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Find the Right Entrepreneurial Community to Silence Your Inner Impostor

Find the Right Entrepreneurial Community to Silence Your Inner Impostor

In normal times, 90% of startups fail. And 2020 was anything but normal. One of the biggest challenges of being a new entrepreneur is the lack of knowledge and experience, which can lead to impostor syndrome, which, in turn, can set you up to fail.

This is where finding a peer group – an entrepreneurial community – can be a huge benefit. The right group will provide an education, networking opportunities, accountability, and will banish fears that you don’t have what it takes to succeed as an entrepreneur. 

Successful people put themselves in the company of other successful people. Sometimes it’s intentional—actively navigating your way to those you want to know—and other times, it’s just a product of success. Doing well will propel you to places where others are also doing well.

Success expert Jim Rohn once said, “You are the average of the five people you spend the most time with.” The company you keep will be a significant driver of the direction of your life and career. If you want to improve yourself, you should regularly be in situations where you might feel inferior, and might struggle with impostor syndrome.

When your inner impostor starts speaking up, it means you’re among people who are going to challenge you, grow you, and inspire you to do more and think bigger. You should not be running from those situations; you should see them for the gift that they are and lean in to those opportunities.

What to Look For in an Entrepreneurial Community

You need a group, a circle of peers who are on a similar journey as you are. These are the people who can identify with your struggles and help you reset your perspective. They’ll help you fight off impostor syndrome.  An ideal peer group for an entrepreneur is made up of a handful people from similarly sized but noncompetitive businesses. 

The similar size is important, because the CEO of a $150 million company deals with a different set of challenges than a CEO of a $2 million company or an independent artist who is managing his or her own career. That’s not to say that you can’t learn and benefit from a person in a different size company than yours, but it can easily start to feel like a mentor–mentee relationship rather than a peer relationship.

I’ve seen a lot of different peer group models over the years, and I believe a good peer group shares three characteristics. Consider the following questions.

Is the Group Diverse?

It may seem at first that the best type of entrepreneurial community would be made up of businesses (and owners) that are like yours (and you) in as many ways as possible. While there’s value in being able to compare your businesses directly to one another, I believe there’s just as much value in learning from businesses that are different from each other.

The peer groups that I’ve been a member and facilitator of have included businesses across a wide range industries. I have learned something from every one of them, and the businesses I have run have benefitted from that broad view of what works and what doesn’t across a wide variety of business models and product or service categories.

Just as important, I have been able to see the challenges that are common across most industries and the struggles that nearly all entrepreneurs face. A diverse entrepreneurial community has given me a balanced and well-rounded perspective on business leadership.

Does the Group Share a Desire for Growth?

I once interviewed an entrepreneur who was interested in joining one of my peer groups. As I asked him about his goals, he said, “I don’t want this company to get too big. I’m making about $100,000 per year now, and if I can get to $150,000, then that’s probably enough for me.”

Hard stop. He was not a fit for our group. It’s not that his choices are wrong; he can do with his company what he wants to. It’s that our group was made up of entrepreneurs who were focused on growing businesses, not putting limits on that growth.

You can’t take a journey with people who want to sit still. You need to travel with people who want to move at a similar pace and who want to go the distance. That doesn’t mean you have to all be building the same type of business or have the exact same long-term goals. It just means that people who are content to plateau and coast are not going to push you to grow, and vice versa.

Is the Group Transparent Enough?

You absolutely must have transparency (and vulnerability) among your group, or it will mostly be a waste of your time. If you’re there to try to prove that you are as good or better than everyone else, you’re going to go into Tour Guide mode, talking about everything you’re doing right and avoiding the areas where you need improvement. If everyone in the group is in Tour Guide mode, there won’t be much learning or improving going on at all.

On the other hand, if everyone is willing to open up and to be very real about where they stand and what they need to improve, you have a real chance of growing together. You can operate as a group of Explorers, each benefiting from the things you are all learning.

Vulnerability is the key difference between an entrepreneurial community that works for you, and one that works against you.  It’s the difference between a community that will feed your inner Impostor, and one that will starve it.

This is also the reason that you need to be in a peer group without competitors and preferably without any vendor–customer relationships. You need to feel comfortable being yourself and talking about your struggles.

There’s a famous saying that has been attributed to a lot of different people: if you’re the smartest person in the room, you’re in the wrong room. The corollary to that is this: if you think you’re the dumbest person in the room, stay there! That’s exactly the place you need to be. When The Impostor inside your head tells you to get out, that may be the best sign that you’re in the right place.


This article has been adapted and excerpted from Overcoming the Impostor: Silence Your Inner Critic and Lead with Confidence by Kris Kelso, with permission from Dexterity Books. All rights reserved. 

Kris Kelso is an executive coach, leadership advisor, and keynote speaker based in Nashville, TN. Certified as a leadership coach, Kris has worked with hundreds of entrepreneurs, business owners, and their leadership teams. 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. Connect with Kris on his website: check out his book Overcoming the Imposter 


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