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

By Amanda Armstrong
Updated August 18, 2010
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Leif Parsons

1. Totally embarrass yourself.
After the publication of my book Reviving Ophelia, in 1994, I was invited to a prestigious party. I got all dressed up; I was so excited to make connections. I had a wonderful time and was elated as I was walking back to my car. Well, that is, until I felt something on the back of my skirt. While I had gotten dressed for the function, I had apparently sat on a stack of clean laundry, and a pair of underwear had affixed itself. I had spent the entire night that way! I was mortified, but at the end of the day, it just didn’t matter. I went to other similar events after that, and as far as I could tell, that incident didn’t change people’s impression of me one little bit.

I tend to think that we are all always one static-cling mishap away from looking like a total idiot—and believing that helps me keep gaffes in perspective. And, of course, these grand embarrassments eventually loosen their grip anyway, leaving you with an ace-in-the-hole story to crack up your friends with for years to come.

Mary Pipher, Ph.D., has been a psychotherapist for more than 30 years. Her latest book is Seeking Peace ($16, amazon.com).

2. Ruffle people’s feathers.
Years ago, when I began working at a business school, I sat in meetings quietly, afraid I would say the wrong thing. Some people spoke up and were scoffed at. I didn’t want that to happen to me, so I held my tongue. I soon realized that my silence implied that I was on board with whatever was being said. I started voicing my opinion, even on controversial subjects, regardless of how my comments would be received. Occasionally colleagues would roll their eyes, but I found that even those who disagreed with me came to respect me for not backing down. Sometimes my ideas will make me unpopular, sure, but that’s better than being a blank slate.

Mary C. Gentile, Ph.D., is a senior research scholar in business management at Babson College, in Wellesley, Massachusetts. She is the author of Giving Voice to Values ($26, amazon.com).

3. Follow trends blindly.
Looking back on my life, I find it hard to think of a fad I did not embrace. When glam rock glittered, I bleached my hair and wore a dangly earring. When punk rock raged, I donned black leather. Not until my 50s did I find my look—I call it Carnaby Street mod circa 1966—which allowed me to hop off the trend merry-go-round. But I am grateful for this process: It took a fashion odyssey to help me find out who I really am.

Simon Doonan has been the creative director of Barneys New York since 1986. He is the author of Eccentric Glamour ($15, amazon.com).

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.