The Roots founder Questlove was easily accessible to the students of the 2023 Disney Dreamers Academy (DDA). The musician, author, and Oscar-winner knows all about chasing a dream that seems unattainable, depending on where you’re from. And he was on hand to ensure the graduating class didn’t adhere to any negative narrative of following one’s passion.ย
This year, DDA gave 100 high scholars students nationwide a life-changing and immersive career and leadership experience. Over a four-day period, the students participated in career sessions that taught valuable life tools, leadership skills, effective communication techniques, and networking strategies. Students also attended in-depth workshops within their specific dreams and disciplines offered in the fields of business, entertainment, and sciences, and even career opportunities within The Walt Disney Company.ย
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PopCulture.com was among many media outlets that attended DDA and were able to speak with Questlove on his journey and how it relates to the Dreamers. He also treated the Dreamers to a special dance party as the finale of the event.
Media question: What’s your advice to the Dreamers?
Questlove: In my time, the way I grew up, dreaming was treated like a four-letter word. It was silly or a waste of time, and you better get down to reality, to terrafirma, whatever your version of reality is. But we were raised by a generation that was raised by a generation that was raised by a generation to live in fight-or-flight and to live in survival. Hopefully, we can have that generational curse of not listening to our heart and always hustling and always scheming, trying to survive and struggle, and really just take time now for ourselves to really decide what it is we want to do. Oftentimes the decisions we make are made on survival thinking. What makes me the most money? That’ll make me happy. What gets me the most power? That’ll make me happy. All those things aren’t true.
And yeah, I used to laugh at people like me that are saying this now, like, “Listen to your heart,” and “Listen to your dreams,” or whatever, but I was forced to do that in the pandemic because everything was taken away from me. One day I woke up, and there was no more touring, no more records, I had 19 jobs, and then suddenly I had three, and I had nothing to do but sit and actually think, “What is it I want to do?” And one of the things I did, one of my biggest fears was writing a book of fiction. It’s easy for me to write about music education, biographies, and things that I know, but to actually not listen to the voice, that, “Ah, man, what do you think? You’re going to be the next Harry Potter? No one’s going to read this book.”
I’ve kicked my dreams to the curb, and suddenly doing Summer of Soul, doing this book, doing seven other things that I do now, I came out of the pandemic a better person. I think a lot of us, we were either going to pivot and make…The universe forced us to listen to our dreams, or unfortunately, some didn’t. But I’m one of those people that decided to be a living example of what happens when you dream.
Media question: The Roots have been around for 35 of those years. How can you tell our Dreamers at home how important it is to surround yourself with a group and how to identify the group that’s going to get you to the top?
Questlove: I treat it metaphorically in terms of basketball. Who’s your starting five? Oftentimes, I know that for myself, I always make sure that I’m the least knowledgeable person in my circle, so that way I can learn from the four people and then they teach me. Even though people think, “Oh, well, Questlove, use your brain, you’re smart.” That’s because I make sure that I surround myself. If I’m the alpha and I’m the person with all the answers, then it might be time to change squad and move on. Oftentimes, we’ll let the guilt set in. We often say, “Oh, I feel bad. I grew up with this person.” But sometimes you’ve got to know who serves you and who doesn’t serve you. Even now, I’m going through a transitional period in which I’m getting a new team, it’s kind of hard. Saying goodbye to the old team doesn’t mean you’re just totally done with them, but oftentimes you grow up and you can’t have fear, you can’t live life with other people’s expectations of what they think about you.
PC: The Roots picnic, the lineup this year is amazing. How has it been to be a part of and watch the festival’s growth year to year?
Questlove: My manager had to remind me that when we started the Roots Picnic in 2007, that it was only for 4,000 people. And I was like, “That’s impossible,” because I think that our guest list for each Roots Picnic in the last three years has been 4,000 people. It’s like, yeah, exactly. Now we’re doing 60,000.
The story of The Roots is us. The second we got our record deal, we exiled to live in Europe. We lived there for four years, and during that period, between ’94 and ’98, America really wasn’t big on festivals. There was an occasional Lollapalooza or Farm Aid or something like that but Coachella and all those things that we do now in America, that wasn’t a thing, so we moved over to Europe because they had over 700 festivals. Every day we were like, “Yo, how come we had to leave our home to survive and make a name for ourselves?” We just kept asking, “Well, why don’t we do this back at home?” Our main goal, more than going platinum or getting rich or whatever, was, “We’ve got to find somebody to do this for us back in the States.” It just turns out that we had to be the change that we wanted to see. I’m really proud of the fact that we have a three-day festival now serving the city of Philadelphia. We’re not charging these…
PC:ย Astronomical prices.
Questlove: Yeah. To maintain all that is almost a 24-hour all-year-round thing, but it’s our passion. That’s what we want to do.
