McKesson: I had done so much policy work as an organizer, and I’d done training for adults and young people. I wanted to do what now is called direct service. I wanted to actually do a concrete thing, and teaching was that for me.
Fadulu: Did you see the first episode of Insecure, when Issa Rae is in the school explaining the “We Got Y’all” program, and afterward the kids just start roasting her? Did you get roasted?
McKesson: I remember I wore this one shirt that I still have. This girl, who was great, first thing she says is: “Why you look like a picnic table?” They’re middle schoolers, so I, like everybody else, endured my fair share of roasting from them. “Why you wearing high waters?”
They wore uniforms. I didn’t. I was a broke teacher, so after a while, they knew my entire wardrobe. They're like, “Oh, you’re wearing that shirt again.” I’m like, “Yes, I am, because I don’t have 180 shirts. You’re going to see these pants again, too, and I will try to switch it up every week.” We were family, and that’s what family does.
Fadulu: How was your transition from being a student to being a teacher?
McKesson: Teaching is the hardest thing I’ve ever done. I was responsible for hiring teachers in Minneapolis and Baltimore, so I’ve now seen it from both sides. Every single day, as a teacher, you fail. Even on the best days, there’s that one kid who didn’t get it, and you tried really hard. What I found with some people who become teachers, especially from places like the Amhersts and Bowdoins of the world, is that you see people whose lives are just one string of successes. Then you become a teacher, and you’re like, this is just hard. There’s nothing about it that’s easy. It gets better. I got better. All my students did really well. I was so incredibly proud of them. They’re graduating from college right now, and I’m still proud of them. I worked really hard for that, and they worked really hard for that.
Fadulu: What was the hardest decision of your career?
McKesson: I was the senior director of human capital in Minneapolis. I made $110,000 in Minneapolis. I left during the protests. It was a leap of faith. I cleared out my retirement. I said, “I’m going to move to St. Louis, because I think it's the right thing to do,” and I quit.
That was really risky, because I didn’t necessarily have a safety net. My father raised us. My mother left when I was three. Nobody in my family is wealthy. I was just praying that, worst-case scenario, I find a good job somewhere, and I’ll figure it out. There was no guarantee that would happen.
Fadulu: Are you glad you made that decision?