The same day I handed in my master’s thesis in electrical engineering at MIT in 2004, I left Boston for Santa Cruz. By August I had a job in Silicon Valley developing flash memory for computers. It was straight out of Office Space: I worked in the basement, and I hated it. Three months later, my father had a stroke. When I was with him in the hospital, I asked myself, Is this really what I want to do with my life? I never went back to that job. I took out a loan and in early 2005 founded ϳԹ Out to teach what I really love: surfing, climbing, and wilderness survival. I lived in my childhood bedroom for that first year, drove all over California, and taught 250 people by myself. Last year my 20 employees and I had more than 4,000 students, and about a third of them were groups from corporations and schools. The work ethic I learned at MIT is actually a large part of why we’re successful—I still put in 12-hour days, but what I do doesn’t feel like work.
HOW YOU CAN DO IT: Get training from an established program like NOLS (look into the outdoor-educator courses listed at nols.edu), then scout out an ideal location for your base of operations. You want to be next to public lands that you know intimately—and that have permits available for guiding services (quotas often fill quickly). Approximate income range: $20,000–$150,000 a year.