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Chapter 1: What sparked the discussion on career regret?
What got you into thinking about the idea of career regret as somebody that's had a very seemingly successful and fun career? Why did you think about it?
So I spent 25 years as a venture capitalist and the four years before that as a sell-side analyst on Wall Street. And through that process, I started writing as a way to differentiate myself. And so I was an early blogger. It was actually a fax, that's how old I am, when I started. And I got in the habit of, when I had ideas, jotting them down and then either developing them.
A lot of them ended up just undeveloped, but if I developed them, they would become a blog post. And there was a period in my career where I was reading a ton of biographies. And I finished this third one and saw a through line with these other two from people that were in wildly different fields. And I jotted those notes down. And that thing kind of
simmered and breathed and took on a little bit of a life. And I got asked by the dean of the business school here in Austin, University of Texas, to talk to the MBA class one day. And I was like, can I do this? And he said, sure. So I pulled it out and developed it a little bit as a PowerPoint presentation. Anyway, they posted that on YouTube. A few people noticed.
Some people that have been on your show, James Clear, noticed. And he posted it on his website. And people started prodding me to develop it as a book. And a few years ago, I decided to begin retirement as a venture capitalist. It actually takes a while, unfortunately. And in that window, I thought about doing this. I thought about doing a book. And a lot of people wanted me to do a book.
A lot of people wanted me to do a VC book or an investment book or a tell-all book on the Uber experience. And I was more drawn to this idea. Um, and a few other people prodded me who said, you know, like go, go do. And it felt more authentic. It felt like something that could have a bigger impact. And I was drawn to that at this moment in my life, I was drawn to this particular thing.
So I spent like six years. working with a co-writer and researcher developing it further and making it this way. But you used the word regret. We did, along the way, I launched a survey on SurveyMonkey that said if you could go back and start over, would you do a different career? And seven out of 10 people said yes.
And I eventually took that to Wharton People Analytics, and they did a more scientific version of it, much broader audience, and came back six out of 10, but very similar. And that notion of career regret's interesting. I had the opportunity to talk to Daniel Pink, who you may know, who wrote a book. He's been on the show about regret. About regret. Yep.
in that book he says the biggest regrets people have and and and he showed me a graph it actually gets worse as you get older towards end of life are regrets of inaction he calls them boldness regrets it's what you didn't do like humans are great at forgiving themselves made a mistake learn from it won't do it again but they ruminate about what they didn't try
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Chapter 2: How does Bill Gurley define career regret?
It has a similar kind of... When looking at the regret minimization framework, what are the things that... What are the common pitfalls that you've seen people do, even both inside of their career and outside of it? You must have reflected on this a lot.
Yeah, I have. One thing that I think, especially with the modern young people, I think one problem that I think exists, because we've built this... I call it in my book, A Conveyor Belt... Jonathan Haidt called it a resume arms race. We've built this pipeline for these kids that's so intense.
I think when they get to their first job, they feel like it's the result of all this investment, and they feel like tweaking any way away from that is throwing away the investment. Does that make sense?
Yeah.
Like a loss aversion type thing?
Yes, yes, yes. I invested all of this to get to this college, to get to this degree. And if I move away from that, did I just waste all that time? And, you know, this is despite the fact that in, there's a lot of studies that have been done, like, I won't get the numbers exactly right, but like five years after college, 40% of people are no longer working in the field that was their major. Yes.
And that number gets bigger at 10. But it doesn't mean that they don't feel trapped or that that number might not be higher if they didn't feel trapped. And when I mention this to young people, there is this weight. There is this weight they feel. like an obligation to, especially maybe- Decisions that they locked in when they were 17. Yeah, well, and that's another thing.
When I was younger, the colleges wouldn't let you declare a major until the end of your sophomore year. Many schools, you have to apply to the major now. So we've moved the decision of what major you're going to pick from the end of your sophomore year to the end of your junior year in high school. Mm-hmm.
Like that's, you know, three years forward and less time to – there's a lot of people, a lot of smart people that just say we don't allow children enough time to explore. And, you know, Haidt says it. He has a chapter called Let the Awesome Play or something. Yeah. Rick Rubin's been pounding on this. He talks about it in his book.
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Chapter 3: What are the key indicators that it's time to change careers?
He's worried that his dad's going to come in there and read him the riot act. And his dad comes in and sits next to him. Here's the whole story. And he says, here's what we're going to do. Let's take that piece of paper and put it right here in your bed stand. And I want you to read it every single day.
And you hear a story like that, you know, and I don't think, there's a lot of people, I think that that's a very hard thing to do. I think that for parents, and I'm a parent of three and I've lived through this phase that we're talking about, Your intuition as a parent, like some in your DNA somewhere, is to look after the economic welfare of this child. You want them to live a good life.
And it's very hard not to associate that mostly with money. And so this thing that Steve Harvey's dad did for him, I think is kind of a really like a very unique thing. I think it's very hard to do. And I hear a story that McConaughey has a very similar story about when he switched from law school to film school. His dad told him, well, don't half-ass it.
And like he said, that was the last thing he thought his dad was going to yell at him. And his dad kind of gave him like this push. And that's what I want the book to do. Like if someone has that inkling that they want to go do something that the world may not think they're capable of or think they should do, I'd love to unlock this latent human potential.
You know what it comes back to? It's quantifiable, observable, and hidden metrics again. The observable metric of financially free, this is how much they earn, this is the track that they would be on. Hidden metric, how passionate are they? Are they happy when they're 35?
So I guess one of the situations that so many people must be in is someone, one version of them successfully pivots and another version of them stays stuck for life. Why do some people successfully pivot and others end up getting stuck?
Well, I mean, you could come up with a number of things. One of them is financial, which we've talked about. You could be overspending. There's a different case where you're stuck financially, like you need your living hand to mouth. I have a profile in the book of Jen Atkin, who I don't know if you know, she is probably the most successful hairstylist of all time.
Not only achieved, touched the top rail of that, but then launched beauty products, sold that company. But She moved to LA with $300 in her pocket. And that's not to say anyone can do that, but there are stories of people with near nothing starting on the very bottom rung and finding their way to be successful.
There's this classic meme of starting in the mailroom in Hollywood and David Geffen and And Barry Diller and all these people started in the mailroom. It's about as low a rung as you have in that business. So I think it's possible. But you may feel stuck financially. You may feel that you can't get there. And then the other one, it could be like this perception.
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Chapter 4: Can someone learn to love the grind in their career?
Precisely. So in your framework, loving the grind is sort of a non-negotiable. Yeah. Can someone sort of learn to love grinding? Or is that innate?
I don't think so. But, you know, when you were talking about your love of podcasting, you know, the word that popped into my brain, and there's a book by this title, was flow. And I just find people that are truly tilting against their passion, they never even think about it as work.
And at times, the experience does go into this flow thing, like where when you're done, you don't even remember doing it. Like you're just that much enamored with the whole thing. And because I've felt that and I've seen it, I just, I really don't know how you could do that.
I suspect some human is just wired in a certain way where they might be able to do it, but I don't know that most humans could. And I don't know, I do think we get a lot of young people to do it for an extended period of time. The meat grinder thing. I just yesterday met with five of the top people I helped start this robotics honors program at Texas, and I met with five of them.
And, like, you know, they're giving you their background, Eagle Scout, and 1580 SAT and all. Like, clearly, this human's been programmed to go take the hill, like, on every single thing they do. But I don't think that's the path to greatness. Like, you know what I'm saying? I just don't think... I don't think just being good at the grind is what it takes to be truly exceptional.
Brute-forcing creativity, sort of white-knuckling your way through miserable successes... It lasts for a good while and might be sort of the activation energy you need to overcome some discomfort at the start. But I would agree, I think. Maybe if you're just so damn competitive, like winning all the time. Winning is your passion. It's a meta passion. That's possible. Yeah, that's interesting.
And that's certainly some people, right? They just want to win. Yes. I think Michael Jordan... would be a good example of this. Have you heard Novak Djokovic's interview where he's asked, why are you so good at tennis? And he says, I just like hitting the ball. I love that. Yeah.
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Chapter 5: What insights do successful people have about mentorship?
Whereas, you know, Jordan invented rivalries. He invented slights against himself. Was it 92 or 93? Very driven human being. He wins some, I think it's his induction into the Hall of Fame. And during that speech, This is the moment that you've worked supposedly your entire career for.
He takes a shot at somebody, right?
He spends the entire speech just revealing all of the slights that from his past and this person and this, but they didn't believe that I'm getting done. You know, even at the moment where you've broken through escape velocity, you're, you're out in space.
still i don't i don't love that that much you know i love it's not the energy that i have yeah so there's a there's a there's a counter example to that there's this thing you can find on youtube where shack was on uh the that famous show that he does with with kenny and and charles and ernie and um inside the nba i think it's called uh the uh
He's at the All-Star thing and there's all these legends there. And he just kind of goes off on his own talking. And he talks for like five minutes and they don't interrupt him. And he's telling his story of how he made it.
and all the people that influenced him along the way and how he views all these legends as idols and he just goes on he's just thought thankful like gracious for four or five minutes and ernie's crying by the time he's done and i love watching it i've watched it probably 10 times i just love the notion that you carry that much um thankfulness for the others that helped you get where you are.
And I think in conveying that it may be in, and it makes him look like remarkable, you know, it really does like that. He, that his brain's wired that way. I felt very proud of him. I have no reason to be proud of him and he probably couldn't care less that I am proud of him, but I, it was, uh, is I like that. I like that version better.
It feels much more pro-social. Yes. I suppose the problem is ultimately what matters is performance, especially in an industry like that. If Michael Jordan... was some middling or pretty poor quality basketball player calling out all of these people and inventing random rivalries to try and motivate himself to go, people would look and say, you're just bitter. And the same thing with Shaq.
If Shaq, who had a version of him that hadn't achieved all of that, was... you know, proselytizing about these wonderful people and how grateful he would be called a suck up.
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Chapter 6: How does AI impact job security and future work?
Yeah. And this is, that's fair. The, the, medium is the message, but the metal is the message very much for this stuff.
Well, and look, that is more of a finite game, right? Like that is, and I did use downhill skiing, but there are like those kinds of competitive sports. You may need to be sharp elbow to climb to the top.
If you're an author, the same thing is not true.
That's right. That's my main point. And most of the careers, most of us chase, that's not, that that's not a reality.
But I also have a principle, always give back, which is why I feel warmly about the Shaq thing, which is I think that the minute you move from the first rung to the second rung of the ladder, if you take the time to appreciate the people that helped you with that movement, you will develop confidence. a process that you will feel really good about at the end of your life.
And your network of supporters will grow faster. You'll have more friends in your corner.
You're seen as the pro-social hub as opposed to the person that stepped on a bunch as they come up. Yeah, you'll be able to weather the bad times and enjoy the good times more. Yes. So you talk about honing your craft. Yes. Kind of interested in what that looks like in knowledge work when there's no clear scoreboard.
Well, here's what I would say is, and I think this relates to this college grind. I think some of these kids are so burned out by the time they get to the end of their senior year in college that they can't wait to not study anymore. Like they view it as, okay, 12 years plus four, 16, I'm done. And they're looking for a break from studying.
And the best in their field, like Danny Meyer, are studying all the time. And So that's a weird contrast. And there are fields where continuous learning is somewhat required. The medical profession is one where that happens. And obviously, there are fields like ballet, where if someone says they work 16 hours a week or a day, we all applaud it, which is weird.
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Chapter 7: What are the key traits of successful founders?
The young AI founders. They've embraced this meme from China, 996. It actually was developed in China, which means 9 a.m. to 9 p.m. six days a week. That's what it stands for. But they used the phrase. And Silicon Valley got lazy in COVID. So you have the situation where the broader culture had moved from being formerly a bit workaholic to being lazy. And despite the...
You know, they literally aren't coming into the office. You can go in downtown San Francisco and look through buildings, you know, because there's so much cubicle space with no one there. And these young kids in this AI world are the ones you're talking about that want that experience. It was some examples of those.
I think almost all of, I'm serious, almost all of the AI companies in San Francisco have this mindset, especially if they have a young founder, like a 20, 22, which is, but I'm agreeing with you. Like this notion that, okay, you don't like it because you don't think there's work-life balance. Do you think it should be illegal for them to do it? Like, I don't.
They get to choose their own life. It's kind of the argument for drug legalization, but it's workload legalization. Exactly. If you're doing it and it doesn't hurt anybody else, you do to your workload as you wish.
But I would say this. If you're... you do need to recognize that you might one day be competing with someone that has that mindset. And that's where I go back to, like, do what you love. Because if you're sitting next to that person... And you're white-knuckling it and they're loving every moment. Yeah, you're probably going to lose.
Because they're at home learning in those extra hours stuff you're not. Like, there's no way to keep up.
Yeah, well, it is... Even if every small... If every iteration of you doing a thing degrades your willpower, drive, whatever, even by the tiniest, tiniest, tiniest amount, it is just a single direction trajectory from you to crash land into burnout.
Well, and the gap is going to grow. And I'll tell you one other thing which I stumbled upon, which I think is an interesting juxtaposition.
If you're a grinder, if you followed the path you were told to follow, you went to the school you were told to go to, you got in the program you were told to go to, you became certified as an accountant or an engineer, whatever this thing is you did, but you don't love it. You're in that place you were talking about. I suspect for those people, AI scares the living shit out of them.
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