Morrell: We're here to today to talk about your book, but I want to start by talking about your public speaking. Certainly you're remembered by our audience for your HBS Class Day speech, you have an extremely popular TED Talk, you're an in-demand speaker generally. In the book, you recount your first speech, though, as a fifth grader in Miss Davis's class. Can you talk a little bit about that experience and what you learned from it?
Gerald: Yeah. My fifth grade teacher, Gwendolyn Davis, was about the most terrifying educator I had ever had up to that point and probably since. I mean, sort of imagine the terror of a first year at HBS cold call, and amplify it by about a million, and that's her.
And so, Black History Month came around, and an oratorical competition, and she assigned homework, and she said, "Everybody's got to write a speech." And the topic was, "I'm the mayor now, and this is my new plan."
At 11, I had never written a speech. I don't think I'd ever really heard a speech except for that little short snippet of "I Have a Dream" that we've been sort of pacified with for half a century, and I surely had never thought about what the mayor ought to be doing. But I was going through a sort of period in my life at that time where everything started to kind of fall apart around me. My dad had started to spiral into sort of drug addiction, my mother who suffered from mental illness had started to disappear. And I guess, if I was a psychologist, I'd say, I, at 11, decided that I would be perfect in everything that I could control.
I remember when my mother started disappearing, I came up with this idea that if I walked the sidewalk squares perfectly, only put one foot inside each sidewalk square and never stepped on the cracks between, never put two feet in the same sidewalk square, that my mother would sort of reappear at home.
And it worked once, actually, which made me even more insane, I guess you could say. So that was just one small piece of this sort of obsession with perfection, which just happened to spill over into this oratorical competition.
My sister and her friends helped me come up with a speech, and I just rehearsed and rehearsed and rehearsed and rehearsed until I could recite the thing without reading it, which I thought was the homework assignment, and I did not want to get my homework wrong. It was simple as that. And so I got to class on the day that we were supposed to turn it in, and I watched all these kids walk up to the front of the class and read their speeches from sheets of paper, and I was horrified. I said, "What are y'all doing? You're going to repeat the fifth grade or something."
And there were so many people reading that I thought after a while that I was the one that was wrong, so now I'm scared that I'm going to repeat the fifth grade.
So anyway, my time comes, and I go up, and I recite this speech that I really don't even remember any of the words of now, and I finished, and I remember Miss Davis was standing at her desk. She had these long, red fingernails and this voice, and she said, "Oh! Casey Gerald, you are it!" And I had no idea what I was really, so I just kind of shuffled back to my seat really ashamed. And that's when I later found out after class that I had been chosen against my will to represent the class in the oratorical competition.
And funny enough, in that competition, at least in rehearsal, I think I forgot half of the speech, standing on the stage. So I've come a long way from that, obviously.
But on the flip side, I think what the book and what this process of writing, it really helped me to work through, was that so many of the gifts that I had come to develop were actually things that were sort of responses to trauma, right? The sort of obsession with being perfect, which is very good when you're reciting a speech, is actually not the most helpful and healthy way of moving through the world, and I think a lot of my classmates at HBS shared this, being the Michael Jordan of the marshmallow test, right? We can defer gratification forever. We can sacrifice as much as we need to, to be perfect or to match what standard somebody has set for us.
And so, I have a feeling about my speaking career that is both very grateful for the skill and for the ability to communicate with people. But also I have this wariness, I think, of the kind of obsession with perfection that led to the career and that makes the career possible in some ways.
And so the book was a chance to kind of free myself from that, hopefully, while also honoring it and honoring Miss Davis's role in all that.
Morrell: I've heard you describe the book as a memoir only on the surface, and that it's really more of an intervention. Can you talk a little bit about that idea?
Gerald: Yeah, for sure. I mean, I was not a writer before this. I had lived myself into a dead end, and so I decided to write my way out of it. I had achieved about everything a kid is supposed to achieve in America: coming out of poverty, going to Yale and Harvard and doing all these other things, but I was really cracked up.
I wouldn't say I was necessarily having a nervous breakdown, but I wasn't too far off, and I was awful sad either way. And a lot of my friends were cracked up. Obviously the world was cracked up too. This was 2016. So I started the book just to trace those cracks, and before I finished, a friend of mine, one of my closest friends from Yale who I had helped recruit actually, who had a very similar sort of quote-unquote Horatio Alger journey from St. Louis to Yale, committed suicide. And a few months after that, he came to me in a dream, and he said, "You know, we did a lot of things that we wouldn't advise anybody we love to do." And I knew exactly what he meant. I knew that the ways that we were trained to live, to succeed, were really killing us in a lot of ways.
And so my job with this book became to make plain those things, right? To counter the ways that we're taught to live or to die and to try to imagine what it would be like to truly live to be a better person, to be whole, to be free, to be a better friend, a better lover, to know God for real, to really find a different way of being in this world rather than the way we were taught to be in this world, which for more and more of us, as we see, is not working.
Morrell: I wonder if you think that the way that your generation was trained or formed, rather, was different from previous generations. Is there something that has made it especially, to co-op your term, "cracked" or broken?
Gerald: That's a great question, and I think something deep and real and profound has happened with my generation. We're recording this conversation on September 11th, and I was a freshman in high school, and so many of us were 14, 15 years old, and that was starting high school. This was the beginning of the new millennium, and that was the beginning.
I remember watching Shock and Awe and the "mission accomplished" banner on the fighter jet. And then you go from there to, I was a summer intern at Lehman Brothers in 2008. You see all of these things that my generation has inherited, all the promises, so many of them have turned out to be false. That's before you even get to the fact that we'll never have Social Security or anything like that.
So the world that we inherited, in many ways, does not exist anymore, and I think there are two things. One, there is a level of psychological trauma that so many of us have just as individuals. I've seen so many suicides, whether it's my friend that I write about in the book. Another friend of mine, I just found, out took his life yesterday. There's a degree of trauma in the body and in the heart of so many people in my generation because the basic sense of trust and security has been ripped away from us, and that happened a long time ago.
But there's also at the political level, a real reckoning that is coming into being. I write about in the book, my freshman year at Yale, the freshman football players. We staged a coup against the upperclassmen because the team really sucked, and the upperclassmen were just really not good at their jobs, and we got kind of tired as 18-year-old boys, of losing. So we said, "Hey, we're gonna take the team over," and just kinda kicked their asses.
And we did that, and by our sophomore year, we won a championship, we went on to be the winningest class in a generation, and we paid the price for it. A lot of us have had surgeries and concussions, all this other stuff. But I write about that as a metaphor for what I think is happening as a political cohort of my generation, which is that there has been a break, and it's still sort of bubbling up. It's still coming into being, but I think the political challenge of my generation is to really, in some ways, reimagine if not reinvent what the promises and what the agreements and what the structures of this country and of our society and of our individual lives are in a way that really works for us.
I think our generation is markedly different because we have come of age at a time where literally the world has come apart, and that's been both a sort of macro issue but also in so many of our personal lives as well.
Morrell: Casey, part of this intervention and this conversation that you're starting with this book comes from your experience, and these are your words of seeing America from the very top to the very bottom. I also wonder how much your experience with MBAs Across America might have played a role in connecting you to a wider perspective.
Gerald: The tagline for this book is "a testament of a boy in a generation that came of age as the world came apart, in a generation searching for a new way to live," and MBAs Across America in a lot of ways was my first sort of attempt at that alternate way.
My first year at HBS, three classmates and I decided that instead of going and sitting in a cubicle all summer doing the right thing, quote-unquote, we'd take a road trip and drive across the country and go to places like Detroit and New Orleans and rural Montana and see what was happening and see if we could use our education not just to make a buck but to make a difference.
Everybody thought we were insane, actually. I mean, here were these four kids who had gone to Harvard Business School, and instead of going to Goldman Sachs or whatever, they were going to go drive across the country for free. I mean, it was just kind of bizarre to people.
And we showed up in Detroit the first week we were on the road. It was summer of 2013. It was the week the city went bankrupt. And I just remember being there that week and meeting those people in Detroit. We met this guy who had decided to save the worst neighborhood in Detroit. The mayor himself had said the neighborhood ought to be wiped off the map. But he had decided to dedicate his life to saving it, and I remember, I asked him, I said, "Kurt, why are you doing this?" And he said, "If you took the blood from my body and projected it as an image on a screen, it would be this work, and it would be this city, so I couldn't stop it if I tried."
Those kinds of interactions we kept having over and over and over again. These people who, with far fewer resources, far less access to places like HBS, had a deep commitment to doing work and living lives that really meant something and really mattered, not just to them but to other people, and it just made us all, I think, feel like phonies in a very serious way. I mean, we had everything. I mean, we had all the degrees and all the resources and everything else, but we had these empty pursuits, more than anything, I think.
MBAs Across America, the three years that we spent on the road, radicalized me in a way, both in a personal sense of having a different standard for my life, but also radicalized me as it pertains to the real malpractice that's been committed at some of the top educational institutions in the country that are not preparing young people to live lives of meaning, live lives of wholeness. And so I would not have the certainty in that for myself or for other people, without the three years that we spent working with MBAs Across America.
Morrell: MBAs Across America, your speeches, TED Talks, this book. Is there a common thread through this work, through your work in general?
Gerald: Yeah, I think the common thread, increasingly, is a question: what would it mean to truly live? What would it mean to truly be whole? What would it mean to truly be free? What would it mean to truly use this time on Earth in the highest and best, might even say holiest, way possible?
I think that's the thread, and I'm as curious as to the answer as anybody who shows up for a talk of mine or who joins MBAs Across America or who reads this book.
Skydeck is produced by the External Relations department at Harvard Business School and edited by Craig McDonald. It is available at iTunes or wherever you get your favorite podcasts. For more information or to find archived episodes, visit alumni.hbs.edu/skydeck.