David speaks with Taylor Pearson, an entrepreneur and author of The End of Jobs.

They talked about:

πŸš€ Deciding not to pursue law

⚠️ The trap of traditional career paths

🀐 The silent risk of staying in a job too long

πŸ“Š The concept of a personal balance sheet

🌍 Experiencing different cultures

🌱 How living abroad affects personal growth

πŸ› οΈ How to build a skill stack

πŸ“˜ The journey to publishing 'The End of Jobs'

πŸŽ™ Listen in your favourite podcast player

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🎧 Listen on Spotify:

πŸ“Ή Watch on Youtube:

πŸ‘€ Connect with Taylor:

Twitter: @TaylorPearsonMe | https://twitter.com/TaylorPearsonMe

Newsletter: The Interesting Times | https://taylorpearson.me/newsletter/

πŸ“„ Show notes:

0:00 | Intro

01:50 | Deciding not to pursue law

04:22 | The trap of traditional career paths

07:33 | The silent risk of staying in a job too long

16:32 | The concept of a personal balance sheet

24:11 | Experiencing different cultures

30:11 | How living abroad affects personal growth

34:57 | How to build a skill stack

40:38 | The journey to publishing 'The End of Jobs'

πŸ—£ Mentioned in the show:

The End of Jobs | https://amzn.to/41MVNUU

Paul Graham | https://en.wikipedia.org/wiki/Paul_Graham_(programmer)

Paul Millerd | https://theknowledge.io/paulmillerd/

The Pathless Path | https://amzn.to/3NOb2ak

Nassim Taleb | https://en.wikipedia.org/wiki/Nassim_Nicholas_Taleb

Fooled by Randomness | https://amzn.to/3tKBgDV

The Black Swan | https://amzn.to/41KSYnm

Anti-Fragile | https://amzn.to/3S8BWfQ

David Foster Wallace | https://en.wikipedia.org/wiki/David_Foster_Wallace

Optimize for Interesting | https://taylorpearson.me/interesting/

Eric Jorgenson | https://theknowledge.io/ericjorgenson-3/

Naval Ravikant | https://en.wikipedia.org/wiki/Naval_Ravikant

Flatland | https://en.wikipedia.org/wiki/Flatland

Full episode transcript below

πŸ‘¨πŸΎβ€πŸ’» About David Elikwu:

David Elikwu FRSA is a serial entrepreneur, strategist, and writer. David is the founder of The Knowledge, a platform helping people think deeper and work smarter.

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Career Hyperdrive is a live, cohort-based course that helps people find their competitive advantage, gain clarity around their goals and build a future-proof set of mental frameworks so they can live an extraordinary life doing work they love.

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πŸ“œFull transcript:

[00:00:00] Taylor Pearson: If you think about why emotions exist, right? Like why does the emotion of interesting exist? Why do we, like, get interested in something, right? Why is that? Why evolutionarily, psychologically, like why would we develop the emotion of interesting.

[00:00:11] Taylor Pearson: His theory was basically something that is interesting is an area in which you have a great capacity for what he calls compression progress.

[00:00:19] Taylor Pearson: So your ability to like take the different components of that and compress it with your existing knowledge and like make something more efficient and useful and interesting is higher. And that's why the emotion interesting exists because it would make sense evolutionarily that you wanna pursue these things which you find interesting because it's an emotion that's indicating sort of a fruitful way to take your skill stack

[00:00:43] David Elikwu: This week, I'm sharing part of my conversation with Taylor Pearson. Now, Taylor is an entrepreneur, an investor, and the author of The End of Jobs.

[00:00:52] David Elikwu: In this episode, you're going to hear us talking about Taylor's early career, his decision not to pursue law, the trap of traditional career paths, the silent risk of staying in a job for too long.

[00:01:03] David Elikwu: We talk about the concept that Taylor has of having a personal balance sheet.

[00:01:08] David Elikwu: We also talk about travel and experiencing different cultures, how living abroad affects your personal growth, and finally, Taylor's journey to publishing his book, The End of Jobs, and some of the core concepts of that book.

[00:01:20] David Elikwu: So this was a really enjoyable conversation. And also, look out for the next parts, because they are also going to be great.

[00:01:26] David Elikwu: You can get the full show notes, the transcript, and read my newsletter at thenowledge.io. And you can find Taylor online on Twitter @taylorpearsonme and in his newsletter The Interesting Times.

[00:01:37] David Elikwu: Now If you love this episode, please do share it with a friend and don't forget to leave a review wherever you listen to podcasts because it helps us tremendously to find other listeners just like you.

[00:01:50] David Elikwu: Okay. So I think one place I'd actually like to start is, so from hearing you speak about your background in the past, I heard that first of all you majored in history, minored in Spanish, and you know, you went, you did some year abroads and then I think you did a year abroad in Argentina, then you moved abroad for work. So before we get to that, 'cause I also wanna ask about your time abroad. I would love to know, you ended up going down, you know, it's a chain of cascading events that led you to doing marketing, but it started with you not wanting to do law and you were a history major, but you were thinking of going to law school and I found your decision making process here interesting. I'll let you talk about it and then I'll ask the questions after.

[00:02:39] Taylor Pearson: Yeah. So, I don't know, I guess I wasn't particularly forward thinking in college. I studied history because I liked it. I just picked the thing I most enjoyed. I took a bunch of classes my first year in the first half of my second year. And I liked history, I liked writing papers.

[00:02:54] Taylor Pearson: I mean, mostly right, you just read books and talked about them and then wrote papers about them. And I thought all of that was really fun. And I got to, I think it was the sort of summer after my junior year, before starting my final year and kind of the default path, certainly at my college. I think this is probably true in the US broadly for the most part, is like, if you do a history undergrad, like law school is a very common path.

[00:03:18] Taylor Pearson: After that, I think there was like 17. I went to a small school. I think there were 17 history majors in my senior year. And I think 13 probably went to law school or something like that. Like that was kind of like by far the most common thing. And, I'm curious what I've said in the past about my decision making framework.

[00:03:34] Taylor Pearson: I think the, I just wasn't excited about it. I think that's where I got to. And it wasn't that risky to like, not do it for a year and think about it and like, go back and take the test or whatever. And so my parents thought I was like just about to go to law school every year for like five years after I graduated college that I would go back.

[00:03:53] Taylor Pearson: I think most of what I recall thinking about it was. I just like wasn't excited about it. And, you know, the way the sort of US university system evolved, like there was like a substantial amount of debt that I was gonna need to take on to do law school. So like, if I did it and didn't like it, it was like really hard to get off the path and do something else.

[00:04:12] Taylor Pearson: And so yeah, I just, I just kept delaying it and delaying it. And then eventually, I don't know, I got to a certain point where I delayed, you know, I delayed it so long and I had other opportunities and it was no longer something I was thinking about.

[00:04:22] David Elikwu: Yeah, that makes a lot of sense. And that's what you said is exactly it. But the thing that I'm interested in is first of all, loads of people going to law degrees. It's the exact same here in the UK and I know from lots of people in the US people end up going and doing law or doing medicine. But I find interesting about what you said and knowing that you have now spent a lot of time thinking about decision making frameworks and a lot of these other things. I'd be interested to know how you think about that same decision, maybe aside from the fact that you already knew you perhaps weren't super interested in it.

[00:04:52] David Elikwu: But the key part I'm thinking of is the fact that a lot of people probably rationalize themselves into doing in law or medicine or some similar degrees, simply because the way the kind of mental model works is that the expected value is quite high in a sense where you probably eat dirt for a few years, you are not earning that much, especially while you're doing law school, everyone's poor, if you're in medical school, you're gonna be poor for a number of years. And then suddenly your pay skyrockets and you are doing extremely well. And then now you are in a very high paying career. And in some of those years, then you just suddenly very quite quickly pay off the debt that you incurred along the way. And I think a lot of people have that framework in mind, and that's how they rationalize themselves into making the exact same decision that you decided not to do. And people just think, you know, because doing some other degrees, you could also rack up a lot of debt for something else that doesn't pay well in, in the end anyway.

[00:05:44] Taylor Pearson: I think, I don't know if I had like the presence of mind. I don't, yeah. I don't know if I thought this at the time, but I think, I mean, I think certainly one lesson I take from that is like, the options you know that are available to you are like, not necessarily all the options.

[00:05:56] Taylor Pearson: I grew up in Memphis, Tennessee. I went to like a small, you know, not particularly notable school in the southeast US and most people from that school went into accounting, legal, I guess, you know, somewhat standard sort of corporate, like working at Wells Fargo, like, you know, kind of that sort of trajectory. And so like, that's kind of what I thought, like, I don't know, like that was just what you did, right? That's just like kind of what I saw people doing. And so I think, I think the first thing I was like, I'm gonna take some time and think about like, do a little exploration and like see what more is going on there.

[00:06:28] Taylor Pearson: And then I think I made a decision like pretty early on in my life to like, I wouldn't frame it in these terms, but like, not view myself as like homo economicus, like an economic agent, right? Like, oh, I do this and this is trajectory and this is the payoff, right? Because like, Paul Graham, the one of the Y Combinator founders and writer has a essay about wealth.

[00:06:46] Taylor Pearson: And like, one of the lines is like, wealth is what you want, right? So like if you had a magic machine and you just told that machine what you wanted and it gave it to you, you would have no use for money, like a dollar, whatever. It would be useless to you, right? You would just tell the machine what you wanted, whatever you wanted and the machine would produce that sort of thing.

[00:07:04] Taylor Pearson: So I think my goal was always to find something where I could do good enough financially, you know, with what good enough meant changing over time. But like, I've always put like a reasonable emphasis on like trying to enjoy my Day-to-Day work and career. I think everyone has certain parts of their work. I don't, I'm not blissful all day, every day at work. And I think being, if I'm going like six months and I'm like really sort of miserable at work, like something has to change here. And if that's like economically to my detriment then try to figure out a way to make that work.

[00:07:33] David Elikwu: Yeah, sure. What scares a lot of people is essentially it's just risk, different flavors of risk. And I think, perhaps we'll talk a bit about abstractions and heuristics later, but very often people kind of get onto a path. You know, we both know Paul Millerd who has the book, The Pathless Path, and this idea of there is a track that you could very easily go on that leads you through university and then you do this job, then you do that job and, you know, life could all be so simple and straying off of that path opens you up to tremendous risk perhaps, or that's, that's what it seems to be. But I've heard you talk about this idea of simultaneously there's a silent risk of perhaps doing the expected or staying in a job too long.

[00:08:14] Taylor Pearson: So, I think one of the writers that was very influential on me early on was Nassim Taleb. He has a number of books, Fooled by Randomness, The Black Swan, Anti-Fragile. And Fooled by Randomness, I think is the best. It's his first book and I think the most straightforward introduction to his work. But he has this, this fun graph of the lifespan of a Turkey. And so, like, of course, like the American tradition is like on Thanksgiving, everyone eats a Turkey, right? And so, you know, if you are a Turkey, he shows this little graphic and it's a Turkey standing in front of a whiteboard and he's got this big chart behind him, and every day the turkey's life gets better, right?

[00:08:47] Taylor Pearson: So the farmer comes out and he puts the food in the trough and you know, the turkey's eat the food and then whatever, waddles around with his friends and it's great life is a turkey's great, right? You know, he's pointed at his chart and it's just going up into the right, right? Everything's getting better. All the days the Turkey comes in. And then of course, Thanksgiving morning, the turkey's life is not so good. All of a sudden everything goes bad.

[00:09:09] Taylor Pearson: And, you know, his point is, you know, if there's lots of things where like, you don't necessarily get like a warning sign, right? It's not like, things start to slowly decline. It's like, things are good, then things are bad, and it just, you know, it just changes very quickly.

[00:09:21] Taylor Pearson: And so I think, you know, talking about risk, I think that's an important concept of, you know, yeah, I think I use the term silent risk, which is like, actually after, after my, my book, The End of Jobs came out, I had a guy reach out to me that I, I talked to a lot that was really interesting. He had worked at IBM for I think 30 years, a long time, 20, 30 years or something. IBM for some period of time had, I think they called it like a lifetime employment policy, but they basically said, we'll never fire you like you started IBM I think, you know, he started IBM at 22 or something for university.

[00:09:52] Taylor Pearson: And you know, at a certain point that changed. He got laid off, I think he was in his fifties, so he was around his like peak earning years. And he was in a really tough spot because a lot of his like career value and career knowledge was, he understood a lot of really specific things about working at IBM that weren't very transferrable to another company, right? It was how certain the hierarchy worked at IBM or certain IBM products or how to manage things politically or certain coworkers, relationships, all that kind of stuff. And so he'd had to sort of go through this multi-year process of sort of reinventing himself and coming up with a new career and, and trying to figure things out.

[00:10:27] Taylor Pearson: And so I think that's, a lot of stuff when people talk about, oh, this is the safe path or this is the safe trajectory, I think it's like what depends on what your definition of safe is and like what is safe really, right? So like pointing to this thing has worked for the last 10 years. Okay, that's a data point, but like, can we necessarily say like, that's safe per se?

[00:10:48] Taylor Pearson: And I think, I mean, I think that's the case with like a lot of jobs. I know there's been, like the US tech sectors had quite a few layoffs and like most people in those layoffs, I don't think saw it coming, right? They weren't saying, they going, I'm probably gonna get laid off 12 months from now, right?

[00:11:00] Taylor Pearson: They thought, oh, this is great. I've got this great job, everything's going well. And it's, you know, maybe I'm not happy, but at least it's safe kind of thing. And so I think, I challenge that with a lot of people because I think, you know, especially if you're, if you love it and you're super passionate about it and it's the thing you wanna spend your life on, like, that's great. Maybe it is risky, but good for you. And if that makes sense given everything else you, your life. That's awesome. Lot of times the safety thing it's like a way of sort of saying like, I'm afraid or I'm worried. And you say like, talking about that directly, you're just sort of like appealing to this notion of safety that like may or may not exist.

[00:11:34] David Elikwu: I think what you were saying just now, well, just a moment ago about IBM made me think of when I, I spent some time a while ago working in China, working in Shanghai. And a friend of mine was telling me that, I think a lot of young Chinese people probably getting into their mid twenties by probably about 25 people start having existential crises. Because there are so many people, there are lots of jobs, but there's also a lot of people. And so whatever job you're doing, by the time you're 25, at least this is how people think about it. That's gonna be the job for the rest of your life. And you know, in Japan, for example, they won't fire you there either. And so it's not like you're going to lose your job, but it's also, it doesn't mean you can switch jobs. So it's almost the, the inverse risk of like, once you pick a path, you are stuck on that path. And that's, that's actually going to be it. It's not even like you have the option to switch paths.

[00:12:25] David Elikwu: But just on what you were saying about just the idea of risk and how people can either the perceived risk that they see is too high or they, or they just don't fully appreciate the value of risk. I think this links to another thing that I've heard you mention in the past, but I think is also from Nassim Taleb, which is this idea that, I think the analogy that Nassim Taleb used was, I mean, it's links to Ergodicity and it's the idea that, jumping off a one foot wall 50 times is not the same as jumping off a 50 foot wall one time.

[00:12:54] David Elikwu: And the way I think about it as well, something that came to my mind, I think in the last week or so, I was at the train station, and you've been to London, you came last year. You know, sometimes on the London underground, you'll see there's gonna be the escalators, but there'll also be the stairs. And they put a warning on the stairs and they tell you exactly how many stairs they are, especially if it's gonna be long. So they'll say, this stairwell has X number of stairs just because you can't see it before you start taking the stairs. And that warning has to be there so people know exactly what they're signing up for once they start taking the stairs. But I think the funny thing is that when you have to take the stairs in an emergency, people obviously end up hating it. But a big part of that reason is because people don't do the small hard thing that you could do every day, which is taking the stairs. And so when you are forced to do a much bigger, hard thing, it feels so much worse.

[00:13:43] David Elikwu: And I think in that same process, people take away the wrong lesson. So every day people avoid taking the stairs, even though, incrementally, like just day to day, it's not that bad. You could take the stairs on a normal day, but people will avoid the small inconvenience of taking the stairs on a regular day. And then on the one day that you are actually forced to take the stairs, it feels like the worst thing in the world. And then once you do that, you're like, oh, I'm not gonna do that again. And so from that point on, then you continue to avoid the stairs. Whereas if you took the stairs regularly on a normal day, just small stairs, then by the time if there's an emergency, there's a fire drill or you actually are required to use the stairs, then you know, it feels relatively easier.

[00:14:24] Taylor Pearson: Yeah. I like that example, and I think of like, you know, I have no data whatsoever to support this, but just like total anecdotal observation. Like, I meet some people that have, you know, talked to some people that are very intelligent people that have worked at like large companies for long periods of time and, you know, in a certain way they just by necessity, right?

[00:14:43] Taylor Pearson: Like you're working at Amazon or something, like your whole job is like two pages, managing two pages on like the seller central dashboard or whatever. You know, a lot of it just like isn't very transferrable to like other things, right? Like it's just extremely specific to that particular company.

[00:15:01] Taylor Pearson: And so I think there's a lot of situations like that where like, to me, I think I can make a reasonable case that that's like quite a risky thing to do, right? As you said, you know, if you start your career, you work for some period like at a, a small company or a startup or freelance or whatever, like the skills you get there tend to be a lot more generalizable, right?

[00:15:17] Taylor Pearson: You know, the equivalent of like jumping off one stair 50 times and like applicable to a lot of other situations in a way that certain big companies. And I'm thinking of you get sort of like put in this really niche specific thing that's just like not particularly transferrable, and like that's a risky thing, right? Because like your economic value, right? Like maybe you're making a really great salary, but like your economic value is very tied to like this particular thing, right? Like one product on Amazon Web services, you know, whatever the thing, you're doing is.

[00:15:48] Taylor Pearson: So I think like, from my view, the important is like, it's not necessarily a bad thing, right? If you enjoy it or you know, you're making a ton of money, whatever, great. You know, good for you. But like, let's not say that this is like necessarily safe or smart or robust. This is like a risky thing that you're doing and you're sort of comfortable with that risk. I don't think that, that doesn't tend to be how people think about it, right? They didn't think about that's like the smart safe thing to do. And you know, something where you're gonna work at a smaller company or start your own thing or whatever it is, is a lot more risky. And I don't think that's like a really reasonable assessment of like career risk, right? That like, having a broad experience of generalizable and transferable skills feels to me like, that's like a much less risky thing to do, right? That your ability you know, turn that do other things with that is much higher.

[00:16:32] David Elikwu: Yeah. But what I find interesting about that though is, I feel like I can see both sides and the irony is that most people don't, and that's why they stay stuck. So the end question I wanna ask you is, you know, how you think people can functionally escape the sunk cost of whatever position they're stuck in or whatever role they're doing.

[00:16:49] David Elikwu: But I think, you know, just going off the back of what you were saying, I spent about five years in corporate law. And I definitely think that people severely underestimate how transferable some of the skills they're learning are, or at least how powerful some of the skills they were learning are if they applied them to other domains. But the problem is they are applying that exact same skillset to the exact same domain over and over again and just optimizing for getting better at that. Whereas if you took some of those skills and you applied them somewhere else, actually you would realize these feel like superpowers. And I guess the analogy that I would give is that it's a bit like thinking that you have superpowers because you get really good at cultivating spiders instead of letting the spider bite you. And then you get to become Spider-Man, like If you took that little bit of risk of letting the spider bite you, the asymmetry of a future where your Spider-Man is far greater than, being the person that gets to grow the spiders. But you are, you still have the same proximity to that, the potential of having that alternate timeline.

[00:17:44] David Elikwu: I know that probably sounds a little bit complicated, but that's kind of the way I think about it, where,

[00:17:49] Taylor Pearson: Not, I love a good Spider-Man analogy.

[00:17:52] David Elikwu: But yeah, go on.

[00:17:53] Taylor Pearson: No, I think there's, I don't know, there is like a, you know, it's interesting, like I've hired people, like directly out of college. Like there are like a lot of work, like how to write an email, you know what I mean? It's like an underrated, an important work skill. Like, it's like a surprisingly non-obvious thing to do, or like, yeah, you know, how to manage your calendar and stuff like that, which like, this sounds like kind of pedantic, but like, it's actually not like if you're like, good at responding to your email and showing up at appointments sometimes, that's pretty good. You can do a lot with that, product of people.

[00:18:20] Taylor Pearson: So I agree. Like, I don't know. I'm like, there's, there's a bit of this like lionization of entrepreneurship in the culture at the moment, and I'm always like really hesitant. I'm always about like sort of not playing into that kind of thing. And I think one thing I was like most people, this is again, my sort of experience, like most people that have like been successful, like working their way up some like competitive corporate career. Spinning that into starting a business or working a smaller company, like just a general like grit, competence, raw intelligence, you know, all those filters. Like you've kind of probably passed through all those filters at that point, I'm like, your ability to make that switch in my experience is like pretty good.

[00:18:55] Taylor Pearson: I think there's usually like a, I don't know, three year transition period or you, there is some transition period of like figuring that out kind of thing. But no, I think that's right. Like there is a certain transferability there. I don't know. I'm curious what you think, like, it seems like maybe the later you wait it's, it gets a little bit harder, especially like given earning expectations, you know, if you're at like 45 or 50 at sort of peak earning years and like trying to do that and get back to peak earning in a new career, that seems like it might be a little bit harder, but I'm not sure. Yeah. Yeah, no, I absolutely agree. And that's where all my friends are stuck. I think that's the thing, right. Okay. So it is both in terms of your compensation and both in terms of the skillset, if you stay long enough just to pick up the skills and then you can take them and apply them elsewhere, I think that's the peak option. Well, that's what I did. I think that's the peak option we will see. Right now, I am still very much feeling jealous of some of my friends who will be listening to this that are still at the firm that I was at, who are earning, you know, very well and a lot of people from, from my cohort.

[00:20:40] David Elikwu: But I think the thing is that the longer you stay just applying the same skillset to the same problem, it almost starts to diminish. I think the potential upside diminishes because then you get trained too much to apply it very narrowly and you don't know it anymore how to apply that skillset broadly. And then on top of that, that's compounded by the compensation that you get. So then the benefit that you could potentially get by leaving and actually trying to, 'cause it does necessitate starting from the bottom a bit, taking that skillset and moving it elsewhere, you do have to learn and you have to start pattern matching.

[00:21:14] David Elikwu: And that requires, yeah, there is the emotional risk there of actually having to, it takes some humility, it takes some, you have to put yourself out there to learn in other domains.

[00:21:24] Taylor Pearson: One thing I've been thinking a lot about lately is like the idea of like a personal balance sheet, right? So like a business will have a balance sheet that like shows all its assets, right? It owns a factory and a, a car and, you know, whatever, and it has this much cash in the bank and, and like those sorts of things. Or like, a person has a balance sheet too, and you can like, think of that in strictly financial terms. You have whatever money you have in the bank and you have a car and whatever you own and that kind of stuff. But like, I think there's like two other ways to like broaden the concept of balance sheet that are interesting.

[00:21:52] Taylor Pearson: One is thinking about like, as you said, like human capital, right? So like, if you're learning very fast, right? You're acquiring a lot of new knowledge, you know, hopefully that's like somewhat transferrable. Like even if you're not making that much money, like you could factor that into the balance sheet too, right?

[00:22:05] Taylor Pearson: Like, okay, maybe I didn't make that much money over this period, or I did that, I made a lot of money and I learned a lot of skills. Okay, that's really interesting, right? But I think, how I'm interpreting what you're saying, right? It's like, you also getting these periods where like maybe you're earning a lot of money, but like the human capital part of your, so like the financial balance sheet looks good, but at a certain point, maybe the human capital side of the balance sheet isn't that much more interesting than it was five years earlier or isn't that much more compelling than it's five years earlier. And like there's a cost associated with that, right. That's a trade off that's being made maybe, I think a lot of people don't think about explicitly. And then I think you could even broaden the concept more and say there's also like, you know, how you feel about your life that's like part of that balance sheet, right? Like, is it, whatever, am I enjoying what I'm doing? Is this meaningful to me? Like all those sort of like existential questions start to come in.

[00:22:51] Taylor Pearson: And so I think it's like, I think about that a lot. I think one, one sort of interesting in investing analogy is, if you're investing in a company, people often do something what's called a discounted cash flow analysis, right? So you'll try and project out the cash flows of the company and its earnings and its cost and all this kind of stuff, and what the profits gonna be, and you'll work backwards from that to determine like what an appropriate valuation is today, right? What I'm willing to pay for this company, and like one of the biggest variables in that calculation is how long you expect those earnings to persist for, right? So if you have a company that's making a lot of money but doesn't have much of a competitive advantage, and those earnings go away in three years, the present value is a lot less than a company that has pretty good profits, but has a very durable competitive advantage and can last over a long time. And so I think, you know, in principle that's true of an individual as well, right?

[00:23:41] Taylor Pearson: It's like if you do something where it's reasonably valuable and you're reasonably good at it, and you can do it for reasonably long time on your, you know, discounted cashflow analysis. It's actually worth a lot. 'Cause it can persist over a long period of time. I think some people get, you know, folks saying like, oh, I can make a lot of money doing this for the next year or two years, three years, five years, whatever.

[00:24:01] Taylor Pearson: But actually, you know, maybe it's better to think about what could I do for the next 20 years? or what would that look to think in that timeframe? You know, and like, what would that look like and how would I do things differently?

[00:24:11] David Elikwu: Yeah, that makes a lot of sense. I'm gonna mix analogies here, but the way I'm thinking about it in my mind is, okay, so on one hand it's a bit like the 80 20 of, in most jobs and in most careers, you spend 80% of the time getting good and then 20% of the time getting griped. But you have to get good first. And once you get good that you've got the 80% and the 20% is just optimizing.

[00:24:32] David Elikwu: And so the other way of thinking about it is getting good at the skill and getting good at the game. The skill is the 80% but that is just onboarding slightly beyond onboarding, but like getting to a point where you are competent and you know you are good enough to be dangerous. That is the 80% and then the 20% is the game. So first you get good at the skill, then you get good at the game. But the problem is that the actual time allocation is the inverse of that. So how long does it take to get the 80%, 20% of the time? And then you spend 80% of the time on the remaining 20%, and that is the rest of the career.

[00:25:05] David Elikwu: And so using law as an analogy, but it applies to other careers as well, is that people within the first few years of being in that career, you do the 80%, you get good at the skill, and then the rest of the entire time span of that career is like working your way up to partner.

[00:25:19] David Elikwu: That's getting good at the game, that's the only 20%. And so I think that's the part where in your analogy, that goes on the other side of the balance sheet where you're not actually building the skill anymore in terms of the human capital. You are just optimizing for the game and just getting good at applying it within this very specific domain. And that is useful as long as you keep playing the game. That is super useful. But once you stop playing the game, you actually realize that you've spent however many years just optimizing for the final 20% and the rest of that time you haven't actually spent that developing on the other side of your skillset.

[00:25:51] Taylor Pearson: Right. No, I like that. That's very interesting, like at that point your trajectory becomes very path dependent, right? You have to stay on that path and keep playing that game for it to sort of be successful in the long run. Yeah, I think there's a, a, blogger I like, his name's Venkatesh Rao.

[00:26:05] Taylor Pearson: He has a blog post, I think it's called the compass in the gyroscope, or that's the sort of analogy he uses. There's the idea of like a, an external versus an internal coordinate system, right? So like a compass is an external coordinate system. You know, you have the north, southeast, west, and you look at a map and you sort of navigate it. And a gyroscope has sort of an internal system, right? It's rolling downhill. I'm not gonna describe very well mechanically how a gyroscope works, but I think people can sort of, visualize it. And I think about that analogy a lot too, because I think sort of to your point of like the skill versus the game is like, it's the more sort of like clear the map is in general, I think it's just like more competitive, right? Like getting to partner at a law firm or being a renowned surgeon in a particular, like, it's really hard. It's just really, it's like being, you know, being a professional athlete, right? Like what percentage of kids wanna be a professional athlete when they're like 10 years are like, it's really hard.

[00:26:55] Taylor Pearson: And so this idea of like a gyroscope or maybe you're, you know, you're picking up some skills here and some skills there. You're sort of following an internal coordinate system that's not leading down a necessarily known map or known road. Paul's like Pathless Path idea, but does still have a certain logic to it, right? Things do stitch together in a certain way in which those skills are complimentary and useful. They are not in a way that is easily explained to someone on the outside in the same way that you know, you may partner to a law firm or you went to go to law school, or you did this or that sort of, specific accomplishment.

[00:27:25] David Elikwu: Yeah, so I'm interested to apply this too. Going back to your career path. So after you left college, I think you spent some time working abroad, and you've mentioned that, or maybe this was, I think actually before that, in your second year of college you had a year abroad and then coming back you had like a reverse culture shock that made you want to go back out again. And I'd love to know more about how you felt in that moment and what felt like the most impactful. Like what did you see that felt, I dunno, life changing or paradigm shifting, that you then came back and felt like, huh, something's different, something's missing.

[00:27:57] Taylor Pearson: I think for me, that experience, yeah, I did. It was my, my third year, my junior year, I spent a year in Argentina. I was a Spanish, at least I was a Spanish minor and my Spanish was not very good. And so I thought if I went and spent a year Argentina, you know, my Spanish would have to be good. I lived with like a host family, like an older woman. I lived in like a spare bedroom in her house and went to the university there.

[00:28:16] Taylor Pearson: And I think, yeah, that was impactful for two reasons. I think one, when I got there, my experience was really bad. Like really bad. Like, I don't know. I can't stress how bad, embarrassingly bad. And the first, I'm depressed is a strong term, but like the first month or two were like really hard like, my classes were in Spanish it's like, imagine if you know but or didn't speak any Russian, you're like, chain down in Russian University. And like, I literally didn't know what they were saying, you know what I mean? Like literally I couldn't understand the words that were coming outta their mouth.

[00:28:42] Taylor Pearson: And yes, it was really tough. And so I would like go home with my like host mother and I would like sit there with like my Spanish English dictionary open and like try and talk to her you know, and I'm like looking up words and like we're pointing, you know, she's pointing at stuff and she's telling me what the word, like, you know, like I'm a 4-year-old basically, right. You know, like a, a young child. And by the end of it, my, I don't know, my Spanish was decent. Like I was conversationally functional.

[00:29:05] Taylor Pearson: But like I could like go to a university class and like in Spanish and like get, you know, 98% of what they were saying and be a functional thing.

[00:29:12] Taylor Pearson: And so I think that was just like a huge confidence boost for me that I had done this hard thing that I was clearly very bad when I showed up and I was like reasonably competent when I left. And so I think that gave me like a lot of courage to like try something else, you know, to do something a little bit different and not necessarily go to law school or kind of go down the default trajectory.

[00:29:30] Taylor Pearson: And I think the other thing relates back to what I said earlier, which is just like, it was a different experience in like ways I couldn't have imagined, right? There's, you know, you talk about like there's the known knowns and the, the known unknowns, and the unknown unknowns, right. So this was a, and it was, it was an unknown, unknown, right? It was different culturally, historically, sort of all those different components in ways I hadn't even really thought about. And so I think that gave me a certain, like maybe there's other things I haven't thought about that are different about how the world works.

[00:29:58] Taylor Pearson: Like, I wanted to explore that some. And so I think, yeah, I think I wanted to go live abroad again after that. Just because that, for me at that point, like that was one way in which that was very visual. Just living in a different culture, people speaking a different language, and like seeing what that was like.

[00:30:11] David Elikwu: Yeah, sure. That reminds me a bit of, like I mentioned, I went to to China as well, and it was a very similar experience, although I had studied Chinese a bit and that was kind of the point. So originally, actually before going to university, my original plan was I wanted to go and work at a Chinese university. I got like two offers through my Chinese teacher to go and, you know, teach English at a university there, and my dad said no. So I didn't get to do it. But, but then during university, then I had an opportunity to go and I was actually working at a law firm there, so to connect two of our, two of our lines. But in the first month, I was doing half days. So I would go to work for the first half of the day and then go to language school for the second half of the day. And at the language school they did not speak English, they would only speak to you in Chinese. And then at work, obviously people are only speaking in Chinese and it was so hard. And particularly that first month was just grueling because you know, people also, like culturally, they would have lunch together at work. And so, yeah, first of all, I didn't even know how to use chopsticks, so I had to learn that in front of everyone. So it's like hugely embarrassing, everyone's sitting around this big table having lunch together and I'm trying to figure it out, it actually took a while. And then going from there to language school where they're only gonna speak to you in Chinese, but you actually get better quite quickly.

[00:31:29] David Elikwu: And I remembered one situation, 'cause you mentioned Russian. They sent me to go and meet with some guys. Obviously the whole point under is 'cause I speak English, right? And so I'm meant to be really good at English, that's how I got the job. I had some of the best exam grades in the world at English. And so they sent me to go and meet these, you know, white people. They were from Russia. And the joke was when I actually got there to meet them, they did not speak English. They spoke Russian and they also spoke Chinese. And so and so, the only language I could speak to them in was Chinese because I was, you know, I'd been learning Chinese. This guy spoke Chinese and also Russian, I know no Russian. And so I was just stuck there trying to try to figure out how to negotiate things.

[00:32:12] David Elikwu: But the other thing, how I was gonna tie that back was you had mentioned this idea that I think also connects to something we were talking about, which is when you go to a new place, you kind of get to try out some different versions of yourself, right? You are unconstrained by your typical environment. People usually know you as one person and in one way, and when you move somewhere else, you get to, not that you have to be different, but you get to try to be different. You get to be a bit more explorative and you can push some of the boundaries that you might typically be stuck within.

[00:32:46] David Elikwu: And it was funny, there was a post that I came across on Reddit that was reshared on Twitter. So unfortunately the person that shared it didn't get to see the, the revelation that occurred, but the person that was making the post was talking about his life and basically he was miserable, right? He had this job, washing dishes, working early hours of the morning, he was just working in this restaurant washing dishes, it wasn't fun. He was arguing with his girlfriend all the time. I think they'd recently broken up. He had these friends that he, he wasn't really friends with them anymore, and they've kind of disconnected and none of them were really doing anything well, either. He'd been trying to save some money to move, but not enough that he could. He hadn't saved enough to move. He had saved enough. What he did was he stopped renting the apartment he was renting. He got a van, he was living in the van, and he managed to save about 15,000, but he didn't feel like he'd saved enough to move.

[00:33:37] David Elikwu: And the comment that I saw, which was now on Twitter, where this post had been re shared, is that this guy is completely miserable, but how happy would he be if someone whacked him over the head and he completely forgot everything about his current life. All the constraints that he sees to the girlfriend that he argues with the job that he, he's supposed to show up at. If he didn't know he had to show up at that job, he just woke up with no memories. Like Jason Bourne, he has a van that he could stay in. He has $15,000 in the bank. Like that is actually a pretty great fresh start. You know, if you didn't know anything else and you have $15,000, you've got a van, you've got some clothes, some belongings, that's actually a much better position to be in than, than a lot of people. But when you are stuck in that position, you can't really see that, like you can't climb out of the situation that you are already in to see things with fresh eyes.

[00:34:26] Taylor Pearson: I know, I think that's hard. For me, that's been perpetually hard, right? You just don't, I think there's a, there's a David Foster Wallace bit where he is talking about, there's two fish swimming that like, just swimming at each other and they swim past each other in the water, and one fish turns the other fish and goes, water's nice today. And the other fish looks back and goes, what the fuck is water? Right? And it's like, well, you know, he's in bits of fish. Why water is nothing? It's like, why would you even comment on it? You know, you're in water all the time, right? Yeah. I think it's, it's hard to see those things and see like, oh, you know, this is like, this is water.

[00:34:57] David Elikwu: Yeah, so in The End of Jobs, your book, you talk about this idea of developing skill stacks and, you know, using that as a way of traversing through the working world. And I think, well, a big part of the emphasis of your book was becoming more entrepreneurial and kind of using the skills that you developed to become more entrepreneurial. I would love to know about your personal skill stack, because you are, you've had a really interesting background and I think, so maybe there's two layers with the question. The first layer is how do you think you've gone about building your skill stack? Is there any way that you've thought about learning things in particular that you found useful?

[00:35:30] David Elikwu: Just because, I mean like tracking some of the things you've been interested in. First of all, okay. Starting with majoring in history, minoring in Spanish, getting into marketing and learning all the skills you need to get there without going through any real formal process. You kind of did that very manually. Going from there to becoming a writer, both publishing your book and also writing quite prolifically online. Then going from there to being an investor. I think at one point you got interested in complexity studies. You seem to have taught yourself a lot of things along that path, so I'd love to hear you talk a bit more about that.

[00:36:00] Taylor Pearson: Yes. Let me see if I can answer sort of both levels of the question at the same time. I think, there's a, a paper I wrote a summary of some years ago, I believe it's called Optimize for Interesting. I think that the guy that wrote, I believe was an AI researcher, and if you think about why emotions exist, right?

[00:36:16] Taylor Pearson: Like why does the emotion of interesting exist? Why do we, like, why don't, you know, you get interested in something, right? Like, why is that? Why evolutionarily, psychologically, like why would we develop the emotion of interesting. And, his theory was basically something that is interesting is an area in which you have a great capacity for what he calls compression progress.

[00:36:36] Taylor Pearson: So your ability to like take the different components of that and compress it with your existing knowledge and like make something more efficient and useful and interesting is higher. And that's why the emotion interesting exists because it would make sense evolutionarily that you wanna pursue these things which you find interesting because it's an emotion that's indicating sort of a fruitful way to take your skill stack as you described it.

[00:36:57] Taylor Pearson: And so I think, that's always sort of been the way I've tried to think about it is like, okay, what am I doing now? And like, what is interesting? That is like somewhat adjacent to that and like, I'm gonna go, that's gonna kind of how be I'm gonna spend my free time. You know, that's what I'm reading about, that's what I'm interested in, that's what I'm looking at. And even though it's not directly applicable to maybe what I'm doing now, it's interesting to me. And so I'm, I'm just gonna sort of take it on some faith that there's some ability for compression progress, that there's something I can do in, in that direction.

[00:37:23] Taylor Pearson: So I guess sort of my career progression, my first job was a, I was a Spanish interpreter. That was my one marketable skill coming out of university. I took a night class my senior year to get, I don't know if I was officially licensed. I had some badge or something but I was doing interpretation. So I did that. It's like, that was sort of my first freelance gig. And then I got a job as an English teacher in Brazil. I said I wanted to go abroad again, so I moved to Brazil and I taught English for a while. I didn't love teaching English for a number of reasons. And so I had gotten interested in digital marketing and, and I just think this was sort of early 2010s, and like search engine optimization, all this stuff was kinda coming online. And I, I went to Amazon and I bought every book on search engine optimization at the time, which I think there were three books. I think there's probably 30,000 of them now. And I built some websites to basically teach myself SEO, I think my most successful website was collegefurniture.net.

[00:38:16] Taylor Pearson: And it was like reviews of like furniture you would use at college, so like futon reviews and nightstand reviews, whatever. And I think at its peak, I think I made like $300 a month or something, and I was like pretty jazzed about my $300 a month from the site. But that sort of set me on like my initial career trajectory, I was able to parlay that $300 in a month wasn't sustainable. So when I left my English teacher a job, I got a job in a marketing agency and I basically, I cold emailed a bunch of marketing agencies and said, Hey, look, I know SEO here's my website, here's all the SEO stuff I did, you know, will you give me a part-time job?

[00:38:48] Taylor Pearson: And so I got a part-time job that turned into a full-time job. I worked there for a little while. I started doing, you know, sort of other digital marketing agency things, email marketing, pay-per-click, a bunch of stuff like that. That got turned into, I got a job at a e-commerce company that was based between Southern California, some in East Asia. We had a team in like the Philippines and Vietnam and China. And so I moved out, I was in Vietnam for a couple years working for them. And I started progression just doing marketing, they had a number of different hospitality equipment brands, so we sold like parking equipment, bar equipment, stuff like that.

[00:39:19] Taylor Pearson: And I ended up running one of those brands. And so I kind of got outta marketing, I was doing more operational stuff. I was kind of overseeing the whole brand and sort of not just the marketing piece of it. And then, that company got sold and at that point's when I sort of wrote my book the End of Jobs and started doing, basically consulting, freelancing stuff around battleship e-commerce, marketing and e-commerce operation stuff.

[00:39:41] Taylor Pearson: And at that time I just got like, really interested in finance. So I just started like reading like a bunch of finance books. I was doing like a little bit of investing like nothing particularly crazy. I got very interested in the cryptocurrency bitcoin stuff. I thought that was very fascinating as like a blend of technology and finance.

[00:40:02] Taylor Pearson: And so sort of my consulting progressed to be a little bit more focused around financial services companies, that sort of industry. And sort of in that process I met my now business partner who was trader by background or a finance person by background and we started a small fund. So that's what I sort of run day to day now.

[00:40:19] Taylor Pearson: But the trajectory there, there's a certain linearity to me looking back, I think, sort of as you mentioned, some of these ideas from like complexity and anti fragility have always been really interesting to me. And I've in different areas thought about how those things apply, but I felt was always sort of on this trajectory of like, kind of what's interesting and how can I sort of incorporate that more into what I'm doing.

[00:40:38] David Elikwu: Sure. What was the process like of publishing the end of jobs?

[00:40:42] Taylor Pearson: So the self-publishing, I know you, you've had Eric Jorgenson on the podcast. He's the CEO of Scribe now. So I was one of scribes very early customers. I don't know how early I was, but it was before it was called Scribe. They had a previous name. So I had, when I published the book, I don't, I've always enjoyed writing, I liked history. I started blogging when I was at my e-commerce job, kind of on the side. And so that was kinda what enabled me. That was like my Saturday project for like three or four years. You know, I would wake up Saturday morning and I would go to coffee shop and I was like working on my blog. And that was, I guess people work on newsletters now, not blogs, but kind of same concept.

[00:41:14] Taylor Pearson: So I had a blog and I had done a fair amount of writing about these ideas of just like, future of work and how the internet was affecting careers and, you know, it was at some level just sort of like a reflection on my own career, my own path, right? Like how did I sort of end up in what was very different from a sort of a law school trajectory that I was like a brand manager in e-commerce company in Vietnam, right? It's just a very, it was a very different trajectory than sort of like where I'd, I'd expect it to be if you asked me five years earlier. And so, yeah, I just decided, it would be cool to like write a book. I had, I'd written a lot about it and so I was like, let's kind of take these things and I'll stitch them together into a book.

[00:41:47] Taylor Pearson: Yeah, I was very fortunate. I had like, some friends that helped me promote it and, it got a bit of traction and did a lot better than I expected, honestly. And I really enjoyed the, I liked writing, so it was painful at times, but overall enjoyable.

[00:42:00] David Elikwu: Fair. If you were to write an update to the book now, what beliefs would you update? So what's changed in your thinking from what you previously wrote? Or is there anything new that you've learned since?

[00:42:12] Taylor Pearson: I think that I have like a whole chapter, like railing on accountants and a month before I published the book, I met my now wife who's an accountant. So I would probably, I would probably change that chapter. There's one major update I would make. My views on the future of accounting have become more nuanced and sophisticated over time. Certainly there's roles for good accountants in the future.

[00:42:33] Taylor Pearson: Yeah, I mean, I think the basic thesis of the book was basically like, the internet opens up a lot of these new sort of like, niche business opportunities that don't work in geographic worlds. So one of the brands at the e-commerce company I worked for was, we sold like, sort of like high-end boutique, well-designed cat furniture. It would be like your cat litter box would fit into like it looked like a mid-century modern, sort of side table, right? So you could like, put it next to your nice mid-century modern couch. And, you know, the cat could go in and like use the litter box or whatever. And that business only makes sense on the internet, right? There's no geographic location. Where there's just a sufficient quantity of people that want to buy enough mid-century modern cat furniture, to like, make that a viable business, right? Like maybe New York or London or Tokyo. But it's not that, like the business works a lot better on the internet because across the world they're like, are enough of those people, right? That have that particular design aesthetic and have a CAD and want their, you know, want their place to look nice or whatever.

[00:43:29] Taylor Pearson: And I just thought that was like, so fascinating. Like that was a viable, like that was a real business. Like, it, it was a multiple six-figure business that could sustain a person and, you know, the head of manufacturing and all that kind of stuff. And sort of through that process, I just met a lot of other people running similar types of businesses, right?

[00:43:47] Taylor Pearson: That there were all these sort of, we kinda get called like long tail, if you will, businesses relatively, niche businesses that were economically viable in sort of the internet era. And yeah, I mean, I think broadly like that's still true. Like there's still a lot of podcasting is certainly one thing that's exploded right in the last 10 years. Like the number of things, there's podcasts for that like are real businesses now is like insane, right? Like, all these really niche, there's a particular like college football team in the US that I like, that's like the team I grew up and like, there's like people that like run a full-time job. It's like there, it's a podcast for people that are fans of this one college football team in the us right? And there's a, you know, whatever, there's a thousand people that are willing to pay $10 a month to like hear the commentary about this team, right? Because they're super into it and they want to hear the latest of what's going on in the recruiting and that kind of stuff.

[00:44:32] Taylor Pearson: So I think that's sort of like core, sort of core thesis intact. I think like the specific examples have probably like evolved. Some like how those businesses get started and where you get into it. But, I wouldn't like change a lot. Like, I think sort of like core concepts are pretty decent and still work. I'd probably just sort of update it, take out the accounting stuff so I don't have to hear my wife tell me about how I was wrong about that.

[00:44:53] David Elikwu: Thank you so much for tuning in. Please do stay tuned for more. Don't forget to rate, review and subscribe. It really helps the podcast and follow me on Twitter feel free to shoot me any thoughts. See you next time.

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