Questlove thought he'd flopped as the White House DJ. Just then, Obama tapped his shoulder

We are often our own harshest critics, replaying what didn’t work and holding onto the parts that didn’t go as planned. Even when things turn out fine, it can be hard to shake the feeling that we could have done better. That disconnect between self-doubt and outside perspective is what Questlove described from a 2016 White House event, where President Barack Obama stepped in with a reminder that adapting is not the same as falling short. In a video shared by @masterclass about a month ago, he looks back at the night and the brief exchange with President Barack Obama that still resonates with him.

"January 2016, I'm at the White House. The one thing that has never happened in my career happened," Questlove said. He had spent 16 weeks preparing what he considered a thoughtful mix of old-school hip hop, jazz, and deep cuts that reflected who he was as a DJ. About two hours into the set, though, he noticed that the younger guests were sitting down rather than dancing, and the energy in the room did not match what he had imagined. Then he felt someone tapping his shoulder. "I'm like, yo, yo, get away, stop," he recalled, assuming someone had wandered too close to the booth. When he turned around, it was Obama.

"He's like, 'Hey, you're doing a good job. I like the old school hip hop and the jazz. Great, great. But you know, they want to have fun too.'" Questlove said Obama gestured toward his daughters, who were sitting and clearly not connecting with the carefully curated selections, and changed gears. "I became the DJ I hate the most," he admitted. Despite knowing that phones and Wi-Fi access are tightly controlled inside the White House, he reached for his streaming device. He searched for songs that would resonate more with the younger crowd. At one point, he said Obama approached again and asked, "Do you have French Montana?" "I'm like, 'Sir, I don't have the clean versions of that,'" Questlove said. Obama replied, "We're all adults here. Play it." 

As the playlist changed, so did the room. "Suddenly those 1,000 people turned into 5,000 people," Questlove said, but internally, he was spiraling. "In my mind, I'm like, wait a minute. Was I that bad that 4,000 people were just sitting in another room like, well, eventually he's going to play something I want to hear?" Live performance often requires that kind of adjustment. This is something psychologists call the "spotlight effect," a cognitive bias that leads people to overestimate how much others notice their mistakes or awkward moments. In classic laboratory studies where people wore an embarrassing shirt into a room full of strangers, participants believed 50–70% of others would notice it, when in reality only about 20–25% did. 

Questlove has spoken about that same night before, including during an appearance on The Tonight Show Starring Jimmy Fallon, where he said the experience affected him enough that he stepped away from DJing for about six months. At the time, he interpreted the pivot as failure rather than flexibility. After the set, Obama took the microphone and asked the room to applaud. Then he pulled Questlove aside again. "He grabs me by the shoulder. He said, 'You have fun?' I said, yeah, it's cool," Questlove recalled.

Obama continued, "You're one of those artist types that had this plan in your head that you were going to wow us with your intellect and the colors you paint in music. You figured out that it wasn't quite working for the people, and what you wound up doing was you wound up serving the people. And there's nothing wrong with that. You used your music and your talent and your resources to figure out how to fix a problem, and that's what's important." When Obama asked once more, "So, do you feel better?" Questlove said the honest answer, at least in that moment, was still no.

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