Seven years ago, four Canadian students scribbled down 100 things to do before they died. “Everyone makes this list,” says Duncan Penn. “We committed.” Duncan and his brother Jonnie embarked on a road trip with buddies Dave Lingwood and Ben Nemtin. The itinerary? Make entries reality—and with each success, help a stranger live a bucket list dream. That led to an MTV show, The Buried Life, a No. 1 New York Times bestseller, and beers with Prince Harry. Here’s how the foursome does it.
Turn dreams into projects. “Dreams feel out of reach,” says Duncan. “Projects have logical, actionable steps. Cross them off until you accomplish the larger goal.”
Work the phones. “I called a ton of ranches and asked to ride a bull (#8),” says Dave. “Everyone said no because I’d never even ridden a horse.” Finally, a pro rider invited him to Idaho, where Dave rode a 1,200-pound bull for five and half seconds.
Chuck your ego. An escape from a deserted island (#88) brought clarity. “We lived off coconuts and made fire from scratch,” says Duncan. “And we learned to care less about our own opinions and work together to solve problems.”
Get uncomfortable. Duncan feared humiliation when he started a dance in a public place (#4). But New Yorkers in Times Square ignored him. “People didn’t even look up from their phones,” he says. “You have to risk embarrassment to push yourself.”
Use creative persistence. Dave gets inspiration from fans. “One couldn’t get a job interview, so she snuck into a conference room and left a shoe with a note: ‘Now that I’ve got my foot in the door, here’s my resume.’ She got the job.”
Pack costumes. The first road trip included a suit of armor to become a knight for a day (#43). They still pack outlandish duds—because Oompa Loompas have better luck crashing the Playboy Mansion (#6) than regular Joes.
Forget second chances. “The poem that inspired our name talks about how day-to-day life buries you,” says Dave. “So many people simply don’t have the freedom to dream. If it’s possible, do it.”
Pay it forward. They raise money for charity and gave a teenaged girl a prosthetic arm. “Helping someone is the greatest feeling,” says Dave. “That will stick with me the longest.”
Duncan, Jonnie, Dave and Ben are all ambassadors for First Descents.