You Must Be Some Kind of Therapist

Swell AI Transcript: 151. Jenn & Wink.mp3
Winkfield Twyman:
I had a conversation with someone. This person said, Blackness is oppression. Nothing else matters. And that completely upended everything I had ever knew, learned, felt, experienced, worshipped about Blackness in America. And that caused my head to turn around like the woman in The Exorcist.

Jennifer Richmond: lived overseas in Burma, Indonesia, China and I've seen what real kind of authoritarianism looks like and I came back to the United States and you know diversity was all the rage and I felt like I must be missing something because I always thought diversity was always all the rage like I always thought that was like the coolest thing about the United States having lived in very homogeneous countries before. I went to this diversity training, again, very open-minded, looking forward to hearing stories that weren't my own, and it was none of that. I literally had been living out of the country, so I was just gobsmacked. I didn't know what to think about it. And I had questions, and I remember having questions, and I thought that that was a sign of curiosity and understanding. And I'll never forget this younger white woman pushed a note across the table to me, and it said, do your homework.

SPEAKER_03: You must be some kind of therapist.

Stephanie Winn: Today, my guests are Winkfield Twyman and Jennifer Richmond. They're co-authors of a book called Letters in Black and White, a new correspondence on race in America. They're also both former professors and writers and interesting people. And this conversation has been a long time coming. Wink and Jen, welcome to the podcast.

Winkfield Twyman: Thank you very much. Thank you for having us.

Stephanie Winn: Glad to have you guys. It's been a while. You sent me your book, gosh, like a year ago. It's so bad. But you've been so very patient. So yeah, let's dive in. So for people who have never heard of your book, can you describe what it is?

Winkfield Twyman: Well, our book, it should be a very simple thing, but in these times, it's a very unusual, uncommon thing. Back in the late 2010s, Jen and I respectively were concerned about the level of polarization in the public discourse about race. I know, for example, and Jen can address this herself, that she encountered a diversity training session in Austin, Texas, which left her dumbfounded and disappointed with the level of discourse. On my end, two things. One, I had a conversation with someone, and it was April 21st, 2018. I remember the date and the year because it's such a dramatic statement. This person said, Blackness is oppression. Nothing else matters. And that completely upended everything I had ever knew, learned, felt, experienced, worshipped about Blackness in America. And that caused my head to turn around like the woman in The Exorcist on the bed. And then two, one of my dear friends, Dan Wolf, we're both Harvard Law School graduates. He wanted to have us talk together before the Harvard Club of San Diego about race because things were so polarized, the discourse. And to my amazement and his disappointment, it was communicated to us that they could not let me address the group or give me a platform because, quote unquote, I might deviate from dogma, unquote. And that also caused my head to spin because to me, Part of being a Black American was always about creative expression. I had, growing up, 15 different uncles, and I would hear 15 different opinions about anything under the sun. What kind of world were we in when the Harvard Club in San Diego feared to let me speak because I might deviate from dogma? And so from that point, I reached out to Jen, and our book was born. Jen, you may want to add upon that.

Jennifer Richmond: Yeah, I mean, it really did start for me. So I came into my professional life as a China scholar. And the idea of diversity, e pluribus unum, I mean, I just, I love that. I've lived overseas in Burma, Indonesia, China, and I've seen what real kind of authoritarianism looks like. And I came back to the United States and, you know, diversity was all the, you know, rage. And I felt like I must be missing something because I always thought diversity was always all the rage. Like I always thought that was like the coolest thing about the United States, having lived in very homogeneous countries before. And so I was like, well, you know, I love diversity. This is back in 2018. So before COVID and some of the more extreme things that we've had to go through in the past five years. And like we said, I went to this diversity training, again, very open-minded, you know, looking forward to hearing stories that weren't my own. And it was none of that. I mean, I literally had been living out of the country. So I was just, I mean, I was gobsmacked. I didn't know what to think about it. And I had questions. And I remember one of the, there's so many stories from this event, but I remember having questions and I thought that that was a sign of curiosity and understanding. And I'll never forget this younger white woman pushed a note across the table to me and it said, do your homework. But I think that's what I'm here. I'm here to learn. And so as a result of that, I'm a writer. I was an analyst, professor. And I felt compelled to write about this experience. And that's how we got started is it was picked up by, at the time, Ariel magazine, my piece. And Wink wrote to me. So a complete stranger wrote me a letter. And we didn't go into it necessarily thinking that this would be a book, but it was such, I think both of us were looking for a real conversation and being able to ask real questions, hard questions, being able to get pushback without judgment, et cetera. And like Wink said, he was kind of going through his own journey at that time. And our conversation like months into it, and these were long letters, most of which are in the book itself. But after about a couple months, four to six months of writing these letters and feeling so relieved to be able to have a voice in this conversation, I said, I think that other people would appreciate hearing that these conversations are not taboo. We can have these conversations in good faith. And we weren't the only ones who thought that apparently. And so Pitchstone picked up our book. But that was that was our beginning.

Stephanie Winn: And the book is a series of letters, a correspondence, a deep friendship, really, that you developed over. Gosh, how long of a time period was this?

Winkfield Twyman: What was the fourth years? I think three, four years. Yeah.

Jennifer Richmond: Yeah.

Winkfield Twyman: Because it came out in twenty twenty three. And I think we first address each other in 2019, I think.

Jennifer Richmond: That's a long time. It is. And we were still writing each other, but we walked through so much together. I mean, in the book, I did a mission trip with my church to Baltimore. And at this point, our conversation had already really had a life of its own. But the things that I saw and experienced in Baltimore, this is the height of, you know, we were 2021, I believe, when we were in Baltimore. And so Wink was kind of my sounding board for everything that was going on that I was seeing in Baltimore, kind of the capture of the moment that we were in in 2021. So yeah, we've been at it for a while.

Stephanie Winn: Jen, how long had you been out of the country when you came back and found that sort of woke takeover of the diversity training?

Jennifer Richmond: That's a good question. I don't have a straight answer, only insofar as I've been in and out of the country ever since I was young. So I would say I had been back in the country my last trip overseas, so I spent most of my time overseas working at flying back and forth. I was living there, then I became a mother, so then it took me there just monthly instead of actually living in China. But I was back, the last time I was overseas was in India in 2019, and I was there for quite some time. And as some of our letters actually were me writing him from India. So it was not long until 2020 that I had, was my last trip.

Stephanie Winn: It seems like because of so much time spent overseas that maybe you hadn't been around to pick up on how quickly the culture was changing in America. I'm hearing that you almost kind of had whiplash from growing up with one set of liberal values with regard to what it means to have respect and curiosity towards people of different cultures, and you're kind of approaching things like that. And I remember having similar feelings about the pace of the language evolving. I can't remember if I was in grad school or where I was, but I remember at some point someone introducing a language guide. And it was this thing that was periodically, it was updated every year. This is the current language you're supposed to use in order to not offend people from every walk of life. And I remember thinking, this is a lot to memorize and this is being updated every year.

Jennifer Richmond: Yeah, and it was like a culture shock. Again, having grown up in these various places, growing up with other diplomat children, I went to international schools, that was the water that I swam in, diversity. So I think it was the slogans, and Wink and I talk a lot about the slogans, and that was kind of our first butting of heads, if you will, in the book is, I used the slogan, white privilege. And he was like, oh, now hold on a minute. And Wink, I'll let you carry that part of the story.

Winkfield Twyman: Oh, sure. I mean, Stephanie, I'm a pretty straightforward No sun, sky. So if you're going to have a conversation with me, you can't use abstractions. You can't use things that are indeterminate. You have to use clear words. And to me, white privilege, quote unquote, was one, the opposite of a honest, forthright conversation between two people, because you're letting some other institution or cultural event define the ways you can communicate. Number two, it just struck me as manipulation. When you change the language or constrain the use of words, you're essentially being a bully because you're freeze-framing a way in which discourse can proceed. But number three, and most importantly, you know, who's privileged? I think there's a lot about being Black in America that awards privilege. And so I refuse to kind of accept that that language because it would presume there's something superior about whiteness and something inferior about blackness. And that's not the case. And I've known that since I was a little kid on Twine and Rose. So, yeah, I don't use certain phrases because I think they frame us into relations of superiority, inferiority. That's just not me. If I want to have a real conversation, we have to talk as equals. Privilege gets in the way, if you will. No one's, everyone's privileged and no one is privileged. It's one of those indeterminate words for me.

Stephanie Winn: So Jen, I'm wondering if at that point in your correspondence with Wink, you were like, was it that you were trying to keep up with the pace of the culture and you're like, okay, this is what I'm learning like as a white lady, I'm supposed to say that I have white privilege. And then you say that to your black friend. And I mean, I could just imagine the whiplash that's coming from like, trying to figure out what society wants of you and what's true and

Jennifer Richmond: That's I mean that that that was exactly right and again what was so funny is I was trying to explain to wink at this part in our juncture in our conversation that I understood, okay, that I had white privilege. And my reasoning behind it was, I don't know what it's like to grow up in the ghetto, right? So I have to say, I was raised in a middle-class family, education was highly valued. I didn't know what it was like to grow up in a ghetto. So therefore, I had white privilege. Well, Wink quickly, he quickly corrected me and said, well, I didn't grow up in a ghetto either. You know, and so this is that was the, I think, jumping off part of the real relationship and the bonding, because we started to see I started with just those few words, I started to see him as an individual. And I think at the time, and even still such to this day, but at the time, people were trying to label black as, as almost synonymous with ghetto. And Clearly, that's not the case, but that is and what a disservice. What a disservice that is to just lump everyone on and make them assume a certain label.

Winkfield Twyman: So many responses I would offer, Stephanie. Number one, I often think about this. Not only did I not know what the ghetto was, quote unquote, and had not grown up in the ghetto, my family had been in a southern suburb since the 1870s after the Civil War. So that was kind of our sense of self. And I think in some ways, when we look at people as individuals, you're better positioned to understand people. I really think that's true. I think that dogma and caricatures and stereotypes dissolve at the level of the individual. And number two, my kids. My kids are certainly not people who have grown up in the ghetto. You know, they're children of Ivy League graduates, grandchildren of professionals, great-grandchildren of professionals, great-great-grandchildren. I could go back to My children are probably descendants of one of the oldest Black American families in the country. Their nine ex-great-great-grandfathers, something like that, in 1790 formed the first self-help society for Black Americans in the country. It's in Charleston, South Carolina. It was called the Brown Fellowship Society. And from that point on, the ancestors had always been achieving an enterprise and business generation after generation after generation after generation. So I think when Jen kind of assumed that I wouldn't share her distance from the ghetto, quote unquote, I think it was really smart for me to not shut her down, but to engage her. I think sometimes there are upper middle class and middle class black Americans that are so sensitized to offense. that they would have read into that all kinds of horrible caricatures and stereotypes about Jen, and they would have ceased the communication. I'm not like that. I'm a curious person. And I think that it's fun to, not to educate people, but it's fun for the people see my part of life, my part of the human condition. And so I wasn't in a mood to shut Jen down. I was in kind of a professorial mood as it were, so. But we have, Stephanie, we have to, I think that's so important. We have to get away from this lazy idea that the Black American experience equals poor and ghetto, because that's not true. That's not true. And I think sadly, Black Americans who don't fall into that caricatured box are reluctant to speak up. They're reluctant to break ranks and share their lived stories because they're afraid of being called inauthentic Blacks. I think Yale Law Professor Stephen Carter once wrote about whether or not he was an authentic Black, given his experience as a law professor and a descendant of prominent ancestors on the East Coast. So yeah, I think it was important for me to not choose to shut the door on Xi'an. but to open the door wide open and have her look into my life, my world. As it is, it's a real life. I'm not a bot. I'm not AI. I'm the real deal.

Jennifer Richmond: But again, those weren't the conversations that were being had. And I go back to what I was saying. The conversation at the time, particularly around these DEI trainings, was this homogeneity in the Black community. And so I don't feel that anyone felt comfortable having these conversations. And that's why after we kind of carried on for a while, I was like, I wish other people. felt this comfortable as I did, so.

Winkfield Twyman: Well, certainly the Harvard Club of San Diego did feel comfortable.

Jennifer Richmond: Well, that's what I'm saying. So, I mean, I think in general, and again, it was lazy of me. It was lazy of me not to look further and just to kind of accept things. But in general, we were being told as white people at the time. That was the narrative. That was the storyline. And I was lazy in parroting it. And if it weren't for you, though, I wouldn't have had the Really, I mean, I think in some ways, too, and this I do think we still continue to see in education, but we've lost the ability of critical thinking. And some of that is just because we're not taught critical thinking. But some of it also is that we have been shamed or shunned into accepting, you know, certain tropes. And that, again, is a disservice for everyone.

Winkfield Twyman: Look here, when I was in the sixth grade, seventh grade, early 1970s, I didn't really have a strong sense of quote-unquote Black identity because everyone was Black. I grew up in an all-Black street. Everyone was a relative. I attended an all-Black church, an AME church. Everyone in my family was Black. But ironically, because of that, Blackness kind of fell away. It wasn't really… an important dimension of my existence. But I remember when I did become aware of Blackness in a positive way, it was reading at grandma's house copies of Black Enterprise magazine. And for your listeners who may not be aware or viewers, in 1970, a businessman in New York City, Earl G. Graves Jr., decided that we needed to do more to make sure Americans were aware of black enterprise, black businesses, black capitalists. And so on a monthly basis, he would recount the stories of black lawyers, accountants, bankers, publishers, construction firms, doctors throughout the country. And for a little kid who was sixth grade, seventh grade, it was such an eye-opening experience because I was shown that to be black in America was to be, quite frankly, a go-getter. It was to be at the height of enterprise. And I think that was really important. And so I never really internalized the idea that blackness equaled oppression, nothing else matters.

Stephanie Winn: thinking about the idea of a ghetto. And what's associated with that, we were joking before we started recording when you guys talked about how neither of you grew up in the ghetto. And I was like, Well, I did.

Winkfield Twyman: Well, there you go.

Stephanie Winn: A little bit of an exaggeration in the sense that like, I lived in like, a nicer part of the ghetto, if you will, like I lived in an area where it was mostly black and more, you know, there was gang activity nearby. There were some more stable middle class families in the area, but also there was poverty in the area, like right on the cusp. I definitely did not grow up in the safest neighborhood, although there were some far unsafer neighborhoods just on the other side. But I think one of the common themes when it comes to poverty and strife and violence and drugs and all that is fatherlessness. And that's probably one of the biggest issues actually affecting African-Americans today. And that was what I had in common. That's part of why we couldn't afford to live in a safer neighborhood is because of fatherlessness. in in my life too but you you don't hear about uh nuclear family privilege you don't you don't hear about two-parent household privilege and and and then in amongst the people who do talk about that stuff there's some concerning trends i don't know if you guys have seen those like bizarre headlines about like If you read to your children, are you giving them an unfair advantage because other kids don't have parents that read to them? Like, have you guys seen that, like, woke nonsense where they're written to the lowest common denominator?

Winkfield Twyman: You used the right qualifier, nonsense. This is so beyond the pale. I probably wouldn't spend much time reading that kind of stuff. For me, I've loved to read. I've always loved to read. I began reading maybe I was five years old, the first word I read was go, and from that moment I kept, I would read a book a day, Stephanie, junior high school, because I loved learning so much. When my children were born, I decided that studies had shown the more words kids hear between birth to three years old, the stronger their cognitive development, so I made it a goal to make sure they would hear, what was it, at least 10,000 words but I can't remember over the course of the term, but there was like a certain finite goal to reach for a maximum cognitive development. And so, for example, we joke about that. When my oldest son came home from the hospital, the very first book I read to him was a treatise, American Constitutional Law by Larry Tried, because I wanted to get into the habit of my kids just not hearing like baby books, but real adult words. And that's been sort of a custom in our family and my wife's family. Her grandparents would always speak with their children using adult language and words. They wouldn't dumb themselves down, if you will. And I think that's a very smart thing if you're a parent, because you want your kids to feel comfortable with a large vocabulary, and reading does that. That's just my thought. Maybe I'm a little too ambitious with the trees, I don't know.

Stephanie Winn: I'm curious about sort of like zooming out to the overall arc of your correspondence and how it has shaped you both as people. You know, I found myself kind of drawn to these questions about Jen of like what it was like for her coming from all these different cultures and then being taught that she needs to say that she has white fragility and then making a friend wink who says, no, you don't. And, you know, those like little parts. But what's the big picture here in terms of sort of where you were both at with your intellectual and moral grappling with these issues when you met each other and what you've learned through your friendship.

Winkfield Twyman: I think that's a great question, Stephanie. I remember growing up and through college and law school and years afterwards feeling I really should keep quiet when it comes to questions of race because the people who really deserve to be heard are those who are suffering the plight of the inner city black And so I kind of self-censored myself because I felt their plight was more compelling, more deserving. I mean, who wants to read about a small-town suburban kid, right? That's boring. That's just middle American. But it was during those years, 2018, 2019, when I thought, no, things are out of control. When your authenticity as a person is being totally distorted, as a black person that I need to speak up. So I think for me, the biggest arc was getting over the self-censorship, that my story didn't matter as much as the story of people who lived, applied to the poor inner city people. And I think that was an important mental change for me, because I think it's very easy for black Americans who have only known affluent suburbs to feel a sense of guilt, to feel a sense of why me, to feel a sense of misalignment with the larger Black American community. And that never really goes away. So to handle those feelings of misalignment, your story to the greater story, I think people cling to things like solidarity, racial solidarity. Jen, you remember this. We were talking to a very privileged Black American person in our country. And we were just talking, and she had grown up in a very comfortable suburb, right? And she had lots of white friends. But when she went to college, she decided that she needed to live in an all-Black dorm. And I think either you or I asked the question of why. And I remember she used the word solidarity. I remember that. She said, well, I'm going to be in racial solidarity with other Black kids. I think that that can be problematic because the logical consequences of that are going to be a feeling of misalignment if your life story doesn't align with the narrative. That's just my thought.

Jennifer Richmond: I had come back before the race thing. If you would have told me I'd be writing about race when I'm a China scholar, I would have said, what? But it's really been so eye-opening. I think it's It's not that I wasn't curious before, I think I was, but you know, I mean, my curiosity was stunted until I had this conversation with Wink. I'll say I also, it was a period of my life where I was in a relationship with someone who was incredibly opinionated and closed-minded, and it gave me an outlet to have these, again, have the conversations, but then to allow my curiosity to reign instead of reigning it back in. And so from there, I mean, everything I've done actually, Stephanie, since this time is to try to continue to promote curiosity and to promote conversation and courage, curiosity, courage, conversation, the three C's there. But, you know, I run an organization called the Institute for Liberal Values. classical liberal values. And part of what I do, our own podcast is called The Dissidents. And so having conversations with people who aren't afraid to speak out, and or providing that community for people who are where they feel that they are more comfortable in speaking their own truths and exploring these ideas. And so that conversation with Wink opened up all these possibilities now that I am currently exploring professionally. So it was a watershed moment for me.

Winkfield Twyman: In 1972, I would have been at grandma's house and we might have been discussing whatever. And there had never been a sense that you had to watch your words or walk on eggshells. Uncles spoke freely about everything. Fast forward to the early 2020s. I remember a sense of foreboding because I didn't want to talk about anything racial inside my family because of their positions. And at one point at Thanksgiving, there's a family member I'm thinking of. I just I just couldn't keep it in, Stephanie. I'd have to be curious. So I asked the family member over turkey and gravy. I asked her, you know, is there a place for the individual in blackness? And I swear, Stephanie, She was tongue-tied. She couldn't answer that question. And to me, that was so telling, because I'm like Mr. Individual. I'm nothing else. So for this family member just to be tongue-tied at the question, is there an individual in blackness, well, it kind of gives you a sense of my internal misalignment.

Stephanie Winn: Hearing both of your responses, one commonality that I hear is sort of overcoming any obstacles that shame might have placed. Like, wink with your answer. that this story arc for you was about starting from a place of my story doesn't matter, I need to keep my individuality quiet for the sake of this thing outside of me, right? the it seems like that's sort of like maybe a shaming message that you would internalize like don't don't deviate from the group think don't share your experience if it's not convenient to the narrative we're trying to tell about what people like us go through even though in your experience you can recall as a child that the magazine you were reading i can't remember what it was called enterprise Yeah, like you recall that successful Black people sharing their stories was helpful to you, and yet you had to kind of dismiss your own experience that sharing your successes was going to be helpful to other people, that all the emphasis needed to be placed on people who are suffering in a very particular sort of cliche way. And not only that, but I would add that the nature of the suffering, the nature of the suffering that was supposed to be highlighted, the ghetto, right? The idea seems to be that this suffering is because of racism, as opposed to, you guys both leading with curiosity, like, let's be curious about what constellation of factors is creating the suffering. If we really want to solve any problem, We have to be curious, like you're saying, about what constellation of factors is contributing to the problem. Oversimplification might obscure solution finding, and that means people stay trapped in suffering. So I just hear you kind of removing that barrier of the cultural messaging and shaming and saying, nope. my story matters. I'm going to go ahead and tell it." And then the same thing for Jen, like you talk about being a naturally curious person, which is something I hear you both kind of keeping coming back to as a shared value. And that was like shamed out of you. You were part of this first very open-minded culture, and then as you witness this kind of like woke takeover of the culture around diversity, there's this idea, oh no, you can't bring your questions here. You were supposed to have done your homework already. I'm not going to tell you what that means, but you're supposed to come prepared. Don't ask questions, right? So that had been like shamed out of you. Yeah. And then you kind of reclaimed it and you found your innocence again. And I feel like right now, anyone, even the slightest bit left of center, who's a white American, is at risk of losing their sense of innocence and their ability to kind of protect the innocence of their heart. Because I feel like when white Americans who are open-minded, who are trying to talk about any of these issues, reveal their either ignorance or their disagreement with the narrative, or they're not coming forth in this sort of masochistic way, that they're treated as if there's this like guilt of original sin on us. It reminds me, I got into this confrontation, not a confrontation, I just got into like a weird conversation at a cava bar in Hawaii of all places. And I could tell wokeness was in the room, let's say. I kept trying to operate from first principles. I was like, I'm just gonna pretend I don't know anything about wokeness. And like, I don't recognize some of the cliches these people are bringing in. And I'm just going to operate from first principles and see how far I can get. I didn't get very far. And I remember there was that like, oh, what's it called? There was like, you know, the Kafka traps that are embedded in wokeness, right? Where like, if you say you're not, then you are. And if you say you are, then you are. And either way, you're we're going to burn in hell. I remember they set up one of those things where I was like, I disagreed with something. I said, no, that doesn't feel right to me or something. And this woke guy was saying something like, oh, well, then maybe that's proof that it does apply to you. He started pulling one of those. And I was like, nope, nope, we're not doing this. Nope. I just shut it down. But it's taken years of practice. grappling with these issues for me to get to the point where like, oh, you're trying to tell me that if I deny being racist, that makes me racist? Actually, no.

Winkfield Twyman: You know, Jen and I, well, remember, I had this experience with a gentleman. I oppose reparations for American slavery, Stephanie. I think it's like the second worst idea in history. The worst was slavery. But I was talking with this gentleman from a graduate of Harvard Law School. And I just mentioned casually that he had invited me to partake, I think, in Harvard's support for a study of reparations. And I just casually wrote that guy back and said, you know, I don't think I'm really down with that. You know, my grandma, born in 1897, didn't need reparations or demand, so why would our grandson? And he literally lost his mind, Stephanie. I wrote him like a one-paragraph response. He came back at me with like a three-page treatise. And I replied, and I got bombarded with 25 pages of source material and everything. And it got to the point where he just wouldn't let go. You remember, Jen? We invited him.

Jennifer Richmond: He wouldn't let go, but he wouldn't listen either. He wouldn't listen. I mean, again, Stephanie, you said something really good. It's probably because you're some kind of a therapist. Yes. But Wink really did help me reclaim my curiosity. I mean, I just put that language around that right now, but this man refused to be curious. He refused to go, well, that's a different story. Like, that's not the story I've been hearing. And here are some of the facts that back up what I've been hearing. But tell me more. Tell me about your story, because this one's new. I mean, there was no cure. He was trying to, I mean, it was like, it's sledgehammer, you know, sledgehammer to wink and just saying you if you don't believe this, you again, this goes back to authentically black. And this gentleman wasn't even Black. He was trying to make Wink authentically Black.

Winkfield Twyman: He was trying to tell me he knew my grandma's story more than I know my grandmother's story. This is a strange conversation. I mean, Stephanie, one of the things I do personally is, and Jen knows this, I've adopted a personal rule, I just don't engage bullies. I don't engage bullies. So when I can tell in the conversation that it's no longer good faith back and forth, it's no longer about curiosity, but you're trying to force a narrative, I just will just say, sign off, no thank you, see you later. And that has worked for me. Do you think that's a good strategy to take going forward? Or is the downside of not engaging bullies is that you eventually end up only talking to Jim?

Stephanie Winn: No, I mean, it reminds me of that conversation at the Cabo bar where I was, I was, I was trying, but I mean, I remember there was a moment where I could feel that he was coming from dogma.

Winkfield Twyman: Yes. Yes.

Stephanie Winn: And, and I started like, I just hinted that there was more. I was like, you might be surprised if you knew some of like my background and where I come from. And he didn't respond to that with curiosity. He responded with, Oh yes, I'm sure you're a very good person. Yeah, I mean, I don't engage with bullies either and you can feel it, right? You can feel people's intentions and like energy and vibe. And I commend you guys for engaging in back and forth in writing. I think it's amazing that you've managed to have such a peaceful and deep friendship over written correspondence because I do not generally recommend people try to solve interpersonal issues in writing. But let's get into at least one of the issues, though, because, Wink, you said you oppose reparations for slavery.

Winkfield Twyman: You got it. Can you tell us why? Oh, my Lord. I once told Jim that I was going to write a thousand essays opposing reparations between now and the end of the decade. I so despise the idea. I'll give you three quick reasons, Stephanie. Number one, I wasn't a slave, my dad wasn't a slave, his father wasn't a slave. You have to go back generations to find someone who actually wasn't a slave. Why would you take money from people who were not slaves, slave owners, and give it to people who were never slaves? That's number one. Number two, it is such an affront to black agency and black enterprise. I mean, the implicit idea is that, well, you must be downtrodden in the year 2025 because of the slavery of a 5X great-grandparent, so we're going to throw some money at you. No, no. Number three, there are studies that show that those type of redistribution of resources, they never last over a generation or two. There's a famous study of the Cherokee. Remember the Cherokees were forcibly removed from their land in Georgia under President Andrew Jackson. Well, the land that remained was now controlled by the state of Georgia. They decided to have a lottery system and award, I forget, maybe 100 acres or 200 acres of land to every free white person who applied. Well, everyone applied. So everyone got this windfall of land. Guess what happened, Stephanie? Although in the first years these people were better off than people who didn't participate in the lottery for land, by the third generation, not only were the grandchildren not better off, they were worse off because they had inherited this idea of dependency. that things just fall from the sky, manna from heaven. So to me, reparations would be the same thing. You're just reinforcing the idea that, well, we can turn back the hands of time, we can give you a windfall, we can make matters right and call it a day. And in fact, what you've done is you've created and furthered a culture of dependencies. That's why I don't like the idea of reparations whatsoever. I think it's horrible. I think it's bad. I think it's wrong. Stephanie, heck, people don't talk about this. You know that there were blacks who were slave owners, right? There were some who owned slaves, right?

Stephanie Winn: And you talk about that in the book. I do. And I think that's the next chapter of our conversation.

Winkfield Twyman: So to me, it's so immoral and unethical for the descendants of not one, not two, not three, but four generations of free black slave owners to be at the public trough to receive reparations. Instead, they should maybe be paying reparations to the descendants of the slaves that were owned by their ancestors. But that's a different story for another time. Am I too excited, Stephanie? What's that? Am I too excited?

Stephanie Winn: So to recap, it's an affront to black agency. It's not relevant to current issues. It would end up leveling out anyway. I think that's actually a really interesting point, both in terms of economics and psychology. Yes. Just what we know about, for example, how most people, several months after either a major windfall or a major trauma, happiness tends to return to baseline. Right. And, you know, similarly, a lot of people have made the argument that if you were to take a rich person and a poor person and either start them out, both out with zero dollars or start them both out with a million dollars, like whichever path you choose, you would notice over time the rich person engaging in the behaviors that establish and maintain wealth and the poor person, you know, behaving in ways that undermine their wealth. So you make a lot of interesting points there, but I want to play devil's advocate for at least two, please do straw has still men still men, especially when it comes to your first point saying well, like my grandmother wasn't a slave and you know, so setting aside for a moment the very complicating factor of the reality that you yourself, as you explain in the book, are the descendant of both slaves and slave owners. You know, setting aside how complicated it actually is and the fact that slavery exists in all cultures going back and that Africans enslaved each other and sold them to Europeans and, you know, everything that like really muddles the issue. If we just set that aside for a moment, Intergenerational trauma, this idea of post-traumatic slave syndrome. So what if someone would say, well, just because your grandmother wasn't enslaved does not mean that you were not disadvantaged as a result of intergenerational trauma because of what happened to your ancestors.

Winkfield Twyman: And my response would be, well, identify the concrete and specific trauma. show me, tell me. I mean, from what I know, I come from a family of property owners, a family of church worshipers, a family that created a street in which everyone was related and was named after our family. I mean, I never sensed growing up that slavery was something that made a difference in the hearts and minds of relatives. I didn't. I learned about slavery in the fourth grade, and I wrote an essay about this for free for my thought. I mean, all I need to know about slavery, I learned in the fourth grade. I mean, it's the year 2025, time to move on. Unless you can offer specific, concrete, vivid evidence of intergenerational trauma, I don't see it. And not only do I not see it, in the book I mentioned several families that actually knew slavery, that rose to the very pinnacle of wealth and influence in our national history. U.S. Senator Blanche K. Bruce from Mississippi, case in point. born a slave by March 1st, 1841, was manumitted during the Civil War, 1862, by his father, who was a slave owner, by the way. And he would become a very wealthy property owner in Mississippi and a U.S. senator from Mississippi. And eventually he would have a son who would go to Phillips Exeter and Harvard and become very prominent in color education in the 1900s. And he would have children All two sons graduated from Harvard Law School in the 1920s. So if that family had a family father who was a slave, who picked cotton in Mississippi in the 1850s, where's the concrete specific evidence of intergenerational trauma mandated by slavery. I don't think it's there, number one. Number two, you would have to read tea leaves to discern, well, is this decision or that decision by a descendant in the year 2025 in some way remotely linked or tied to intergenerational trauma? I don't see it. Stephanie, I think the real trauma is what we learn about slavery over and over again. I actually think the trauma comes from recreating the experience. I've written about the need for, tongue-in-cheek, slavery blockers. Because if you could create a system whereby every descendant of American slavery just received a slavery blocker, So whatever the word slavery was uttered in the classroom, the world classroom, they wouldn't hear the word or they wouldn't be able to read the word. I wager that in 10 to 20 years, you would no longer have this dependency on slavery as a reason for more achievement. There would be other reasons, but American slavery would be taken out of the picture, as it should be in any event. Go ahead, Jim.

Jennifer Richmond: So I was just saying, I pushed back on Wink on this idea of post-traumatic slave syndrome. And he kind of turned it on his head and said, well, what about you? Do you have post-traumatic slaveholder syndrome? But that really got to the heart, I think, in our conversation on individuality. And I think Wink did a really good job of it. to to read the tea leaves. I mean, you've got people who black and white who have come from nothing and made something of themselves and have come from something and made nothing of themselves. And so do you see these stories more in black America? I don't, I don't, I don't know that that, that holds. And Wink would say, Why couldn't you see that as fuel for advancement, fuel for entrepreneurship? And is that just, is that, does that, is that based on your personality? Are some people more likely to see trauma or challenge as something to rise, you know, for them to rise to or something to, you know, push them down. And is that an individual trait more than a post-traumatic slavery?

Winkfield Twyman: The idea is post-traumatic growth syndrome, not post-traumatic slave syndrome, trauma syndrome, but post-traumatic growth syndrome. There are people, because of their personality and character, who are turbocharged by challenge and adversity. I write about those people all the time on my sub stack. But yeah, that's what I think, Stephanie. I think that unless you can show me the concrete evidence, I'm not persuaded.

Stephanie Winn: I'm thinking of the roles of culture and family as protective mechanisms with regard to the aftermath of slavery. Because the fact that slavery was traumatic is pretty indisputable, but you know, how many generations does that ripple down through and to what extent and how I think when it, you know, when we're looking at risk factors and protective factors, you guys are talking about the role of choice, but I hear you saying, Wink, that you come from a stable family and a family that was rooted in one place for a long time and had its traditions that kept the family and the culture thriving. And I'm thinking, I wonder what makes the difference and what you think makes the difference between Black Americans like you who are thriving and don't feel that slavery and their ancestry has made that big impact and those who are not and do. Is it all belief? Is it all narrative? Or could there be a component such as the extent of the abuse that took place or how badly the abuse disrupted family structure and disrupted the traditions that people turn to for comfort and renewal?

Winkfield Twyman: Well, let me take a stab at that. What makes the difference? I'm going to offer two points. One point I think is not a hot take. The second point might be more radioactive. I'll just throw out and leave it at that. But the first point, I think, Stephanie, I think families inherit more than a name or more than an ethnic heritage. I think families inherit personality. I think personality flows down through certain families. For example, there are families of lawyers, there are families of doctors, there are families of dentists, there are families of ministers. I know that. There are several ministers in my family. I wonder if there is something about a quirky, nonconforming, a creative personality that shields one from any lingering effects of American slavery. One of the things about my family is, God, they were quirky. They were eccentric. Aunt Amy, A mathematical genius passed and advanced through three grades in school. She eventually would become the crazy aunt in the attic, but be that as it may, she was very smart. She was a genius. Then there's Uncle James Scott. Uncle James Scott, who had no social awareness or intelligence, but for one thing, He loved real estate development. That was his thing. He lived for real estate development. Another uncle who never loved his mother. Why? Because his mother felt he was less successful than another brother. So he was driven to achieve because he tried to find his mother's love throughout life. Another aunt, my aunt Charlotte, always, always, as long as I remember, would sit in the very back of the church in the same pew, the same seat for like 10 or 20 years. And when the minister ended the service, she was the first person out that door as quick as she could, because she had business things to attend to. Those are quirky traits. And they were in this one family. I think that shielded the family in some ways from the lingering effects of slavery, because people recognized that we're all unique, we're all individuals. Aunt Amy is not Uncle Scott, is not Uncle Willard, is not Aunt Charlotte. And so I think that's part of the answer. Another part, and this is more of a hot take part, which I really hadn't thought up too much, but I think, and Jordan Peterson has talked about this, Stephanie. Could it be that a component, whether big or small, might be just a cognitive ability? And I raised that point because when I was in the sixth grade, I remember I was just a driven kid. I remember I would read a book every day. I would try to ask the most questions in class. I always was curious and wanted to know about the larger universe. One day, my sixth grade teacher took me to the principal's office. And I knew I wasn't in trouble because I was a great kid. I was a nerd. But she took me to the principal's office and sat me down. introduced me to this wonderful woman. And then for the next 30 minutes, that woman just quenched me. She asked me questions about this, that, and the other. I remember the very last question she asked me was, have you ever read The Pilgrim's Progress by John Bunyan? And I said, no, but I'm dying to read it as soon as I leave this office. And as a result of that interview, which is really kind of an IQ assessment, the county diagnosed me as gifted and talented in the gifted and talented program. And I was just simply one of many people in my family that were quirky and eccentric. And I think sometimes a high level of curiosity aligns with uncommon level of IQ. Could it be that for whatever reason, we don't have as many people who are black Americans at the far right end of the bell curve? And so we see some of these consequences that we think are the lingering effects of American slavery, but they're actually more the lingering effects of personality and things like curiosity and cognitive ability. It's the curiosity that creates the smarts, the giftedness. That's the way it works. So people are questioning people all the time, as my uncles and aunts did. It's going to raise your ability to be inquisitive about the world and to do better on tests and whatever.

Jennifer Richmond: Yeah. You know, Wink, I was going to mention something, and you mentioned this in the book. I think you call him baby felon. Oh, yeah. Yeah, double hot. But you I mean, you you're sitting you're talking about all your family that's so curious, quirky and whatnot. But you also have people in your family line who who could potentially say, Oh, I've got, you know, hang their hat, their criminal activity on post-traumatic slave syndrome. So how do you square that, like in your immediate family line, you have people who aren't quirky and I mean, could they have somehow suffered from PTSS whereas you didn't?

Winkfield Twyman: And that's a great question. I love that question, Jen. And the answer is, if you grew up in the same house with the same sets of parents and grandparents, you're subjected to whatever faint whispers of slavery there might be. So that's not going to be the defining angle, right? Because everyone has the same relationship to slavery, if you're a brother or a sister or a cousin. So to me, that's not a defining factor because everyone has that same relationship. Now, you could argue, and this is a good argument to make, Well, it's your personality. That if you have a particular personality that cares more about curiosity and the outside world than dogma and racial solidarity and racial consciousness, there might be a different outcome. In other words, the argument can be made that certain personalities may let in the leery effects of American slavery more than other personalities. And maybe, Jen, that's the argument you would make is that it becomes a factor of personality. Maybe that's it. Maybe that's it. But yeah, Stephanie, Jen knows all my stuff. I definitely have a few relatives who have not always been very successful or achieving, but I chalked it up to one, just the way they are, two, peers, their peer pressures. Yeah.

Stephanie Winn: You guys are speaking my language. Personality, intelligence, and choice. make up for a lot of where we end up in life. And personality is that mix of nature, nurture, and that.

Winkfield Twyman: But Stephanie, notice what I did though. Notice how I was hesitant to use the words cognitive ability in this discussion and how I made sure that I backtracked and said, well, it's a factor of the curiosity and the introspection and the quirkiness. It's because I think there's this great hesitation and reluctance to talk about cognitive ability when we talk about race. But I think for me, that's probably something that lurks below the surface. But I think, once again, I think it's a factor of personality. If you have parents and uncles and aunts that are questioning you every day, like it's moot court time. Like when I raised my kids, we raised our kids, I would always ask my kids, what do you think? What's your reason? I would never let my kids offer a position without telling me, well, what's your reason? What's the underlying argument? And, you know, dinnertime became kind of a mini moot court, because you force your children growing up to use their cognitive abilities, their argumentative skills, their logical skills. And I think that's why my kids, you know, did kind of well. My oldest son just graduated from Stanford as an MBA. My middle son will be completing his master's at San Diego State. And my youngest just graduated from Yale this past year. And we're a black American family.

Stephanie Winn: Many of you listening to this show are concerned about an adolescent or young adult you care about who's caught up in the gender insanity and therefore at risk of medical self-destruction. I developed ROGD Repair as a resource for parents just like you. It's a self-paced online course and community that will teach you the psychology concept and communication tools the families I've consulted with have found most helpful in understanding and getting through to their children, even when they're adults. Visit ROGDRepair.com to learn more about the program and use promo code SUMTHERAPIST2025 at checkout to take 50% off your first month. That's ROGDRepair.com. So we said we were going to circle back to this point about slavery and that you, Wink, have both slaves and slave owners in your genealogy. I do, I do. And I think there's a lot of, you know, myths that you dispel in your books. So I just want to give you the floor.

Winkfield Twyman: Well, you know, it's interesting. I've had few knock down, drag out intellectual battles with my children. But one battle, which continues to this day, would be over George Washington. I discovered, because I love genealogy, that George Washington just happens to be a second cousin seven times removed. That's right. And to me, that was like, wow, that's neat, because I was a history major. I enjoy stuff like that. And I remember I was in Charleston, Virginia, shopping around for something. I saw this wonderful oil portrait of George Washington kneeling in prayer at Valley Forge. And I thought, wouldn't it be great to bring it home and hang it on the wall? So I purchased it, took it home, wrapped it up under the Christmas tree. Christmas came, and I was ready to unwrap it and to place it on the wall. And a particular family member said, do you own slaves? I said, yes. He's not going on our family wall because he owns slaves. No slave owner shall be on our wall. And I thought to myself, what do you do about it? It's George Washington. Our national capital is named after him. You know, there's a Washington Monument. There's a Washington Street in every town. There's a Washington State. But the family member would not budge. And so I remember in despair. writing about that family dispute to the Richmond Times-Dispatch in the Chicago Tribune. And I wrote about the harm of clinging on to slavery so much, so much that it denies you the blessing of recognizing and honoring all of your ancestors, regardless of their race, regardless of their relationship to slavery. So, yeah, yeah. To this day, we never really have reconciled, although George Washington proudly stands on a wall in my office. So not at home, but in my office. So I went part of the doubt there.

Jennifer Richmond: I think that was one of the really interesting things too that happened as a result of this correspondence is Wink is so interested in genealogy that he had me do my own genealogy and find, you know, I had several black, you know, family members or, you know, descendants of slaves in my genealogy, who I reached out to and then was able to have, again, a real conversation with someone who was at some level related to me. And I think that realization too, I think was so important. And it's really interesting that it's kind of okay for white people to have that realization and to look back at blacks in their family history. But Wink, I think in some cases, your family has decided to blackwash or whitewash your family history because they won't recognize anyone who's white as true family versus someone that looks like me. You know, I mean, it was, it was way much more of a, again, I don't want to use the word watershed too much, but I mean, it was an eyeopening experience and completely different for you.

Winkfield Twyman: Stephanie, we will never reach unity as a country. in terms of race until Black Americans come to the table and just embrace all of their ancestry. I mean, it's already there. The DNA in me, it's already there from Daniel Brown, from George Twyman III, from Colonel Richard Lee I. It's you're just acknowledging your complete genetic composition. You're not pretending you're 100% black, and you might in fact, only be 48% black, I'm thinking of somebody in particular. To me, that's just, that's just self hatred. That's just, I'm not sure what that is. It's almost like you need to carry the burden of the great, great, great, great grandmother who may have been in a forced sexual relationship. Because of that, you just can't recognize anyone in your family tree unless they are a black American. To me, it's ridiculous. And I think if we, as black Americans and white Americans, recognize our common genetic heritage, we would find we have more in common. We would have that sense of family extend beyond the borders of blackness to include the larger world. I'm really big in engaging the larger world.

Stephanie Winn: Well, let me get kind of philosophical for a moment here. I think some of this comes down to notions of good and evil and wanting to be able to split off and project the parts of us that we're afraid of or that we feel loathsome toward onto other people, particularly a group of other people who are kind of faceless and nameless to us, like another race is kind of the perfect scapegoat. And, you know, if you see yourself as black and not white, then whites are a race different from you, even though, like you said, you're probably actually both. And it's very easy to kind of cut off any parts of yourself and put them onto that other group, including our fear that this darkness lives within our heart that is capable of doing terrible things. But I am more afraid of people who haven't reckoned with that sort of inner demon. I'm more afraid of them because there's so much more potential to project the shadow onto other people than those who have grappled with that. And so when it comes to slavery as a, you know, pernicious form of evil, we can we can look back in hindsight from the comfort of the 21st century and say, yeah, that was really terrible that people ever did that. We're coming from a time when we have are you guys familiar with the concept of ghost slaves? So the idea is that if, and I'm going to distort this idea because it's actually been a while since I learned it, this is my interpretation of the concept of ghost slaves. If you have a comment, feel free to leave it on YouTube or Spotify if you have something to add respectfully to this discussion. But my understanding of the concept of ghost slaves is that if all we had was, let's say, 18th century technology, If we didn't have electricity and running water and plastic and, you know, all the things that make our lives easier, we would all be working a lot harder, doing a lot more manual labor and being a lot more physically uncomfortable for a much lower standard of living. And the idea is that with all these lights running around me right now, the temperature control in my house, the cleanliness of my clothes thanks to this miraculous machine in the next room, and all of the modern conveniences, not to mention high-speed internet, the fact that I'm talking to you guys using this technology. I mean, there are so many comforts and conveniences that we have that would have been shocking to our ancestors. And the idea of ghost slaves is that the demands that those technologies placed on the environment and on people in distant parts of the world are, you know, they're like ghosts to us because we don't see them. And there may or may not, depending on the technology or the luxury or convenience that we're talking about, there may or may not be actual human beings who are harmed by our lifestyles or animals, depending on how much sentiment you have toward non-human creatures. But we are definitely placing a burden on the environment. And the amount of energy that goes into probably just the technology to have this conversation right now That's like the amount of energy of people plowing fields by hand, you know. So and someone's feeling that cost. And we know that that slave labor does exist. Slavery is not a thing of the past. Slave labor exists. children and all kinds of people are being exploited all over the world for us to have this modern lifestyle. And we don't feel directly responsible for it because we are not the ones making those decisions. And it's not right in front of our faces and everyone else is doing it. But I think there's so much hubris in this idea that, you know, when when we're in our modern, comfortable homes with our, you know, infinite amount of food that we can have delivered to our house when we're living this comfortable lifestyle and we say, oh, George Washington, he owned slaves. Therefore, we don't acknowledge him in any way. It's this idea that if you existed during George Washington's time, you definitely wouldn't have slaves. And I don't think anyone who's assuming that about themselves has taken a really honest look in the mirror. Because if, first of all, not I mean, as you explain in the book, like not everyone of a certain era did own slaves. But if you were in a certain class or had a certain amount of land to manage or things like this and you were to voluntarily forego that thing, that technology, that human technology that everyone at your level in society had access to, you would be disadvantaging yourself in the same way as me today choosing to live without internet or electricity. So I'm not saying that that justifies slavery, I'm not saying slavery good, slavery acceptable, but I'm saying it takes a tremendous amount of arrogance to think that you would have made a different decision if you were in George Washington's shoes or anyone else's shoes because it's like Are you voluntarily living today in a way that is lighter on the planet and lighter on human beings in distant parts of the world? You know, those children slaving away in mines to get the silica for your cell phone. I mean, you know, like that, that's what that makes me think of. And I hope that I can say that without people hearing that as a justification of slavery. It's not. It's just saying, Who are we to condemn our ancestors when we were not in their shoes?

Winkfield Twyman: I agree, and I think that takes a certain, and except to compliment Stephanie, I think it takes a certain insight and empathy and perspective taking, perspective taking, if you will. You can see yourself in the shoes of a George Washington or Thomas Jefferson or Patrick Henry. Could it be, Stephanie, that there are people who simply lack that ability of perspective taking? They're just unable to do that.

Stephanie Winn: I think, I mean, and you said earlier that the conversation around IQ is something that, you know, you prefer to put it in certain terms, but below a certain IQ, people do lack the ability to take perspectives and engage in abstract things. I don't know if you guys saw that video of the lady with Down syndrome that was going around. This is a little bit of a tangent, but there is this video of this woman with down syndrome being very angry, in like a Greta Thunberg sort of way, saying like, you presume I can't do all these things and so you don't give me the opportunity to try and so I don't, but you should treat me like I am capable of doing all these things. And I analyzed the video like, okay, what is, I looked up the average IQ of someone with Down syndrome. It's about 55. People with Down syndrome on the whole are generally not capable of abstract reasoning. So one of the things mentioned here is understanding Shakespeare. That's actually probably out of reach for someone with Down syndrome. Similarly, she was talking about things like drinking alcohol and having sex. Yes, people with Down syndrome absolutely can drink alcohol and have sex. However, their naivete places them at greater risk than the average person of being taken advantage of or harmed if they put themselves into situations where there's alcohol and sex involved. So this message is not necessarily harmless. This message that we should treat people with potentially very low IQs as if they're capable of the same thing as people with higher IQs, Like people could be harmed if that message is interpreted incorrectly. So that was something that came across my radar this past week and it just, it feels connected because when you say, are certain people cognitively not capable of perspective taking, it's, yeah, I do think some people are cognitively not there. I think a lot of people also just choose not to exercise that capacity and could definitely become better at it, but their arrogance is in the way.

Winkfield Twyman: Oh, wow. Oh, wow. Their arrogance is in the way. That's deep.

Jennifer Richmond: Arrogance. And I would say, Stephanie, I think also we've become more, with all these technologies, like you were talking about, and with social media, we've become more disassociated from each other. You know, I mean, talking on a screen, you're talking over Twitter and all these other ways that we've chosen to communicate while we communicate so much more than we ever did. It's at such a superficial level without any depth.

Stephanie Winn: Quantity more than in quality.

Jennifer Richmond: Right, right. And so I think that in a way, it's almost like playing violent video games. We're lacking empathy.

Stephanie Winn: Well, when you talk about the dissociative element of this virtual communication, there's a few elements to that. One is that it's often asynchronous. It's weird. As someone who spends as much time online as I do, I really prefer synchronous communication. So I spend most of my time on video calls, whether it's like this recording a podcast or whether I'm doing a consultation, because at least even if we're not in the same place, at least we're in the same time, at least we're in real time together. And I value that. So there's there's that lack of synchronicity. And then there's a lack of context, like physical context. That's why I shared a picture on social media today of this project I have in my office. It's a beading project. I'm making jewelry just because I realized I post so much really heady stuff on X and people have no idea what I'm physically doing. You know? So yeah, I feel sad that we're missing that being simultaneously present with other human beings in the same environment where context is present, both, you know, social context, reading each other's cues in real time, but also just that we're feeling the same air on our skin that, you know, we're hearing the same sounds of nature outside, but

Jennifer Richmond: You know, my friend Angel Eduardo one time said, with regards to context, he said, you know, the context, we're just talking about generationally, the context of 2025 is so different than the context of 1875, but we're treating it like it was the same.

Stephanie Winn: I once spoke with someone who has a passion for historical fashion and made like this person chose as a hobby to make clothing that was similar to the clothing that women would have worn in the 18th century. And I just thought that was so interesting. And I remember hearing her share about it. Like I wanna feel what they felt on their bodies. Like I wanna feel the textures of those cloths on my skin. And I remember I found myself using the phrase hitting like visceral empathy. We're missing that tactile component of things. We're just missing like the sensory relatedness on so many levels.

Jennifer Richmond: And you mentioned something earlier, even though with letters, clearly we're not in the same time period, it's not synchronous. But I think what was so useful or helpful for us was it took, because this was such a heady topic, it took us, I had to sit there and digest what he had said. So it wasn't something like in a conversation now, I might jump the gun or speak off the cuff. I mean, I had to really take in what he was saying and respond in a meaningful way. And I think that even though letters, again, aren't one-on-one, face-to-face, it was so much better than the conversations being had on social media. I mean, there was context. It was rich in context.

Winkfield Twyman: Right, right. Now, having said that, of course, there were times when I felt that I shared part of my story, my experience, and it was completely new to you, Jen, completely new and foreign, and I did my best to educate you, and I hope you got it. For example, I'm thinking of Jack and Jill. Jack and Jill. Are you familiar with Jack and Jill, Stephanie? You are now, of course, having read the book.

Stephanie Winn: Remind me.

Winkfield Twyman: But Jack and Jill is this association of black moms. It was formed in 1938. And the Black moms formed this association because they wanted their kids to have playmates with other Black kids who might be the children of doctors and lawyers and dentists and professors and what have you. But the associations continue to this day. There are about maybe 30,000, 40,000 members nationwide. But the reason I bring it up is In my life, my life really is not racial, Stephanie. I don't go around thinking about race.

Stephanie Winn: Even though you wrote a book on it. I know.

Winkfield Twyman: Can you believe it? It's crazy. It's craziness. I told you about that. I mean, my default position is like no racial consciousness. However, there was a way in which I was always reminded of race for the past 10 or 20 years in my house. And it's because my wife came from a different background. She's from a very strong, black, middle class, upper middle class family. And one of the things they belong to is Jack and Jill. So she made sure our kids joined Jack and Jill. She was a member of Jack and Jill. My mother-in-law was a Jack and Jill member. My grandmother-in-law was a family member of Jack and Jill in Brooklyn. And so I tried to communicate that part of my life, which was really the racial part of my life, to Jen. And I wasn't surprised. It was like totally new and strange and alien to her. But I hope I succeeded in sharing that dimension of my life, my otherwise non-racial life. Did I succeed, Jen, or is Jack and Jill still kind of a mystery to you, in a sense?

Jennifer Richmond: Well, you know, when you first mentioned it, I thought you were talking about nursery rhymes. So that's how foreign it was to me. And that's when, you know, Wink had me read a book called Our Kind of People. which was stories of Jack and Jill. But again, these are stories, I feel like we have flattened the black experience into being just one experience in the way that we talk about the black experience. I mean, that, our kind of people was, I mean, here I was, you know, a full grown adult, a mother, I had no idea of this world. that you're now talking about with Jack and Jill, but also, you know, black sororities and fraternities and whatnot. And I mean, so I became so much more educated as a result of the conversation. But it's it's just so funny because there's even books out there that talk about it like our kind of people. But yet there's we have flattened the black experience to one of just this victimization narrative, again, to a huge disservice to the diversity within the black community.

Winkfield Twyman: Now, I'm curious because in some ways, Stephanie may have grown up more immersed in Black culture than I did. So I wanted to ask Stephanie this question. When you were growing up in Los Angeles, had you heard of Jack and Jill or Alpha Kappa Alpha or the Belay or Alpha Phi Alpha or Phi Beta Sigma? No? That's interesting to me. That's very interesting to me. because there are definitely black networks in Los Angeles for whom that is the center of their social life. That is kind of how they make adult friends. That's how they find marriage partners. That's how friendships are kind of created. So it's interesting to me that that's new to you. That's interesting. There's a gentleman who you know, Michael Bowen, who I know from Free Black Thought, and he's a member of Alpha Phi Alpha. And when I talk with Michael, he instantly gets it. He recognizes all the names. So I think it's an interesting sign that you could grow up near the ghetto in Los Angeles, but still that part of black life could be far removed from you. To me, that's kind of interesting in a way.

Stephanie Winn: I mean, I was it was mostly coming through my peers. Yeah. You know, so like if their parents belonged to societies, I wasn't necessarily hearing about that. I think I was getting like. 90s Black youth culture and 90s pop and R&B and like a little bit of like Bloods and Crips. That's a little bit different from Black kids. I mean, I know about how like Black kids love their shoes. and basketball and like, you know, those like tropes and cliches. And like, I mean, honestly, there are even some elements of my cultural upbringing in that environment that I have not been able to successfully integrate into my personality because all of this like racial tension has made me feel like I'm not allowed to Like, for example, I grew up around, like, oh, no, he didn't. Like, I grew up hearing, like, certain expressions like that. And, you know, you your language, depending on the context, often has elements of the slang that you grew up around. But there there's moments that I have, like, a little, like, 90s black kid voice in my head that, like, wants to say something that and it won't come out my mouth because I'm like, oh, you're not allowed to talk like that. I mean, that was part of the double bind that I

Winkfield Twyman: But isn't that horrible though, is that you can't be your full self in the current environment. I mean, that's part of who you are, but you have to self-sense.

Stephanie Winn: I don't feel like I can, like, this sounds strange because I have created a life where I have a lot of freedom, like moral and intellectual freedom. I'm self-employed. I'm able to support myself as someone who has a podcast and a consulting service where I'm being truthful and real. But I guess one way I heard it described well that related to me is if you have a broad variety of life experiences that you have a lot of surface area to connect to people on. And I don't feel like there are very many contexts where I can share all that surface area. And I think that's fine. Like we're multifaceted as human beings. But yeah, it like surprises people when like 90s hip hop comes on and I feel it in my body in a certain way. Yeah, I feel like I have a fragmented identity in some ways and I want to say like the one of the double binds that I grew up in as and I'm fascinated by the subject of double binds and I incorporate it into a lot of my work and one of them was like, Like, I don't know how I would articulate it actually, but I remember getting the message that like, even though I was surrounded by black culture that I wasn't allowed to participate, but then it's like, well, then what, what do I do? So like, I remember like being on the bus, going to middle school and the, they would play like 90s hip hop and R&B on the bus. And I knew all the songs because I was hearing them just as much as everyone else. And kids would sing along. And I remember one day after months of silence and being pushed off of my seat, and I like started singing under my breath, like singing along with the R&B song. And this girl next to me was like, you know this song? What? You have a good voice, sing louder. Like, but I was like, I'm allowed to? I don't know. I thought you guys all hated me. Like, I don't know what I'm supposed to do. Am I allowed to like this music? Like it was just

SPEAKER_03: That's so funny.

Stephanie Winn: And it's interesting, as an adult, every now and then I'll catch wind of someone else who had a similar experience growing up being one of the only white kids in a black neighborhood. And I'd love at some point to have a podcast episode with people with a similar background. I've met a few of them on Twitter, but we haven't really deepened the dialogue.

Winkfield Twyman: What's ironic to me, just listening to this, I love the story of Stephanie, in some ways I'm more privileged than you were, than you are, because I grew up in the stereotypical housing area, leave it to beaver kind of Southern suburb. So for me, the culture, the people were just Southern middle class people. Leonard Skinner was a big band when I was growing up. Led Zeppelin was a big band when I was growing up. For me to be like everyone else was just unremarkable. I was never rejected by my classmates. And so ironically, I benefited because the larger world is a white world. So when I go off to college at UVA, it's just more of the same. When I go off to Harvard Law School, it's more of the same. When I work for Capitol Hill for a member of Congress, it's more of the same. In my current job, it's more of the same. So in a way, I'm privileged compared to you, because I could always just be my full youthful childhood cultural self, but you in some ways have to hold back.

Stephanie Winn: Well, it's a privilege to have a cohesive family and a culture that can sustain itself, that can uphold some stability for the family and society, that teaches you how to be and that you can carry that culture with you into different environments and have it work for you. And for me, so I mean, I was the only child of a single mom. in a black neighborhood where I received very mixed messages about how welcome I was. And then, and then every other environment I was in from there was like a completely different environment. Very different norms, different rules and expectations. And, you know, so I grew up with kind of like a fragmented sense of identity.

Winkfield Twyman: Now, I'm going to be honest. I mean, one of the things I recall growing up was it meant a lot for me to raise my kids in the larger world. So, for example, we always chose the best schools we could find in San Diego. They were always private schools. My kids were always the only black kids or maybe one or two black kids in their class. And when it came time to college, it was pretty clear. I made it pretty clear that, no, you're not going to apply to a Howard or a Spelman. We want you to go to a school that's part of a larger world. And I think in some ways that was a wise choice on my behalf as a parent, because why would you want your, even if you have the choice, why would you choose for your kids to grow up in a racially isolated elementary or junior high or high school if the larger world isn't like that. You want your kids to be able to function in the larger world as if it's a fish in water, as if it's no big deal.

Stephanie Winn: That connects to something that was like on the tip of my tongue 10 minutes ago and I can see that Jennifer has a thought too. Can I share this one? Yes, please. So it's like, so America's called this melting pot for better or for worse. You know, European Americans like me are pretty disconnected from our respective, you know, for me, it's like Irish, Welsh, Russian and Ukrainian roots. Like, I don't have much connection to those roots. um you know black americans are separated from their african roots and for better or for worse we're like a very young new culture and not super cohesive It seems like one of the blessings though, because I do think there are some downsides to that, but one of the blessings of being an American is that you get to choose which elements of any given culture that you do have any relation to, like which elements to keep and try to nurture and which to let go of and blend into the wider American culture and reinvent yourself as an individualist. And so when it comes to whatever black culture means, which Wink, you've rightly pointed out, means a completely different thing to you having grown up where you grew up and when you grew up than it meant to me. But like, if there are things that are dysfunctional, then America offers an opportunity to let it go and reinvent yourself and find a different way. culture, right? And then if there are elements that you love, that sustain you, that sustain life, that can, you know, serve as a foundation for the creation of more beauty in the world, then you get to keep them and grow them and enhance them. We have that choice. And it seems like some of the, I guess, criticism that I hear from you and other, for lack of a better word, like heterodox Black thinkers is this, like, I guess could be maybe paraphrased as like, let's choose wisely what culture we want to identify with and facilitate more of and what culture there's actually not much value in perpetuating.

Winkfield Twyman: Well, I think that's so true, and I learned that from my parents. My mom chose to lead where we had lived for some time to move further out into the suburbs. Why? Because she felt that the suburban schools were better than the city schools, and taxes in the suburbs were lower than taxes in the city. That was my mom's choice. That became my life experience. So I'm always, Stephanie, a little bit perplexed. I know someone who is Black, who grew up in, let's say, the Bay Area. And when I talk about my small town upbringing, and I'll share my story, she'll lament that she grew up in a difficult part of the city. She could relate to some of your experiences. And I would ask her, well, Did your parents just think about moving to the suburbs? And she gives me this look like, who would do that? Or how could you do that? Which is not something my parents, my parents didn't know, learn about this. In 1970, the choice was clear. We can stay here, we can move there for the kids. What will your choice be? And so sometimes I'm amazed when I don't see that same agency among Black colleagues. And then number two, what was number two? I can't remember. It'll come back to me later.

Stephanie Winn: But yeah, I sort of cut Jen off earlier. So Jen, what were you about to say?

Jennifer Richmond: Well, I was going to say, Wink, it's so interesting because you do talk about how much you've nurtured your kids, how much you've let them be part of the wider world. But as you readily admit, they have chosen, though, their Black identity over and above this worldly identity. Mom, think mom and mom-in-law.

Winkfield Twyman: It's not a family. A family is not just the dad. It's not just the mom, in many cases. In many cases, it's two people working together to create some kind of a sense of family. And the kids will pick and choose, right? So what does dad think? What does mom think? Let's mix it all together and create our own sense. So yeah, so I think you're right. My kids may have made different choices, but that was probably because they chose other parts of the parental menu to draw from. So, oh, we were going to talk about, it just occurred to me, Stephanie, you were going to talk about the baby felon. I think that's what you were thinking about.

Stephanie Winn: Baby felon. Yes. You were going to talk about baby felon.

Winkfield Twyman: Oh, okay. Oh, you're a good therapist. Cause I tried to avoid it, right?

Jennifer Richmond: Oh, well, we hit baby felon and that just post family relationships.

Winkfield Twyman: Thank you, Jen. Thank you.

Jennifer Richmond: You were talking about every, everyone being quirky and I'm like, yeah, but you still have some, that's true.

Winkfield Twyman: You have some baby felons in your, but it's, it's, it creates a weird, uh, family dynamic at times. Uh, Stephanie, because it's almost like, And this is true for many families, I'm sure. You have two family components. There's one family component in San Diego, which you've spent 20 years developing, creating, and you're happy and the kids are out there doing their best. And then there's another family component, say back in Virginia, that you didn't have any hand in, but you're still related by blood. And there's all kinds of poor choices being made and inexplicable outcomes. And you just kind of shake your head and you just… I remember, this is in the book, I remember there's a family member who's very bright. And I will say this, I think my family, we were not only quirky and eccentric, but I do think we were smart. I think we were smart people. I've been told that by one or two people, that the Twymas were known for their intelligence and their smarts. So anyway, this woman is smart, off-chart smart. In fact, she was solicited for the gifted and talented program, but the problem is, she was from a very troubled, disadvantaged, single-family household. And so I always felt like she wasn't making the best choices aligned with her raw intelligence. If she had lived in my house in San Diego, she would now be who knows where she would be, someone's medical school. But as the case was, she grew up in a different setting, she made different choices, and she broke my heart, Stephanie, I'll tell you why, broke my heart. Because she was so smart, I thought, you know what? She needs to be in a boarding school, a New England boarding school. She needs to get away from all the craziness and the chaos and the dysfunction and just be able to excel, use her raw intelligence to do well. I made contacts for her. I reached out to boarding schools for her. I got an application from the ABC program, a better chance for her. Nothing. She refused to fill out the application, refused to follow through. And I just eventually decided, well, you know, you make choices. But it was very frustrating because I really love potential. And this was someone who probably smarter than me, probably, but just was making bad choices because of the environment in which she found herself. Very frustrating. But what can you do about this, Stephanie, right?

Stephanie Winn: Every family is different. I remember this story.

Winkfield Twyman: Yeah. What can I do? You can't make someone fill out an application for a boarding school, even though if she had gotten in, she would have had full tuition, full boarding paid for three or four years. Think about that. But she refused. to follow, I think she was afraid of something different. I think she was accustomed with familiar. I think she was close to her mom, was a single parent. So I think that those were reasons why she didn't decide to engage the larger world. But what are your thoughts about that, Stephanie?

Stephanie Winn: What was the most direct or harsh confrontation that you ever had with her?

Winkfield Twyman: Oh, that's a good question.

Stephanie Winn: The most like tough love.

Winkfield Twyman: Oh, I'll tell you.

Stephanie Winn: Come to Jesus conversation.

Winkfield Twyman: Oh, you know what? She got very angry. We've had difficult conversations. One, I remember she was very angry. I had written an essay about her circumstance and about the poor choices of her parents. And she had demanded, demanded that I retract and withdraw that essay. And I thought, no, no, no. Is it true? She said, yeah, it's true, but I want you to withdraw that essay now. And I declined to do so because, you know, literary freedom, creative expression, it was written truth. I didn't name any names, but that was probably the most difficult conversation.

Stephanie Winn: Well, hearing that, I can imagine that even though you protected her identity that she probably felt pretty humiliated. And maybe that this was more about your need for self-expression or like some needs related to your writing career rather than like about her and I can imagine some of the defensiveness coming from there. I guess the reason that I wanted to ask about the come to Jesus moments that you may have had is that, and this is my bias coming from some of the shortcomings in my own upbringing, but I think a lot of people need, I think young troubled people need more come to Jesus conversations than people are willing to have with them. And I often, a lot of my work entails guiding parents towards carefully planned interventions. So I don't recommend people just losing their shit and saying things they regret and lashing out and destroying relationships. That's not what I'm talking about. And depending on where a family is at when I start consulting the parents, I often will tell them that they need to rein it in. But for some people, it's the opposite. It's that they tiptoe too much. And, you know, considering that in this instance, we're talking about parent-child relationships, which is a bit of a different thing. They're, you know, often inverted power dynamics, parents afraid to express their authority and to express their genuine heartfelt emotions. So I often, you know, once I understand the dynamics in a given family, will help them get to a point of being willing to say something a lot more direct and risky. And I guess I think that too often we presume that others know what's in our hearts without actually telling them, you know, we're all guilty of that. Like, in relationships, we want our significant other to read our mind. And I and I get that, you know, I want mine to read my mind, too. But but notice, I don't know.

Winkfield Twyman: this conversation, which is very deep and good and important. This is non-racial. This is like a human conversation. This is a human interaction thing.

Stephanie Winn: So I think that's so important. And the consulting that I do, like I have, I have worked with people from every major religion. and many different cultures. I feel like I probably more as a consultant on the gender issue than as a therapist. I'm like listening through thick accents to first generation immigrants. And man, let me just say they have it. They have it rough. Like first generation immigrants from completely different cultures. who are raising their child in America and then their kid declares that they're trans. The parents are often so lost because they're just, you know, they're still figuring out how to be American, like basic American stuff and basic English. So, yeah. Yeah. I mean, it's it's human. And I think maybe that's kind of like the overarching message, right, is that the identity politics stuff is Although I will give the benefit of the doubt that many people who do engage in identity politics have noble intentions and probably do really genuinely see themselves as very caring and empathetic people, I think it's a huge mistake to go down that path because that's where we really lose sight of, as you say, Wink, the individual.

Winkfield Twyman: Right, right, right. I mean, to be honest, because I've thought a lot about these issues since Jenna and I began writing back in 2019. But I think at this point in my life, I've kind of settled upon the following personal philosophy of life. I mean, I think that life really comes down to or is about three things, three dimensions. I think it's about preserving human dignity, right? I think it's about creative expression because, as you suggested earlier, there's a certain shame in self-censorship. How many years did I just keep my mouth shut and my hands from the keyboard because I was not of the plight of the black inner city? Who did that fault really in the end? And then three, the individual. We're all individuals. It's the one thing that unites all of us across race, class, ethnicity. And so, when I look at the universe and problems, I try to look at it through those three dimensions, name and dignity, creative expression, and the individual. And there's no place for dogma. There's no place for slogan words because that just, it misaligns you. It creates a distorted reality, to quote Monica Harris with FAIR. We've all been living for too long in a distorted reality created by those with, as you suggest, noble or good intentions. But even the best of intentions can sometimes create the worst of outcomes. So we have to always be mindful of what are the consequences of how we choose to frame reality, how we choose to think about reality. And I think that for me, I feel most alive and self-actualized when I really am not a racial person, when I'm really just getting to the nub and the heart of who I am as an individual. And so, yeah, Stephanie, you're right. It's ironic that one of the least racial people, likewise, would write a book over four years about race. But I think it's because I was so unsettled by the impact dogma and slogan worlds in my own personal space. I never raised my kids to think blackness is oppression, nothing else matters. If anything, I always raised them to kind of engage the larger world, to believe the world was your oyster, to understand that you're just the latest link in a series of family members going back to the 1900s and the 1800s and the 1700s. I think kids benefit when they know they're just part of a part of a cycle of family generation and that your duty in life is to carry the mantle for the next generation and so on. That's kind of how I was raised. I always had a sense that They were my parents and grandparents and great-grandparents and great-great-grandparents. And my duty as a dad and a father was to create a great foundation so that my kids would carry forth a mantle into the future and my grandkids and great-grandkids and so on. And that's been my life philosophy so far.

Stephanie Winn: I think that's a beautiful note to end on. Do you have anything to add, Jen? Any lingering thoughts?

Jennifer Richmond: No, I think that is also a great note to end on.

Stephanie Winn: All right, well, thank you both so much for your time today. And of course, listeners can find the link to your book in the show notes. Thank you so much. It's been a pleasure. Thank you for listening to You Must Be Some Kind of Therapist. If you enjoyed this episode, kindly take a moment to rate, review, share or comment on it using your platform of choice. And of course, please remember, podcasts are not therapy, and I'm not your therapist. Special thanks to Joey Pecoraro for this awesome theme song, Half Awake, and to Pods by Nick for production. For help navigating the impact of the gender craze on your family, be sure to check out my program for parents, ROGD Repair. Any resource you heard mentioned on this show, plus how to get in touch with me, can all be found in the notes and links below. Rain or shine, I hope you will step outside to breathe the air today. In the words of Max Ehrman, with all its sham, drudgery, and broken dreams, it is still a beautiful world.