5 Mistakes Everyone Should Make

Five successful people, ranging from a noted psychologist to a legendary tastemaker, describe their most startling (and most revealing) blunders.

4. Be willing to fail—doing something you love.
In 1997 I had just graduated from law school (with tons of student-loan debt) and was interviewing for high-paying positions at big firms. The problem was, my heart wasn’t in it. So I took myself out of the running in order to build a small Internet publishing company with a friend. After a year of barely staying afloat, our venture went the way of a 404 ERROR message. I was broke and unemployed, and Sallie Mae was hot on my tail. I wondered what endeavor I should try next.

It sounds crazy, but once again I decided to throw caution to the wind and just do what I wanted. I began working as a trial attorney for the U.S. Department of Justice. Over the next few years, I held a wide array of fascinating jobs that I took because they captured my imagination: serving in the military, reporting from Iraq for the Washington Post, and, most recently, becoming a full-time author. Some might consider me flighty for changing careers so often, but I contend that the key to professional happiness is asking yourself two simple questions every single day: Are you passionate about what you do? And if not, what are you going to do instead?

Bill Murphy Jr. is the author of The Intelligent Entrepreneur ($27.50, amazon.com).

5. Carelessly put yourself at risk.
I’m a terrible skier, and I’m not being hard on myself when I say that. Small children and monkeys are more coordinated than I am. So it was with unbridled terror that I once found myself alone on a black-diamond ski trail in the middle of a blizzard. (Long story.) With nobody to carry me down, I didn’t have a lot of options. So I wept—and had a fairly supplicating talk with God about my imminent death. (I believe I made a series of promises involving church attendance, reduced alcohol intake, and forgoing swearing.) And, finally, I skied—slowly, with zero elegance, and whimpering like an infant the entire time—down the mountain. It wasn’t pretty, but I did it.

The point being, sometimes you have to get in over your head to realize that you’re not really in over your head at all. Two years ago, I got a job that I desperately wanted but had no idea how to do. So I took it, endured several panic attacks, and eventually learned the ropes. My choices were either figure it out or get fired. The bottom line: Most of the time, a high-risk situation won’t kill you, because you are stronger than you think. And it’s never a bad thing to be reminded of that.

Amy Ozols is a cultural commentator and writer for Late Night With Jimmy Fallon.