Questlove Says He No Longer Feels Pressure to 'Take Every Job' After Living 'Check to Check' as a Kid (Exclusive)

The multitalented Roots drummer opens up to PEOPLE in this week's issue about the highs and lows on his journey to the top

It'd be easy to assume Questlove has never been busier.

Between prep for his Roots Picnic music festival in June, his day job at The Tonight Show (his group the Roots are the house band), running his publishing company AUWA (he's set to release his first novel for kids, The Rhythm of Time, through Putnam, an imprint of Penguin Young Readers, on April 18) and his multiple movie projects, he certainly has his hands full these days. But this is the multitalented musician's workload scaled-back.

Between 2015 and 2017, he estimates, he had about 19 different jobs, including music professor at New York University. "It made great fodder for press," he tells PEOPLE with a laugh.

With girlfriends, though? Not so much.

"They'd say, 'If you accept this position at NYU, we're not going to have a relationship,'" he recalls. "I thought — because I lived in fight-or-flight as a kid, living week to week, check to check — I had to take every job that came down the pike."

Related:Questlove Announces Children's Book Debut with Middle-Grade Time Travel Novel 'Rhythm of Time'

It wasn't until the pandemic that Questlove found a new perspective.

"The universe told me to stop and listen to what's in my heart. If it makes you excited, that's what you go for," he says of his mindset now.

During lockdown he wrote The Rhythm of Time and also completed his directorial debut, Summer of Soul, a documentary about the 1969 Harlem Cultural Festival that he calls a celebration of "Black joy." The film won him the Best Documentary Oscar in 2022, taking him from "hiding in plain sight," he says, to a new level of visibility.

"Playing the shy, Clark Kent-meek role, that's not serving anybody," he adds. "I saw the happiness that Summer of Soul brought to people, and I know that I have a mission. I have to be the change I want to see."

Says his longtime friend and collaborator John Mayer: "[Questlove] has become more than a musician. He's a teacher and a historian for a new generation."

Born Ahmir Thompson to musicians Arthur Lee Andrews and Jacquelin Thompson, the Philadelphia native got his first taste for the stage while on tour with his parents.

"They did not believe in babysitters — babysitters weren't popular until the '80s," he says. "I had to go to work with them when they would play in nightclubs from 8 p.m. till 2 a.m. On top of that, they wanted to keep an eye on me, so they'd have me get onstage and play the tambourine and cowbell as a 6-year-old."

When he was 12, he got to play Radio City Music Hall with his dad's band after their drummer broke his arm in a motorcycle accident.

"They took me to Macy's, got me a suit jacket, and I was my dad's band leader drumming for the show," he says. "All he had to do was pay me in $150 and some records, and I was happy."

After graduating high school, Questlove formed the Roots with his classmate Tariq Trotter (now Black Thought). They released their first album, Organix, in 1993, but it wasn't until six years later that they found mainstream success with their Erykah Badu collaboration, "You Got Me."

Landing their job on Late Night With Jimmy Fallon in 2009 brought stability and a larger audience.

"That was our first real break," Questlove says.

Since then the Roots — who have included 20-plus different members over the years — have remained by Fallon's side even as he moved from Late Night to The Tonight Show in 2014.

"From high school until the month before Late Night, we were living on the road for 250 days out of the year," Questlove says. "We were together too much, and at the time, my manager's entire solution was two tour buses. We would joke that there was the Gryffindor and Slytherin tour bus. That's how we lived our lives, which, yes, it gave peace to the group, but we only saw each other during showtime. Fallon allowed us to slow down and be adults for the first time in our lives."

Related:Questlove Makes His Directorial Debut with Summer of Soul: 'This Was My Chance to Restore History'

The band went to therapy together: "a real thing, not just for Metallica," he jokes. "As Tariq and I grew as human beings, suddenly the shows became fun again."

When the pandemic shut down in-studio production on The Tonight Show, he worked remotely from a friend's farm in upstate New York and found new creative energy.

"It was my chance to become an 8-year-old again," he says. "I got to dream and fantasize and play without the stress of 'Am I going to make it?'"

He was inspired to start writing The Rhythm of Time, about a seventh-grade rap fan whisked back to 1990s Philadelphia.

"I always fantasized about writing the book that I wished I read as a kid — a time-travel book about a music geek. But because I didn't know enough scientific jargon, I always dismissed it," he says.

Related:Questlove Says He Found the Woman Who Started His Record Collection at 5: 'She Planted the Seed'

As Summer of Soul began sweeping awards on the festival circuit last year, he had a hard time adjusting to all the attention.

"I would think, 'Oh man, everyone hates me now,'" Questlove recalls. "They were excited in the beginning, now it's like, 'He's here, you know he's taking it.' I, again, starting thinking, 'This is why I don't deserve this.'"

Then, at the Oscars, his big moment was unexpectedly surreal: He won right after Will Smith slapped Chris Rock onstage.

"I didn't even realize what was going on until maybe 90 seconds in," he says. "When you're nominated for an award, you're not in your right mind. It took me maybe two months to really get what happened."

Though he used to keep his awards (he also has six Grammys) in his bathroom — a move he describes as a "performative humble act" — Questlove sees things differently now: "I've really had to face myself and say, 'You won this Oscar. Now what are you going to do with your life? Are you going to crawl in a corner, or are you going to stand up to the challenge?'"

Whether he's tackling addiction in his upcoming documentary about singer Sly Stone or class differences in a planned live-action remake of Disney's Aristocats, Questlove wants every project he takes on now to have a "teachable lesson."

Surprising perhaps even himself, the entertainer says he's also envisioning taking a real break. But that day, he notes, likely won't come until 2027, after the completion of those two films as well as four others.

"Then I'll be satisfied," he says. "I definitely want to slow down and just enjoy life, find love, start a family, all those things. But for now I've come too far to drop the ball."

For more on Questlove's journey, pick up the latest issue of PEOPLE, on newsstands everywhere Friday.

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