Jeb Corliss says he’s “impossible to be in a relationship with.” He’s a professional BASE jumper and wingsuit flier—who’s learned to very carefully analyze and control his emotions, including fear. “People don’t realize that feelings get you in big trouble,” he told me during our conversation at his condo near the beach in Marina del Rey, CA.

For the past two decades, Jeb has made a living doing things that, to most of us, seem crazy. Like jumping out of planes or off of cliffs and flying through the air, often through narrow spaces or trying to hit targets close to the ground. He was first drawn to BASE jumping after seeing it on TV when he was a depressed and suicidal teenager. “It was this concept of, wow—very few people in the world are willing to do that. And if I do it, well then I’ve done something that very few people would ever be willing to do,” he told me. “And if I failed, well then, I got what I wanted.” 

Jeb has had a few brushes with death. In 2012, he slammed into a rock outcropping while soaring down from the top of Table Mountain in Cape Town, South Africa. He was sure that he was going to die, but instead broke both of his legs. Some of his friends haven’t been so lucky. Earlier this year, fellow wingsuit pilot Jhonathan Florez—a friend who Jeb says “barged his way” into his life—died during a practice jump in Switzerland. “I’m kind of back to just being a total anti-social, just on my own, kind of thing,” Jeb says. 

In our conversation, we talk about what motivates Jeb to keep risking his life, at 39. And we talk about why his near-death experience left him thinking…about retirement savings.