Imposter Syndrome

Imposter Syndrome: a symptom of the human ego, a major contributor to the human condition.


I launched my first internet-based startup in 2005 and never looked back. MySpace was poppin and Facebook this online community for college students that used "networks" defined by your .edu email address had something really special about it. 

I was already a non-technical entrepreneur in a very technical world, which meant that I was completely beholden to someone else to actually bring my idea to life. Talk about feeling like an imposter on your first day as a founder in a world that sounded like gibberish and ran by engineers. I was an artist-hustler with a big heart who excelled at sales.

I did undergrad in Psychology and a masters in Integrated Marketing Communications both at Florida State University in Tallahassee, FL. Great school, great times but I always felt a bit inferior academically up against institutions like MIT, Harvard, Northwestern, etc. I had come to value academic achievement in my 20's and wished I would have put more focus on it.

So when I got to "the valley" for the first time in 2005, I was constantly insecure about the fact that I went to a state school in Florida. I also thought that if you went to a great school you were better, smarter, etc, so it caused me to put people on an automatic pedestal just based on where they went to school. So I felt like I was an imposter every time I was in a room full of ivy leagues and Stanford grads.

One other place this was amplified was when I would pitch investors. Most of them very well accomplished academically, and then they pass on you; you can imagine the imposter syndrome there. 

I still feel like this at times but I know it's more about my own insecurities and not because people are better because of their .edu. I have come to realize that we all suffer from the same human condition and suffer equally despite our external, social, economic differences.

I know it sounds crazy but the rich and poor person suffers equally just about different topics. One is suffering because they have no food to eat, the other is suffering because they have too much food to eat.

One of the downsides of feeling like an imposter in entrepreneurship is that you feel shitty for a long time through your journey. The upside is that you keep climbing mountains, some familiar, and some completely new to you.

As a serial founder, the imposter syndrome has caused me to suffer, and has driven me forward. At times it's fueled me to prove others that I was worthy. Others it was about validating to myself that I was not insane and smart, etc.

It's hard to know completely if this is actually a decent strategy overall as a maker of progress, but I can say that it has proven over and over again to be very unhealthy physically and spiritually.  

The thing about being a founder is that you're truly trying to bring something to life that didn't exist before, while fixing all the collateral damage happening around you based on this chaotic, however unavoidable process of starting a company that involves humans to work.

The imposter syndrome is relentless especially when you haven't "been successful". Especially in places like Silicon Valley, LA, London, NYC, etc. Silicon Valley and NYC having the most intensity around this in my opinion.

The thing is that MOST entrepreneurs have "failed" ventures at one point or another. And failure is something that you have to get used to in order to live a life as an entrepreneur. And the imposter syndrome is often times involved somehow in your suffering after a venture "fails".

Thoughts are common like: "maybe I'm not good/smart/attractive/educated/equal enough?" Maybe I'm not one of the lucky ones? Maybe people like me don't achieve these kinda things?

The challenge with the startup world particularly in Silicon Valley is that success is defined by a small set of achievements. Things like whether you've sold your company before, are a billionaire, raised money, etc. So anything outside of these things are stereotypically failures. 

So what's the cure? I don't know. But I think it's something that is tied to one's overall happiness and self acceptance.

Mindfulness and the practice of unconditional love is definitely something that can help.

But I think the most lethal habit here is comparing yourself to others.

If we can figure out how to not to do this in an unhealthy way, I believe we can successfully fight imposter syndrome.