Entrepreneurs are Different from Executives

By Barry Pruitt

I’ve started two handfuls of small companies, and I’ve won some, lost some, and sold some. This pattern bookswas an odd one for my wife, an American Express manager at the time. How could I live with the uncertainty, the ups and downs, the “some place to be” versus “nowhere to be” pendulum that seemed to be my life? Being an entrepreneur, like being a parent, can offer some of the highest highs … and some of the lowest lows of your life. For entrepreneurs it can be exhilarating. It’s exciting to find problems and offer solutions, to compete, to build teams. Still – I could never quite explain it to my wife until she, too, became an entrepreneur.

I was recently reminded of this journey in conversation with John Warrilow, author of The Automatic CustomerJohn pointed me to his articles in Inc. Magazine, and when I read this one, titled “The Single Biggest Difference Between an Executive and an Entrepreneur,” I found the explanation that I wished I’d been able to share with my wife many years ago.

Here’s what John wrote in March 2015:

Last week, Patrick Pichette, Google's CFO, announced he is retiring at the age of 52. In an unorthodox resignation letter, Pichette revealed that he and his wife are keen to travel and share more time with family and friends.

Before spending the past seven years at Google, Pichette held an executive position at Bell Canada and did a stint with McKinsey. Presumably, Pichette has earned enough money to live comfortably for the rest of his life, but it still struck me as odd that, at the relatively young age of 52, he characterized his departure from Google as "retiring."

Entrepreneur vs. Corporate Executive

And therein lies one of the biggest downsides of choosing a career as a Fortune 500 executive: there is no pause button.

Executives have careers they nurture and care for over time. There is a linear path to the top and when you opt off the career ladder, you "retire."

Contrast that with the winding road that is the entrepreneurial life. Most of the business owners we work with at The Value Builder System are not preparing their business to sell so they can "retire." Most of them will sell, take some time off, and then start another business.

By choosing the life of an entrepreneur, you've opted into a roller coaster ride with many ups and downs, but one of the benefits is that you don't have to treat your career as one long, linear arc.

Personally, I like to look at my career in 10-year chunks punctuated by periods of extended down time.

Life in 10-year Chunks

When I got to the end of a 10-year run in my last business, I sold it, because I knew my strengths tilt towards starting small companies rather than managing a relatively big one. But instead of immediately starting another business, I took some time off. We moved our family to Europe and experienced a different culture for three years. I wasn't worried about being passed over on the career ladder because I knew I wasn't going back to a job. Instead, I was pretty sure I'd be starting another business.

Now I'm three years into another 10-year run with The Value Builder System, after which I hope to sell the company and take another long break.

The Pause Button

The "life in 10-year chunks" philosophy is usually a bad fit for the corporate world. In a corporate job, you're on a ladder and once you opt out, it is difficult to opt back in again. There is no career pause button. The half life of your skills and networks shortens with technology and there is someone coming right up behind you to take your job. And he or she will not be keen on you coming back to your company to compete for the next rung on the ladder.

Sure, some companies like Microsoft offer a seven-year sabbatical program but they are typically limited to a number of months, not years.

By contrast, with a career in entrepreneurship, you get no corporate safety net, no pension, no company car, but the one thing that--at least for me--makes a career in entrepreneurship more attractive is that you do get a pause button. You get to start a business, hopefully sell it, take a long break and then start something new, without having to worry that you won't be able to re-enter the job market.

Your entrepreneurial instincts are timeless. The ability to see opportunities in inefficient markets, and to sell and convince others of the way forward, are not credentials that atrophy with time. Once you have them, you have them for life, which makes enjoying your well earned sabbatical between 10-year chunks that much sweeter.

Thank you, John! Now all entrepreneurs can better explain the pendulum life of being an entrepreneur and, when needed – hit the pause button.

Barry Pruitt


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