A young friend, who had just completed her second graduate program at the University of Texas in Austin, asked me how she will know when she finds her true place in life.

Anne is worried about starting down some career path, only to discover after years of toil that she should have traveled in another direction. Her dad had begged me to discourage Anne from seeking any more expensive education. He is an MD, and a wonderful guy, but a little, shall I say, “rigid.” Meanwhile, Anne’s mom was in favor of her doing anything, so long as it was close to home. Anne’s mom has never stopped going to school and runs multiple neighborhood associations. She’s the mother hen of all mother hens.

Isn’t it wonderful when someone asks you a question for which you are the least qualified person on the continent to provide a meaningful response? I wanted to give Anne solid career advice, but my own professional endeavors have consisted of bumping into jobs serendipitously, and then hanging on with both hands. Whenever I was dropped from a job, or attracted to another, I did little self-evaluation in terms of the appropriate fit or future opportunities. And I never looked back to consider what might have been had I followed another path.

In retrospect, I guess it all came down to how I saw myself. When it came to careers, who was I? Since I had never posed that question during my decades of labor, it’s only now that I recognize I always defined myself as a writer, or a salesman, or both. I’d taken almost any offered job that tantalized me more than the previous one. And then, I’d go about finding a way to include writing in that job, and figure out a way for me to sell something to somebody. The latter skill kept me employable, the former kept me interested.

So I told Anne the truth about me, and my own haphazard careers. Then I asked her whether my confession was of any help. She gave it some thought, and then replied, “No. But my parents made me ask you. They think you have it all together.”

Anne likes me. She wanted to give me a second chance at this mentoring thing. “Isn’t there anything you can give me to guide me in the right direction?” she asked.

Such pressure! I thought about how young and gifted Anne was, and how she could take off in one of many directions and be a huge success. So what did she need? I jotted three words on a card, and gave it to her with a big hug:

“Permission to fail”