Singer-songwriter Margaret Glaspy joins Zoë and Brendan to talk about the strange and surprisingly rich overlap between running and making art. She shares how watching her mom run planted the seed early, growing up close to the Western States course, how Courtney Dauwalter and Addie Bracy helped draw her into ultrarunning, and why learning to sit with discomfort has changed far more than her athletic life.

Margaret also talks about quitting social media, writing songs on a typewriter, finding solitude in anonymous hotel gyms, and the logistical challenge of training while touring in a van. Plus: the financial risks of falling on your guitar-playing hand, the unexpectedly deep musician-to-ultrarunner pipeline, and what Margaret might learn from how ICU nurses train for ultras.

Sam Robinson writes the Substack Footnotes, works as a content designer at YouTube, and has a PhD in seventeenth-century science, religion, and philosophy, which makes him exactly the right person to ask why we're all trying so hard to optimize a sport whose whole appeal is that it's beautifully pointless. Zoë and Brendan get into the tension with him: distance running rewards incremental gains and deferred gratification, and it's also the least efficient way imaginable to get from point A back to point A. Sam talks about racing above Stinson Beach with his head down, missing the view; about eating a protein bar in the shower at 4:58 a.m. to make a 7:30 meeting; and about how a three-year-old and a torn meniscus have both forced a slower relationship with the sport.

The back half turns to Sam's piece on the fragility of type two fun and the male friendship crisis, what happens to shoulder-to-shoulder friendships when the run club scatters and the knee gives out, and whether shared mileage alone can hold a community together. Along the way: Robert Caro, Oliver Burkeman, Benjamin Franklin prosecuting his breakfast, and the unsettling possibility that morning-routine influencers have never actually seen American Psycho.

Read Sam at footnotes.substack.com. This episode is brought to you by Running Warehouse - join our club here.

Heather Hansman is an award-winning outdoor journalist, an Outside columnist, and the author of Downriver and the bestselling Powder Days. Her new book, Fierce Country: The Untold Story of Three Women Who Ignited America's Love for the Wild, is out now.

In this conversation: the therapist who mapped the heroine's journey, and the very famous mythologist who told her women don't need one; Georgie White swimming Grand Canyon rapids in 1945 in tennis shoes and a couple of hard candies; why there always seems to be exactly one available spot at the top for a woman, and what that has to do with the way we talked about Rachel Entrekin winning Cocodona outright; topophilia, or what happens when the love of your life turns out to be a landscape; and whether the American myth of the lone tough guy summiting the mountain is, frankly, a pretty boring story.

This episode is brought to you by LMNT. Go to drinklmnt.com/UltraSignup for a free sample pack with any order.

Featured race: the Bear Canyon Trail Run in Sandy, Utah, on Saturday, October 10. Formerly the Corner Canyon Ultra, now with a new name and a new course. The 11 Mile Classic climbs over 4,000 feet in five miles, the 20 Mile Challenge runs that loop twice, and there's a 5K if you'd like to keep your quads. Every dollar raised goes to an individual or family facing serious hardship, nearly $70,000 to 13 recipients since 2013. Registration closes Wednesday, October 7. Sign up at UltraSignup.com.

The Trailhead is part of the UltraSignup Podcast Network.