Scott Stillman is a 53-year-old writer, backpacker, and desert wanderer who built his life around walking canyon country instead of working full-time. He’s the author of I Don't Want to Grow Up and seven other books. (scottstillmanblog.com)

Scott traces his evolution from skateboarding teenager to normie bank employee in Ohio to full-time freedom seeker in Colorado. Along the way, he explains why he’s always prioritized time over money, how he and his wife built a life around working as little as possible, and why most people are asking the wrong question when it comes to careers.

We get into the specific ways he pulled this off, from compressing an insurance sales job into two days a week to negotiating a car sales role down to weekends only. Now living in Durango, Scott earns a living from his books—spending about two hours a day on social media—and spends the rest of his time hiking, backpacking, and disappearing into canyon country. He also explains how writing accidentally became his path to freedom, the role a good editor plays, and why he ditched photography to start documenting his experiences with words.

We also get into the philosophy behind his work: why “this reeks of privilege” is the most common critique he hears from young people on TikTok, why he thinks that’s missing the point, how starting with a beat-up car and a few hundred dollars can still lead to a life outdoors, and why you don’t need to have your whole life figured out—you just need to go.

Full transcript: dirtbagrich.com/scott