Overcoming Self-Doubt as a Solopreneur

It can be tough trying to start a company without any cofounders. It requires as much demonstrable skill as it does willpower to make it through the rollercoaster that is a pre-revenue startup.

In fact, starting a company by yourself is the number one mistake that kills a startup according to Paul Graham.

So am I just hard-headed and destined for failure?

If we look at why Paul Graham recommends finding a cofounder, I think we can better address that question.

You need colleagues to brainstorm with, to talk you out of stupid decisions

This is 100% true. If I didn’t have a great support community, knowledge from 100’s of people who have done it before, and a Product Manager to keep me on track, I would be in one of two place — A.) still building out features and never preparing to launch or get feedback, or B.) somewhere in Hawaii living on food stamps.

The point being, you need a community to bounce ideas off of, to keep you driven, not necessarily a cofounder.

The low points in a startup are so low that few could bear them alone.

I’ve found it really important to have close friends and family that support what you’re doing. Even if they’re simply asking how things are coming along, it can make a huge difference in morale.

It’s important to remember that although at times it can feel isolating, there’s always a support team waiting behind you to pick you back up when you stumble.

And lastly, it’s a job not your life. This is equally true for people that get consumed by their work and become overwhelmed by anxiety when something goes wrong or they start to fall behind. It can be hard to separate your “life” from work when you spend 10+ hours a day working, but it’s important to distinguish the two.

If something goes wrong at work — if you get fired, if your startup fails, is it really the end of the world? Probably not. Sure it’s embarrassing and you might feel some societal pressure for not succeeding, but you get another job and you go on with your life.

So it’s important to separate the two and take some time for yourself. Personally I hike or climb to clear my head and get back on track when things go astray.

Dealing with Imposter Syndrome

I deal with imposter syndrome on the daily. People ask me, “what do you do?”. A proud, outgoing entrepreneur would say, “I founded this great company that does XYZ — we should connect, maybe I can help you with etc..”.

Me? I’m not an entrepreneur. I don’t fit the build. After a quick stutter, I usually respond with, “Oh, umm I work at a software startup”.

We have trouble labeling ourselves. There’s this societal expectation that you must achieve some milestone before you are something. You’re not an engineer until you get a piece of paper telling you so. You’re not an author until a publishing company prints your work. You’re not a martial artist until you’ve placed in a tournament.

For entrepreneurs? Either raising a large round from VCs (AKA giving up equity or taking on debt) or becoming largely successful and having a recurring revenue in the millions.

I emailed a TechCrunch writer regarding what I had built and the initial traction that seemed promising and his response:

…could be a solid business but not the kind of product innovation I typically write about. If you get to $5M ARR let me know.

Five million dollars in annual recurring revenue. That’s when you’ve made it.

He’s not wrong. With the tech bubble growing, it takes more and more to build something that anyone cares about, and that’s fine. It just contributes more to the imposter syndrome.

The imposter syndrome is something that is deep-rooted in many of us. Society tends to label us by our occupation and it’s hard to break that mould and you often feel like an imposter when you do.

Think about. Who you are, to society, has always been a reflection of an occupation.

What do you want to be when you grow up?

I bet you didn’t say, “I want to be a husband with 3 great kids living in Colorado near a ski resort.” You probably said you wanted to be a firefighter or some other occupation.

Same goes for questions today:

What are you studying (AKA what occupation are going into after college)

What do you do? (AKA what pays the bills?)

Learning from Others

Although I’m still guilty of feeling as if I’m an imposter, I think there’s value in knowing you’re not alone. Many very successful entrepreneurs, entrepreneurs that have been on How I Built This, have felt this same feeling during the early stages.

The importance is to continue pushing, don’t be afraid to put your neck out there, and everything will work out in the end.

’Til next time

Do you have tips or a story on how you’ve overcome self-doubt in the past? Share it in the comments below for others to learn from.




Co-Founder and CEO of Cloud Campaign. Spilling my brain about bootstrapping a SaaS startup in a crowded market. www.cloudcampaign.io

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Ryan Born

Ryan Born

Co-Founder and CEO of Cloud Campaign. Spilling my brain about bootstrapping a SaaS startup in a crowded market. www.cloudcampaign.io

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