Best of 2022: Tim Klein | The New Science of Navigating School, Careers and Life

Tim Klein: Labor economists have known for about 80 years that anything that involves a pattern or process or repeatable actions, anything that can be done in the same way over and over again, will eventually be automated by technology. We're seeing this with GPT-3, where like there, the writing technology, there's so much of our life being automated.

Srini: Movements

Tim Klein: built thriving businesses, wrote best-selling books and created insanely

Srini: Interesting art. For more, check out our 500th episode.

Tim Klein: archive@unmistakablecreative.com.

Tim Klein: Thank you, Tim!

Srini: Thanks much for taking the time to join us.

Tim Klein: Oh, I'm super, super excited to be here. Thanks for having me.

Srini: It is my pleasure. You were actually my first interview after a one-month hiatus after ten years of not taking a break from the show.

Tim Klein: So nice to see you again!

Tim Klein: It's the big one I love. Yeah

Srini: You have a new book called How to Navigate Life, which, as I was saying to you, is now officially in my top 10 book recommendations for 2022 for anybody. But before we get into all of that, as having listened to the show, I want to start by asking what I think is a very relevant question, given what this book is about, and that is: What did your parents do for work and how did that end up influencing where you've ended up with your life and career?

Tim Klein: Yeah, they influenced me a lot, so my parents are very much hippies from the countercultural generation of the sixties and seventies. They're both from New York City. My dad was a New York City cab driver and they decided to move up to rural Vermont and try to do a yeoman farmer lifestyle, like going back to the land.

Tim Klein: And so that's where I'm from originally in Vermont. And yeah, my mom was a Potter growing up. She had her own pottery studio and she helped run an art co-op. And my dad was a public servant and was a House Representative in the state of Vermont. And so they both instilled in me this rugged individualism and really empowered me to go my own way.

Tim Klein: And yeah, I think in our book with me and Ben, we talked, I've been in education for a long time. And I think what they did for me is they didn't put a lot of pressure on me at all. And they really, my dad said the only thing he did as a parent was he trusted me to figure it out. And it was very simple advice, but that was actually very profound.

Tim Klein: And, like, when I dug into the research on what students need to be successful, it actually was spot on. So, yeah, that's my parents in a nutshell. Yeah.

Srini: Okay. A New York City cab driver is one of those professions that's pretty much nonexistent today. Thanks to technology, which I know you talk about - creative destruction - later in the book, which we'll get into, but from both having been a public servant and a New York City cab driver, which in many ways is another massive public service until services like Uber come along.

Srini: What did your dad teach you about human relationships?

Tim Klein: He really taught me that they were everything like my dad. If there are any Vermonters listening, Tony Klein, was like a big fish in a small pond, but he was a huge character. And he was very much a high-level thinker.

Tim Klein: He was really good on policy, but he was really a public servant in the sense of he was there to serve people. And I think that's something that's gotten lost in politics and everything he saw; serving people was the number one thing he wanted to do. He was a great orator. He was a great speaker.

Tim Klein: He could tell a most astounding story, but I think his purpose was that he loved doing things for individual constituents; anyone coming to him with an individual problem that they had. So he was really all about people first in what he did, and he was all about solving problems.

Tim Klein: And he also was not afraid to shake things up at all. He's not afraid to ruffle feathers. And I think he instilled that in me as well. And I think that worked, 'cause he couldn't hold down a job. He was the type of guy who would come home one day as a carpenter or as a roofer and be like, "I couldn't do it anymore."

Tim Klein: Quite had to find a new one. And my mom didn't like it, but she supported it. And I think for better or worse, he's instilled some of that trailblazing in me as well. Yeah. So typically I think the perception, at least mine, is that if you're a New York City cab driver, you're a blue-collar worker, which makes me wonder, what was the narrative about education when you were growing up with your parents?

Tim Klein: So that's really, so both my parents it's really interesting are like the youngest of three kids and they were the youngest by a good amount, like seven, eight-year difference between them. And so my dad was growing up in a Jewish, immigrant family, super hard-working, both his sisters, one is a very prestigious psychologists.

Tim Klein: One is a very prestigious lawyer. They have Ivy League degrees. And so yeah, he had to go in these huge footsteps and he just said, "F that," and he wasn't gonna do it. And so he just totally rejected it. My mom rejected it. And they very early on rejected the path toward wealth, status, and power.

Tim Klein: And I never had, so they never literally put any pressure on me academically. It's funny, 'cause I went to the University of Chicago. I was a teaching fellow at Harvard University. Like I've been at all of these super prestigious universities. They could not have cared less about my academics growing up.

Tim Klein: Honestly, there was no, it's just not what they valued in me. It's not...yeah, go ahead.

Srini: No, the reason that came up is I remember you were saying you're of Jewish descent and having listened on the show, we've had a lot of people also who are Jewish on the show, and from what I understand, growing up Jewish isn't very different from growing up Indian where the narrative is Dr.

Srini: Lawyer engineer, as you just proved by talking about your dad's siblings. So what do you think it is that enabled that spirit—I'm gonna go and do my own thing, despite the fact that they were raised in an environment in which that is the conditioning?

Tim Klein: Oh, man. That is a great question. I think it was a product of the time like that; that countercultural revolution of just like rejecting it in the sixties and seventies. Also, my dad was terrible at school. He was like, I think the second worst in his class in high school; he barely graduated high school.

Tim Klein: He only went to college to avoid the Vietnam draft. And so it was like, I don't even know if he could have embraced that academic performance and like trying to achieve at all costs even if he wanted to. And so I think as a way I think he knew he wasn't gonna win at that game. He was never, ever going to live up in the footsteps of his sisters.

Tim Klein: And so he just decided not to.

Srini: Okay. So you got into the University of Chicago as a Berkeley undergrad. I know exactly what it takes to get into the University of Chicago. And from what I hear, it's a brutal academic environment. So, where does that drive to get to that come from inside of you?

Srini: Like what?

Tim Klein: Sparked that? Let me be clear. So I went to graduate school at the University of Chicago and I went to their social work school a lot of these Ivy League schools have a lot of graduate schools where they don't tell you the acceptance rate for them. And there's a very specific reason because they're a lot easier to get into than undergraduates.

Tim Klein: And I fell. Yeah. So in high school, I went to Ithaca College. It's a great place, but I literally never applied myself at all in high school or undergraduate; I just did just enough to get by so that I wasn't going to raise any red flags or draw undue attention on me to my poor performance.

Tim Klein: So it was just like, I did as little as possible, but I actually decided to go to the University of Chicago 'cause I'm from Vermont originally, but, and then I went to college in upstate New York, but then after college, I went and moved to Chicago. And I just through happenstance, decided to, I got a job at a Boys and Girls Club in the oldest public housing development in Chicago, in the Julia L. Hamer Projects.

Tim Klein: And coming up, I hear that Vermont is the whitest state in the country; it's 98%. So I'm like, "Glow in the dark white!" Going to Chicago, working in public housing, and being the only white person there, opened my eyes to systemic inequities and the students I was working with at the time. I was in the games room, hosting pool tournaments and bumper pool, and trying to make sure they weren't breaking ping pong paddles.

Tim Klein: I was working with these young people who were amazing. They were really funny, charismatic, and super compassionate. Even though they couldn't have been more different from who I grew up with, they reminded me of me and my friends growing up, but they were having massively different outcomes, right?

Tim Klein: The year I was in Chicago, 185 Chicago public high school students got shot that year. And wow. Like all my friends were just in the default mode of graduating high school, going to the University of Vermont was like just going on that path. I was seeing students with the exact same capabilities.

Tim Klein: That's what I grew up with, but they were having very different outcomes. And that kind of made me see some invisible systemic inequities, systemic structures that were negatively impacting them. And I was getting an advantage from it just because I was lucky and where I grew up and who I was.

Tim Klein: And so it was that trying to address systemic inequities that got me to the University of Chicago. Yeah.

Srini: It's funny because I, and you've probably heard me say this on the show numerous times. I think that one of the things that have happened over the past few years as I've had all of these conversations is just a much, much higher level of awareness of just how privileged of an upbringing I had.

Srini: It's not like we were rich, but if your dad's a college professor, you're definitely not suffering. And I realized what a contrast that was to so many people. One thing that I think was interesting, there are two things that I wanted to ask you about is you had this co-author, Bell, and the contrast between what both of you were taught was pretty funny because I read hers and I was like, yeah, that's my story.

Srini: I read yours and I was like, "Yep, definitely not."

Tim Klein: My parents. Yeah. It's such a funny story; we both work together. We've written this book together. We're like two peas in a pod. We do a ton of work together in the Purpose Lab, which she runs at Boston College. So, Bella, she's the Dean of the Lynch School of Human Development at Boston College, she has a Ph.D. from Michigan, but it's like an immigrant family, where it's like, she--and I don't want to speak for her story, but it's in the book where she talks about it--it was like, you come and you have to be a doctor and you go on that path for financial stability and security. And yeah, she decided to be a psychologist and it was like, "Is that a real doctor or not?"

Tim Klein: So it's just like the level of, yeah. Yeah. So it's like the level of expectations put on her was really high. And what's really interesting is 'cause like her motto, which we call the performance mindset in the book, is where like the purpose of life is to be successful.

Tim Klein: And that's viewing life as this zero-sum, hypercompetitive game or race. And the goal is to win, to beat everyone. And that race worked for Bill until it didn't. And we just contrast that with the way I live; we call it the passion mindset where I was literally living.

Tim Klein: I thought the goal of life was to be happy, to live completely in the moment. And if I was doing what I was supposed to, I was only doing what I wanted to do. And if I didn't want to do something, I wasn't going to do it. And that worked for a while until it didn't, because it just led to a very self-indulgent, self-centered lifestyle where it was just like, I had to keep upping the ante on what I was doing to find that next high or whatever.

Tim Klein: And yeah, it's been this beautiful balance that we've found because we come from super different backgrounds. But we've really met in the middle in how our work comes together to support young people.

Srini: I wanna come back to all of this because this is really getting into the core of the book, but there's one other thing that you talk about at the beginning of the book, and that is that you are like this badass tennis player.

Tim Klein: Yeah, yeah, "quote-unquote," yeah, go ahead.

Srini: I wanted to know what that experience has taught you about the skills you gained from it that have transferred to your career and life in general.

Tim Klein: He plays very rarely. And so I started and I just went to start playing tennis as a way just to not be coached by him, which was a jerk move, looking back on it. But anyways, I started playing tennis in Vermont. I started tennis at 10 or 11 years old, which was super early in Vermont, but that's incredibly late.

Tim Klein: Yeah. So yeah, I say, quote-unquote, "great" tennis player, because the thing that's interesting, which I don't even talk about in the book, is my dad was a fantastic father - super involved in sports. He was my basketball coach, soccer coach, baseball coach - all that. And then, as an act of defiance, I went and picked up tennis, which he didn't know anything about.

Tim Klein: Anyone who's playing competitive tennis. So yeah, I just go through, I'm in Vermont, I went 53 and four, I think is the record. I lost four times in my entire high school career. We won a state championship, I was runner-up in doubles. I'm top ten in the state. And yeah, I think when I looked back on it now, I was miserable the entire time I was playing because the goal was to win and I was so stressed out and I was so angry and the entire 99% of the time I was actually playing tennis, I was miserable.

Tim Klein: And then I would win the match and I would get a moment of relief just until the next match, and yeah, that's influenced me a lot. I think.

Srini: Have you ever read the Andre Agassi memoir? Yes. He actually opens the book by saying, "Let me let you in on a secret: I hate tennis."

Tim Klein: Right?

Tim Klein: That's literally the opening of the book. And he talks about right in that book, his dad chose for him. He was gonna be this amazing tennis player. He likes Jerry Riggs, the tennis machine. So it can shoot a hundred miles per hour balls at him so he can get the best return of service. And it's his dad who was ahead of his time in how he was thinking about success, because he was like, "I'm going to start super early. I'm gonna get this competitive advantage. I'm gonna make my kid hyper-focus on tennis to be the best, 'cause he's going to outcompete everyone." And we're actually seeing that mentality everywhere in education.

Tim Klein: It doesn't matter if you're an engineer, robotics crew, or anything else we're in; it has become an incredibly hypercompetitive sport now where you have to be in the top 1% to be successful. And as Andre Agassi wrote in his book, he talks about his depression, his anxiety, and his burnout. I think he wrote that book 10 years ago.

Srini: I think I remember, and I may have mentioned this before, one of my oldest roommates, one of my oldest friends, had a daughter right before she was born.

Tim Klein: But the mental impact he talks about. There. We are seeing so many young people and young professionals having that same mental response to pressure that they're feeling now, whether it's depression and/or burnout. Yeah.

Srini: They were living in San Francisco and they put their daughter on the waiting list for a school before she was born. Yeah. For kindergarten, they moved to Chicago. I think she was five years old. And the school called not to say that she had been accepted, but that she was off the waiting list for the school.

Srini: And then we're putting unborn children on waiting lists for schools. Like, what is the world coming to?

Tim Klein: Yeah. And then, yeah. What happens when they get off the waiting list? That five-year-old has to interview to prove, oh, I've heard. Yeah. To prove they have what it takes to get into this school.

Tim Klein: So, let's get started. Does everyone have their materials?

Srini: Yeah, no, I've heard well, so let's get into the book, and there's one other question I want to ask, which I think will make a perfect segue into the book. You have Bell as a co-author and you have these wildly different backgrounds. And what that kind of sparked for me was, my parents are first-generation, and I'm second-generation, obviously.

Srini: And I'm wondering, with people who are children of immigrants, who now have children they're bringing up in the United States, are you starting to see a change in that narrative of "go to school, get a job" - what you call a performance mindset - or is that just being passed on from generation to generation?

Tim Klein: To generation?

Tim Klein: Yeah, I don't want to speak for all, for my experience. I've actually found that immigrant kids, a lot of the time, especially low-income and middle-income ones, are actually more purposeful in what they're doing because a lot of the time they can see and they've witnessed the sacrifices their parents have made to come here.

Tim Klein: So a lot of the time they don't take education for granted and they take it a lot more seriously than a lot of students who were born here who just hadn't, their parents didn't have to make that pressure, but we are seeing a pushback in that performance mindset because I think more and more young people are feeling like the game is rigged and a lot of them are.

Tim Klein: Yeah, yeah. We, I think when you bring up Varsity Blues in the book (not the movie, for those listening), it reminds me that every game is rigged in favor of people from privileged circumstances. I know this because I was one of them.

Tim Klein: Yeah. And I think what's so interesting about that Varsity Blues scandal is that you look at the people involved in it. And it was the most privileged people, the most connected people—of, one of the daughters who didn't even know her parents were rigging the game to get her into USC. She is, she was already making six figures as a brand influencer on YouTube and Instagram.

Tim Klein: It was like, yeah, they didn't need, they didn't need this help at all. They were going to be fine, no matter if they went to college or not. But I think what I find really interesting about the Varsity Blue scandal is everyone is feeling this anxiety and this uncertainty and fear about their young people being able to feel successful.

Tim Klein: And it says something about this moment in time that even the richest, most privileged, and most connected people still will risk jail time because they don't feel like they're stable enough. Whether that's correct or not is the perception that they aren't. It really speaks to this moment where we're at with what, who can be successful, and how many people feel like they can be successful and live meaningful lives.

Tim Klein: Moving forward. Hmm. I think that makes a perfect segue into the book. And the thing that I really wanted to start with is why has it taken so long for [this issue] and I still don't believe that what you're talking about in this book is even close to pervasive in the university system, yet. I know this because my dad's a college professor.

Srini: I'm literally using his office 'cause he's pretty much retired at this point. But, and why like honestly I, as a Berkeley undergrad, nothing you talk about in this book was ever talked to me about thinking about navigating life this way. The only thing that I was taught is pretty much what you call the performance mindset, which you basically say people with a performance mindset view life as fierce cutthroat competition. The mindset is ubiquitous and today's parents also refer to us as snowplow parents, a term that while it captures our determination and skill in leveling any and all obstacles that stand between kids and success, we make a helicopter.

Srini: Parents look like amateurs.

Tim Klein: Yeah, I think so. I'm a clinical therapist by background. I've been a school counselor for a long time. I've worked in both undergraduate and graduate settings. So I've been working, and both Bell and I have been working with students one-on-one at every phase of the education journey.

Tim Klein: And I think one thing we realized in our work was that students are under unbelievable pressure to be successful. As we've talked about, they know exactly what they want to do. And I think what we realized is that we've never taught young people how to decide. We've never taught them how to make big decisions in life and over the last 30 or 40 years in education, without even us knowing it, the purpose of K-12 education has been college.

Tim Klein: It was like the only reason you get really good grades, are you pad your resume. You do community service to get into the most selective college that you can get into. And we, and for a very long time, we've never questioned why I wanna go to college. Because we just assumed the better college you go to, the more money you're gonna make in your life.

Tim Klein: And so we've gone so long without questioning the purpose of education. We never taught young people how to be successful. And that's why Bill and I talk about it in our research. We're in the midst of a college and career navigation crisis where students are working harder than ever before, but they're adrift.

Tim Klein: They're lost, they're dropping out of college. They're switching their majors, they're switching their jobs and to us, it's because we've never taken the time to help them choose for themselves. What do they want to do with their lives?

Srini: Yeah, it's funny you say that because obviously, as I said, you get told, "Be a doctor if you want a good life," growing up Indian.

Srini: And I remember going to give this talk to my high school AP English teacher's class. And the question I got over and over again was, "What am I supposed to do with my life?" And I was like, "Oh my gosh, seriously? You've not even lived a fraction of your life, and you're worried about how you're gonna spend the rest of it?"

Srini: You don't have enough data points to figure that out. That to me has always been the most shocking thing, is that we put so much pressure on people to make choices about their entire lives when they've only lived a fraction of it.

Tim Klein: Yeah. Yeah. And the research bears that out where I have a six-year-old or a five-and-a-half-year-old and a three-year-old.

Tim Klein: And they're super purposeful. They're very intrinsically motivated. They're just curious about the world and they do whatever they want. And Bell's research has found that kids up until around 7, 8, or 9 years old, just play right. They just play and they just experience the world. The process of it.

Tim Klein: And then around fifth and sixth grade, they go from play to performance. Because they get this idea that okay, I'm playing for keeps now; my grades matter, my standardized test scores matter. And they really have this feeling that what I do as a seventh or eighth grader can influence the trajectory and the opportunities I have as I get older.

Tim Klein: And so it really is we've created, it started I think with No Child Left Behind and this boom on standardization and standardized test scores, but we've really turned the education system into this linear path where you have to be checking off these boxes and you have to be going in one straight direction up and it really sends this message that you.

Tim Klein: If you don't know what you want to do, and if you don't know where you want to go in life, you're lost. And if you're lost, you're losing. So, a lot of the time, students it feels better to say, "I'm gonna go be a doctor," even if you've never spent five minutes shadowing a doctor, or you don't even know what they do on a daily basis.

Tim Klein: That feels, yeah, that just, that feels much better as an answer than "I have no idea what I want to do with my life." So, young people, yeah, grasping for bad ideas, because it's better than no idea at all. I think I probably may have said this before. Like I remember when I told my mom, I was like, "Mom, I don't want to be a doctor."

Srini: I hate going to the hospital. I get sick all the time. 'Cause I used to get frequent colds and my mom said, "Don't worry, you'll develop immunity."

Tim Klein: Like very practical.

Srini: Like a typical

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