auren Ober ’96 is the host and producer of American Public Media’s hit podcast, Spectacular Failures, about some of corporate America’s biggest business blunders. Before that, she hosted NPR’s The Big Listen, produced an award-winning weekly newsmagazine and, as a freelance radio producer, contributed stories to public radio shows and podcasts including NPR’s All Things Considered, Morning Edition, Criminal, and 99% Invisible. A graduate of Syracuse University, American University, and the Transom Story Workshop, Lauren describes her path as “unconventional” — and says that Winchester Thurston helped instill confidence for the journey.

Q: “Breaking Boundaries” is the theme of this issue of Thistletalk. What are some boundaries that you have broken?

A: I have taken a sort of unconventional route to where I am now. I worked in print journalism, made a big shift into radio journalism and audio production, moved to Washington D.C., and began working in public radio. When I had a show on NPR, I was one of only five female solo show hosts. There aren’t that many women heading shows, and there certainly aren’t any like me—I’m a gay woman, and I’m closer to the middle of the gender spectrum—but I have the confidence to know, sure, why couldn’t I helm a national show that is on public radio stations across the country?

Q: How did WT help to prepare you?

A: I went to a large public high school. My parents didn’t see it as a fit, socially or academically, so I visited Winchester, was accepted, and went from a class of 400 to a class of 36. Winchester was like a breath of fresh air. There was a huge amount of trust, and when you are trusted with time and responsibility, you step up into that. It builds confidence. It allows people to take risks that are calculated, and gives the experience of being able to feel your way through things.

The school was pushing against the norms of high school education, and I benefited from that boundary breaking: We walked to Oakland to see an art film, took Japanese history classes with someone who had lived there, and African history with someone who was Ghanaian. All of these things are beyond the scope of traditional high school education.

Q: Did this inspire your curiosity?

A: I come from a deeply curious and engaged family; WT supported that foundation. That’s important; it said, ‘Yes, the direction you’re going is good, here’s more of it, and here are things that you might not have known you were interested in, like African history.’

Before Winchester, I didn’t know what Diwali is or what classical Indian dance looked like; now I know how Japanese tea services are done, and about their cultural and religious underpinnings, because we did one in class. The first gay people I ever met were through a school presentation; one year later, WT started a Gay-Straight Alliance. There were many ways in which WT was ahead of the curve. Conversations were happening there that were not happening elsewhere. For somebody like me—who wasn’t interested in the movie version of high school—it was very appealing.

Q: You’re currently hosting the nationally syndicated Spectacular Failures. Have your thoughts on failure evolved since you’ve begun hosting the show?

A: I’ve learned that failure is just a thing that happens. You don’t have to imbue it with meaning, to say, ‘Oh, I need to fail up.’

I have seen real reluctance and fear, on the part of young people, to get anything wrong. I’ve been fired from a job, and I lost a job because my show got canceled. Of course, these things make you feel absolutely terrible, but this is where resilience comes in. You pull yourself back up and figure it out. In an academic environment, creating a supportive space where people can take risks, make mistakes, know that things will fall to pieces and it’s not the end of the world—being able to fail small—is important. Then when bigger things happen, you know how to deal with it.

Q: Final thoughts on how WT contributed to who you are today?

A: When you have curious and engaged and thoughtful adults fostering that in kids, it makes all the difference. WT allowed me to be me, in whatever ways that manifested itself. I truly did feel it allowed me to fully explore who I was and could possibly be.