It was supposed to be Questlove’s night. He was DJ’ing for one of the most powerful men in the world, at one of the most famous homes in the world, the White House. He had been imagining this moment for a decade, working on a set that spanned from the 1930s to today, with lots of classy jazz.
And then he got a tap on the shoulder.
“I’m feeling like I’m gonna get a MacArthur genius grant for this set,” Questlove told attendees at The Fast Company Innovation Festival. He didn’t confirm that it was President Barack Obama, due to a non-disclosure agreement, but he gave some pretty hefty clues (and an Obama-esque accent). “‘The host’ taps me on the shoulder, and he says, ‘You’re doing a great job.’ But then the host points to his kids, and they’re not having it,” said Questlove. “These kids want me to go ratchet.”
So he was forced to change his set in the moment and play more popular hip-hop songs. “It broke my spirit,” he said, laughing in the way someone does when they’re kind of joking but mostly not.
For Questlove, the story is now a lesson in managing expectations and dealing with spur-of-the-moment changes that force you to adapt or flail. It’s something that the cofounder of The Roots, which has a longstanding improv-based gig on The Tonight Show with Jimmy Fallon, comes up against often. As do the creative directors of streetwear fashion brand Kenzo–Humberto Leon and Carol Lim–who joined Questlove on stage.
Though Leon and Lim (who also founded the brand Opening Ceremony) come from a different industry than Questlove, all three discussed a shared proclivity for ending up in unexpected situations, and using those experiences to subvert expectations.
“People pigeonhole you,” Leon said. “They try to put you in a bracket of what they think you’re good at.” When Leon and Lim got into fashion, they considered themselves underdogs because they didn’t have the same formal fashion-trade training and experience as their peers.
But they’ve learned to use their different perspectives to their advantage as a problem-solving tool. “When you have formal training, it can be walls you can’t break down,” Leon said. “We were like, Let’s challenge that.”
Questlove’s experience is the opposite: He’s a classically trained musician who has chosen to take a gig in late-night, in the background, rather than headlining Madison Square Garden.
“Kanye would be on stage, and I would always wonder if our peers looked down on us,” Questlove said. “But then I realized that with my pop-culture curiosity, I’m perfect for this job. Recently, me, Lin-Manuel Miranda, and Jimmy got lost in a rabbit hole of Weird Al Yankovic polka songs. We’re like three adult nerds.”