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?
I spent 25 years as a venture capitalist and the four years before that as a sell-side analyst on Wall Street. Through that process, I started writing as a way to differentiate myself, and so I was an early blogger. I got in the habit of jotting down ideas, and a lot of them ended up undeveloped, but if I developed them, they would become a blog post. 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 in wildly different fields. I jotted those notes down, and that thing kind of simmered and breathed and took on a little bit of a life. I got asked by the dean of the business school here in Austin at the 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. 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 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. A few other people prodded me who said, you know, go do it, 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. But you use the word regret. 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 and People Analytics, and they did a more scientific version of it, much broader audience, and came back six out of 10, but very similar. That notion of career regret is interesting. I had the opportunity to talk to Daniel Pink, who you may know, who wrote about regret. And in that book, he says the biggest regrets people have, and he showed me a graph, it actually gets worse as you get older towards the 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, learned from it, won't do it again. But they ruminate about what they didn't try. And so I've thought about this long and hard now since I've been working on it for six years. I fear our current education path has become a bit of a conveyor belt. We're pushing these children into this meat grinder, and we're pushing them towards jobs that are typically called safe jobs, at least before AI. And I think they're learning to grind. That's what Angela Duckworth's been saying now. The perseverance part we've taught them. But if they don't have the love for it, it turns into burnout. And so the purpose of this book that I wrote is hopefully to give as many people permission to go do what they want in life. And look, I'm sure it won't touch everybody, but if there's a subgroup of people who read this and have the conviction that they can go succeed in this thing they love, I think that'll be a huge impact on the world. Like, I think the people that do that are the people that just love what they do. And not only are they more successful, but I think they radiate a bit and spread positive energy.
Well, they're magnetic as well. They become a role model for other people. That's right. Go and do, oh, he took a chance on that thing that he wanted to do and wow, it didn't work out and his life didn't blow up or it did work out and he's really happy.
Thinking about the fact that we seem to regret inaction, boldness regret. Have you reflected on why you think that is? What it is in the human mind that causes us to prefer decisiveness over...
I was hoping to bring up one of the many biases I've read about in all the behavioral science books, but I'm going to go to a different place, which is I think we ruminate a lot. Our brains constantly are replaying things in our minds. And maybe that's what dreaming is too. But I think because of that, it's very easy to imagine these what-ifs, to build a story, especially a positive story around the what-if that didn't get done. And then you compare that to your current life. And unfortunately, that can create anxiety, but I do think that might be part of it.
You'll be familiar with the Zeigarnik effect.
Oh, cool. So, there was a psychologist who began studying waiting staff, and they realized that these waiting staff had unbelievable recall while the tables were still open. You know, you've ever been to a restaurant and you see some waiter come up and they're stood, no pen, no pad, no iPad, hands behind their back, and you go, 'This guy's crazy. Like, he's insane. I'm definitely going to get something wrong.' And sometimes you might go, 'I'm going to... we'll take the sprouts, but extra bacon, no goat's cheese,' but you want to just see if... all right, it's a no pad. And the study ended up finding out the Zeigarnik effect, which is an open-loop, closed-loop bias that exists inside of the human mind. While the tables were still open, the servers were able to recall what the orders were very closely. And as soon as they went, you know, nothing at all. You know, a perfect example in almost everybody's life with this, I'm quite bad at this actually but it still holds true, hotel rooms. Let's say that you're moving from city to city to city. You're not bad at remembering the hotel room of where you are now. But if I was to say where did you... which hotel room did you stay in two hotels ago? I have no idea. It's the same reason why cliffhangers work at the end of TV shows to get you to watch the next one. The open loop, the human mind abhors an open loop. And I get the sense that... I see what you're saying. When it comes to boldness regret, the main thing that you have is an open loop. Now, the human mind abhors open loops and uncertainty and ambiguity so much that we'd rather imagine a catastrophe than deal with the uncertainty. That's what a lot of anxiety, sort of future projected regret kind of is, right? I don't know what's going to happen. So I'll imagine the worst thing, and at least for a moment I have certainty, even if the certainty is horrible. And this is the same thing I think in some regards but in reverse. What could have happened? What could I have done? And there's an interesting way to flip it on its head. When Jeff Bezos was trying to convince himself to go start Amazon, he had this incredible job at D.E. Shaw, and David Shaw didn't want him to leave. So he was trying to talk him out of going. And Bezos has this thing. It's on YouTube. You can go watch it, but he self-proclaimed, it was very nerdy, but he called it the regret minimization framework. And he just imagined he's 80 years old and was trying to get advice from his 80-year-old self about what to do. So he put himself in that future place where he might have that boldness regret. And in my own career, I had two different jobs I started and then switched before I got into venture capital, which was definitely my dream job. And in both of those cases, a couple years in, I paused and reflected, and I only thought about this as I've been promoting the book. I paused and reflected, do I want to do this for 30 years? And was able to fast-forward that in my brain, and I was unhappy with that reflection, which encouraged me to think about what's next. When it comes to the regret minimization framework, which I love and I kind of can't believe isn't bigger. I'm aware it is among people that read the sort of stuff that you do or maybe I do, but it is a really wonderful idea. And I guess Jeff's got other stuff that he can be well known for. So perhaps, you know...
Well, it's actually quite synonymous with one of the seven habits of highly effective people, begin with the end in mind.
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?
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 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. 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 they feel, like an obligation to especially decisions that they locked in when they were 17.
Yes. 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 are you going to pick from the end of your sophomore year to the end of your junior year in high school. 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 Them' or 'The Loss of Play' or something. Rick Rubin's been pounding on this, he talks about it in his...
We looked at Jean Twenge's work, Generations.
Yeah. So, Generations is really fascinating. This stinks of you. Highly recommend it. You really...
And she talks about extended adolescence. Sort of twins with some of Haidt's stuff. You've got a real interesting duality going on, which is in one world, you've got these kids that are sort of being forced to become adults more quickly than ever before, where we expect you to know what you... potentially the set of railroad tracks for the rest of your life, the next 30 years of your career. And you're only 17 and you got to know and apply. And then at the same time, kids are moving out of the house later. They're getting their driver's licenses later. They're getting employment later. They're getting into relationships at lower rates. Less alcohol, less casual. All of the things that we would have typically associated with being an adult are not present as we're trying to force structural adulthood onto them. Was socially very immature, professionally expedited, and he ties them together.
Jean Twenge. Yeah, for sure. I think that... Oh, actually, no, no, no, no, no. Great point. And I don't know, and I don't think so. Now there might be some rebellion going on that, ah god, like everything just feels like I need to get my act together. How can I do these other things? I just so much of my cognitive real estate is taken up. I could see that. Maybe that would be a compensator. Yeah. Like I mentioned, I think when about 10 years after Duckworth wrote Grit, she said that she wished she had positioned it as 50/50 passion and perseverance. And if she could do it again, she'd put more on the passion because she thinks we taught a whole generation of the high-performer children how to grind. Like we taught them to persevere, which is...
Well, and so I get that. Grit was a massive book. I don't think that she should lay at the feet of her pen the issues of this stuff, but I think one of the reasons why from a personal development standpoint it's a bit more seductive to over-index on the perseverance than the passion is that passion feels more difficult to engineer.
So, oh, how do I get the thing, the line, the stuff right? It feels a bit more egalitarian to say no matter what it is you're doing, if you hold hard enough you can get through.
I do think it is the hardest question, finding it. Like finding it and knowing it, you know, knowing it's a little easier, but finding... there are a lot of 17-year-olds who appropriately, if you ask them what is your passion, what do you want to do, they appropriately say I don't know. Because it's the truth, they don't know. But I think that's okay, it's just we shouldn't force the question upon them.
You've got this line, life is a use it or lose it proposition.
Well, I mean, it's tied to the boldness regret, right? Like you're going to get to the end and then it's done. And only if you think in the way that Bezos did with his regret minimization framework are you going to hold yourself accountable for that line. You know, the recognition that life moves much faster than any of us realize and then it's done. And you can get locked in even sooner if you spend up to your limits. You can freeze yourself in a job like that you can't leave, and you can do it with personal commitments as well. My second career was going to Wall Street, and I can't tell you the number of people I worked with on Wall Street that had for their age ridiculously high salaries, but they had the place in the Hamptons, the summer lease, like they tried to get into the membership club. Like they spent right up to the limit, and now you can't switch, you know? You can't switch.
Yeah. You're locked in at this very high burn rate, which means you need to keep pouring fuel in the top of it.
Yes. Yes. I have like for young adults that are lucky enough to have a job with a decent salary, I would heavily encourage them not to spend against it just so they can have the flexibility to do other things. Move cities, change jobs.
All of which may be the right path for them.
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Yeah. It's weird, isn't it? Because flexibility is actually a really difficult thing to show off. It doesn't... And even flexibility is only show-offable in so much as you can take a photo of you on a plane or you at a holiday, which again is not quite the flexibility that we're talking about here.
Yeah. So, I've always thought about this, the difference between hidden and observable metrics.
We'll often trade a hidden metric for an observable one.
You know, trade the quality of our sleep for a slightly bigger pay packet. We'll trade the hours of peace that we have on a Saturday for position improvement. We'll trade... I mean, you know, some people will trade a caring, supportive wife for a very difficult, younger, hot one. You know, the trades are everywhere.
Yes. I think that's a good framing.
So, is... many people, especially people who maybe aren't so fired up with their jobs and their careers, might think, I can get my fulfillment elsewhere. Why should I care about my career? It's just the thing that I do from 9 to 5 or whatever, 8 to 4 every day. Why should I try and optimize that? Is being fulfilled at work a luxury?
I guess what I would say is I have an immense amount of respect for someone who adopts that mindset, the one you described, especially if they're really thriving in something that they may not perceive to be an occupation. That could be a religious community. It could be volunteer work that they do. I would highlight to them there might be a career in that, you know, like if they wanted to be around it all the time. But my main goal isn't to tell those people they aren't being successful. Like if they're happy and passionate about that lifestyle, like that's great. I'm not casting any shadow on that whatsoever. If you are the type of person that is either unhappy with your work, like so much so that it's impacting your quality of life, or even better, if you're someone that has this inkling, this little notion in their brain, but maybe doesn't have the confidence or the permission, they don't feel like they have the permission to go do it. That's who I want to read my book. Like, that's who I really, really want to read my book. There's a great story, there's a couple of these actually, but I'll choose the Steve Harvey one. I don't know if you've seen this, but you know who Steve Harvey is, the comedian who does Family Feud now.
He tells this story, I think he told it on Oprah, that when he was seven, the teacher asked them to, for an exercise, to write down on a sheet of paper what they wanted to be when they grew up. And he claims he got called last, and the teacher said, but the others she read, but for his, the teacher made him come to the front of the room and read it out loud. And apparently he had a stuttering problem, but it said I want to be on TV. And she thought he was not taking the exercise seriously, and she condemned him for writing that so much so that she called his mother, and he got in trouble when he got home. So, he got sent to his room. 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. Hears 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 bedstand. 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'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 that 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, 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 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 does some people successfully pivot and others end up getting stuck?
Well, I mean, there's... 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 just stuck financially, like you're living hand-to-mouth. I have a profile in the book of Jen Atkin, who I don't know if you know who she is, probably the most successful hair stylist of all time, like 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 mail room in Hollywood, and David Geffen and Barry Diller, all these people started in the mail room. You know, 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, you know, it could be like this perception, McConaughey had this perception that his father wanted him to be a lawyer. It's probably just that Matthew had told him he was going to be a lawyer and he was supporting that. But that weight can be there too. Like you may feel, I think there are certain cultures where being a doctor is considered really important, like being an academic was. So you may feel pressure from your family as this is the thing people in my family do. And I've seen that and I've met people who have that weight upon them. Those are all kind of things that could restrict this movement.
What about the fear? There has to be a huge chunk of people that just, what if this doesn't work? It's sort of ambient. Yes. Ephemeral, this fugue fog thing that's come down on them.
But if you'll allow me to give you a little history of how or why I would say I spent six years turning the original presentation into a book, and I had this thing I really wanted to achieve, which was to embed as much stories and narrative into it as possible. And I was listening, I know you've had Morgan on, how...
And he was on a podcast called Why We Write talking about...
And so the book is divided, it's structured unlike most books. It's divided into two parts but they interleave. And so every other chapter is an Atlantic-size article about someone that started on the bottom rung with intention and made it to the top. And the reason I wanted to include those is precisely for the reason Morgan talks about, which is I think these things stick in your brain more. Like a lot of the books in the category that have done extremely well in career read like a textbook, do A, do B, then do C. They don't have this kind of spirituality to them that I think can infect the brain a little bit more. Does that make sense?
It's 100% correct. I mean, Ben Shapiro's famous line of 'facts don't care about your feelings' is as backward as it could be. That feelings don't give a single [__] about the facts.
Yeah. So we have eight, nine, or 10, I should know the exact number but I can't recall right now, of these profiles, and I alternate them with the principles. And it's, I wasn't thinking about it like candy and vegetables, you know, or something, but you get some of both.
It brings the ideas to life.
Yes. And I think the reason I told that long story was an answer to your question about fear. I think seeing this many stories, and they're all, by the way, I chose every one of them from a field that your parents would probably tell you not to go into. I intentionally skipped, you know, investment bankers and doctors.
Yeah. All the stuff that everyone knows is nice linear progression.
Yes. I have none of those in there for this reason, because I wanted to help people get past the fear by giving them the motivation and the method to do it.
Well, you're certainly right about changing people's opinions with beating them over the head with frameworks and justifications. It just straight up does not stick.
Yeah. Mantras and quotes and stuff can do, they're a nice compression algorithm I think for bigger things. But really what you're optimizing for, and this I'd be interested to know if you agree with me on this, I think you're optimizing for memorability.
Yes. And I just don't think that regardless of how well written, whimsical, insightful something is, it doesn't... the human brain, the keyhole isn't the same. It doesn't retain things quite as easily. The aphorism and stuff is nice. That's kind of like, you know, the tune from a song. It's the lead melody from a song that you can hold on to. But if you give somebody a story, how are you going to forget that? Years ago, and I don't know when it started. Actually, it's funny. I just said I don't know where it started and then something popped in my brain. I fell in love with these long-form non-fiction articles. There's a website called Long Reads, that has best of, and it's a lot of Atlantic stuff, that kind of thing. The thing that popped in my head was there was a New York magazine article. Suge Knight and Snoop and I think Biggie were on the cover of New York magazine when I was... it was in '93 or '94, and it was 20 pages. That may have been the first one that got me into this. But that led me to a book called The New Journalism. And there's another one called The New New Journalism about these writers that kind of left being beat writers on newspapers and started doing this longer-form journalism and how it brought stories to life. I think Truman Capote's highlighted in that. Tom Wolfe put together the first one, and then the second one has Krakauer and Lewis and like all the modern...
But now we've seen this pivot into Substack, right? That people that were previously hardcore journalists have made their entire careers on Substack. And then if you're somebody like Bari Weiss, you've done this sort of double U-turn thing and loop back on yourself enough and you end up in charge of CBS, or Matt Taibbi and you end up in charge of the Twitter files or whatever.
Uh, so talk to me about the risk of starting over in your 30s or 40s.
Yeah. You know, the idea of not just what am I going to do, but you know, I should have had my life together by now. Is really, you're telling me I'm going to start again at 37? I'm going to be at the bottom of the pile and I've got all this sunk cost fallacy from before. What are people going to think of me? What's the real risk of starting again in 30s and 40s?
Well, one thing I would encourage you to do, there was a book I read when I was really in, I think back in business school, called Shark Proof by Harvey McKay. He wrote, he's known for his sales book, but he wrote a book about careers, and he said to keep your dream job. This was an older book, so he said keep it in a Manila folder in a file, but you could create it in a Google Doc or something, where you're just keeping notes, like well if I do it one day, you know, and everything you learn, people you might talk to. I think you just pile more and more stuff in there, and it'll start to feel more real, like you can begin the process before you make the leap.
And then the second thing, I'm going to say three things, the second thing I would say is if you have some curiosity that's occupying your downtime, that's a really interesting tell. You know, when I was an engineer, I got a computer engineering degree and I was working at Compaq Computers in Houston. That was a big hot company back in the day. And I was going home at night and I had started, I'd learned about stocks and I was trading stocks. You know, I'd read One Up on Wall Street. I had this book, I forget what it was called, this book. You just get this book with all these one-pagers on every stock. Like that's what I was doing in my spare time. So if you're doing something like that in your spare time, like it's calling you, you know. And then the third thing, there's a chapter in the book actually titled 'Never Too Late.' And we list about 20 people that did post-40 pivots and we go deep on four of them. My favorite being local Austinite Bert Beveridge. Bert's nickname is Tito, so that'll tell you who he is. But seismology degree, undergrad, worked in oil and gas for several years. Ended up down in South America where he got frightened by a few experiences. So he hung that up out of fear and the boom-bust cycle. Became a mortgage broker. Didn't really love it, you know, and not sure he equated his identity to being a mortgage broker. And one night, this is such a, like it's part of why I love self-help books and ideas so much. He's watching a PBS special that says, 'Take out a sheet of paper, draw a line down it, and put the stuff you love to do on the left side and the stuff you're good at on the right, and see if you can find a through line.' And he's looking at this sheet of paper and realizes he wants to start a spirit company. He's got like chemistry on the right. He's like hanging out at bars on the left. And he didn't know jack [__] about launching a spirit company. And it turns out Texas is probably the worst place you'd ever, at the time there was no one that had a license for a spirit company in Texas. But of course, Tito's is now the most bestselling spirit in North America. He owns 100% of it himself.
No way. The whole thing's bootstrapped.
But it's such a great story. Like, it's just such a great story. And now, you know, he's at the phase in his life where he's giving back and launching foundations. And this is my point. Like I say, I had a young person at Johns Hopkins raise their hand and say, 'But I don't want to chase my passion. I want to be purpose-driven.' And I thought to myself, you know, every profile in the book, these people are touching more lives than they could have ever imagined.
I don't want to chase my passion. I want to be purpose-driven.
I think it's part of a new movement to just like feel good about yourself. Like, my main goal in life is to help other people.
Serve. Yeah. Okay, that's interesting. Well, it's like no, it's noble on the surface, and there's certainly some things, you know, in the same way this person has high burn rate, family to support. You don't have the luxury in quite the same way. This person, there are some jobs that just suck. Yeah, there are some jobs you're serving your country or, you know, I'm sure lots of people love street cleaning, but I would imagine that some people do it more out of a sense of service than they do out of a sense of passion.
My only point was these people that are able to climb from the bottom rung to the top and do it in the right way end up touching hundreds and hundreds of lives.
They're serving in a much more seamless way that's leveraged as well.
Yeah. Yeah. Yeah. Yeah. It's, I mean, one of my favorite on that front is I, many years ago, because I was involved with OpenTable, I met Danny Meyer, who's the famous restaurateur in New York that also built Shake Shack. He has a great book, Setting the Table, if people haven't read it. But if you talk to people in the restaurant industry and they worked even for a year at a Danny Meyer restaurant, it's like meaningful to them. Like it's on their resume. They talk about it all the time. Like there's almost this church of Danny Meyer for everyone that rolled through it. That's got to just feel amazing.
What is it about his demeanor or culture or ethos?
The book talks about this kind of understated sensibility to hospitality. Like just trying to read the room on each and every customer and really understand, you know, what they're trying to optimize and to help them do that as much as possible.
But his journey is about more than that. That's what his book's about.
His journey is about being hyper-curious and an excessive learner. Like every single step along the way, including today, he's still doing it. You know, last time I talked to him, he just got back from Europe, he'd taken all his chefs on a tour of Europe together. Jotting notes, taking learning, like just constant learning.
Which I think is... it's also, that's the second principle of my book is continuous learning, but it ties in with the first one. The best test as to whether you found your passion is does the learning feel free? Like would you do it instead of watching a TV show? Like is it something you enjoy so much that continuous learning is just you enjoying life, you know, and if you find that, you found your passion.
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Joe Hudson's got this line, enjoyment is efficiency, he says. And I think I liked it.
I think it's really, really true. Yeah.
People have this relationship between discipline, motivation, and obsession.
Discipline's always there but there's a lot of friction. Motivation, the friction gets removed a little bit but it's sort of harder to grab a hold of. You don't really know where it comes from. Maybe it's a rock playlist or maybe it's the right amount of caffeine or something.
And obsession is friction inverted, as opposed to you having to push through resistance. The resistance pulls you toward it.
That's exactly right. And the problem I think, or the reason that obsession is difficult, is that obviously if it's pointed in a non-positive direction, that's how you become obsessed with politics or porn or your toxic ex or something. But if it's pointed in the right direction, what from the outside looks like a superhuman amount of discipline, from the inside feels almost like you haven't chosen it. You know, I'm not choosing to do this thing. You know, I mentioned before we got started, there's not been a single house I've lived in for a decade that I've not turned one of the bedrooms, including most of the ones that I slept in, into a podcast studio for a decade. My house back in the UK has got a podcast studio in it. The one that I live in right now is still podcasting. Eight years in, a thousand episodes. Every single house has had, every Airbnb that I've stayed in, I get there and I'm researching hotels to see if the depth of the table can withstand my MacBook, the stand and the tripod because that's what I want to do. That's what I want to do. I want to have these conversations. So, okay, my entire life gets warped around it. I'm sure you'd be familiar with the single-ordinating principle. I think Bezos has got one and I think Musk's got one. And Bezos's was always, 'Does this make the customer experience better?' So everything, every single decision in Amazon was threaded through this sort of single eye needle. And Musk says, 'Does this get us closer to Mars? Does this get us closer?' And by the way, both of those people did something that is super extraordinary, which is they took an innovative company, grew it to hundreds of thousands of employees, and kept it innovative. It's two of the only examples I know of.
They didn't get laden down with diseconomies of communication and lumbering behemoth bureaucracy that always lands in big companies. And it must be some heuristic like the one you described that allows them. In fact, I was just listening to Elon on Cheeky Pine, I think.
Yeah, this came up. This came up like every leader wants to know how he does it. That's why I think Collison was asking him, 'How do you lead?' He goes, 'Well, I'm down deep in.' He can't be deep. There's 200,000 employees. And Elon jokes, yeah, there's 200,000 employees. Like, you have to have some heuristic, simplifying heuristic that can spread through the organization. Spinning too many plates. Yeah. Exactly. Yeah. It's pretty impressive. It's super impressive.
Okay. So, career pivot fear. Someone is in the career, not super fired up, or I used to be and it just feels like it's time for me to grow now. What are the indicators that it's time to move? And what are the things that they should keep in mind to maximize their bravery, give them a little exogenous amount of morale?
So, on the, do you know, I mean I love this test of, is do you see yourself doing this 30 years from now? Because if the answer to that is no, you should get busy. What's the line from Shawshank? Like, 'Get busy living or get busy dying.' Like, if you know that's true, like, well now is when you should start. I'm not saying jump, like quit tomorrow, but like start building the plan. And then there's all kind of things you can do in designing your next move. Dave Evans has this exercise where he says create three to five scenarios and battle card them of what you might do next. Like, you know, fill them out. AI can really help, right? Like, you could build a 20-pager on each one of these career paths. What might I like? What might I not like? What are the three things people love in this career? What are the three things? You can steer it all, right? You can ask people in those fields. You can go find them. So you could role play being in each of these. There's a heuristic in the book that I borrowed from Ben Gilbert at Acquired, a lot of podcasters, where he had side hustles at all his jobs. So at each job he went to he would ask the employer, 'If I do it on my own time, can I do this other thing also?' And there's something really great about that. One, in each of his cases he ended up doing something pretty remarkable in the side hustle. At Microsoft he created Microsoft Garage, which became this way for Microsoft to stay relevant with founders, and he met all these founders, like all this kind of extra goodies came from that. But I think it all, like, so you learn more, you learn maybe two, you get two shots on goal instead of one. And I think the employer makes you look proactive so it reflects positively on you. When he ended up at Madrona, VC, asked him if he could start a podcast and look for that lead. And I just had dinner with both of them and they were in Austin and man, they're happy. Like I got to tell you, like they are really happy people. So similar to you and your obsession, and they fell into it through that, through getting there through that way. So I think those are some things you can do to test and then look, what are you doing in your spare time? Like are there any signals there? Those are all great ways. I wouldn't quit if you don't know where you're going. That doesn't make any sense.
Yeah. It's such a good shout to say, what are you thinking about in the shower?
Yes. What are you doing in your spare time? I keep on watching pickleball drills. I just keep on thinking about pickleball and I'm really interested in the sport and I'm interested in how it's growing and I love playing it with my friends. But even when I'm not playing it, I'm always thinking about it a lot. Let me, maybe there's, you know, maybe there's something going on there. Let me share this fun story I just stumbled on because I was using some hacker techniques to promote the book and that led me to talk to this gentleman and when I pinged him he said, 'Oh, please send me the book.' He goes, 'I saw the video a long time ago and it changed my life.' And I said, 'Well, tell me that story.' And he was a real estate lawyer and he loved football and he loved offensive plays and offensive diagrams in football. I love this story because it fits with my thesis that the best stories are in jobs your parents would tell you to never go do. He launches a website to help people manage and develop football plays and then he builds software and then he starts a podcast. He has 900,000 followers and this is what he does all day now. He talks about offensive football plays with the best and the brightest in the field. He's known throughout the industry. What a great story. Like how awesome is that?
It's so great. Like, I think people don't realize that you can actually, there are careers in a lot of places. A lot of people want to be in Hollywood or music and they think they can't do it because they're not talented. But there's a hundred support jobs for every artist that's out there and there's tons of work to go do. You know, if you really love being around that stuff, there's tons of opportunity.
Well, especially given that you can fail at a job that you hate, you can underperform in an industry that you don't want to be in. Yeah. So the prospect of potentially doing okay at one that you love is infinitely better.
I think so. I think so. That goes back to life is a use it or lose it proposition. Like, give it a go. And then the other thing to know about failing in that is humans are like this, the research in psychology says humans are really good at forgiving themselves. Like, you're not, the failure is not going to, you're not going to ruminate on it forever. Especially if you tell yourself, well, I'm proud of the bravery to make the call.
No doubt. Isn't there some evidence from psychology that humans prefer just making decisions generally? That if you make a decision, you tend to be happier. Someone's, let's say, it's a maybe a slightly less momentous decision between one city and another. The city that you're in now or moving. On average, people that move are happier. And I think part of that is just, well, life is, like novelty and variety are pretty fun. It's different and no doubt exciting. And even if it's objectively a little worse, subjectively it's all new.
Yes. I like that. I liked it. I just had a similar life experience. I spent 25 years in the Bay Area living in one type of community and when I moved to Austin, I moved downtown in a high-rise, completely different vibe. And it's invigorating. Like it's awesome.
Yeah. New place for coffee, new place to work to take your calls, your morning walk. All that's different. That's great. I agree with that sentiment. So, you quit a successful job at Compact to start again. How do people know when they're plateauing versus they're just a bit bored or something?
Yeah. A few people have asked me this question. Once again, I think the 30-year forward exercise gets you away from that because it's asking a different question. One thing I'm really big on is, and there's a different chapter dedicated to this, is developing peer relationships. And we can go into why I think that's such a huge unlock, but one of the benefits of having a group of peers, especially if they're outside your organization, so these are people on the same career path you're on, but are maybe a bit distant, they're at a different company or whatever, and if you have a community like that that you really trust and support one another, they can help you with that question you just asked, like, am I failing and I'm never going to succeed because I don't have the right talent for it? Do I maybe have a shitty boss? Is their experience different? Like, you can, it's a great group of people to ask those questions of.
It's almost like being able to run a little split test of yourself. What are the things that are different in your experience and how much of those are fundamental to the role?
Exactly. Yeah. And how much of that is transient that I could just finesse my way out of? There's 10 other reasons why you should build that group, but that's it. It's good at helping with that problem that you just described.
How do you deliberately upgrade your peer group without it being transactional? How can you make like-minded friends and peers without them thinking that you're constantly just wanting something?
Yeah, it's a tough question because I think the number one reason people are bad at forming these peer groups is they've been taught to be a climber and they've been taught to almost, been taught to be a bit sharp-elbowed and to outgun the next person.
Yeah. And we borrow a lot of our mental frameworks from finite games that have a beginning and an end and a single winner. And careers just aren't that way. Almost any industry, if it's not downhill skiing, there's lots of winners. You know, there's tons of winners. Podcasting is a great example of that. There's tons of winners in Austin. And so if you can build a peer network of like-minded people that you trust, and the great test of do you trust, would you share your best ideas with them? Like that you've learned this new thing that you just unlocked in your job? Would you share it with them? You should actually, I believe, but a lot of people wouldn't. And so, if you once you get to that place, it's a really special place. There's a story in the book about Chris Del Conte, who's the athletic director here at the University of Texas, and when he broke into sports administration, he was in the development office. He went to a conference, like, and it's a great place to meet peers. He went to a conference and met with a couple of other young men who were also at the beginning of their career. They exchanged numbers and started a text group and over time they added a few more people to that, got up to like seven or eight. They're all eight, all eight of them are D1 athletic directors now and they all started on the bottom and if you follow them along that journey, their learning elevated each time, each year they met, each time they texted, the problems they were encountering, they were sharing, they were explaining. It got to the point where they would do weekends away with their wives and invite in guests, you know, you talk about external learning, who's holding mini-conferences on their own nickel and bringing in external guests to help educate them so that they could rise and thrive together. It's just so, I just like, I get like, there's another story that's perhaps more modern for the younger crowd. Mr. Beast did this when he was 17. He found three other people that were trying to hack YouTube. They're basically trying to figure out the game of YouTube and they were on a Skype call for 16 hours a day together. And he says if there were a fifth person in that room, they would have made a million dollars also. Like it was just because the stuff they were uncovering was so usable and just deterministic, just no one else knew it. And he used a phrase I love. He said, 'You know how they talk about 10,000 hours?' Referring to the Malcolm Gladwell book. He says, 'We got 40,000 hours because we were sharing it all.' That's not the exact math, but it's a cool reflection of the moment.
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I think you do both. I think you do both. They serve very different purposes. The co-learning journey, I mean, peers give you co-learning. They give you support, which I talked about. They give you reflections, so you can ask those questions. Is this the same in your job? You're vulnerable with peers. You wouldn't do that with a mentor, right? Like especially if you get the peer group in the right place. You tell them I'm struggling here. So I think it's just a different purpose. With, I think mentors are extremely important, but I think the idyllic version of a mentor is a bit broken because we encourage a lot of young people to cold call too high where the rejection rate's going to be 98% because the CFO of this company doesn't want to be friends with you.
But it happens constantly. And so what I encourage people to do is divide mentorship into two different categories. Have aspirational mentors and just like that file folder for your dream job, create one for each of them. Like study them like a kid might study Star Wars characters or something. You know what I'm saying? Like really get enamored with these people that you idolize as aspirational mentors. And one, you're going to learn a lot studying them. And by the way, the resources are amazing right now. YouTube interviews, podcasts, like AI, you can learn faster than you ever could have learned before. So study them. If you ever meet them one day, the fact that you studied them this long is going to prove super useful. And then for the mentors you actually want guidance from, like tone it down a bit. Like go two levels below what you thought you were supposed to do. And you're going to meet somebody who's so thrilled that you recognize that they were successful and worthy of giving advice that your hit rate is going to go up 10x or more. Like the probability that you're going to get them to do the work is so much better.
I noticed that when I first started the show in 2018, and it's still not early, it felt late but you know now it feels early-ish. It was so flattering for people to be invited on a podcast. You know one of the other, such a funny trick that I still use now so the world can have this one. I realized that flattery was one of the big drivers I think for bringing people on the podcast, especially no one knows who it is. It's this random British guy asking if you should come on. I always used to ask people, 'Can you please put me in touch with whoever handles your podcast adverts?' And it's some small researcher at University of Arizona. And they're like, 'Oh, well, it's just me that handles my...' I'm seen in the echelons of those that would have an assistant or perhaps a receptionist that would handle my podcast ads. So, and that's still now. Please pass me on to whoever handles your podcast ads. And that's actually another good one I think just generally for any outreach to somebody. You want to be in front of the right person and especially if you're starting to pitch up toward mentors, that right person who actually handles that thing might not be them. So, you know, reaching out, 'You please put me in touch with whoever handles Bill's inquiries for coffee or whatever it might be' to the admin inbox because the last thing that you want is some complex question that the person who handles the inbound email thing or the LinkedIn DM requests, is it them or is it going to be somebody else looking to get put in touch with the person who handles their partnerships or whatever it is? If it is them, they feel flattered. And if it's not them, the delegate person passes you on to the right department.
And this isn't in the book, but if you ever meet the delegate person, pay as much attention to them as you possibly can. Like learn through them. Oh yeah. Learn all you can about them. Like be generous and kind and thoughtful, you know. It will pay off big time.
Good story around that from the show. David Goggins, you familiar with David Goggins?
Okay. So, he's ex-Navy SEAL, endurance athlete, probably one of the most sought-after podcast guests on the planet. In the last probably six years, he's done two podcasts. One of them was mine and the other was Rogan. He brought a brand new book out. His first book sold gazillion copies. Brings a new book out. And for nine months I'm back and forth with a person on his team and checking in, seeing how everything's going, seeing the marketing, this, this, this. And then he cancelled every other podcast appearance except for Rogan. And they tried to cancel the one with me as well. And I got this message, 'Really sorry, David's just going to have to, we're not going to be able to make it work.' And I was like, 'Look, I will do whatever it takes. I'll move heaven and earth. I'll come to you. I'll bring you to me. We'll change the date. We'll do whatever it is.' And they said a couple of days later, I got another reply, 'Okay, we're in. We'll be able to make it work.' And when I turned up, David, he's sort of a stern, stern, hard guy. Comes up, 'Very nice to meet you.' The first thing he says after that is, 'I just want you to know the only reason that I'm here is because of her.' And pointed to the person that I've been emailing.
So in your framework, loving the grind is sort of a non-negotiable. 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. And the meat grinder thing. Yeah. I just yesterday met with five of the top, 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 it's 1580 SAT and all, like clearly this human's been programmed to go take the hill 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 success. 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, and maybe if you're just so damn competitive like winning all the time is...
That winning is your passion. It's a meta passion.
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.'
Yeah. Whereas, you know, Jordan invented rivalries, like he invented slights against himself. There was, was it 92 or 93...
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 from his past and this person and this, they didn't believe that I'm getting... you're even at the moment where you've broken through escape velocity, you're out in space, still...
I don't love that that much, you know, I love...
It's not the energy that I have.
Yeah. So there's a counter example to that. There's this thing you can find on YouTube where Shaq was on that famous show that he does with Kenny and Charles and Ernie, Inside the NBA I think it's called. 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 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 thankfulness for the others that helped you get where you are. And I think in conveying that, it maybe makes him look remarkable, you know, it really does, like that his brain's wired that way. I felt very proud of him. Like I have no reason to be proud of him and he probably couldn't care less that I am proud of him, but it was, 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. You know, 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 proselytizing about these wonderful people and how grateful he was, he'd be called a suck-up.
That's fair. The medium is the message, but the medal is the message very much for this stuff.
Well, and look, that is more of a finite game, right? Like that is, then I, you'd use downhill skiing but there are like those kind of competitive sports you may need to be sharp-elbowed 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 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 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. But so you talk about honing your craft. 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 day we all applaud it, which is weird because if you said that about an engineering career they'd say you're a bad human, you know, but whatever. So this notion of learning constantly in your spare time, I think it's just the best test of whether you're truly obsessed with what you're doing. Do you remember when Elon took over X and he did that announcement post and he said, 'We are looking for people who want to work on the hardest problems possible as long as they can at an unrelenting pace to try and change the world.' And there was a lot of quote tweets of this saying we're throwing it back to a version of work-life balance that is completely primitive. This is abuse. This is horrendous. All the rest of it. And don't get me wrong, there are certainly some bosses in some industries that will drive their employees so hard that it's irresponsible. But if you're stating it upfront, what all of those people that quote tweeted it and complained about Elon's horrendous working conditions failed to understand is there are people out there to whom that sounds like a dream. Yes, they want to work 18 hours a day fueled exclusively on high-quality stimulants and Chick-fil-A, especially if they get to hang around with the smartest people. They want to be pushing each other and they want to send it. They want to send the living out of it. You know who's doing that right now, which is super interesting? The young AI founders. They've embraced this meme from China, 996. It actually was developed in China which means 9:00 a.m. to 9:00 p.m., 6 days a week. That's what it stands for. But they used the phrase and Silicon Valley got lazy in comparison. 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 eating their lunch.
Who are 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 it, 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 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, 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 out of them. Like they view AI as grind versus grind. It's gonna crush me. It's going to, I'm going to lose my job. Look at this world that's unfair. Now, if you contrast that with someone who is a proactive, independent climber who's trying to build their craft, their world, they're a continuous learner. For that person, AI is a jetpack. Like, they can now do more things faster that they wanted to do and they can achieve more than they were able to before.
They get to run extra fast. Like, so two people maybe in a same station in life, AI looks like the opposite to them.
A threat or a nitrous turbo boost.
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Cool. So, guidance doesn't sculpt us into something new. It exaggerates who we were already. The pattern is almost cruel. The ones who least need the medicine are the ones most likely to overdose on it, while the ones who need it desperately are immune. Advice doesn't land evenly. It finds the path of least resistance and tends to be absorbed by people who already lean in its direction. So, I first started thinking about this when considering the post-MeToo instruction of 'don't be pushy with women.' And I realized that it made conscientious, anxious guys even more timid.
While the dudes that were blowing through boundaries just didn't take heed.
Exactly. Or another example of the prescription to just work harder.
Yeah. That gets devoured by the insecure overachiever who's already bleeding effort into every crack of their day while the genuinely lazy person just coasts past it unchanged. The call to take more responsibility encourages the one who always thinks that it's their fault to carry even more of the load while the ones who constantly point the finger elsewhere never change. There's a bunch of reasons. People filter it through their existing traits. It amplifies predisposition instead of correcting overbalance. We all want to be good, so we sort of over-index guidance that flatters our self-image. But I think the most influential one is that the pieces of advice that match our inner fears are the ones that we believe the most. So an anxious man doesn't just hear 'don't be pushy.' He feels that it confirms the fear. Any move he makes is already too much. The sensitive man doesn't just hear 'open up more.' He feels it confirms the worry that he's emotionally inadequate, even when he's already oversharing. And for what we're talking about, the insecure overachiever doesn't just hear 'work harder.' They feel it confirms the suspicion that they're never enough regardless of how hard they try. And this to me, the disproportionate way that advice, you call them advice hyper-responders, right? The same piece of advice goes in very different directions to two different people. I do still think that developing a grind capacity is important.
But if you don't have the passion part, if you don't actually care about it, you can drive really, really fast in a direction you don't want to go.
That's the problem that you will look back on a career where you white-knuckled a ton of lorded but largely unfulfilling wins.
Yeah. And look, I'm somebody that I don't think you feel this if you switch jobs at three years, but when you reach a true retirement, and I'll be 60 next year, and when I decided that, okay, I loved every minute of being a venture capitalist, but it's time for me to pass it on to the next generation and move out of the way, it's reflective like, oh, I'm there. I think it's hard when you're 25. I think one of the benefits of being 18 is you don't see the end of times at all, and that gives you all kind of superpowers to play. There's some point at which you realize there's an end to all of this, and for this particular thing about your career, I think the sooner you can feel that the better, just because if you do want a different at-bat, you want to frontload that fear a little bit.
