As Me with Sinéad — 13: DeRay Mckesson

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Author, educator, and activist DeRay Mckesson sits down with Sinéad to talk about what teaching taught him about activism, how being an uncle keeps him in touch with his roots, and the computer game that shaped his creativity and organization.

As Me with DeRay Mckesson transcript

[01:12] Sinéad Burke: Welcome to As Me with Sinéad. This week’s episode of the show was with the extraordinary DeRay Mckesson. Without him and without his podcast, this one may not exist. It’s poignant that this episode is airing around Christmastime because it was two years ago that I did an interview at Christmas time for Pod Save the People. It was on the phone. I’d been such an admirer of DeRay’s work that it really was a privilege to speak with him. I can’t really remember anything I said on that call. I was incredibly nervous, but it was just such a joy to learn from him. Little did I know that the person listening to that show, and also his producer, Jessica Cordova Kramer, two years later would found Lemonada Media with Stephanie Wittels Wachs. And in February this year offer me the opportunity of a lifetime to host this show, As Me with Sinéad. So thanks, DeRay. If you don’t know DeRay, he is an activist, an author, an uncle, a friend, an educator, an organizer. And in this episode, we talked a lot about teaching.


[02:15] DeRay Mckesson: Teaching was also the only thing where the effort doesn’t change the outcome. So everything else before teaching, if I stayed up working on that paper, the paper is better. If I crammed for the test, did better on the test. Teaching is like — you can stay up all night and you’ll give some of the worst lessons — like, the effort wasn’t it. So I really had to figure out how to be smarter about planning, and teaching helped me figure out how to calibrate my energy to actually change the outcome and not just like pour in with the idea that more is always better. Teaching taught me that more is sometimes just more. 


[02:42] Sinéad Burke: I couldn’t imagine ending the year without airing this lovely conversation between me and DeRay. He has taught me so much about advocacy, and whether advocacy must always be physical, or can they be more accessible ways to demonstrate one’s advocacy and to be an advocate. And how can you be part of a system without being conditioned by it? On my mind this week is taking time to look forward to 2020. What is it going to hold for us? Whether it’s an election in the U.S., whether it’s the ongoing challenges we face in creating policies to ensure that climate change is not as overwhelming as everybody’s predicting it is. If you’re on my side of the pond, looking at the implications of Brexit and what that might mean for the north of Ireland and the island of Ireland. And it can seem overwhelming. So what I’m thinking about this week is how do we mind ourselves within tumultuous times? What are the strategies we need going forward to, well, do the work? Are you ready for this week’s episode? Let’s go!


[03:47] Sinéad Burke: Welcome to As Me with Sinéad. This afternoon we are joined by the extraordinary DeRay Mckesson, who is known for all sorts — his blue vest, his advocacy, his organizing, his book, his podcast Pod Save the People. But today we are going to have a different kind of conversation. Welcome, DeRay. Thank you so much. 


[04:08] DeRay Mckesson: So good to be here. 


[04:10] Sinéad Burke: I suppose I have known of your work — and have genuinely been inspired by your courage and you’re willing to be vulnerable in such public spaces. And I have learned a lot from that. And I think in moments when I was unsure if I should step forward, and despite all of the privilege that I have, I really took great motivation and confidence in what you do. And I’m conscious that people know you for lots of different reasons, whether it is your book, your advocacy, whatever it is, Pod Save the People — how do you describe yourself? How do you define yourself? 


[04:43] DeRay Mckesson: I think of myself as an activist now, an organizer now. I used to lead with being a teacher. Teaching was one of the hardest and coolest and most exciting things I’ve ever done. So all my work in education has been and continues to be really important to me. Today I spend more of my time around issues of mass incarceration and policing, so I think of myself primarily as an activist and organizer in the work. And then the other ways I think of myself as like a brother, I’m a son, a good friend.


[05:12] Sinéad Burke: What are the qualities you are most proud of that you have or that you’ve honed? 


[05:17] DeRay Mckesson: If there’s anything I’m most proud of is like my sense of imagination and wonder. I think that like in the hardest moments, I haven’t lost the ability to dream. Sometimes the dreams get really big and weighty and that becomes hard. Like, the enormity of what I think is possible versus what is here today. But I’m proud of that. And I also I think over the years, I’ve gotten much better at showing up. What does it mean to be present, and what does it mean to be fully present and not need reciprocation, but just to be there? 


[05:44] Sinéad Burke: Both of those — imagination and being present and showing up — for me, I don’t think they’re quite natural characteristics. They have to be honed and defined. Or perhaps they came from your own environment growing up. Are you conscious of like when you were younger building on that or somebody commenting on that?


[06:01] DeRay Mckesson: I think that cartoons had something to do with imagination. I just saw so many worlds that like didn’t exist, but they were cool. In SimCity I remember building a city. And that was, like, oh, I can build a neighborhood. That sort of wonder. And that was sort of the beauty of the early Internet, you know, or early days of video games or Saturday morning cartoons. I think that’s where it came from. Then I was in student government from sixth grade to senior in college. And it was in student government that I saw like the ability to, like, plan and do the most for — you know, whether it was a pep rally or policy things, like, we just got to do such big things and it’s like, oh, the world can be like this. That has stayed with me and led me for so much. 


[06:38] DeRay Mckesson: And being present, I think, you know, especially growing up, I was in so many rooms where I saw what it was like when people weren’t present. I was like, I don’t wanna be that guy. You know, I saw what it was like when people only really cared about you because they wanted something from you. They didn’t really want to get to know you. And I’ve just been so blessed to be in so many rooms with so many incredible people. And like, I just want to know, right, I want to know what makes you tick. I want to know like how you express frustration. What joy looks like for you. Do you cry? Like all these things I just want to understand better. And understanding you better helps me understand the world better.

[07:08] Sinéad Burke: I want to go back to where you were talking about The Sims, because I think that’s one of the many things you and I probably share — 


[07:13] DeRay Mckesson: SimCity. The Sims, too, but the Sims cam sort of way after some SimCity. 


[07:18] Sinéad Burke: Ok, so tell me about SimCity. 


[07:20] DeRay Mckesson: Do you remember SimCity? 


[07:21] Sinéad Burke: No. 


[07:22] DeRay Mckesson: Where you build a city? 


[07:23] Sinéad Burke: No, I remember The Sims quite tangibly. 


[07:25] DeRay Mckesson: So The Sims was like, you built a house, right? SimCity was like you literally build a city. And then they would let us zoom in to a house. But it started with where is the police department going to go, the fire department gonna go, where are the roads gonna go? How are you gonna — like, it literally was there is this blank land and you built a city. 


[07:43] Sinéad Burke: So what did yours look like? 


[07:44] DeRay Mckesson: Oh, well they looked like a whole — because you could build the city in the future. They were like all these types. Just like in The Sims you can, like, build a million types of houses. You can build a million types of cities. So it was great and incredible. And then The Sims came, which was also — I mean, it seems now like Sims 5 million expansion packs. So that is it. But it’s still that idea of you get to build it, like make a world, you know, and like,


[08:06] Sinéad Burke: But what did your world look like? Do you have any memories of like — or was it just — 


[08:10] DeRay Mckesson: No, because it was like you could — you just needed like the city not to crash and burn. Like that was sort of the goal. Like you could design it so poorly that like nothing could work. But The Sims was also really cool, too. Do you remember when — I mean, I haven’t played The Sims in so long, but I remember like making your Sim go to work. Then they come back. Now it’s like they get married, have kids. That wasn’t in the — I don’t remember that from the first Sims. 


[08:29] Sinéad Burke: And there’s this terminology called woo woo now involved in The Sims. Yeah, you should look that up. 


[08:37] DeRay Mckesson: Clearly I’m an older Sims player. What’s the woowoo? Yeah. So it’s just beautiful. Like I remember just the play of that. As a kid to be like, oh, I just like made a family. I’m like waking up. I’m like, I’m gonna put them to sleep. And like turning the game off. 


[08:50] Sinéad Burke: All of these social norms that we were conditioned to conform to without even realizing. 


[08:55] DeRay Mckesson: And like the make believe of it. You’re like, you were God for a little bit. 


[08:58] Sinéad Burke: But nobody was self-employed. Nobody was self-employed. 


[09:02] DeRay Mckesson: Until you had the cheat codes, and then you could afford all the food. 


[09:04] Sinéad Burke: I didn’t have the cheat codes. I was very naive. 


[09:08] DeRay Mckesson: Were you even playing The Sims? You can’t play The Sims without the cheat codes. 


[09:10] Sinéad Burke: I’m the eldest of five. I have three sisters and one brother. And we didn’t get the Internet until, gosh, I was probably nine, 10, 11, maybe. I know. Archaic times. And we used to have this router in my house when we had dial up that you were only allowed like, say, 30 minutes of time because there were so many of us. But your sibling would be standing next to you waiting for a their time. There was a sign in/sign out sheet. And you were like so much time. 


[09:33] DeRay Mckesson: Your parents had to have been organized.


[09:34] Sinéad Burke: They are organized as individuals. But I remember kind of thinking then, you know, I would love to know through The Sims — there was this lens through which you could understand who other people were feeling. Or if your Sim was feeling sad or hurt, there was an understanding as to why that is. 


[09:50] DeRay Mckesson: And it was like the planning — do you remember if had a couple of people in a house, it was like, OK, if they go to work at this time, and this person was at work at this time, I have to fix these other things up at the house. You know, it’s like all that just coordination that was just so, in hindsight, incredible, you know. 


[10:04] Sinéad Burke: But you use the word organizing there. And that term of being an organizer, or being involved in organizing, is still quite new to me. How do you define that? Like what does that mean to you? 


[10:14] DeRay Mckesson: So there is a set of things that we believe to be true when it comes to organizing. Some of it is the stuff that everybody thinks about, which is like taking action, building relationships with people, those sort of things. I think the thing that defines the difference between like people organizing people or activists is this idea of like, are you building power or not? Not that being an activist or an organizer is better than another, but activists take action. That is what they do. That is like their skill. They, like, push. They take action. They move. Organizers do that and they help build power. They say, like, you know what, we’re trying to build the skills of the people around us, and the capacity of people around us, so it’s not just me doing really good work, but it’s all of us. With the idea that the more and more that we build power and share power, the stronger all of us will be. 


[10:57] Sinéad Burke: And has that dissonance between the two of those entities always been very clear to you, or were you kind of almost flirting with one and the other, or were you always considering yourself within organizing? 


[11:07] DeRay Mckesson: I don’t know if we’re ever always just one of them, you know. So I think that there were moments or like I was an activist, like that’s how I show up. I’m like, you are organizing your community, I’m really just here pushing. Right. And that’s cool. Like I’m in a place like, that’s my goal. And there are other places where, like, I’m organizing really deeply. One of the things that we say about young people often is that young people have the experiences before they have the language. I think I had the experiences before I had the language. I was like living in both worlds, not understanding what the difference was between the two.


[11:32] Sinéad Burke: And was that experience directly from being involved in student government? 


[11:36] DeRay Mckesson: Oh, no. This is recent. This is like in the past five years. You know, because people use the terms and they weaponize the terms and it’s like ‘you’re not’ — I did it. And the reflection is like, what is the what, right? Like what’s going on here? And then when I sat down to start to define the terms, it’s like, OK, this is the difference between organizer and activist. This is what building power looks like versus not building power. This is what building authentic relationships looks like versus building relationships with people who do one concrete thing. Like very different, very different outcomes. I learned that language like rather recently in the span of my life. 


[12:11] Sinéad Burke: Were you conscious of your ability or willingness to not just vocalize your own needs or wants at a young age, but those for other people? Like running for student government seems so quotidian in many ways, but actually, not everybody puts themselves forward even to be a representative within the school system. 


[12:28] DeRay Mckesson: I think I’ve always loved teams. I like playing team games. I like playing team video games. I’m just a big fan of teams. Mostly because when teams work, you see people’s best self come out in a way that is just beautiful. Like it rarely comes out that way otherwise. But like teams that have do this thing were like people’s magic gets to show up. And I’ve been on so many teams where like individually, people are good and fine and interesting, and the team like is just sharp. So I think I’m one of the things that I learned pretty quickly is that I had an ability to help people really shine in a team setting. That like when we got everybody together, I can help create the conditions where, like, you just did your best and we all did our best. So student government was a part of that. Working in school systems were part of that. Teaching was that, you know, if there’s anything I understood that ability early and I love it. Like, I love a good team. I like seeing people get together and do things that they thought were impossible and like helping to facilitate that.


[13:26] Sinéad Burke: And how does that — the conditions for bringing people out into their best selves. How does that manifest? 


[13:31] DeRay Mckesson: A host of things. I think some of it is to understand that conflict is a part of the work and not run from it. And knowing that conflict isn’t always us trying to kill each other, that our ideas can be a conflict without us being in conflict. So, you know, when I was the chief human capital of the school system, it’s like we’d have these really complicated problems. And I bring the leadership team together and we just fight about it. And we’d fight from like we’re all trying to get to the best place, but we fight in a way that was really, really about the work and not about a person. So what does it mean to, you know, I was a chief and I’d be like, I just don’t understand. I don’t get it, does somebody else get it? Oh, I get it. Or I’d say this is where my interpretation is. And somebody would be, like, I think you’re reading it wrong. And we would sort of push, and in modeling the collective push, it made us all better. Or another thing that I used to do a lot, especially when I didn’t understand something, is like ask somebody else from the team to paraphrase it. So I’d be like, Sinéad, what do you think you just heard? And then it’s like if your paraphrasing was something bizarre because you didn’t understand it either, then we need to regroup, you know. Or we’d have people put all of the options that they thought. So how do you create the conditions — one of the ways to create the conditions is like just amp up the intensity so that, like people’s best self just like feels like they have to come. 


[14:37] DeRay Mckesson: The second is this idea of what does it mean to over-communicate? So you can be in whatever meeting you want to be in, I don’t care. Like there’s some meetings that some of you have to be in, but if you want to come, be where you want to be. And like, I’ll make sure everybody’s looped in because you’ll make better decisions with better information. So there are a lot of people who lead teams and they sort of hold these things really close to them. But it’s like I’m going to be the chief tomorrow whether you like me or not, you know, like I’m gonna be here. So the best we can do is like everybody have the information to make the best decisions. I don’t feel threatened by you being in a position to make really good decisions. So that turned out to be a really big win. The third is that I would share a lot of space.


[15:09] DeRay Mckesson: So there were some meetings that required me and my thoughts. There are a lot of meetings where people just invited me because they thought I was a person with power. And I was the person of structural power, but Shawna probably was a better person in this meeting, right? D.L. was probably the better person. Jerome was — right? And I didn’t lose anything by saying like, Jerome, I want you to go to a meeting and like, if you need me, I’ll come, but I think you got it. And that wasn’t because I didn’t think the meeting was important, but because, like, you just were the better person. And those sort of things allow people I believe step into their best self. The other thing — and I think this is something I don’t take for granted — is that I knew the work really well. So, you know, when somebody was late for the front desk, I will go cover the front desk. And like I was the chief. So like, there were many layers between me and the person who worked to the front desk. But modeling this idea that when the phones were like too busy, I was like on the phones answering phone calls about people’s health insurance, you know. Like when it got too busy for the team, I stepped in. And I think that that helped show people that, like, if I’m doing it, we all can do it. 


[16:03] Sinéad Burke: It’s building that culture and that community. Was being a teacher in any way, a microcosm or a laboratory almost for the learnings of what you’re doing now?


[16:15] Teaching — I learned a lot of things. One is this idea of like what does it mean to regroup? So teaching is really interesting because you fail every day, and you don’t have a whole lot of recovery time. So it’s like I taught the same lesson three times and then there would be the end of the school day. I do some after-school stuff. I get home around five. I’d eat, grade some papers and I had to be back up at school at six. So it was like you just didn’t have a ton of time to, like, reflect and read — like, you had enough. But like, it just wasn’t a ton. Whereas most things — if you think about the time between your big projects, there’s time. There’s not like seven hours, it’s a lot of time between big projects, you know. Teaching you don’t. So I learned how to quickly reflect and adjust and like hold myself accountable and those sort of things in a way that I just didn’t understand before. Teaching was also the only thing where the effort doesn’t change the outcome. So everything else before teaching, if I stayed up working on that paper, the paper is better. If I crammed for the test, did better on the test. Teaching is like — you can stay up all night and you’ll give some of the worst lessons — like, the effort wasn’t it. So I really had to figure out how to be smarter about planning, and teaching helped me figure out how to calibrate my energy to actually change the outcome and not just like pour in with the idea that more is always better. Teaching taught me that more is sometimes just more. 


[17:30] Sinéad Burke: More after the break. 


[19:39] Sinéad Burke: What was the most challenging part of being in the classroom?


[19:43] DeRay Mckesson: Oh, everything. I was a very good teacher and it was hard. It was — 


[19:47] Sinéad Burke: What does it mean to be a very good teacher, though? 


[19:48] DeRay Mckesson: So we had a great classroom culture and my kids did really well academically, but I worked for it. It wasn’t like, you know, there are some people who will tell you they’re great teachers and they just like woke up like that. It was like I worked hard. Whew! One of the hardest things was the acknowledgement that it was my responsibility that every kid learned. It wasn’t enough that most kids learned. So on any given day most of my kids got it. Even when I wasn’t my best, they could sort of find something in the midst of it. Like I remember Terrell not learning how to add fractions for months after the fraction unit and he finally got it and I said thank you, Jesus, you know. Like it was those things where it was the responsibility to every kid, not just most of the kids. It was like an easy commitment to say, it was a hard commitment to put in practice because — Terrell’s a great examples of this — like a month later and I knew he still couldn’t at a fraction. So it’s like I could fail you, right. I could keep failing you on the test because, like, you literally cannot do it. Or I could say, like, he just didn’t get it, but we got it, right? And like, it’s not his fault that he didn’t get it. Like, I just didn’t figure out how to teach it right. So I got to keep at it, you know, and it was understanding that the easy way to just give him a zero for the unit. Like, the honest way to be like keep figuring it out. And like, I remember the day he got it, and could explain it, and it wasn’t just sort of rote memory. And it was like, this is what it is. Right. But it was a much easier commitment to make in theory than in practice. 


[21:07] Sinéad Burke: And what made you then segue out of being physically in the classroom every day?


[21:12] DeRay Mckesson: Yeah, I wanted to figure out how to make sure that every kid had a great math teacher and I couldn’t do that in the classroom. So I went to go work at the system level in human capital to try and figure out how to recruit teachers better and train them better. 


[21:23] Sinéad Burke: Why math? 


[21:25] DeRay Mckesson: Random. In New York sixth grade is technically elementary. So I was a sixth-grade teacher, so technically certified as an elementary teacher, but math was the only content I taught. Me and my sister both became middle-school math teachers. Like random. It was random. 


[21:39] Sinéad Burke: Was there any real love for math growing up? 


[21:42] DeRay Mckesson: Not a love for it. I think they were maybe good teachers and I was really bad at math. I swear I never learned how to divide fractions until I became a teacher. I literally was like I remember reading that section in the book. Or dividing decimals. I didn’t learn that. 


[22:00] Sinéad Burke: What was the turning point. What gave you the hook in to be able to do it? 


[22:04] DeRay Mckesson: I mean, I had the teachers guide, but I think what made me even a teacher was that like I didn’t take for granted when they said they didn’t understand. It wasn’t about them. It was like I was that kid, you know? I was the kid who sat in class and like was smart and literally just like the teacher would model one way. I’m like, I don’t get it. Or they would do it so quick and I’d be too embarrassed to raise my hand. It’s like I got it. You know, I completely understood. So in class, I think we made our class really special — and this is definitely an organizing lesson — is that this idea that practice plus feedback equals growth. Right. That practice without feedback is not helpful, but practice and feedback, like, you can do anything. And my classroom became a place where like practice and feedback were everything. Like we practiced a lot. And it was like, how do you practice without the threat of failure? So they got grades on my classwork and stuff, but I remember when I was in middle school. It was like you answer these 20 questions, you got a grade on those 20 questions and that’s your classworkfor the day. And like I was so nervous about potentially messing up, but that didn’t encourage me to ask questions. So I didn’t want my classroom to be like that. But you just like practice. And we didn’t do number grades on classwork or anything, actually. I just circled. We did these circles. I was like, if they got it wrong, I would circle it. So you didn’t want to get a lot of circles, but there wasn’t a number, you couldn’t fail with circles. So by the time a test came or something, like you’d practice so much already that like you were fine, you know. You might not get an A, but you weren’t going to fail it because like we’d already done it. There’s only so many trick questions you can ask in math. You know, if you can solve an equation, you can solve an equation. I can make it complicated with fractions, but if you can solve it, you can solve it, you know. And that was really cool was to see them practice, like, what it meant to create a space where kids can explore and mess up and get a lot of feedback about it and they could take that with them. 


[23:45] Sinéad Burke: And evolve further and move it along. 


[23:47] DeRay Mckesson: Yeah, and do things that, you know, I taught all of sixth-grade math by Christmas my second year. Like the whole year’s worth. 


[23:53] Sinéad Burke: And how long should that take? The full academic term? 


[22:55] DeRay Mckesson: And then I did a seventh-grade algebra from January to June. So people would come into my class and see like these 11-year-olds doing all this incredible math. 


[24:01] Sinéad Burke: Did that ever cause friction in the staff room?


[24:03] DeRay Mckesson: I mean, if they were mad it didn’t get back to me. There was a seventh-grade English teacher who was incredible, she taught English and she did a lot of great things in her classroom. So she and I spent a lot of time together. And she was an easy believer in me and I was an easy believer in her. We started at the same time. So when I would be teaching like factor polynomials, like really complex algebra to my 11-year-olds, and I had 30 kids in each class, and she would come in and like help for a day, like the day that I was like delivering the content. And I would go sit at her class and help, too. And so she and I had a really good thing going on. And the principal I think was just excited that kids were learning. The test scores came back and my kids did really well. So that worked, you know. I think that one of the things that was probably hard was really the classroom culture. So I was sort of like, I think I get that classrooms are the first places that kids who want power looks like outside the home. So creating a class where like you didn’t have to raise your hand to go to leave, like you did go to the bathroom whenever you wanted to. Like, I just didn’t care. You also could always choose your own seat. Like I didn’t care. It was like when those things were like, you’re gonna be in trouble if you talk to him all day, so like, sit where you want to sit, I don’t care. You’ll both get detention. 


[25:02] Sinéad Burke: This is the process. This is gonna be the outcome. You decide.


[25:06] DeRay Mckesson: And I think that was hard for other teachers who were just used to more control. Because they would be like, ‘well, in Mr. Mckesson’s class I can do it.’ And it was like that just wasn’t important to me. I just needed them to like focus when they learned and they did. 


[25:19] Sinéad Burke: I grew up always wanting to have a teacher who looked like me. And I think that was probably one of the big pillars as to the reason why I wanted to be a teacher. And my greatest challenge of being in the classroom was not the children I was teaching, but it was everybody else’s assumptions. Like, are you gonna be able to do that? Because, again, the world had said that, you know, if you want to be a teacher, you got to be told enough to turn on the light switch. If you want to be a teacher, you got to be tall enough to hang up the artwork. And it’s such a key space, I think, not only just to teach about power, but also kind of justice and reflect what the world could a need to look like. 


[25:54] DeRay Mckesson: Yeah, I agree. And because a man — I’ll never forget I was much more emotionally all over the place my first year. Like I just hadn’t worked with groups of kids. Like kids temper tantrums and then I’d be yelling and then I figured it out. I’m not yelling, I’m not screaming. 


[26:08] Sinéad Burke: When they go loud, you go quiet. 


[26:10] DeRay Mckesson: Yeah, pretty sure I didn’t get it. So I wrote one of the things that I had to do. It’s like I had to start speaking my emotions because so few kids had had a male teacher before. Any sign of disapproval from me would be like, everybody’d be crying, you know? Because they were still kids. So I would have to say, like, I’m not mad at you. I’m just really disappointed in that decision you made.


[26:28] Sinéad Burke: I’m disappointed in your behavior. 


[26:30] DeRay Mckesson: I’m really frustrated that you made that choice. And I had to talk those things out for my kids in a way that I really learned and grew from. Which is cool. And like, I took math serious, but I didn’t take myself too seriously. Some things were funny. You’re like, that was good. That’s a good joke. 


[26:47] Sinéad Burke: We’ll be back just after this break. 


[29:00] One of the things you just said that was really interesting, that idea that there aren’t that many male teachers. So in Ireland, if there’s a graduating class of elementary school teachers, it’s usually 90 percent women and 10 percent men. And they are mostly, if not all white and mostly if not all able-bodied and non-disabled. Did you feel a sense of responsibility with that? That idea that you were an individual who perhaps had a huge responsibility, or was that something you were cognizant of? 

[29:27] DeRay Mckesson: In some ways, yeah, but not. Actually, I think I was so nervous about making sure they learned, you know, that that was like when I walked in, like, I hope they get this. That was really nerve wracking. 


[29:39] Sinéad Burke: You have done such extraordinary things since. And you said there that, you know, one of your main focuses now is to help people build their skills. How do you divide your time, though, if you’re trying to be present and trying to be conscious of what’s going on in the online zeitgeist? Is it very disciplined and organized or —


[29:56] DeRay Mckesson: Well, online I’m really diligent about who I follow. So that’s why I follow just a small number of people. Not because I’m one of those, like, I want the numbers — but because I want to make sure that anything comes on a timeline makes sense to me. Right. That like I’m like feeding my spirit in the right way. So very rarely does something come on my timeline that like is so wild that it’s something I didn’t want to see. So that’s important to me. And then I do have enough downtime where I can, like, call somebody and be like, hey, this is what I thought. You know, just talking to Sam about the presidential candidates. Because I think we were going back and forth about some of the proposals and it was like, oh, I didn’t see that. And he’s like, oh, I did it. Or like if something that somebody else had on the podcast about this number. And I was like, I didn’t remember that number. He was like, oh, this is where it came from. I was like good push, I never heard that. So those sort of things are important. Yeah. 


[30:40] Sinéad Burke: And what made you say yes to doing the podcast, or what made you do the podcast? 


[30:44] DeRay Mckesson: Long time ago at this point. I wanted to create a place where people could like learn. They could hear conversations go back and forth. We don’t talk about the news until we record it. So every week we’re all pushed, like we are all like, whoa, that’s a great argument. That is cool. We’re all learning every week. I wanted people to be part of the learning process that we were going through. 


[31:02] Sinéad Burke: What’s been the most memorable lesson? 


[31:04] DeRay Mckesson: Oh, so much. I remember asking Brittany and Sam originally and then asking Clint to join. It was just an idea. Like I had this vision of what it could be. I think this it. And it worked. 


[31:15] Sinéad Burke: What did you initially start out with it being? What was that vision? 


[31:19] DeRay Mckesson: It’s what it is now. So I was like, I want to get a couple of people together and talk about the news that they didn’t know the week, but that was important to them, and we’ll discuss it. You know, the editing is what got better. Shout out to Jess. And like the logistics around the pie got much tighter. But the idea is the same idea from Episode 1. And like that, I’m proud of that. I’m proud that like every week we talk about a set of issues that are important to the world but like you probably haven’t heard of. And I meet people all over the country who are like, I didn’t know. Or like, you know, I’m always surprised at how many people — they can go anywhere to get Trump news. You don’t need DeRay’s take on Trump. I can do that. That would be interesting. It’s definitely a current events topic. I don’t know how much that equips you to be a better fighter. I wanted to create something that would actually equip you to do like different work. 


[32:01] Sinéad Burke: And speaking of that, and a different work, I think there’s lots of people who would like to be organizing, or would like to be an advocate, or would like to be an activist. Or would like to even have the bravery, or the courage, or the confidence to kind of step forward and have a difficult conversation, or to be a bit more forward in having a voice. What advice would you give? 


[32:23] DeRay Mckesson: I’d say, like, start where you are. I think that people — one of the things that’s unfortunate about the way the Internet has functioned is that people think that it always starts off big. They see the, like, $50 million announcement, the $50 million dollar organization started by — none of those things exist, like they’re impossible without everyday people deciding to take a stand and creating space. So all this work around criminal justice that’s spawned in the past five years started from everyday people in St. Louis saying they’d had enough, right? They created the conditions for all this other stuff that like now we consider big, but like it was regular people. You think about Montgomery. In Montgomery, the bus boycotts, was everyday people without a 501c3, without a lot of money. Like they create the conditions for all this stuff to form. So I remind people that like you have the power to create the conditions for everything else. Like you do. The biggest thing I ever did in Ferguson was make peanut butter and jelly sandwiches, you know, and like people don’t see that. They don’t remember it. I don’t even know if we took pictures that day. But the work is already in front of you. The question is like, do you see it or not? 


[33:24] Sinéad Burke: And can you step forward and do it?


[33:26] DeRay Mckesson: Yeah, well, you walk into the risk. 


[33:27] Sinéad Burke: You spoke about sixth graders being in this lovely moment where they get to reimagine everything that’s possible. You’re a sixth-grader for a second. What do you wish or hope to imagine for. Either what’s next for you or for the world? As idyllic as that sounds. 


[33:42] DeRay Mckesson: If I could go back to sixth grade and I — I guess I had some good teachers in sixth grade. My world was still pretty small in sixth grade. I would want sixth-graders’ worlds to be like a little bit bigger. Just to like know more, to see more, to be exposed to more so they can ask those questions, you know?

[33:59] Sinéad Burke: What questions? 


[34:00] DeRay Mckesson: Any of them, whatever question they care about. I think about — I don’t think I’d really been out of the state in sixth grade. My world was like sort of just home. I didn’t know that there were more colleges in Morgan and Hopkins. I just didn’t. We lived in like a very small part of the world, you know, like it was like I went to my grandmother’s house. I went to school. I went to some other random places in the city, but like nothing too random. Whereas now, it’s like I would love to think about what virtual reality looks like. To allow kids to, like, play on the moon. You know, I think about — when I ran the after-school program, we took kids on college trips, you know, as fifth graders and sixth graders. That wasn’t a thing when I was in sixth grade, you know. So I’d want those opportunities. Like I want every kid to be able to benefit from those. I remember the first sleepaway — like we took all these kids on this trip over the summer. It’s like they’d never been with, like not a parent, you know, to a trip. And like we took them on college visits and it like normalize this idea, like you’re on a college campus. It’s like so simple. 


[34:54] Sinéad Burke: I think that idea of dreaming big and making all of our worlds bigger is not just something that sixth graders can do, but we all have a responsibility to do for ourselves. DeRay, it has been such a treat to have you on As Me. 


[35:08] DeRay Mckesson: So good to be here! 


[35:13] Sinéad Burke: You see people on social media and you get to know their work, maybe even their persona, but I just really love to DeRay talking about being an uncle, his relationship with his sister, and who he was and who he became as a teacher. A person you should know this week is Vicky Phelan. Vicky is an extraordinary woman who has changed Ireland this year. She took to many a public stage and shared her very personal experience of living with cancer. And so often we expect people to invest in emotional labor and burden in such a public way in order for things to change. And not only did Vicky step up, but she did it with such grace, humility and empathy. Vicky is on Twitter. You can find her at @phelanvicky. That’s all for this week’s episode. We have another one coming out next week, and that will be it for me from 2019. Thank you for joining me on this wild journey. Anna Wintour hates the word journey, I should stop saying it. But it has been wild. 


[36:17] Sinéad Burke: As Me with Sinéad is a Lemonada Media original and is executive produced by Jessica Cordova Kramer. Assistant produced by Claire Jones and edited by Ivan Kuraev. Music is by Jerome Rankin. Our sales and distribution partner is Westwood One. If you’ve liked what you’ve heard, don’t be shy. Tell your friends or listen and subscribe on Apple, Stitcher, Spotify or wherever you like to listen, and rate and review as well. To continue the conversation, find me on Instagram and Twitter @thesineadburke and find Lemonada Media on Instagram, Twitter and Facebook @LemonadaMedia.

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