Emily Pennington is a 37-year-old freelance writer, former Hollywood assistant, and full-time outdoor nerd who once lived in a minivan for a year to visit every U.S. national park. (@brazenbackpacker)

In her 20s, Emily bounced between creative careers—first as an actress, then as a circus performer, then as a film producer’s assistant. The job paid okay, but the work felt meaningless, and after losing several friends to sudden deaths, she started questioning the whole plan. She cut her expenses, saved aggressively, and quit in 2020 to hit the road full-time.

That trip, which started as an attempt to reboot her life, turned into a book (Feral) and a new career as a freelance adventure writer. But the realities of making a living as a writer are far from glamorous. Emily breaks down exactly how much she made from her Outside Magazine column and book advance, how she cobbles together an income from travel writing and gear reviews, and why she still occasionally wonders if the whole industry will collapse. Emily also discussed the burnout of monetizing your passions, the constant anxiety of freelance work, and how she preserves time for hikes that aren’t “content.”

Now based in Boulder, Colorado, she’s finally settled into a routine that gives her the freedom she was looking for—working Monday to Thursday, keeping her weekends sacred, and skiing in the middle of the week whenever she wants. And because she can’t stop picking up new creative projects, she’s also fronting a folk-punk band called Trouble's Braids.

Full transcript: dirtbagrich.com/emily