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Recently I failed to win a fellowship that would have underwritten two years of creative bliss. I would have been able to write that novel and not worry about the mortgage or the repairs that in my ramshackle old house I've come to expect. The letter was apologetic and brief. I wanted to crawl under a rock. I wallowed. I blamed. I bought new shoes.

After a decent amount of time spent feeling extremely sorry for myself, I started to sort out what I could salvage. I still wanted to write my book, and suddenly it was clear that my future should not rest on the decision of an anonymous panel of judges. What I need to do, I thought, is figure out some other method of accomplishing the same goal, even if that required making a way out of what, at the moment, felt like no way at all.

In school, where we learn the F word, failure packs such a wallop because it seems to be the end of the story. That letter was our grade, our identity. Some of us never outgrow that notion. The mere fear of failure, my friend Kathy says, has hobbled her choices in work—and, sometimes, relationships—for much of her life. But as the four women here point out, failure turned out to be the beginning of their stories, not the end. Failure redirected them to triumph in some vital part of their lives. They took the blow, felt awful, and then not only found a way to learn from the mess but ended up in a far better place. What each of them has recognized is the paradox that success requires a willingness to risk failure.

Subject #1: Terry Gross
Who She Is: Terry Gross is the host and an executive producer of Fresh Air, the award-winning interview show on National Public Radio. Gross, 50, has been hosting since 1975—more than half her life—talking to a wide range of guests, from Al Green to David Sedaris to Jimmy Carter. All of them are subject to Gross's mild-mannered but hard-hitting questions and her relentless enthusiasm for substantive conversation. She loves what she does. It wasn't always that way.
What She Told Us: "When I have guests on a show, I like to talk to them about their failures—not to show them up, but because that's part of what defines us."
Her Failure Story: "In college I thought I wanted to be a writer, and then I realized that my writing wasn't nearly good enough to justify that ambition. And then I got caught up in things like the antiwar movement and the women's movement, and watching movies and going to concerts and poetry readings. And suddenly I was stuck needing a career.

So I figured I would become a teacher. Not because I felt called to teach but because I knew how to do that. You take your classes. You become a student teacher. Then you take a test. You're assigned to a school and, poof, you're a teacher. I knew there wouldn't be insurmountable obstacles to getting a job.

But I happened to graduate at a time [1972] when there was a glut of teachers. I didn't get an assignment till the day after election day. I was given a job teaching junior high school at the toughest inner-city school in Buffalo, and I didn't have a clue how to be an authority figure. I had spent my undergraduate years challenging authority. Suddenly I was the authority. I wanted to be the kind of teacher I had always wanted to have. So I showed up in my purple corduroy jeans and work boots. Now, this was not the teacher that my students needed. They were mostly very poor. Many came from broken families. They needed order and structure in their lives. And I needed anarchy in my life because I had come from a very structured, very middle-class family. What I needed and what I was ready to give were exactly the opposite of what they needed.

For instance, when they saw my purple corduroy jeans and work boots, they ribbed me about seeing me at the Salvation Army. One of the students finally told me he thought I was saving my good clothes for the people I really cared about. So I ran out and bought myself some nice clothes—pleated skirts and sweaters that matched. And, oh, they loved it. People showed up at the door just to look at me.

I was a disaster as a teacher. It was constant chaos in the classroom. I'd hand out books; students would throw them at each other. There were usually more kids in the hallway than in the class. One student accused me of having a heroin habit. That spread through the system, and the teachers sent a letter to the superintendent of schools, saying I was suspected of being a junkie.

I was the hippie of the school, and there were all these preconceptions about hippies and drugs. They said that since I wore long sleeves, it was probably to hide track marks. Of course the kids were wearing coats in class all the time because they were afraid if they hung the coat up, it would get stolen. It was just one paradox after another.

Anyway, around my six-week anniversary, the supervisor from the board of education came down to watch me teach. And as the students were filing out, they overturned a bookcase, sending a clear message that things were not working out. The students knew the message they were sending.

So I was...I was fired. I was fired. I'd desperately wanted to quit, but I was afraid to. I heard a voice in my head—I think it was my mother's—saying, 'Don't be a quitter.' And I kept thinking, 'Maybe it will get easier. Maybe I'll get better. Maybe someday the students will like me instead of telling me that they'll slash my tires after class.' It was like I was in a movie—but it was the wrong part for me. I didn't know how to play the part. I would just stand there and watch as if I were in the audience. This was a lot of what was going wrong: I would just stand there and observe, as opposed to taking action.

Next: How Gross' failure has shaped her successes

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