Winners Do Quit. Here’s When.

Mark Overbye
4 min readApr 13, 2021

Want to stock up on Virgin cola? Gone. How about buying Virgin Vodka, Virgin Wedding Dresses, Virgin Clothing, Virgin Cars or Virgin Cosmetics? Nope. Richard Branson has started over 100 companies. And he’s shuttered 15 of those.

If Mother Teresa didn’t abandon her Albanian convent in 1946 to live among Calcutta’s poor, she wouldn’t have been awarded the Nobel Peace Prize 33 years later.

From 1900 to 1908 Albert Einstein worked at the Swiss Patent Office. In 1909 he moved on to pursue science, accepting an associate professorship in theoretical physics at the University of Zurich. So enamored by radiation mathematics, gravitation and thermodynamics pursuits he became an Austrian citizen in 1911 to become a full professor at Charles-Ferdinand University in Prague.

Michael Jordan left the Chicago Bulls after winning 3 NBA Championships to play baseball for the Chicago Whitesox. In 1994 he left the Whitesox, returning to the Bulls and won 3 more NBA Championships.

When she was 50 years old, Julia Child wrote her first cookbook after a career in advertising and secret intelligence.

John Glenn orbited the earth in 1962, culminating an aviation career highlighted by 6 Distinguished Flying Crosses and 18 Air Medal awards. Twelve years later, at age 53 he became a US Senator in Ohio, a role he held for 24 years.

I’m a fan of Vince Lombardi, but I believe his advice that, “Winners never quit and quitters never win” is among the most misguided advice of the past century. We all know too many people slogging away in jobs they dislike or roles they despise because they mistakenly believe things will improve or being tagged a quitter is more distasteful.

Someone close to me once said, “Bad news doesn’t get better with time.” How do you know when to quit? You quit when after being fully vested you realize you’re not getting where you want to go. You quit when there are more fruitful opportunities down a different path. You quit when you are open to new ideas, information and points of view and are able to consider contradictions and challenges with a fresh mindset.

Sometimes you need a ferocious storm clearing your shoreline to clarify your purpose and reveal those opportunities. Too often the mentality of, “Another day in the salt mine,” clouds your options, then 10 years goes by. Finding your clarity of purpose and taking action results in your greatest happiness and job satisfaction.

In Q3 2020 Warren Buffet sold about 188,000,000 shares of stock in 10 companies. He also bought about 178,000,000 shares of stock in 10 companies different from those he sold. When asked about his trading practices Buffet commented, “ Well, the best thing to do is buy a stock you don’t ever want to sell. But that only takes you so far…You might want to sell a stock because a better opportunity comes along.” Embedded in Buffet’s success is being able to say good bye to propositions that he believes won’t pan out.

Buddha said, “You can only lose what you cling to.” Clinging fiercely to your current situation prevents seeing new opportunities. The mindset of, “We’ve always done it this way,” must be discarded to be able to see how to evolve to do it better or discover new ways to win customers, develop new products or services and gain traction. The trick is to loosen the grip on today, ask a lot of questions about mission and purpose, then be willing to embrace budding opportunities able to blossom into greater potential.

Ships waiting for an absolute confirmation of uncertain weather conditions before departing the harbor will be left behind by those optimistically willing to explore ports unknown. Same in life and business. Realizing that the forward view is the only view, you can jettison thoughts and actions that don’t contribute to realizing your objectives.

I once had a job I didn’t like and wanted to quit. It paid well, the work fell into my sweet spot and the time demands were reasonable. But the president was a horrific manager and didn’t know the business, how to manage or solve problems. I had a fine deck chair on the Titanic.

A trusted mentor said, “It isn’t about what you’re leaving, it’s what you’re moving toward.” Easily able to count the many reasons I was unhappy, at the time I couldn’t answer what I was moving toward. He put a massive burr under my saddle. Today, I seek to be optimized for joy, knowing what motivates me in ways that best serve those I work with.

The only thing standing in the way of your company being the best it can be, or you as a person, is your willingness to cast off fears, define what you want and trim your sail to get to that port.

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Mark Overbye

A man in the arena I CEO Anthem Marine I Chairman USA Waterski and Wake Sports Foundation I C Suite Scribbler