This story is part of our ongoing “First Steps” series, where we share extraordinary stories of men who transformed their bodies, minds, and lives with a focus on the first steps it took them to get there (because, after all, nothing can change without a first step!). Read all of the stories here.

Below, former millionaire Bill Bradley, 64, tells Men's Health how going bankrupt in 2005 left him searching for a "new identity" in life—and how working through his pain and discomfort (both literally and figuratively) as an endurance athlete helped him find purpose.

I OPENED MY first video store in Santa Rosa in the '80s using a bunch of credit cards because nobody would lend me money. Over the next 20 years, Bradley Video grew to 11 stores, it became one of the top independents in the country, and at my peak I was worth around $5 million. Then, in the mid-2000s, physical video stores began to die out, and in November 2005, at the age of 45, I was eventually forced to declare bankruptcy.

It was a crushing blow. That store represented my identity for two decades, and losing it felt like losing a part of myself. To make matters worse, I was also navigating a divorce, which left me feeling completely shattered. My self-esteem plummeted; I went from confidently addressing large audiences to feeling invisible. I returned to my father's business in a sales role, but I struggled to even make eye contact with others. I felt utterly defeated.

Quitting has never been my strong suit. I realized I needed to reinvent myself, and my mind drifted back to the pride I felt after completing my first Ironman-distance event. In high school, I was a track athlete, and I continued my training, running about 10 hours a week until the bankruptcy hit. I had long contemplated attempting a 50-mile race, yet doubt lingered—could I actually finish it? What would others think if I fell short again? Then, five months post-bankruptcy, a friend reached out with news about the Ruth Anderson Memorial 50-Mile Run in San Francisco. He said, "Bill, you've been wanting to do a 50-miler for ages. The ideal opportunity is tomorrow."

“I'd rather be doing these really PAINFUL and DIFFICULT things than be NUMBING myself with ALCOHOL .”

At that moment, my weekly running routine was limited to just three hours, which was hardly sufficient. To complicate matters, I was also dealing with a case of poison oak in a rather sensitive area. I was definitely not at my best. However, I felt an urgent need for a challenge. I reached out to my friend's father, a retired physician, who bluntly advised me that attempting to run 50 miles under such circumstances was a terrible idea. I went to bed feeling defeated, convinced that I wouldn't go through with it. But at 3 a.m., a spark ignited within me. I set my alarm for 5 a.m. and decided to tackle that 50-mile run as if my very existence depended on it. And in many ways, it did. Once I completed the run, I strolled down the street with renewed confidence, making eye contact with others once more. It was as if I had emerged victorious from a great struggle.

After the 50-mile race, I tried to run 100 miles at the Western States Endurance Run in the Sierra Nevada Mountains. It was 105 degrees, I didn't know how to deal with the heat, I got hyponatremia (an electrolyte imbalance that causes the level of sodium in your blood to become dangerously high), and I didn't finish. Two months later, I ran the Headlands 100k in Marin County, just north of San Francisco, which felt great. And once you get in with these ultrarunners, you start hearing about other races. My next race was 100 miles in Alaska, which took two attempts to complete, and I actually ended up finishing five hours after the cutoff. I rarely manage anything on the first try! But the more I challenged myself with bigger and harder events—like running the Badwater Basin in Death Valley at the height of summer—I began to notice just how much better I was feeling.

I've definitely evolved since then. I have a morning routine now. I'll start the day with a Wim Hof-style cold plunge, I'll meditate, do some visualizing. I have a vision wall of my goals, affirmations, and people that inspire me. It's pretty damn effective. If that kind of thing didn't work, advertisers wouldn't spend millions on billboards. I even travel with a rollout version that I'll tape up in my hotel room before a big race.

I confront all my greatest fears head-on. I've scaled Denali, despite having an intense fear of heights and falling. Ironically, that’s precisely why I embraced mountain climbing. I’ve tumbled into a 25-foot crevice and experienced frostbite so severe that my thumb turned black, requiring visits to three doctors before one finally assured me I could keep it. The thought of returning to those heights and facing those challenges terrifies me. Yet, I still push myself to do it.

I have attempted to swim across the English Channel five times. During my fifth try, a storm caused me to lose sight of the support boat. For my sixth attempt, I arrived in peak physical condition, but the weather was so terrible that I never even got the opportunity to start. That experience really took a toll on me, and I decided to step away from the challenge for eight years. Now, I'm back in training to take it on once more. For the past six months, I've been swimming in San Francisco Bay without a wetsuit and without any breaks. Just yesterday, I swam for an hour in water that was 52 degrees Fahrenheit—colder than I've ever experienced. I kept pushing through, reminding myself that what doesn’t kill you makes you stronger.

When the bankruptcy happened, my dad reached out to me every single night. Later on, I asked him, "What made you call so often?" He explained that he was concerned about my deep depression and wanted to ensure I was okay. I had maintained my sobriety for 15 years prior, and my loved ones were anxious about the possibility of me reverting to drinking. This worry pushed me to take drastic measures to rebuild my self-esteem: I'd choose to face these incredibly challenging and painful experiences rather than dull my feelings with alcohol.

That's the advice I would give to anyone who's encountered a major setback and is looking to regain their confidence. For me, it began with completing a 50-mile run, but it can be anything; it doesn’t necessarily have to be related to sports. If you're an actor, it's essential to jump back into auditions. You need to actively participate. It's when you're in the arena, facing challenges head-on, that you truly start to reconnect with who you are.