As much as secrecy contributes to the problem, it may not be in the interest of you personally or of your company generally to have this conversation in a public forum — at least, not until your track record of success is well established. When Thor Miller and Lane Becker, founders of the well-known company Get Satisfaction, write a book called Get Lucky and attribute their success to a healthy measure of good fortune, it’s thought provoking and honest. When someone you’ve never heard of tells you that they’re not very good and they hope they get lucky… you might be more inclined to take them at their literal word. Honesty is good, but early in your CEO career, it may be best to keep your fears about your own potential unsuitability to your circle of close friends.[4]

As a parting thought, consider the lessons of the Dunning-Kruger effect: researchers Justin Kruger and David Dunning determined that low-skilled people tend to suffer from poor self-assessment skills, just like highly functional people suffer from IP. In the case of these poor incompetents, however, the assessment was reversed: the lowest performers would assess their skills the most highly. So take heart in your self-doubt: if you were truly an incompetent fake through and through, you would probably think you were perfect.

[1] P.R. Clance and S.A. Imes, “The Impostor Phenomenon in high achieving women: Dynamics and therapeutic enterventions,” Psychotherapy: Theory Research and Practice 15 (1978): 241–247.

[2] Joking.

[3] It never occurred to me until he said this that the diseases of over- and underconfidence manifest this same symptom — the inability to ask questions.

[4] Then again, some entrepreneurs build passionate fan bases by practicing radical transparency about their fears and insecurities — ultimately, you need to follow your own truth for this decision.