This is Why Most (if not all) Entrepreneurs Struggle With Impostor Syndrome

By Kris Kelso

Many people are surprised to learn that impostor syndrome tends to be more prevalent among high achievers—people who are ambitious and competitive and who push the boundaries; people who are not satisfied with coasting through life; people who take risks and try new things. These people are more likely to wrestle with impostor syndrome. 

You might think it would be the other way around, that the more ambitious and driven you are, the less likely you are to feel like a fraud. But the opposite is true. Unambitious people don’t struggle as much with feeling like a fraud because they simply don’t care. They’re not trying to improve; they’re fine with coasting through life and keeping things the way they are. There’s no reason to feel like a fraud if they do the same thing day in and day out for their entire lives. 

But the greater—and in particular, the more visible— your success, the more likely you are to feel like you’ve pulled off a great charade. At some point along the way, you’ve probably been in over your head or unsure of the next steps, but managed to figure it out. 

In my experience working with hundreds of entrepreneurs, I have found impostor syndrome to be the one challenge that is nearly universal among them. Most successful entrepreneurs have struggled with self-doubt and had moments when they weren’t sure that they actually knew what they were doing. Here are a few reasons that entrepreneurs, as a group, are one of the most likely to experience impostor syndrome. 

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1. They’re Breaking New Ground 

Entrepreneurs, by definition, are often in the position of trying things for the first time and figuring them out along the way. They create things that didn’t exist before, or they take old, established products and systems and turn them on their heads. 

This leads to a lot of trial and error and a lot of failures and mistakes. Every successful entrepreneur has a long list of failed experiments—some huge and others small—in his or her past. It can be easy to feel like the failures define an entrepreneur, while the successes (which are usually fewer and farther between) may just be the result of luck.

But failure is not the opposite of success – failure is part of success.  It’s an important step in the process. 

2. They’re Almost Constantly in Sales Mode 

Entrepreneurship involves a lot of selling. The most obvious sales job is selling products or services to potential customers. In the early phases of a business, an entrepreneur may be the only salesperson in the company. They might be selling a product that isn’t yet as high quality as desired, or a service that is not completely defined and tested. 

But that might be the easiest sale an entrepreneur has to make. They also have to sell a vision of the future, of what they’re setting out to build, and of possibilities that haven’t yet been realized. 

Entrepreneurs have to sell their ideas to potential employees who they want to come join their company. They have to convince people to come alongside them, sometimes working crazy hours for little pay and sparse benefits, and to believe that the rewards on the other side of success will be worth the sacrifices. A small percentage of entrepreneurs will raise money from investors, which is essentially selling a stake in the company’s future for cash right now. 

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The problem with all that selling is that you’re always presenting the best version of yourself, your team, your idea, and your business. You are highlighting all the positives, while you know deep down there are plenty of negatives as well. You know there are cracks and flaws in the plan. You know there are things you haven’t figured out yet, and there are assumptions you have made that you can’t yet prove. 

3. They’re Put on a Pedestal 

Entrepreneurship has become in vogue in our society, and entrepreneurs are sometimes celebrated as superheroes. 

A CEO named Toby Thomas used an illustration that has become my go-to description of entrepreneurship: a man riding on a lion. 

People look at the man on the lion and think, “This guy’s really got it together. He’s so brave!” And all the while, the man riding the lion is thinking, “How in the world did I get on this lion, and how do I keep from getting eaten?”

The imagery here is remarkably accurate. I cannot count the number of times I’ve been given accolades, admiration, and verbal high-fives for the risks I’ve taken and the things I’ve accomplished as an entrepreneur. Yet on the inside, I’m not celebrating; I’m usually freaking out a little bit. What looks to others like strength and boldness feels to me like a series of near-catastrophes. 

Entrepreneurs are celebrated for being the risk-takers they are, but that celebration often feels undeserved. It feels fraudulent. 

That combination—having a close relationship with uncertainty, being continually in sales mode, and being glorified by others—puts entrepreneurs on a crash course with impostor syndrome. It provides plenty of material for the inner critic to work with – plenty of options to convince you that you’re not really who everyone seems to think you are. 

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The good news is that when you feel like a fraud, that’s often a sign that you’re taking big risks and doing great things.  Impostor Syndrome can be a sign of boldness, rather than weakness.  Once you realize that the feeling of being an impostor puts you in the company of many other smart and successful people, it doesn’t seem quite so bad.  You might even begin to believe that feeling like an impostor is a good sign that you’re not one.


Kris Kelso is an executive coach, leadership advisor, and keynote speaker based in Nashville, TN. He is also the author of Overcoming The Impostor: Silence Your Inner Critic and Lead with Confidence (Dexterity, January 19, 2021). Certified as a leadership coach, Kris has worked with hundreds of entrepreneurs, business owners, and their leadership teams, and he is an advisor and instructor at the Nashville Entrepreneur Center, a Facilitator / Coach with The Alternative Board, and a contributing writer for The Nashville Business Journal. 

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