Can you think of an example from your childhood when you remember thinking: This is how I'm supposed to act? What messages were you getting at home?

Well, in some ways I think we were lucky as kids because my dad was very present in our lives and even when my parents got divorced, we lived with my dad. We didn't live with my mother. And my dad, I think, presented a really balanced kind of masculinity to us that was very inclusive. He was an artist. He made some of his own clothes and was into fashion and creativity.

He also was a manufacturing worker who worked on assembly line, so he did kind of a stereotypically manly job in the day but at home he was really creative and expressive. And so I feel like we always felt like we had the permission to be artists. It was three boys and one girl that my dad raised, and we always felt like we had the permission to be confident in doing that kind of thing.

Get the think newsletter. This site is protected by recaptcha

But then, also you go to school and I feel like in school, particularly in high school, athletics was more valued. Particularly in Ohio, I think, because football is so huge there and basketball is pretty important, too. We all love sports, but I wasn't a very good athlete, so in the sense that athletics was so valued in high school, I wasn't valuable.

But I always found my voice through art, and found my way of expressing myself through art.

A young man with a plan. Seth Poppel / Yearbook Library

We hear a lot how to be a black man in America, and parents really worrying about their children and worrying about how they go out into the world. Was this something your parents worried about?

I grew up in a relatively safe neighborhood, but there was a lot of stuff happening that I wasn't even aware of. As I got a little older, I was less sheltered and I started to realize a lot of my friends were getting locked up. They were getting involved with selling drugs. I have several people that were close to me and my family that were locked up when we were young.

It became very clear to me in my later teen years and early twenties that I was very close to people who got caught up in the wrong life. These were people who became involved in the criminal justice system in ways that were really dangerous. It cost them their lives in some cases, and cost them their freedom in other cases.

And so even though I felt sheltered at the time, I quickly realized that I was pretty close to people that weren't so sheltered.

So you walked that line, but were on the other side of it?

Yeah. And I think my parents did a good job of making sure we didn't follow that path. But we weren't far from that path.

Do you feel like there were some challenges that, looking back, you could have avoided?

Well, my situation was unique because I was also really young. I started high school when I was 12 because I had skipped some grades when I was younger. And so part of me being the best person I could be had to do with overcoming that youthful shyness and social awkwardness that came with me being two years younger than everybody else.

When I went to college, I was definitely a fish out of water. I was from a small town in the Midwest. I went to a big city Ivy League school in Philadelphia. And so, it was like culture shock and also being younger and also not having a lot of money when the vast majority of kids at Penn did have money.

There's all kinds of things, all kinds of challenges going on that make you feel insecure and like you don't have your footing exactly yet. But I think music was always that place where I felt most confident. It opened doors for me to be more social as well and overcome my shyness.

John was his high school's class salutatorian in 1995. Seth Poppel / Yearbook Library

After graduating, when you got your first big break and started to climb the music charts, did you know that activism was going to be a big part of your role as a public figure?

You know, actually, I wrote an essay when I was 15 that almost eerily predicted exactly what I wanted to do with my life. Crazy enough, it was for a McDonald's Black History Month promotion. I wrote this essay and I won the local competition and they gave me a little scholarship and put my essay in the newspaper. And what I said was: "I plan to make black history by becoming a really successful musician and using my position as a musician to make change in my community, use my voice to bring about change and uplift my community."

So I literally wrote that when I was 15 and I'm truly manifesting it right now. But it was definitely not a completely easy path to get there. It took me six years of really trying pretty hard to get a record deal to get one. When I got one finally in 2004, it took me a little while to figure out my voice politically, in terms of how I wanted to communicate with the public and what issues I wanted to get involved in.

I did a lot of reading and thinking about what was going on in the world politically and just thinking about what I was passionate about and what areas I felt like I could make change in. I started to speak out more and more, and obviously I'm doing it a lot now. But it's something I always wanted to do, it just took me some time to learn exactly what I wanted to say and develop a platform where I could do it with impact and with some effectiveness.

People growing up now are growing up in a very different time than people who were growing up in the seventies and eighties. What advice would you give someone on how to navigate that very difficult journey from a boy to a man?

Well, I think part of it is to learn, to listen, to pay attention to other people and not only learn from books and from outside media, but also listen to your classmates. Listen to women. Listen to people who are different from you and develop a sense of empathy for the things that they're going through. I think we should all be humble and we should all listen to each other and learn from each other.

I don't say be fearless, because everybody has fears. I think it's an unnatural thing to tell someone to not ever be afraid. But I think it's important to work through your fears and overcome them by doing the things that make you afraid, doing the things that challenge you and push you and will eventually hopefully help you learn and grow.

This interview has been condensed and edited for clarity.