The Man. The Myth. The Imposter?
What happens when your shadow runs away.
Like a shadow, Imposter Syndrome follows you wherever you go. Like Peter Pan, I’ve been trying to catch mine my whole life.
I’m 40 years old, but I can vividly remember the first time I caught a glance of my shadow. I was eight years old and falling behind in math class. Everyone understood with ease things that took me days to learn — but I was too scared to ask for more time or explanation. I’m sure the fear of being seen as not smart kept me from raising my hand and drawing attention to myself. So I went on pretending everything was just fine — and my shadow, a shadowy version of myself, brought a cheat sheet to our multiplication quiz and helped me cheat my way through the times-tables.
It was a moment that internally split me in two: I started to believe that I wasn’t much good at anything, and anytime I was able to impress someone, pass a test, or succeed, it was my shadowy magician, stepping in to distract and misdirect. My shadow was a constant reminder that I would only ever be good enough by sneaking my way through, by hook or by crook.
I never really recovered. I struggled with math for the next few years, and it was only compounded when we picked up and moved from the States to Canada. Maybe I had done an excellent job of hiding my struggles, or perhaps the students in my new class were further ahead; either way, I fell even further behind, and no teacher was slowing down the class to help me. It didn’t matter much because that would be my first and last year in Canada. We moved again, to England, and the problem continued to grow. But this time it wasn’t just Math; the school threw me into a homeroom that was taking both second-year French and German.
Now not only was I drowning in math, but I was also drowning in French and German and too afraid to say anything to anybody. My shadow helped me in those years. Whenever my parents asked about school, my shadow would respond with a joke or a half-truth, something to make everyone smile or laugh. As my shadow made everything seem just fine, I kept treading water as if my life depended on it. No worries, I only had to endure that hell for two years before we moved back to the States.
One of the patterns of young imposters is their inability to ask for help and the propensity to tell fibs or half-truths. When I arrived at Redmond Junior High, I had a history teacher who was enamored to have an English kid in his class (I picked up an accent in England, mainly as a survival tactic), especially one who was well read in modern world history. That too was a survival instinct; I thrived in classes that were not math or foreign language related. This history teacher was also the advisor of the Honor Society, and when he asked if I had had a 3.6 GPA or higher in England, of course, I fibbed and said that I had. In his eyes, I was smart — brilliant — , and I didn’t want him to think of me differently. I couldn’t remember the last time someone saw me as exceptional, and I didn’t want to lose the feeling — even if my shadow was constantly jabbing me in the ribs, reminding me it was all a lie. It was the first, and last semester I would be in the Honor Society or anything similar until I made Dean’s List in college.
I survived High School, but barely. On a steady diet of C’s and D’s in Math, Chemistry, and French, I scraped my way to a diploma. But my Imposter Syndrome affected not only my grades but also on me as a person. I had a few close friends at school besides my shadowy companion — one named Greg Matyas, or as I affectionately call him “Greggie.” knew I was a genuine kid, but a fake. Outside of Greg, I kept everyone else at arm’s length. As a coping mechanism, I had two drugs of choice: sleeping and skipping classes. I did both of those a lot.
Did anyone know I was faking it? I don’t know because my shadow was pretty good at telling half-truths, flat-out lies, or very entertaining and plausible stories. However, Mr. Bearman, my chemistry teacher, did pull me aside once to let me know that I “would amount to nothing.” Those words hurt and did for a very long time. He wasn’t wrong. If I kept hiding from the things that were holding me back, how would I ever amount to anything? I walked across the stage at graduation feeling like a fake. For the next five years of my life, I grappled with my shadow, trying not to let it run away or define me.
When I eventually went to college at 23, I didn’t skip classes or use sleep to avoid school. I had the freedom to choose my classes each semester. I piled on the History, Social Sciences, Public Law, Design classes and even a few introductory Computer Science classes — as long as they didn’t have too much math. I excelled, but before I had to take any math classes, I left college to pursue a career in the tech world.
My unruly shadow followed but took on different shapes, sizes, and behaviors. I felt it when I got married: I was sure my wife was marrying an imposter, and she would inevitably figure it out. I felt it, again and again; while doing jobs that were way above my pay grade, going from intern to project manager to product manager. It’s not unusual for people in the tech world to jump jobs every couple of years, but it felt too much like my childhood. My shadow was my constant friend and foe, keeping up appearances even when I was learning on the job, but continually reminding me that I didn’t belong and could be found out any minute.
In 2011, I co-founded a startup called Space Monkey, and a day didn’t pass that I wasn’t sure I was going to get ratted out as a fake. Every investor meeting felt like I was watching as my shadow pitched Space Monkey, and each time an investor passed, I felt both frustration and a little relief. Sure, I didn’t get the funding, but at least they wouldn’t get the time to see right through me — to make me prove myself.
Then there came a day when I was pitching a group of VC’s on Sandhill Road. I had an out of body experience where I was watching everyone in the room listening, taking notes, asking in-depth questions about cloud infrastructure and my shadow was rolling through my pitch and answering their questions without hesitation. At that moment, I realized I was the expert in the room; my shadow, my cover for the big fake I was under it all, wasn’t a shadow at all — it was just me. It was the part of me that had been growing, watching, putting in the work. After years of believing I was an imposter, I had been learning, gaining experience, and slowly becoming an expert in my field.
Become the best in the world at what you do. Keep redefining what you do until this is true. -Naval Ravikant
I’ve often heard entrepreneurs say “fake it till you make it!” and I would respond with a large eye roll. The truth is you should LEARN IT TILL YOU MAKE IT. To learn, you have to embrace feeling vulnerable, being stuck, failing, being wrong, and experiencing uncharted bodies of knowledge; it’s the only way to tame the shadow of imposter syndrome. You allow your shadow to take over because you want to assert fake control over your situation — but it won’t work. You have to embrace the journey of learning. I wish I had a teacher who recognized this in me when I was feeling lost. In all the moving around, being dropped into school after school, feeling like I didn’t belong, what I needed most was a feedback loop with someone who cared about my journey and believed I wasn’t destined to fail. In the education system, kids are quickly labeled as ‘good students’ or ‘bad students,’ destined to succeed or fail, and once you’ve been marked it’s hard to see yourself any other way.
As an adult, I can see that those labels — ‘good’ or ‘bad’; ‘overachiever’ or ‘under-achiever’ — are shorthand ways to categorize people without taking the time to invest in their potential. Caring about how someone is performing means constant feedback that doesn’t just feed into a predetermined idea we have of them. Everyone has good days and bad days; the important part is that we create a loop that can give honest, constructive feedback on the bad days, and encouragement on the good ones. One that pushes us to grow and confront the most difficult challenges. For so many years, it was my shadow — my fear, my insecurities, my conviction that I was destined to fail — that was keeping me from diving in and working through the hard parts.
In 2014, we sold Space Monkey to a larger tech company, and instantly, I felt the shadow of my imposter take over again. I found myself going from a little startup CEO to an executive with a large budget, thousands of salespeople, a manufacturing operation to build 100,000 devices each year and a product team that would double each year. I felt out of my comfort zone and knew I had a lot to learn in a short amount of time with little margin for error. My shadow started to appear everywhere — in my breakfast cereal, my rear view mirror, my employee’s emails.
But here is the truth: every day Jeff Bezos is running a company bigger than Amazon was last week, last month or last year. There is nothing wrong with not having the experience or expertise needed on day zero — every day is day zero when you are doing something new. What matters most is that you don’t act on the negative behaviors that imposter syndrome can enable, and those behaviors are different for everyone. Mine happens to be avoidance and false bravado. Instead, embrace the opportunity to stretch and grow with the process of doing something new. It’s okay not to have the answers, it’s okay to ask for help, and it’s even more okay to fail, to pick up and try again. We are all at our best when we stretch ourselves and stand taller than our shadow.
Sometimes people with the growth mindset stretch themselves so far that they do the impossible. — Dr. Carol Dweck on Christopher Reeves teaching his brain to regain movement.