Jack Schott is a 36-year-old summer camp consultant, former camp founder, and self-directed learning advocate who spends a lot of time thinking about money. (jackschott.com)

Jack occasionally earns $1,500-$3,500 in a single day by running corporate trainings and camp staff workshops: work that doesn’t always light him up, but work that is very useful for buying time, freedom, and very possibly, another summer camp that he can direct.

Jack describes the tension he feels between wanting to do meaningful work and not wanting to be tied down. At his most purposeful, he was co-running a camp in upstate New York with his ex, building cabins by hand and forming deep relationships with kids and staff—but he felt trapped. Now he’s trying to design a setup where he can direct a camp each summer without needing to live on site year-round.

He also shares how he thinks about money strategically: not just for personal comfort, but as a tool for long-term impact, particularly in making camps more self-directed and less top-down. In this vein, he describes how an average 22-year-old could quickly build a high-flexibility career from scratch by cold-emailing lawn care companies (or a similarly "boring," everyday field of work).

Jack is less focused on outdoor adventure than past guests, but he’s laser-focused on building a life of flexible work and purposeful contribution. His version of "dirtbag" is getting to play outside with kids, every single summer, for the rest of his life.

Full transcript: dirtbagrich.com/jack