Diana Proemm is a 54-year-old ski bum, adaptive sports professional, dual US-German citizen, and lifelong wanderer who has spent three decades saying yes to unlikely opportunities. (dianaproemm.com)

Diana describes leaving Ohio in the mid-1990s, bouncing between ski towns, remote lodges, and outdoor jobs, and building a life through curiosity, persistence, and conversations with strangers. From working in Alaska’s grizzly bear country to hitchhiking through Chile, volunteering on organic farms in New Zealand, and repeatedly selling nearly everything she owns, Diana’s story never really settles down.

Along the way, she became a certified recreation therapist and adaptive sports director, helping people with disabilities access the outdoors while slowly piecing together enough financial stability to keep chasing freedom. We discuss seasonal work, Workaway gigs, online income, living cheaply abroad, why she believes many women underestimate what they're capable of, and the social dynamics of working with wealthy clients at the Yellowstone Club.

Now living in the Austrian Alps, Diana reflects on getting laid off, starting over in a new country, and maintaining faith that the next opportunity will appear when she needs it. At an age when many people are planning retirement, Diana doesn't know where she'll be next year—but that's never stopped her before.