Why You Should Make More Mistakes

April 23, 2013

broken egg

Think about the last time you made a mortifying flub at work. The email that went to the entire company instead of its intended recipient, or the words that – even as you heard them come out of your mouth – you regretted saying to your boss.

Whether you stumbled 15 years ago or last week, the misapprehension and dread it inspired probably feels just as fresh as when the mistake first happened.

Big errors are burned into our memory so that we can learn from them. And even the most successful people make major missteps. In fact, judging from a series of original posts by LinkedIn's Influencers on their top career screw-ups, it would seem the higher-profile the business leader, the more serious their workplace disasters. Heavyweights like Deepak Chopra, who alienated himself from the Boston medical establishment with a well-timed dump of a file folder, or Peter Guber, owner of the Los Angeles Dodgers and Golden State Warriors, who fired Jeremy Lin before he became Jeremy Lin.

What sets apart industry leaders with colossal blunders in their past from the simply error-prone is the ability to use mistakes to get better at what they do. Angel investor and writer Chris Schroeder learned to slow way down and always have someone check his work when, early in his career as an investment banker, he put his and his company's reputation behind a report that was based on a bad calculation. When Jetblue chairman Joel Peterson was a senior partner at the world's largest real estate developer, he saw the housing crash coming but was at odds with his founder and didn't make a strong enough case to slow growth. The unfortunate outcome for the company taught him never to tiptoe around problems.

Having a sense of humor about your mistakes doesn't hurt either. Former Merrill Lynch president Sallie Krawcheck isn't afraid to talk about how her offbeat-looking cat cleaned her "nether-regions" behind the Bank of America CEO in full view of a very high-profile crowd. NewYorker.com editor Nicholas Thompson was fired from his first job as an assistant producer on one of the country's most respected television news programs on his first day. "I might be the only person who worked at 60 Minutes for less than 60 minutes," he writes.

This career arc — a fall from grace only to be redeemed later — clearly talks to some part of our brain. There's a reason why movies, novels and epic poems rely on the three act structure: The hero is introduced, comes up against an obstacle, and just when things look darkest — triumphs. It is in that moment between Acts 2 and 3, when it looks like there is no way back, that the lessons emerge.

So what are those lessons, and how bad can it get? Here are some of the 60 blunders in this featured series:

  • CNBC journalist Herb Greenberg botched a drug raid as a rookie reporter at the Miami Herald.
  • Charlene Li, Founding Partner at Altimeter Group, had a boss who really, really stank. After agonizing about it -- she decided to tell him.
  • Dan Rosensweig, CEO of Chegg, sold his company to CNET, and accepted a job at Yahoo – a great chance to sell his CNET stock and ensure his family’s future. At the last minute, he changed his mind, burning bridges at Yahoo while CNET’s stock crashed.
  • Science House EVP Rita J. King, took a job at a newly-opened AOL call center as a vulgarity censor after her car broke down in Albuquerque. She writes: “Had I really given up my adventurous voyage for daily viewings of latex nuns in gas masks?”
  • Richard Moran, CEO of Accretive Solutions had an epic reply-all blunder in which he meant to tell a trusted colleague exactly what he thought of a certain client, but instead, told the entire company -- and the client.
  • Likeable Media CEO Dave Kerpen was humiliated publicly in 29 episodes of reality show Paradise Island.

The full series will give you a flavor for the dazzling array of slip-ups it's possible to make, and how you can do better than just recover from them.

What's your best career mistake, and how have you helped it get better what what you do? Share it with us on our LinkedIn Company Page or tweet it to @LinkedIn with hashtag #mybestmistake.

Photo: Ribarnica/Flickr