An Entrepreneur's Biggest Enemy

May 21, 2008

4 Min Read
An Entrepreneur's Biggest Enemy

By Mitch York 1

I had a dream last night. It was one of “those” dreams. I was walking down a crowded Manhattan street in my BVDs. At first thinking it was normal and then, with increasing dread, realizing it was anything but (unless you are this guy). And then I had a second dream last night. My brother was there. We were in college. It was around finals time. I asked him if he knew when our history class was meeting, because I can’t remember ever going this term. I don’t even know where the classroom is, and I haven’t done any homework—and the final is tomorrow!

While many people have dreams like these, perhaps as nature’s way of helping us work out our insecurities, we also take our fears into the world and give them lots of fresh air and exercise. I know many entrepreneurs who are their own worst enemies. Some of the things we do:

We’re not worthy. A financial planner I know wants to acquire clients with at least $500,000 in assets to invest. When she asks for a referral, she hedges the amount by saying that if the prospect does not have $500,000 but has the potential to get there, that is also a good referral for her. But what she really wants are clients with $1 million to invest. So why doesn’t she ask for those referrals? Is it because she thinks she’s not worthy of those clients? Absolutely not! Quite the contrary, she knows she can bring enormous value to people with that level of assets. So why doesn’t she ask for referrals of people with $1 million…or $2 million…or $5 million in assets?

We wallow in it. When we screw up, we often beat ourselves up to an extent that would make a Singaporean policeman blush. How did I not catch that typo? Why didn’t I know that customer was going to give the business to my competitor? Why did I have to open my mouth in that meeting? Why didn’t I say something in that meeting? How did she get that promotion–I should have gotten it. Why did I get the promotion–I didn’t deserve it. Instead of forgetting about mistakes and defeats and moving on quickly, we are likely to re-play in our minds whatever the bad episode was. If only we could get royalties for all that mental syndication, we could retire, at least in our BVD dreams.

Don’t ask, don’t tell. We have great trepidation about asking customers to tell us the truth as they experience it. Many entrepreneurs are uncomfortable asking for business because they don’t want to risk being rejected. So they make their presentation, they finish, they ask if there are any questions, and then….they leave the building. DOH! I should have asked for the order! After a sale, they get nervous about following up to see how the customer liked their product or service, out of fear the client may have hated it.

What should entrepreneurs do about facing their fears and insecurities? It’s such an individual and idiosyncratic problem that there are no one-size-fits-all answers. But there are worthwhile books on the subject. Some of my favorites are: Taming Your Gremlin, Feel the Fear and Do it Anyway, and The Four Agreements. The first book asks you to recognize that you have some irrational thoughts that are part of your DNA–and there is no sense trying to eliminate them because you can’t. But you can put these “gremlins” in their place. The second book gives tips on working through fears because the reality of doing what you are afraid of is less painful than the paralysis that fear causes. The last book gives you core guiding principles that, if you really internalize them, make it possible for you to walk into fire in the business world with no fear at all.

I don’t think there is any way to completely overcome the human problem of being our own worst enemies, but if you are going to be successful in business, you have to make it a priority to beat back your insecurity gremlin whenever he gets out of the trunk, slithers into the back seat, then into the seat beside you, and then puts a slimy finger on the wheel. Oh geez, I feel another bad dream coming!

Contributing blogger Mitch York is a personal friend of The VAR Guy. York coaches executives who are evolving into entrepreneurs. Find York — and his personal blog — at


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