Dr. Darnell Leatherwood: Chasing Greatness So Others Can Live Their Best Lives
When Dr. Darnell Leatherwood talks about his purpose, he doesn’t hesitate:
“The purpose that God has put on my life is to help other people live their best lives.”
That one line says a lot about who he is — and how he leads.
On this episode of Village Talks with host Damien Howard, Dr. Leatherwood steps out from behind the titles — PhD, education scholar, board member of My Brother’s Keeper (MBK) Chicago — and walks us through the experiences that shaped him.
He connects his childhood in East St. Louis, his path through business school and the University of Chicago, his time in Englewood classrooms, and his current leadership with MBK Chicago into a clear throughline: use every bit of education, access, and power to serve others.
This is his story, and what it means for anyone trying to build something bigger than themselves.
From East St. Louis to the University of Chicago
Dr. Leatherwood spent the first 18 years of his life in East St. Louis — “the boogie,” as he calls it.
Those early years, he says, gave him the survival skills and grit that would carry him into completely new spaces later.
He became the first person in his family to go to college, enrolling at the University of Illinois at Urbana-Champaign. There, he majored in business management with concentrations in entrepreneurship and business process management.
Damien admits he’d forgotten that business background — and suddenly a lot made sense. The way Darnell thinks about strategy, resources, and building something that lasts was grounded in that early training.
After Illinois, he transitioned to the University of Chicago for a master’s in social sciences, then eventually a PhD in social policy and social welfare at the Crown Family School.
But the path was not a straight academic climb. Between his master’s and his doctoral work, he stepped away from campus and into Englewood.
How Two Years in Englewood Changed Everything
During his gap between degrees, Dr. Leatherwood taught in two schools in Chicago’s Englewood community — one elementary school and one high school.
He started as an assistant teacher in the elementary school, then moved into a community engagement role as the Community Action Council representative. Later, he became an algebra teacher at the high school.
Those two years, he says, “changed my life.”
Why?
Because theory met reality.
He wasn’t just reading about social policy; he was meeting students and families whose lives were shaped by those policies. He wasn’t just thinking about systems; he was confronting what those systems felt like at 8:00 a.m. on a weekday in a real classroom.
That experience grounded his scholarship. When he went back to the University of Chicago to pursue his PhD, he wasn’t just chasing another degree. He was thinking about the young people he’d taught in Englewood — and how his research could ultimately shift conditions for students like them.
Why He Never Wanted to “Do Education” — And Why He Does It Anyway
Ironically, for someone now recognized as an education scholar, Dr. Leatherwood resisted that label early on.
“I never, ever thought education was the only way for people to be successful,” he explains.
That belief is one reason he didn’t set out to study education as a field. He didn’t want to fall into the trap of treating school as the single path to a meaningful life, especially for Black communities that have been “disenfranchised and underserved historically in the United States.”
But something shifted during his time as a McNair Scholar at Illinois.
He initially joined the McNair program for a simple, honest reason: the stipend. As he puts it, “Back in college, we was like, $750 what? I’m doing McNair.”
Once inside the program, two things happened:
1. His undergraduate research advisor, Professor Bill Trent in the School of Education, exposed him to education as a serious topic of inquiry.
2. He met a graduate student named Olanipekun, a Black man pursuing a PhD.
Seeing someone who looked like him in a doctoral program flipped a switch.
“I was like, what’s a PhD? And when I saw that he was doing it as a Black man… I was like, oh, I could do a PhD too, then.”
Representation expanded his sense of what was possible. What started as a move for extra income became a doorway into a new vocation: using rigorous research to push for better outcomes, especially for Black students and families.
Freedom, “The Bag,” and the Real Goal
One of the most powerful parts of the conversation comes when Dr. Leatherwood talks about freedom.
His grandmother planted the first seed. When he was young, she told him:
“Baby, you’re not going to work a nine to five.”
He didn’t understand it then. For him, like for many of us, a 9–5 job seemed like the default option.
Looking back, he now believes she meant something deeper: that he was “going to be free.”
That idea was sharpened years later in a conversation on his back deck with an older sister figure. He remembers telling her how much he wanted to “get the bag.”
She stopped him.
“She said, you’re talking about getting the bag like, I’m getting the bag, but I want what you got.”
He was confused. She had resources, credentials, visible success. What could he possibly have that she didn’t?
Her answer stunned him:
“You are free. I got the bag, but I’m not free.”
People, she told him, often believe that making money will make them free. But she saw in him something they couldn’t buy — the ability to “do what you want when you get ready.”
That moment reframed his pursuit:
“The bag ain’t for me.”
For Dr. Leatherwood, wealth is not about personal escape. It’s about positioning himself to say yes in ways that change other people’s lives — paying off a mortgage, opening a door, funding a program.
He’s still clear about his own ambition. “I’m already called to be great,” he says. “I’m going to be great without anybody’s permission.”
But that greatness is tied directly to service.
Called to Help Others Live Their Best Lives
When Damien asks him what he is “searching for” — the way anime protagonists like Luffy, Naruto, or Goku are always chasing a higher goal — Darnell’s answer is simple:
“I want to do God’s will in my life.”
Pressed further on what he believes that looks like, he doesn’t hesitate:
“The purpose that God has put on my life is to help other people live their best lives.”
For him, that purpose has two parts:
1. Serve directly with his time, insight, and presence.
2. Build his own capacity — influence, decision-making power, and resources — so he can help at scale.
Right now, he gives what he calls whatever “God deposits in me” to the people who come to him. Questions about money, relationships, sex, life direction — he listens and responds from that well of lived experience and wisdom.
At the same time, he’s working intentionally to grow his authority and access, so he can eventually be the one who can say, “Yes, here you go,” and change a family’s reality with a decision or a check.
That is not about ego. It’s about stewardship.
Taking Radical Ownership of Your Life
Dr. Leatherwood is honest that his own life is not flawless.
“I’m divorced,” he says plainly. “That was not something I felt was honorable. I didn’t feel proud of that.”
But he refuses to stay in shame. He treats the pain as resistance — the same kind you meet under a barbell at the gym.
“Because I work out, resistance gives me an opportunity to get stronger, if I don’t overdo it.”
The key, he insists, is ownership.
“People be mad… complaining… ‘my life sucks,’” he says. Then he adds a line many of us try to avoid:
“You play a role in that.”
Our context, he argues, is “a byproduct of what you’re doing.” That doesn’t mean we control everything. It does mean that waiting for change without changing our own actions keeps us stuck.
His challenge is direct but hopeful: “You can do something about your situation if you just make up your mind to do something.”
Leading With and Through My Brother’s Keeper Chicago
Today, one of the key places Darnell lives out his calling is as a board member of My Brother’s Keeper Chicago, alongside Damien and other community leaders.
MBK began as a national initiative, but in Chicago it has become a local, collective effort to support boys and young men of color — and their families — with the relationships, opportunities, and resources they need.
What makes this board unique is the alignment of spirit.
Damien notes that many of the men around the MBK Chicago table share that same “Robin Hood” instinct he sees in fellow board member Kareem “Clo” Wells: using personal relationships and access to bring resources back to the community.
For Darnell, it’s another arena where he can connect his scholarship, his leadership, and his commitment to building power on behalf of others.
MBK Chicago is about collective impact — people coming together, “stronger together,” and then, as Damien puts it, putting “walk or actions” behind the talk.
Greatness, Anime, and the Pursuit of Something Bigger
There’s a playful but revealing thread in this conversation: anime.
When Damien asks for his favorite anime character, Darnell struggles to narrow it down. Instead, he names a “prototype.”
He’s drawn to characters like:
– Goku, who “just wants to be the strongest.”
– Naruto, who wants to be Hokage, the leader of his village.
– Luffy from One Piece, who wants to be king of the pirates.
What attracts him isn’t the powers. It’s the pursuit.
“They’re going for something,” he says. “They’re searching for something that nobody has obtained for a long time.”
That same energy lives in his own life.
“I want it all,” he says at one point. Then he adds the question he carries with him:
“Why not?”
Not why him. Not why dream that big. But why not use his gifts, his education, his access to the fullest — if the result is more people living free, whole, and well-supported lives?
Practical Takeaways for Your Own Journey
You don’t need a PhD or a board seat to apply what Dr. Leatherwood shared. Here are a few places to start:
1. Redefine the “bag.”
Instead of chasing money for its own sake, ask: how could more resources help me free others, not just myself?
2. Take ownership of your context.
Wherever you feel stuck, look honestly at the part you can change. What is one decision, habit, or relationship you can shift this month?
3. Seek (and be) visible examples.
Like seeing Olanipekun in a PhD program opened a new path for Darnell, your very presence in certain spaces can do the same for someone else. Look for people ahead of you — and notice who might be quietly watching you.
4. Use resistance as training.
When something hard shows up — a failure, a loss, a painful transition — treat it like weight in the gym. Ask: how can I come out of this stronger, not bitter?
5. Build capacity to say “yes.”
Think long term about how to grow your decision-making power and resources so that, when the time comes, you can change someone’s life with a conversation, a connection, or a check.
6. Plug into a village.
Darnell’s work with MBK Chicago is a reminder: community matters. Find or build a circle where your ambition and your service can both grow.
If you’re interested in how tools and communities are working together to expand access to mentoring and support for young people, you can learn more about how organizations are scaling mentoring at https://www.sel-plus.com/selvie.