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.

  • Amanda Armstrong

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).