Battling Imposter Syndrome for Entrepreneurs

I had an entrepreneur write me today responding to my Medium post about battling depression as a startup founder. From all outside perspectives this young founder is building a successful business. $10K in monthly recurring revenue in just a few months on a hybrid SaaS/services model is pretty damn good.

The problem is he doesn’t feel that way. Just like other founders who get to that stage, the feelings of success are outweighed by the feelings of not being good enough.

His brain is telling him he should be happy with his business growth, but his heart is telling a different story. When starting a business entrepreneurs have a sense of elation. A new idea in it’s earliest stages invigorate them and breed a ‘nothing can stop me’ mentality. For me, these feelings were matched with the decision I made to quit my day job, further adding to the feeling of freedom I had that I was going to pick myself up by my bootstraps and, well, bootstrap my startup.

Days, weeks, and months go by and after getting over the initial hurdle of getting to revenue, things began to change.

$0K/month turns into $5K, then $10K and then $20K/month, but with each increase in revenue, there was no matching increase in the amount of confidence I had in myself or my business.

It created further disappointment because I didn’t really understand why I felt that way. Why was I so pissed when people said “hey, your business is going great! Why aren’t you happy?”. Friends and family just didn’t understand why I wasn’t going out with a huge smile on my face because I had ‘made it’.

Ultimately there was one reason that stopped me from feeling the joy of a growing business.

Imposter syndrome.

Every feeling of joy we had as a company, whether it was a new sale or growing margins, was met with an equally but longer lasting feeling of fear. “What if this is all a sham? Who the hell am I to build this? I’m not experienced/smart/creative/good enough to have this.”

The roller coaster of emotions I was on as a founder turned into a mine cart hurtling deeper into the depths of the imposter syndrome I was feeling.

Several founders feel this way but many are afraid to admit it, and for good reason.

We’re not supposed to talk about this stuff.

Everything is supposed to be great! Every cocktail mixer, pitch event, or networking meetup we go to we’re encouraged to talk about how amazing things are! How ‘freeing’ it’s been to start a new venture and how there’s nowhere to go but up! The problem is to outside observers, the starting point of ‘going up’ is from where you are on the outside (revenue, buzz, social following), not what you’re feeling on the inside.

How to Overcome

There’s three things I do regularly to overcome the still lingering feelings I have of imposter syndrome. I say ‘still lingering’ because even though my business is at 22 employees and $100K/month I still have feelings that somehow this house of cards I built will come crashing down. It’s not a valid emotion but it’s very difficult to change how you feel in the moment.

1.These Are Just Moments in Time

How you feel in the moment is often not reality. People are driven by emotions, and as founders it’s easy to be on an island and let feelings in a moment overtake your day, week, month or year. Acknowledge that you are going to feel terrible about yourself or your business sometimes, but take a breath and realize what you’re feeling is just a moment in time, not necessarily a truism you should take to heart for the long term.

2.Ask Yourself “What’s The Worst That Could Happen?”

When I started feeling down for whatever legitimate or illegitimate reason my mind would race to the worst possible scenario; losing my house, my credibility, my career, my family, friends, reputation, financial well-being, etc.

Most of these concerns were not real.

The real worst case scenario was that I might have to shut down my business, maybe lay off a few employees (all of which would find other jobs really quickly), pay off a business credit card or two, and find a job. That’s it. Was I going to lose my house? No. Was I going to ruin my reputation? Definitely not. Was the world going to end? Nope.

My mind would race to these illogical things but when I forced my mind into an honest conversation I knew my emotional worst case scenario was not really the logical worst case scenario.

3.Tell Yourself “I’m Doing More Than My Peers”

The last thing I do to stifle my feelings of imposter syndrome is to tell myself I’m doing great. So often we get caught up in the people seemingly better than us making billion dollar companies by the time they’re 18, but we don’t look around and think about how we’re still doing pretty damn well.

Most people will never create a company. Most will never take risks. Most will never put their finances, career, relationships or emotional state on the line to start a venture that has a small chance of success.

Personally, I’m a competitor. It’s very hard for me to not look around at others in my field who are more successful than I. That’s okay. What’s not okay is obsessing over that fact while ignoring that we entrepreneurs are still pretty damn incredible, especially once you start making revenue.

One Last Thing

You are worth it. You have earned this. If you’re dealing with imposter syndrome know this is just a moment in time, and there are things you can do to push aside moments of emotional turmoil in favor of feelings of accomplishment.

I served in the U.S. Army for 4 years and one thing we always told ourselves is that less than 1% of the U.S. population has or will ever serve in the armed forces. Similarly, you as an entrepreneur are a very small percentage of the population who will ever start a business.

That alone is something you should be proud of. Startups fail all the time. The people remain, usually coming out the other end better than they were before.


Jake Hare is the Founder of Launchpeer & Excursionly. He writes about startups & growth hacking at JakeHare.com. He’s consulted Fortune 500 companies, is a former homeless teen, and proud Army veteran.