Trapped By My Success

Trapped By My Success
Photo by Frederic Köberl on Unsplash

One of the prime attributes of any successful entrepreneur is a sense of restlessness.  We always want to be engaged; planning, implementing and improvising to achieve our goals.  This is extremely important when we are in startup; like a prizefighter we counter-punch, side-step, and plot for an opportunity to deliver a knockout blow.  This restlessness keeps us motivated.  But what happens when our venture becomes successful?  How do we keep this sense of restlessness from undoing the good work it helped to create?  How do we keep ourselves from constantly gazing over the next hill looking for more exciting challenges in the next opportunity?

I’ve been a CEO for over 11 years now.  It is the longest I’ve stayed at one company and the longest I’ve been in one position.  I earn a standard of living that far exceeds what I have any right to expect considering my upbringing on the wrong side of the tracks.  But in the past few years I’ve struggled to stay focused on continuing to grow my company like I used to, burned out by the constant grind of operating a business in today’s environment.

Watching it Grow

In the early years it was a crazy amount of fun.  My partners and I decided to forego outside funding and bootstrapped our company’s start-up.  The company would succeed or fail off OUR efforts, and we didn’t want it any other way.  We literally ran checks down to the bank to deposit to make payroll, brought and repaired third-hand office furniture, and kept house-fans on the servers so they wouldn’t overheat.  Many months we did without money so we could afford to pay our staff.  In these heady times our restlessness was assuaged by the constant struggle to keep the company afloat and moving forward.

By the middle years it was all about building on the strong foundation we created.  Confident in our ability to grow the company ourselves, we spurned venture capital and acquisition opportunities, our logic being no one could grow the company like we could because no one would CARE about the company like we would.  So, here we are, eleven years later. The company continues to grow, but our functions within it have changed.  Where before we strategized and changed the company’s course based on gut instinct and prevailing winds, dodging the rocks in the water and keeping the ship afloat; now we stay mired in administrative “quicksand” guaranteed to suck the air from our lungs.

What Now?

So why don’t I kick this company to the curb, sell out and build something new?  Well, that’s the curse of success for an entrepreneur.  Once we reach a level of achievement, we fall victim to the malaise of maintaining what we have, rather than pushing to build something new and better.  Successful business people have inner doubts like everyone else.  My inner critic tells me all the time I can’t do it again.  It was a fluke, dumb luck, and my partners were carrying me (although that last one is probably the truth!).

I stopped “loving” my current company several years ago.  Like any parent, I’m proud about what we have accomplished and relish the experience of growing this business to success, and I remain totally committed to its protection and desire to prosper.  But also like any parent, I’m ready for this grown child to leave home.  And the worst part of this?  I struggle to share these feelings with my fellow partners even though I suspect they harbor the same thoughts.  To complain about this gilded cage in the face of all the prosperity this company has provided for me seems whiny at best, downright ungrateful at worst.

So, what do I do now?  How do I shed these “golden handcuffs” that keep me chained to this company I helped create?  Well, all I can do is to look at the “big boys” of business, the current entrepreneurial “Mount Rushmore” of persons like Richard Branson, Elon Musk and Thomas Edison. I don’t limit myself to just this one company.  Instead, I use the benefits it has given me to prepare for the next “big” thing in your life; find new interests, gain knowledge, and prepare the path for future successes I will walk on one day.  Entrepreneurs have to be challenged.  Like sharks, if we stop swimming, we die.  Nothing should hold us back, not even our success.


Carolina grad, business owner, Master of the Oblivious, "Rural Renaissance Man", dog lover, family man, geek...

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