Brian Whitmore

In 1997, at the age of 27, Matt Damon won his first Academy Award for Best Screenplay (“Good Will Hunting”). After Damon won the Oscar, he went home, sat down on his sofa, and looked at the award. As he looked at it, he was suddenly overwhelmed by a heartbreaking thought: “I remember very clearly looking at that award and thinking, ‘Imagine chasing that, not getting it, and then getting it finally in your 80s or your 90s with all of life behind you and realizing what an unbelievable waste of your life.’ It can't fill you up. If that's a hole that you have, that won't fill it.” “My heart broke,” Damon said. “I imagined another one of me [not getting that award until I was] an old man, and going like, ‘oh my god, Where did my life go? What have I done?’ And then it's over.” Takeaway 1: Many rich and celebrated people talk about chasing money and recognition, getting it, and realizing that it didn't feel like they thought it would. That it didn't, as Damon said, fill the hole they had. One of my favorite analogies for this pattern comes from Sam Hinkie. Hinkie was asked about what he's learned from reading Robert Caro's books—about some very rich and famous people. “I think of it like the Pacific Salmon,” Hinkie said. “They spend their whole life making this journey upstream to spawn in this one spot. And as soon as they do, they die. That's largely what Caro shows you.” The outcome is always a tiny percentage of the total experience. Matt Damon stood on that Oscars stage for eighty-one seconds. That’s 0.0000641% of the four years he spent working on Good Will Hunting. To let 0.0000641% of an experience determine one’s happiness or satisfaction, as Damon said, is an unbelievable waste of your life. Takeaway 2: If not things like money, awards, and celebrity, what should we strive for? “When we were writing 'Good Will Hunting,'” Matt Damon said, “Ben [Affleck] and I always talked about just wanting to love it. We would say, 'If it's just a tape on our mantel that no one ever watches, we want to love it.' We kind of stumbled into a very wise strategy, which is to try to get most of the rewards from the work itself.” Since you control the process, the effort, the work more than the outcome, Ryan Holiday once told me, “The work has to be the win. Ultimately, you have to love doing it. You have to get to a place where doing the work is the win and everything else is extra.” - - - “It's such a gift to be able to do something and to love it for the sake of it.” — Rodney Mullen Follow @bpoppenheimer for more content like this!