19 #Woke : The Other Side of Freedom w/ DeRay Mckesson

We sit down with activist, educator, public speaker and host of Crooked Media’s Pod Save the People DeRay Mckesson to talk about working while woke and his first book, “The Other Side of Freedom” that is available 9/4/18!

Length: 12:15

Host:  Zach

About DeRay

Order DeRay’s book here

Pod Save The People

Crooked Media


Zach: What’s up, y’all? It’s Zach with Living Corporate. It’s Monday, September 3rd, the day before a few things drop. One, Beyonce’s birthday. Two, my birthday. Three, Black Panther on Netflix, and last but certainly not least is DeRay Mckesson’s book The Other Side of Freedom: The Case for Hope. About the book, Henry Louis Gates Jr. says “On the Other Side of Freedom reveals the mind and motivations of a young man who has risen to the foray of millennial activism through study, discipline, and conviction. His belief in a world that can be made better one act at a time powers his narratives and opens up a new view on the cost, consequences, and rewards of leading a movement. Now, I feel as if you’ve gotten to know the Living Corporate team this season. For those who know me, they know I’m a genuine admirer of DeRay’s work. I love his podcast on Crooked Media called Pod Save the People. So shout out to Brittany, Sam, and Clint Smith III, or Clint Smith “Aye-aye-aye.” For me and many folks in my generation, DeRay was the face of a new type of activism that was mobilized through social media. The honesty and, by direct correlation, courageousness of speaking truth to power on such accessible platforms was a major point of inspiration for Living Corporate. Because of this, I’m excited to tell y’all we actually got him on the show to talk about working as a socially-conscious person of color in Corporate America and about his journey in writing his book, The Other Side of Freedom: The Case of Hope. So what you’re gonna hear next is an interview I had with DeRay. His book is also one of our Favorite Things, so make sure you check out the links on the show notes and our website, and make sure you preorder it. So while you’re jamming to B-Day you could also be reading this book. See y’all on Friday. Peace.

Zach: And we’re back. And as we discussed before the break, we have DeRay Mckesson. DeRay, welcome to the show, man. How you doin’?

[Sound Man throws in cheers]

DeRay: It’s good to be here. I’m good. I’m good.

Zach: For those of us who don’t know you, would you mind telling a little bit about yourself?

DeRay: Yeah. My name is DeRay Mckesson. I’m an activist, and I have a podcast called Pod Save the People. I used to be a teacher, and I’m committed to the work of social justice.

Zach: I follow you on IG. You don’t follow me, but it’s cool. I get it. I saw a post you made about a note that you got from the FBI after they visited your home in 2016. Can you talk to us about the biggest impacts that purposed activism has had in your life?

DeRay: Yeah, I think that–I think that one of the most powerful things about the protests for sure, and I think about when we were all on the street in 2014 in the early days of Ferguson and everything since is that it’s helped empower [people who] didn’t believe they had power before. I never would’ve [inaudible] before then. I just, like, didn’t–I didn’t think about that as a way to sort of force [inaudible], and now I would check on [inaudible] our government only exists [inaudible]–and we’ve seen over the last three years is people [inaudible] protest [inaudible] how the world can be better and what their role can be in making it better.

Zach: So you’re not a stranger in these federal or social media streets. In fact, you and I connected some time ago. I believe that we were able to make that connection because you’re able to engage in topics around social equity in really courageous but still very approachable ways. You’ve mentioned in the past your work with Campaign Zero and of course the work that you’re doing with Pod Save the People. Wonderful podcast. One of my–my favorite podcasts actually. And the things that you touch and that you curate, I think that–I think they have so much impact because they’re so practical and they challenge people of color as well as non-people of color to engage and be part of the solution. Think about Living Corporate–and our audience is primarily people of color in the working world–are there any things that you believe middle-class or affluent people of color are not doing in mass but that could be done to support the movement and the work?

DeRay: I don’t know [inaudible]–and I’m gonna start from, like, a place of lack, but I think that where can all grow, especially as somebody who used to work in [inaudible] the school system of Baltimore, you know, which was one of the chiefs in my 50-people team and, you know, it’s a billion-dollar organization is that always remembering that confrontation doesn’t always look one way. So there are ways to show up in rooms where things happen that aren’t about equity, aren’t about justice, aren’t really about our community, that don’t focus on us and don’t center us but should, and we can push and challenge, but it doesn’t have to be a sit-down. It doesn’t have to be a storm out of the room. It doesn’t have to be a yell. I think about some of the meetings where I’ve been really successful it’s, like, asking the really awful question, right? It’s, like, not letting people off the hook and making them to do the cognitive work as approached to preaching to them. Like, those are things that we can do in all settings that are really powerful. The second is that the systems and structures are designed to drown out individuals and, like, make individuals believe they don’t have power. That is, like, how the game is set up. What we can do is, like, remember that, like, people have a lot of–like, individuals, individuals who come together to form collectives like [inaudible]. Think about one parent who emailed in at the beginning of the school year when I was the chief human capitol who requested something very specific. She was the only parent we heard from. She was right, and if not for her email we wouldn’t have redone this whole plan, but, like, she emailed it, and it was perfect, right? It wasn’t about volume. It was about, like, the content, and people just don’t know that. They don’t realize that systems often take the feedback, but one of the reasons why they don’t tell you they take the feedback is ’cause they don’t want to deal with 10,000 of you. So that’s that, and the third is that, like, you can learn all of these issues too. So I would say to most people, like, find an issue that matters to you that you believe in. Like, try to learn as much about it as possible because that will actually set you up to, like, think about problems and structures in people’s lives and really in a powerful way.

Zach: So continuing a little bit–’cause I want to talk a little bit more about people of color in these places, right? So I count myself as somewhat socially conscious. At the same time though I still work in structures that really weren’t built for me, so let me ask you this. Do you think that there’s a way to challenge the systems we’re pushing up while still climbing within them? I ask because it seems counter-intuitive on its face to me. I say this as someone, like I said, in the work. I’ve had very explicit conversations with colleagues who respect Living Corporate’s mission, but they’re afraid to even kind of publicly support it because they think it’s gonna mess their bag up ’cause they don’t want to necessarily talk about those things. Like, what would you say to that?

DeRay: Yeah. I don’t know if I have anything new to say besides, like, knowing that confrontation doesn’t always [inaudible]. Like I said, people often think about challenge as, like, some dramatic thing, but I’ve been in rooms with people I really–you know, I made a decision when somebody came in. I was like, “Even if you say no, can we talk this out and, like, think through it this way?” I’m like, “Yeah, let’s talk it out,” and, like, “Oh, I didn’t see it that way.” Like, I think that sometimes we think about challenging in the workplace as some grand statement. It just doesn’t have to be like that. The outcome–we just need the outcome to be the outcome. So there are some meetings that are like–I just wouldn’t let the question go. So I knew it was the wrong decision, but if I came out and said, like, “I think that you’re making a dumb decision,” the person would respond in a way that just was not–I wouldn’t get the outcome. I would feel better, but I wouldn’t get the outcome. So what I can do is say, like, “Hey, what if we play with this option? What if we do this option? Can we talk about options today?” Like, that’s actually a way for me to push the thinking and, like, get to where I want, where there are some meetings where you just have to say, like, “No, we’re not doing that,” right? And, like, if you want to do it that way, then we need to go talk to this person. So, like, just knowing that there are ways to push and challenge, and everything doesn’t have to look the same.

Zach: You know, I’ve had some coworkers who will run up on me and show me a Facebook post or a racist article or something–the latest thing the president said and go, “Zach, that’s so racist. That’s so bad,” or they’ll even brag about, like, the latest protest they were a part of, but at the same time some of those same people might not necessarily feel comfortable speaking up when [inaudible] morning meetings or cursed out or disrespected in other ways. So certainly you have experience in building meaningful coalitions. What advice would you give to the everyday perhaps well-meaning, aspiring ally on how they can put empathy and allyship into practice?

DeRay: Yeah. Whiteness is a shield, and they should use that shield in a way that, like, serves people. So, you know, it often [inaudible]. A lot of white people don’t realize that. Like, you and I both know what it’s like [to not be listened to and not be heard?]

Zach: Right.

DeRay: A lot of white people just, like, don’t know. Like, they don’t know what it’s like to, like, literally not be listened to and not be heard. That’s, like, a new thing. They aren’t, like, ignored, right? So some of it is, like, helping people just see, you know? In classrooms, one of the things that we do is we sit in the back of classrooms and, like, we can tally up the number of positive to negative things that the teacher says, and that gives a sense of what’s going on in the classroom. Same thing in board rooms and in meetings. We can tally, like, who gets called or [inaudible] power is working in a given space. So you’ve got to step into the discomfort, and there are moments when, like, you know that something’s off, and again, like, confrontation doesn’t always have to look the same. ‘Cause you can say, like, “Oh, no, I wanted to hear you first.” Like, you can share your space. You can share power. You can create space. You can create power. Like, I think there are a host of things that people can do that don’t have to feel like that or even actually be [inaudible]. The impact is really powerful.

Zach: No, I agree with that, and it’s something that you’ve–again, you’ve reiterated it a few times, but I do think when we talk about the work or we talk about, again, kind of pushing up again these systems and things like that, we often think about something really combative or antagonistic, and it doesn’t always have to be like that. That’s something that kind of reminds me–like, a common thread in the things that you say, especially on Pod Save the People, that just the human element of it, right? Like, actually being able to build that connection. Like you said, giving up space for that person. “Hey, I wanted you to talk first.” You’re doing a lot there without you having to necessarily be in any way negative, quote unquote. So let’s do this. Let’s talk about The Other Side of Freedom. It happens on Beyonce and I’s birthday, September 4th. So air horns for that.

[Sound Man obliges]

Zach: But why a book? Why now? And what do you want people to take from it?

DeRay: Yeah. So I was–you know, I’ve been reflecting on all of the places I’ve been, and I wanted to share them because I’ve been to a lot of places. I’ve been in the street in a lot of cities. I’ve been a teacher. [inaudible]. I think about, like, what are the lessons? Like, what are the [themes?] This was my attempt to look at all of the stories and then say, “Here are the tools that I took out of them.” [inaudible] is, like, a sermon that’s called [inaudible] Story. I loved the title, but I didn’t know what it meant, and I listened to it, and he talks about sometimes you can tell your story [inaudible] so all you see is the pain not the purpose. I’m at a point now where I can think about the big lessons and themes that I got. [inaudible]

Zach: So it seems like book writing is a lot of work, right? Like, I’ve seen your posts. You know, I’ve seen your posts on Instagram. You’ve posted the various edits and revisions that the book went through, and then you went to the copying center, and it just seemed like a lot to do. In your journey of writing your book, is there anything you learned about yourself?

DeRay: I learned a ton of things. You know, some things–I spend most of my time writing online. Like, writing on Twitter. [inaudible] all the way out, you know, in essay for the reader and the writer, and I needed to process a lot of things, so it was important to me about writing [inaudible], and I had to process a lot of feelings and emotions. And writing about my mother. I talk about my mother a lot, but I’ve never written about in this way so I needed to do–like, I was pushed in my own personal space. So that was really healthy. And, like, things about the essay on the police. It’s, like, there’s a lot of research we [never put anywhere?] I want it put somewhere. So yeah, the book was really a growing experience.

Zach: DeRay, this has been a great discussion, man, and I want to thank you again for coming to the show. Before we again, do you have any shout outs?

DeRay: Please buy the book. I’m excited. Have conversations with people about the book, and we have a lot more to do.

Zach: Absolutely, yeah. So the book is called The Other Side of Freedom. DeRay, we’ll make sure that we put it in the show notes, and then we’ll also be listing it on our website as a Favorite Thing so people can make sure that they have no excuse not to get it. Thank you so much for your time, man.

DeRay: Thank you so much.

Zach: All right, peace.

DeRay: Bye-bye.

Kiara: Living Corporate is a podcast by Living Corporate, LLC. Our logo was designed by David Dawkins. Our theme music was produced by Ken Brown. Additional music production by Antoine Franklin from Musical Elevation. Post-production is handled by Jeremy Jackson. Got a topic suggestion? Email us at livingcorporatepodcast@gmail.com. You can find us online on Twitter, Facebook, Instagram, and living-corporate.com. Thanks for listening. Stay tuned.

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