The Five Hesitations of an Entrepreneur

Life & Work

When I look back on my experience as an entrepreneur, I find that there is a predictable pattern that rears its ugly head anytime I stop short of achieving something.

These “hesitations” are the grinding force that makes you come to a halt. They stand in your way. They keep you from moving forward. Worse, they mess with your head. These hesitations all suffer from the same problem: They are largely manufactured. They seem like huge, insurmountable challenges all the time. When really, just a little creativity would move you toward the right solution.

They are:


Time is a hesitation because you’ll never start if the project seems too big. You think it’s beyond your capacity, but really, that’s a simple illusion. It may only take a few cycles (weeks, days, hours) if you break it into manageable increments.

Talent is insidious because it eats away at you. If you can’t do something, you feel like a failure. The lie here is that you should be the one to do it. Daniel Priestly, a massively successful entrepreneur and author once said (my paraphrase), “I don’t have any skills. You couldn’t hire me, because I can’t do anything. But I know how to set the vision and put the team together to get the result.”

If you have even one skill, then, you have more than him, and he’s wildly successful. What’s stopping you?

Timidity. There are many reasons to be timid. Maybe you’re nervous, afraid you won’t be able to make it work, afraid of meeting new people, or any number of things. This is a generic fear that causes a never-ending pause. But here are two cool things — first, think back, and you’ll find almost everything amazing in your life happened on the other side of fear/courage. Second, the same chemical reaction that causes you to feel fear also causes you to feel excitement. Simply choose to be excited about the possibilities rather than afraid of the pitfalls.

Tentativeness is a close cousin of timidity. It refers more to the action or process. It’s a hesitation because you might be letting a tentative approach get in the way of going all-in on something. And there are very few ways to succeed in life without an all-in approach.

Lastly, tribe — the notion that the right people aren’t around you to get the job done. Maybe you don’t have the right clients or the right team member(s), and this is causing you to hesitate. But this is totally in your control. You can decide on and get the right clients, you can hire the right team (or make profit-sharing or equity deals if you don’t have the funds). There’s always a way around.

All of these hesitations come down to:

The right frame of mind
The ability and willingness to surround yourself with the right people

Almost none of these hesitations manifest in a way that the results you desire are physically impossible to achieve.

That, my friend, is a freeing feeling.

Feb 9, 2024

About Me

Hey, I'm Steve — a Christian, entrepreneur, thinker, and creator. Thanks for stopping by!

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