How to Run 100 Miles: A Film About Persistence

Just over a year ago today, I signed up for my first 100-mile ultramarathon with a guy I’ve been friends with for 18 years, my old pal Jayson Sime. If things went well, we would, in the span of exactly two years, go from not ever running an ultramarathon distance to completing the 102.9-mile Run Rabbit Run 100 in Steamboat Springs, Colorado. If things went well, anyway.

I’ve known Jayson’s story for almost as long as I’ve known him—he grew up one of six kids raised by a single mother, battled dyslexia, got bullied in school, learned to fight literally and metaphorically, and worked his way to a successful career as a political organizer and later, a motivational speaker and coach. For years, he’s been in my ear with career and life advice, telling me to fake it till I make it and not be afraid to bite off more than I can chew (or be afraid and do it anyway).

I figured a 100-mile ultramarathon would be the perfect metaphor to tell the story of Jayson’s life, as well as provide an opportunity to explain ultrarunning through the eyes of two people who aren’t exactly natural runners. Things went sort of according to plan for part of the race, and then—well, you can watch the film if you want to see how it went for us. I hope it makes you want to dream up something big, lace up your running shoes, call a close friend, or all of the above.

A big thanks to the folks at REI for getting behind this story and making the whole thing possible, and to the team that put in the long hours to make it: Hilary Oliver, Aidan Haley, Ian McLeod, Matt Sedivy, Peter Mulcahy, Forest Woodward, Eric Bucy, Brody Leven, and Bodie Johnson. To find out more about Jayson’s story, check out his website at