02/06/2012 03:49 pm ET Updated Apr 18, 2012

Success: Taking Risks To Follow Your Dreams

Dear young person,

When I was your age, I made a raft of decisions that older folks (and even some of my peers) thought were monumentally stupid. Here are just a few:

1. At 22, I married my college boyfriend.
2. At 24, I dropped out of graduate school even though I had a fellowship.
3. At 26, I left my job in advertising to backpack around Europe.
4. At 28, I changed careers. I did this again at 32, 36, 42 and 50.
5. At 34, I had an unplanned pregnancy and decided to keep the baby.
6. At 35, I switched to freelance writing in order to stay home with my child. Eleven months later, I was forced to declare bankruptcy.
7. At 37, I left a cushy editing gig at Time Warner to work for a fledgling website.

And so it goes. Some of these choices worked out better than others. The college boyfriend and I divorced. The unplanned pregnancy produced one of the most amazing people on the planet. The website, iVillage, went public.

But here's my point: Now that I'm over 50, all these events have been reclassified.

No one says I was stupid. Instead, I was courageous. I had moxie. Cojones. I didn't let the bastards get me down.

Sequential failures have been redefined as essential steps on the road to success. In fact, the bigger the snafu, the better it has turned out for me in the long run.

The only truly stupid choices I made were a) disrespectful or unfair to others, or b) disrespectful or unfair to myself.

With these two caveats, I would urge you to follow your heart. Take risks, big ones. Even if it means acting like a complete idiot.

Because no one is going to remember how stupid you were.