(upbeat music) I'm Cal Newport, and this is Deep Questions, episode 186. I'm here in my Deep Work HQ, joined by my producer, Jesse. Jesse, when this episode airs, so not right now, but when this airs, I will hopefully be a much more relaxed person. You know, as I've talked about on the show, and you know all too well, I have been in this busy period at Georgetown.

All good things, we're recruiting, we're on campus again, we're meals and seeing people, but it's unusual for me, basically every day I'm on campus all day. It's a lot of moving parts, and that's not usually the way I operate best, and it's a lot stressful, it makes me anxious, I don't sleep very well, when I have a million moving parts going on in my schedule, and ambiguous logistics, my body just rejects that.

It's like rejecting a transplanted organ or something, it's like, ah! But on Tuesday of this week this comes out, that winds down, so when this episode itself airs on Thursday, just imagine me joined like a nice cold beer somewhere with my feet up, and my laptop with my email inbox open, just smashed in a corner.

Just straight up office space, beat it with bats, won't be needing you ever again. So I'm looking forward to that, I'm looking forward to the future version of me, that's listening to this episode. So last week we introduced a new segment, which was crazy or deep, people seem to like.

So the idea was we introduce a idea, we try to figure out is this like a deep idea, it's embracing the deep life or is it just crazy? And so last week, just a quick update on last week's, last week's I talked about how I was reading, 'cause I felt like it was important for my work on the deep life, that I finally read Thomas Merton's Seven Story Mountain, and I had it on my Kindle and it just wasn't working, I wasn't getting into it, and so I bought a version, but not just any version, I bought a first edition, first print version of the book, I figured having the version that people who first encountered that book, read it on, would somehow help me read it, and it has by the way, it's been going well, it's a beast of a book, it's 400 something pages long, but 1948 hardcover books is not airport business book spacing, this is not the like, well, let's kind of double space it and make the margins and put some pictures, this is, these pages are wide, and the spacing is narrow, so it's 400, you earn those 400 pages, I'm about 200 something pages into it, and I think it's really helped to have a hard copy, but here's the update, so Jesse, someone wrote me after that episode, and said, they sent me a photo, they had the exact same issue, the Kindle wasn't doing it for them, and they went out and bought an old hardcover version, and they sent me a photo of it, they had it, they had done the exact same thing, so I think that really makes sure that deep, not crazy was the answer on that one.

- Yes sir, that's good stuff. - All right, so let's do another crazy deep, now this one is about other people, maybe about me one day, this is something I've been hearing about a lot, so Jesse, you're the arbiter here, all right, writers opening up bookstores, I'm gonna give you some background on this, okay, so friend of the show, Ryan Holiday, has his bookstore in Boss Drop outside of Austin, what's it, the Painted Porch, other writers have done this, Anne Patchett has a bookstore in Tennessee, Anne Rice, who actually I think just recently died like this year, but she had a bookstore in New Orleans, the latest addition to this long list of people, authors doing bookstores is, remember we did Brandon Sanderson, who did that Kickstarter for the whatever million dollars, Brandon Sanderson, who wrote "The Name of the Wind", I just want Jesse to get a lot of mad emails by misappropriated, giving the wrong name for his book, no, no, of course, Brandon Sanderson, who wrote "The Lord of the Rings" trilogy, Brandon Sanderson, author of the "Harry Potter" trilogy, I just want Jesse to get emails from mad fantasy fans, but anyways, Brandon Sanderson, who I know who he is for sure, posted an FAQ and a reader sent this to me, it's really interesting, and actually I would recommend people Google this, because he actually gets into like, here's how many copies I sold of this book, and this is how many copies I sold of this book, and he's getting to the economics of the Kickstarter, and he just opens up the kimono, and was like, here's how much money I make, and here's how much money I think I'm gonna make on this Kickstarter, but in the FAQ, they're asking him, what are you gonna do with the money?

And he goes, as we talked about, he goes to the math, and like, look, this money is going to pay for the books, so like, it's not like I get to keep all this money, but what it's gonna give me is maybe a slightly higher royalty rate, but whatever, he said, one of our ideas is we're gonna start a physical bookstore, so Brandon Sanderson is also gonna start a physical bookstore, so a lot of people do this, a lot of people do this, so before I go out and buy some Tacoma real estate, let me ask Jesse, crazy or deep, for a writer to own one of the least profitable, most precarious businesses you can buy today, your own bookstore?

- Deep. - Deep? - Deep. - You support it? - I support it. - All right. How would we make that work? See, I think if we podcast out of it, that would help name recognition. - It'd kinda be like the version of Mr. Money Mustache's, you know, office that he has in Colorado.

- That's true, Longmont, yeah. - You could have some cool things in there. - Yeah. - Put a little gym in the back. I think the key is, maybe Ryan told us to, but the key is you can't depend on the book sales to be what makes it work.

- No. - That's the reality. But if you already have a name and you're known and there's other things going on there, I mean, okay, so right away I was thinking if we podcast out of there, just think about our overhead and lease payments for this HQ, you could just imagine that as money in the pocket of the bookstore, right?

So like, okay, we could kinda pay the bookstore for that. So that's already gonna help a little bit. And co-working space, this is like the Mr. Money Mustache thing. Like some of the things that happens there is he has people come and work. You wouldn't need many, but like some really nice co-working spaces, I don't know, we could figure it out.

Or just like lose a little bit of money on it because it's awesome. - Yeah, it's pretty cool. - You could just sit like in a nice chair and like read and sip coffee and be in the middle. It would have to be in the middle of Tacoma Park.

I mean, I think-- - Yes, 'cause you could walk there. - Yeah. - Or you're in between coffee shops. - Yeah, all right. All right, so Jesse gives that, audience, you can weigh in. Jesse gives that a deep, not crazy designation, writers starting their own physical bookshops. So-- - What does Ryan say about his?

- I think, I mean, Ryan's advice is don't buy property to start a bookstore two months before a pandemic hits. I would say that would probably be his main advice because that's pretty stressful, but I think it's rock and rolling now. Yeah, I think it's going well. But Ryan has that great reading list email newsletter.

He has like 100,000 subscribers. And that now points people towards buy the book through Painted Porch. So I think that helps, right? So like he just has this great relationship with a lot, big readership who takes his reading recommendations or whatever. But also I think, I'm sure if we talk to him, if we got him on the show to talk about it, it's like the way I would think about it too, which is, it's not just a, part of the value of this place is not just the dollars that come in from book sales, but it's like a place for him to work.

It's a place for him to do his podcasting. It's a place for him to leave his ranch and do his interviews. Like that's pretty valuable too. Like there's that, I think it's that double dipping value of like, as a writer, this is a place for me to go and it can be at the center of my operations and my brand as a writer.

So if you think about it more like reasonably priced, this is terrible economics. We're gonna get yelled at by so many like actual people who know about business, but here's, okay, let me try to justify myself, Jesse. You think about it like it's reasonably priced office space because it's subsidized by the book sales.

So it's, you know, so if you had a bookstore that was losing you, you know, $2,000 a month, but you had your whole writer business out of it, you'd be like, this is a pretty nice space for $2,000 a month. Like you could think about it that way. I think that's probably terrible economics and is, but that's my justification.

- What's the closest book store around here? - I mean, there's a Busboys and Poets here, which has limited book selection. That's in Tacoma. But otherwise I go to Politics and Prose. - Yeah, which is like two miles away. - Yeah, yeah, I go to Politics and Prose. There used to be some old timers were telling us there used to be a used bookstore here, long time ago.

So there is precedent. And you know, Ryan does, he doesn't try to do the Politics and Prose thing, which is you try to have a fully fledged inventory. So it's 60,000 books, whatever is a fully fledged inventory. Ryan does only curated face out. So it's like their thing, because it's like the reading list email newsletter made physical.

So you go into his store, it's not like, oh, I'm looking for this book. And so I'm gonna go to this bookstore that has 60,000 books and hopefully find it. It's more like, I wanna get a good book. And so if I go to Ryan's store, it's all curated.

It's all books he likes, it's all face out, which is kind of an interesting model. I guess you're selling more of an experience or something like that. All right, so we'll have to start a bookstore, I guess. - Sounds good. I'll work the cash register. - Yeah. All right, but anyways, we have, we have calls, which I'm looking forward to.

Briefly before we jump in the calls, let's talk for a moment about Magic Mind. Magic Mind sells this magic little elixir that comes in these small bottles that you take once in the morning to give yourself a smooth, non jittery, focused energy. So you can either replace your morning coffee with this or have it along with your morning coffee.

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You know, Jesse, something I didn't realize is that the founder of Magic Mind, James Bechara, I talked to him, right? I like to know who I'm in business with and selective about my sponsors and enjoy talking with him. But it turned out like this was his thing in Silicon Valley before he started this company.

He was known as the nootropic focused substance. Like, you know, it matters what you intake in your body because your mind is your best instrument. Like this was his thing. So for Silicon Valley types, like, oh, it's James' company. Makes sense. So that's Magic Mind. And again, if you go to magicmind.co/deep and use that discount code, Deep20, you will get 25% off your purchase.

Magic Mind is your best choice when it comes to getting more done in less time. I also wanna talk briefly about Monk Pack, Keto Nut and Seed Bars, a go-to snack when I need some food, but I don't want a sugar crash. The Monk Pack Keto Nut and Seed Bars taste really good.

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So try it for yourself and you'll see, we even have a special deal for you, our listeners. You will get 25% off your first purchase of any Monk Pack product by visiting monkpack.com and entering the code DEEP at checkout. They are so confident in their product that it's backed with a 100% satisfaction guarantee.

So if you don't like it for any reason, they'll exchange the product or refund your money, whichever you prefer. So to get started, go to monkpack.com. That's M-U-N-K-P-A-C-K.com and select any product and enter that code DEEP at checkout to save 25% off your purchase. All right. Jesse, I think it's time to do some calls.

We have a brand new piece of equipment in the HQ here. Joe, the audio engineer extraordinaire gave us some sort of magic box that sits between Jesse's laptop and our soundboard to help do something with the questions that are coming in over it. I think it makes the question smarter.

Is that what the box does? - Questions are pretty smart, but yeah, it makes it clearer. - Yeah, it makes it clearer. So, which means like almost certainly when we play this first question, you're just gonna see flames. It's like shoot out from the mixing board onto my head and then my hair is gonna catch on fire because that's about where we are technically speaking.

That's my impression of like Joe here working our equipment and we're there. He's like doing all this complicated stuff and then I'm slowly reaching over to press something. He's like, "Don't touch that." And that's basically it. - You guys were having some good conversations. I was just kind of in the background just understanding maybe 20% of what you guys were saying.

- I know. This is the skill of a nonfiction journalist and writer. I can sound confident about almost anything. So you probably picked up. I can pick up from like the things you're saying, like vocabulary and put them into a structure and then mimic them back in a way that sounds like I know what I'm talking about.

It's all a parlor trick. Because like, that's what it is if you're writing like a big long form piece or a book, or like you have to bring in all this information and sound confident about it, but you know, like you can't master every single thing you're writing about.

So I am a professionally trained BS artist. Like I had lunch the other day with a critical theorist and I know some critical theory, but like this guy was like cutting edge critical theorist, you know, and I was just able to pick up from the conversation. These are names of complex theories and be able to like, I bet I understand what that means and how this would relate to it.

And kind of sound like I knew what I was talking about, like a little bit with, you know, post-humanism and right, anyways, right. It's complicated, irreducible, irreducible systems. But that's my thing. I can like very quickly get enough out of you to sound like I kind of know enough.

But if we talk for five more minutes, you're gonna be like, wait a second. You don't know anything about this. So it's a skill that is useful in like a very narrow, very narrow applications. All right, so who do we have here? What do we got for our first call?

- All right, the first question we have is about day batching. So we'll take a listen. - Hi, Kyle. I'm Giacomo, a UX designer with a background in adult education. I have two questions for you. First, what are your thoughts on day batching? Jeff Dorsey, ex-CEO of Twitter, uses this approach.

Would you recommend day batching to someone that, like me, has several hats to wear? And second, how do you find balance between planning and spontaneity? One of my favorite thinkers, Massim Nicolas Taleb, discourages readers on planning their time. He suggests to let your curiosity, BS detector, and boredom avoidance guide your activities.

Just make sure to set limits on things that do not help you focus, say social media. Since I know that you're familiar with his work, I've read your thoughts on his book "Antifragile." I wonder if you have any recommendations on this approach. Wish you and your family a merry, merry Christmas.

- All right, well, first of all, Jesse, I think the cat's out of the bag that we build up these questions over a long period of time before we answer them. They might've heard the evergreen nature of this question, the hat, merry Christmas. - Yeah, it's funny. I mean, I have a big audience and it's, you know, I get a lot of questions that go through.

- Yeah, yeah, but I'm glad we got to it. I think it's a good one because there's two pieces in there. First of all, day batching was a term I didn't, I hadn't been using, but I'm gonna use it now. So Giacomo, you've invented a term that I like, day batching.

And so for people who don't know what he's talking about, day batching is essentially where you say, this day I work on this, this day I work on that, right? So you're dedicating whole days to one activity or one job or one type of role. And Jack Dorsey used to do that.

I guess he probably still does, but he was doing that. I guess he's no longer the CEO of Twitter, but when he was the CEO of Twitter and Square, he had different days for the different companies. I'm a big believer in it. I'm a believer in it when that is applicable to your situation.

And the reason why I am is because it does a great job at avoiding unnecessary context switching. This is the biggest issue when you wear multiple hats or like me have 17 jobs. It's not that the total amount of work of these different hats or jobs adds up to be too much.

It's the context switching. I'm trying to work on this role, but also answering emails about that role. I'm trying to switch from this type of activity to a completely unrelated activity in the same day back to back. There's a real cost in terms of how long it takes for you to adjust your focus.

It also just creates drag and you burn out easier. So when you have a full day dedicated to just one thing, that's all you're doing in your mind. Your mind is just in that context and it can completely forget, expend no energy on open obligations, questions, and work from the other context.

You're gonna get a lot more done. You're gonna be a lot less burnt out. So when it is possible, when you have multiple clear roles, I like that configuration better than, for example, half day, half day, right? So if you want to compare this to, I work on this role in the morning and that role in the afternoon, that's worse than this day is for this role, that day is for that role, right?

So I like the idea of day batching where possible. We do something like that here at the podcast. So, I mean, I've talked about this before. For now, while I'm in an academic semester, I give the podcast a half day, one half day per week. So it's not a full day.

I can't afford a full day, but, what do you say, Jesse, like an extended half day probably, right? You know, sort of like today we're doing noon to five. Yeah. And then I say, that's all I do during that time. And I try to consolidate as much as possible to that time when I'm here and Jesse's here and let's get through the things, let's talk things through.

I want to be just in that context while I'm here. And then I try to optimize it. Like, let's make as much progress as we can, but within that time. And actually that's a side effect of this is that this is an unrelated issue, but it's a fixed schedule productivity issue that when you give yourself these fixed limits, it still enables ambitious growth because you can say during this time, I want to do as much as we can, but it also puts limits on that time.

So you're not just spending all of your time, you know, working on it and it takes over the rest of your life. So I like day batching. I like day batching when it is possible. And if you're going to do it, do it. Have separate email inboxes. Don't let any of the old world come into the new world, if at all possible.

I think it's a great hack. All right, so what about this Tlaib question, planning versus spontaneity? You need to keep in mind that Tlaib is in a rarefied position in terms of the flexibility he has with his time. So we have to have some wariness generalizing a complete non-plan curiosity driven approach to your day.

That's not going to be relevant to 99% of the working world, where it's, well, I have this job with all these obligations and there's deadlines and things have to get done. And in that situation, what is the binary? Organization or no organization? You're going to try to have an intentional way of making sense of the stuff on your plate, some sort of system and plan for trying to get things done at a reasonable level of quality and timeliness or not.

And not means chaos. So once you have non-trivial amount of things on your plate, you have to do some sort of organizational system to avoid chaos. If you have nothing on your plate, then yeah, don't bother, I suppose. But once you do, you need some sort of system to avoid chaos.

And these are the type of things I talk about. Now you want to have capture, configure, control, et cetera, or whatever it is you enjoy. I think there's a different issue here, however, and this might be what Tlaib is actually leaning towards, which is, do you want to map out like everything you're going to do with your time?

Like here's my master plan, I have my work, but even outside of work, I'm working on this project and that project, and there's no room for spontaneity. And he's saying, that's a problem. That I would agree with. So the work you have to do, it's better to have an organizational system versus not.

If you don't, then it's just chaos. And the work doesn't go away, it just gets done worse and you're more stressed. But in terms of where you have control, your time after work, your weekends, maybe you've pulled back your job, not to be a full-time job, Tlaib's warning probably is one worth heeding.

Don't fill every minute of the time you have control over. Don't say, I'm going to figure out in advance, here's what I'm going to do with all the other aspects of my life. Give yourself some room there. I like that idea for spontaneity. I'm going to read, I'm going to see how I feel.

I'm going to go to the woods and we'll just see what happens. I think there's some merit to that as well. I actually talked about that in my third book, "How to Become a High School Superstar." I had an idea I called under-scheduling. And I was pitching this idea to high school kids, American high school kids.

Have less on your plate than you have time to accomplish. This is very scary for kids who are worried about college admissions. But in that extra time, you can be curious and explore and stumble and wander into things. That was the key to becoming interesting and you want to become interesting.

And so I think we're on the same wavelength. But what I'm saying is, Giacomo, the stuff you have to do, organize the hell out of it. In fact, that'll probably leave you more time to wander, but then be cautious or conservative with how much you structure the time that remains.

All right, Jesse, what do we got coming up next? - All right, next question. It's about burnout. He's a student, so did some time blocking. We'll take a listen. - Hi, Cal. First of all, thanks so much for your podcast. I think it's incredible and it's definitely changed my life for the better.

And it seems many others were very grateful. So my question is about burning out and making sustainable work for long periods of time. I, after last semester, after time blocking, towards the end of my time block, blocking towards of the end of the semester, I overdid it to meet a bunch of paper deadlines as a computer scientist researcher, just like you.

I definitely think I overdid it and worked too much and that burned me out. And that was a little bit mainly because, you know, I'm getting to be better at productivity planning, scheduling, et cetera. I think I fixed that. But now I need like two weeks of vacation, which is a week longer than I wish I needed.

So my question is, how do you make it sustainable to do time blocking? Especially when, for example, when I see how you keep in the face of repetitive tasks, like you need to face the same thing again and again and again, like programming. And, you know, I need to program all the time.

I need to do math all the time. And I don't know if it gets repetitive, but how do you manage to have to do the same thing many times without burning out? For example, your podcast, I'm sure you ask the same questions so many, answer the same questions so many times.

Sometimes I marvel how you don't get bored at doing this. Thank God you don't, but tell us the secret. Thank you so much. You're wonderful. - Well, let's start with that last mini question first. So yes, I do come back to the same topics often. And I call that the Dave Ramsey strategy.

I learned it from the Dave Ramsey Personal Finance radio show, which is very popular. I think it's like 8 million average daily listeners. And he comes back to the same things again and again and again, and it's actually at the core of the show, remembering that A, not everyone's listening to every episode, but B, people often want reinforcement for a lifestyle that is appealing and hearing it again and again is not negative.

It's actually positive. That being said, I think you'll notice that Justin and I are pretty careful in our question selection that we evolve the set of questions that we work on. So like within a period of, I don't know, a month or so, you might hear the same question again and again.

But if you go back to six months ago, you'll see the overlap is kind of less. You see as we change our focus, the questions change focus, we sort of drift around. So it's not like we're answering the exact same questions every time, but that's the philosophy there. And I don't mind it.

I mean, I think everyone has their own take on it. I like refining my answer and I think it does some good. All right, let's talk about this burnout issue. 'Cause I think there's two things I wanna tell you. One, especially in academia, seasonality is fine. I work really hard for a deadline and then I do almost nothing for a week or two afterwards is actually I think not an unusual scheduling move for an academic.

It's very seasonal job. Busy periods, unbusy periods. Summer is low, fall exam period is high. Paper deadline is a really busy period. A month after the paper deadline is where you're recharged. So I want you to lean into in the academic life being uneven and the key to that is leaning into the rest as hard as you lean into the peaks, leaning into those troughs as hard as you lean into the peak.

So don't be worried about taking two weeks off. You can have months that are slow and months that are hard, yin yang, balance that out. And I don't want you to worry about that because there is necessarily in your chosen career intense busy periods surrounding deadlines, et cetera. Secondly though, and this is gonna be a different take on this issue.

So you have two ways of tackling this burnout. One of the powers of time blocking, so getting really intentional about your time and in particular when you do time blocking with weekly planning and weekly planning with quarterly or semester planning is that it enables you to work less hours.

So where a lot of people get in trouble and I've been here before is you get organized so you're doing time blocking with your day based off a smart weekly plan, based off of a semester plan. You're getting things done. You're getting a lot of bang for your time buck because you're choosing when you work, you're not distracting, you're not context switching and you're getting things done at a fast rate.

The instinct a lot of high achievers have is great, now I can fit more into my day. And you're not compensating for the fact that it's higher energy, it's higher demand, it's intense what you're doing. And then you overdo it. And you're like, I always worked eight hours days.

Why am I now so exhausted? Because before you were working eight hour days but you had email open and you would go down internet rabbit holes and you were at the coffee maker. Now that you're time blocking, it's this 90 minutes you didn't look up and then you had a 10 minute break and then you were, it's all so packed.

And so what you need to do once you get organized and structured about your time is to use that newfound superpower to work less hours. It's what's gonna give you confidence to say, I'm not working on Friday this week 'cause I have a weekly plan that's in line with my semester plan and my time block plan makes sure that on Monday, Tuesday, Wednesday, Thursday, I'm getting done what needs to get done.

And so with complete confidence, I can take Friday completely off. It's what lets you say, I'm gonna stop working at three every day this week because I have some new crazy workout routine or I'm gonna start training for a triathlon and I have a group of runners and then we're gonna do the bike training or whatever you're gonna do.

It gives you confidence to do that because you can see the plan, you can see how it's gonna unfold. So you have a lot of flexibility as a computer science student, as a training academic. Let time blocking and the associated time management strategies give you much more interesting control over that time.

I want your schedule to look decidedly different than all your friends who, instead of going into grad school with their training, went to finance jobs or went to developer jobs. I want you to have a schedule that feels very different. Whole weeks where you're not working, days you don't work, afternoons you don't work.

Like where you're taking control of your schedule. You're taking advantage of that intense focus that you're able to get out of your time block to build a schedule that's very sustainable and interesting. So put those two together. Seasonality is fine, hard periods balance with easy, don't feel guilty. Two, don't work so much.

You listen to my podcast, you're good at what you do, you're good at structuring your time, take advantage of that. And just keep in mind, when I was in your position, when I was a grad student at MIT studying computer science, I was doing multiple other things. I was writing books, I was running a three time a week essays on the Study Hacks blog.

Once we had a dog, I was doing like long walks and exercise. I never worked outside of nine to five hours. I didn't work in the evenings except for before deadlines. I fit that all in. So the actual amount of computer science work I was doing was maybe halftime at best.

And again, it's because time blocking, weekly planning, these things work. So Brando, lean into your flexibility and build a cool schedule. I've learned, Jesse, to stop telling PhD students that are stressed about their dissertation. To stop telling them that, A, when it came time to write my dissertation, instead of just generalizing work I'd already done, I started a new thing from scratch.

And B, I wrote a book at the same time. Because I was bored. 'Cause we were writing your dissertation, they're like, this is all you should be doing, is writing your dissertation. And I was like, okay, I mean, I can spend a few hours on this a day. What else am I supposed to do?

And I used to get, there's such a subculture back then of, I call it the dissertation hell subculture. Where it's all just self-flagellating grad students about like, no one has gone through a harder trial than I have gone through writing a dissertation. 'Cause I am not sure if this chapter is good or how long I have to research.

And I was like, guys, this is a crazy easy job. You have a lot of time to write this one thing. I'd already written three, I was on my third book at the time. I was like, I've already written two books, unrelated. Like, it's not so bad. Most grad schools want you to get the PhD.

It's not, we are going to, good luck, getting past our murder boards of investigations. They're like, yeah, we know you, you've published a bunch of, it's fine, good, yay. And so I never got that dissertation hell. I was like, this is an unforced error. This like, we have to self-flagellate and pretend like this is the hardest thing anyone's ever done.

But I learned graduate students going through it don't appreciate me talking about writing my book concurrently with my dissertation. And it doesn't make them feel better. Just makes them kind of mad at me. - I can imagine. - Yeah. - All right, speaking of which, what do we got next?

- Okay, next question. It's about basically earning money versus building things and discusses Andrew Yang's book, "Smart People Should Build Things." - Hi, Cal Newport. I am a huge fan of your work. I wanted to ask about advice in "So Good" that they can't ignore you. You quote Sivers suggesting that when making early career choices, people should consider money as a mutual indicator of value.

I recently read the book, "Smart People Should Build Things" by Andrew Yang, which provides an example of where this mindset may be hurtful to society. He argues that a desire to maximize career and financial capital drive students from elite institutions to end up taking more specialized large city and company jobs that have dubious beneficial, if not outright negative real world impact.

They might instead provide the most value for society and potentially feel more satisfied if they took harder jobs in less known cities. For example, a student graduating from an Ivy League might be doing leverage buyouts for a large investment banking firm in New York making $200,000 a year, as opposed to running financials for an energy startup in Detroit at 60K.

While Andrew Yang focuses on jobs in the financial and consulting sector, his advice seems to be relevant across most industries. I'm curious how you would reconcile his perspective, your advice from "So Good" that they can't ignore you. - Well, I like this question and I'm gonna answer it in two parts.

So first, I'm gonna clarify the Derek Sivers idea that I talked about in "So Good I Can't Ignore You" because I think you have a misinterpretation. And once we fix the interpretation, you'll see that it's not in contention with Yang's idea. And then let's talk about Yang's idea by itself.

All right, so this is one of the most, this Derek Sivers quote I use in "So Good I Can't Ignore You" is one of the most, I would say, misunderstood ideas from my books. So I use this quote where Derek said, "Money is a good neutral indicator of value." And a lot of people interpreted that to mean money is a good neutral indicator value, indicator of how valuable or good a job is.

So that if a job pays more money, that is a better or more valuable job than one that pays less. That's the interpretation I think that would run counter to Yang. Because that interpretation would say, yeah, an elite specialized job is gonna pay more than a more pragmatic, less specialized job.

So the elite job would be better. So that would run contrary, but that's not the interpretation I meant. So what Derek meant with that quote and the way that I actually use that quote is when you are trying to evaluate if a particular product or idea is good, you see if people will pay for it.

And the idea that's there is that the alternative is to ask people, is this idea good? Is this product good? And Derek's point, which I agree with, is that people will give you bad advice. They don't want you to feel bad. They'll be like, yeah, yeah, your idea to start a bookstore sounds great.

You should definitely do that. That's definitely not crazy, right? Or yeah, yeah, your startup idea sounds good. You should quit your job and go do that startup. Follow your dreams. Let's do it. Let's get after it, right? It's easy to say that. And Derek's point was people don't care about giving you positive feedback, but people do not give up money easily.

They won't give you money unless they actually value it. So you see, I do a pop-up bookstore. Did I sell any books? Oh, now I could see the people around here actually wanna buy books from me. Or here's my startup idea. Well, why don't I do it on the side in a limited way and see if we can get clients to give me a check?

'Cause if no one's writing me a check, then this service must not be that compelling or they must not trust me to do it. So that's what Sivers was doing. It was when you're trying to get feedback on an idea or product, put it into a situation where people have to pay for it.

And if they do, then you say, okay, this must be useful to people. And if they don't, they don't. And the way that Derek deployed this concept in his own career is that he had a lot of shifts where he transitioned from one type of job to another. And he used this principle to help figure out whether or not he should make the shift.

So he left the desk job to be a full-time musician, for example. And he waited until he was making a sizable fraction of his income at a desk job, a sizable fraction of that income as a performing musician on the side. He's like, okay, that's my indication that I must be good at this.

And then he quit and did that. And then he started a music company called CD Baby as a pre iTunes custom CD company. And he ran it on the side until it was making a certain amount of money. And he said, okay, that's how I know this is a good idea 'cause it's making a certain amount of money.

Now I will quit music and do this full-time. So he used money, not people's opinions as the best indicator whether an idea was good or viable. That's very different than trying to rank order things. So he wouldn't say, how much money would you get for various things that tells you what's better?

No, no, he's like, you come up with the idea that I love this idea because I love what it stands for. I think it's gonna impact the world. I like the lifestyle. I think it's important, but I need the sanity check that it's actually viable. And the way I do that is to see if people will pay money for it.

So it's not a ranking thing. It's a sanity check for an idea. Is that idea sufficiently valuable that you can actually run with it? Now let's talk about Andrew Yang's book, "Smart People Should Build Things." Yes, Yang is right. I like that argument. I think he's right in it.

And it's something that we should emphasize more. I saw this upfront. I went to an Ivy League school, okay? And I know these are stories, just gonna get myself in trouble with people. So let's hope no one I know is listening to this. I'm gonna tell some, literally some stories out of school.

But so I went to an Ivy League college and I guess I was naive, right? Because I came out of public school, a handful of people went to Ivy League schools from the public school. I was like, okay, you know, this should be good. Whatever, I come in there all naive.

A lot of really smart, interesting people, as you'd imagine at one of these schools. I just assumed that we were all gonna go off and do like really interesting things. Like I was writing books and I was gonna go to grad school at MIT and write books and become a professor.

And my wife who I met there, who was also from a public school and sort of similarly naive about this, went into, she had studied, she went to like a educational nonprofits and there's something she had studied. And we had another friend, so our third friend who was our third sort of like just stumbled into Ivy League school from some public school, went into journalism.

And I just felt like everyone was gonna do that. Like you're gonna write books and become journalists and professors and thinkers. And outside of that small group, everyone went to Harvard Law School. And I remember being surprised by it. I was like, you're all just going to Harvard Law School?

Like you all just are, everyone's just becoming a lawyer and the ones who didn't went to finance or consulting. But I remember so many of my friends went to Harvard Law School. I was like, you don't, do you guys really want to be lawyers? Like, I've never heard you talk about this.

Like, this isn't your, like some thing that you're into. And this is why I was naive, is that there's just a whole culture that like, you grow up, if you grew up like upper middle class and go to a private school and your parents are like high paid professionals, it's like, this is the whole point.

You go to these prestigious schools so that you can get the elite specialized jobs at the lawyers, at the big firms or in finance or in consulting. And I didn't know that, no one told me that part because I kind of just stumbled into this Ivy League school and was like, this means I get to write books and go to grad school.

And everyone else was like, this means I get to go to Harvard Law School. So this is why Andrew Yang's book resonated because I don't know how many, how many like high price specialized law partners we need. I don't know how many people we need using their intelligence to make financial instruments that are so complicated that no one can understand them so Goldman can make it unprecedented profit margin off of them.

I had a friend from school who went to work for a prop trading desk at one of these firms. And he was assigned one CEO, like one company. And like his whole job was to just learn everything possible about this guy, listen to every public statement he did, every investor call he did, and even learn the tone of his voice.

Like I think he's worried just so they could make like the best decision on trading this particular stock. I don't know, this guy wrote for the humor magazine with me. Smart, funny, interesting guy. Is that really what the society needed was making sure that the, you know, Goldman prop trading desk was gonna get a little bit of an edge on trading Radio Shack or whatever.

So I actually am one of these sort of, you know, I don't know, hypocritical Ivy League populist on these types of things. Is I think people should go do interesting things. These smart people who go to these schools and probably they do now, this was a while ago. Don't go to Wall Street, don't go to law school.

You're not gonna like being a lawyer. Let me just cut to the chase. You're not gonna like it. If you're good and go to a good law school, they're gonna give you a job that's gonna be terrible. You're gonna have to work so much and it's terrible. And you're gonna have to go to a country club at some point, it's not good.

And let me tell you about Wall Street. Like, yeah, you're gonna make a lot of money, but like you're gonna be kind of a little bit douchey broey probably. And they're gonna make you do spreadsheets until three in the morning and you're gonna be depressed. Like I can just cut to the chase.

Like go do something interesting, write books, become an academic, start companies. More people should start companies. Do the Elon Musk thing. He was like, I'm just gonna go invent cool things 'cause it should exist. It also makes life more interesting. So yeah, I'm not the preacher to teach you, but I'm in the Andrew Yang school that you should, if you're smart and you go to one of these really good schools is go do interesting things, go build things or produce things that are useful.

I mean, I will say I think Georgetown where I am now is good about this. We get more civic minded people. We send a lot of people in the public service. They come here to go in the public service. And so I think we get more of that to Jesuit ethos pervades the institution.

Like you're getting educated so you can improve the world. I think that's fantastic. But I think that memo needs to spread. So I'm in favor of what Yang says, go build cool things, go write books, don't go to Harvard Law School. Jesse, is this where I say, okay, now time to talk to, let's go to our sponsors.

We have a new sponsor here, Harvard Law School. Oh no. Again, thwarted, thwarted. Goldman, the Goldman Sachs proprietary trading desk. Man, I gotta vet these things. I gotta vet these things. They're actually, speaking of sponsors though, let's talk about a real one we have, which is stamps.com. So let's say you do follow Andrew Yang's advice.

You do go start a business. You're employing real people. You're building interesting things. You're not just doing financial derivatives. If you were doing that, and I think Jesse, you will appreciate this transition. You don't wanna waste your time with repeated trips to the post office, right? I think that's chapter three of Andrew Yang's book.

So with stamps.com, you can skip that trip and focus on what it takes to bring your business to the next level. As I talked about in Monday's episode, stamps.com allows you to print official postage right from your computer. So you don't have to go to the post office to send it.

In addition to giving you access to the post office shipping services, you also give access to UPS shipping services right there from your computer. And they give you big discounts. 40% off the UPS rates, the postal service rates, 76% off the UPS rates. So whether you're an office and the invoices, a side hustle Etsy shop, or a full blown warehouse shipping out order, stamps.com will make your life easier.

You just need a computer and a printer. So stop overpaying for shipping. So you can put your attention to making the world a better place and showing those Harvard Law School lawyers who's boss by going to stamps.com. Sign up with promo code DEEP for a special offer that includes a four week trial, free postage in a digital scale, no long-term commitments or contracts.

Just go to stamps.com, click that microphone at the top and enter the code DEEP. Now, if you did end up ignoring Andrew Yang and going to Goldman and Harvard Law School, and now you're anxious because your life is devoid of useful meaning, no matter, you're gonna get in trouble for this.

You need Headspace. You need Headspace's guided meditation app to help you refine your center and calm down that anxious mind. I am a Headspace fan. I talked about on Monday that I was using Headspace during this recent busy period that just calmed down my sympathetic nervous system. I was using their breathing related guided meditations.

They walk you through how to breathe and how to think, very calm voice, and it was quite effective. Headspace has meditations for many different types of uses, including focus, it's relevant for Deep Questions listeners, guided meditations to help you get ready to focus, guided meditations to help you sleep, guided meditations to help you breathe better or fight anxiety.

It's something I think we all could probably use a little bit of now. Headspace is scientifically proven to help you manage your feelings and mental health. Recent study proved that in just two weeks, it reduces stress by 14%. So this actually does work. So however you're feeling, try Headspace at headspace.com/questions and get one month free of their entire Mindfulness Library.

This is the best Headspace offer available, but you have to go to headspace.com/questions today. That's headspace.com/questions. All right, speaking of questions, Jesse, I think we've got time to fit in one or two more. So who do we have next? - All right, next question is a 35 year old looking to change careers and potentially abandon some of the career capital that he's accumulated.

- Hey, Kyle, hope you're doing great. My name is Sebastian. I am a 35 year old man from Uruguay. And my question was regarding switching careers as a 35 year old. I work as a location sound recordist for film and I was thinking of changing careers because of money.

I didn't know what the job offerings would be like in my field when I first started. So as I got deeper into the field, I realized that there's a lot that I don't control. And you end up being a freelancer and you don't know where you're going to be offered a job.

And all you can do is network and well, that's all the control you have. So I'm trying to switch over to web development and start from scratch. I think, well, I can use the wisdom of I have accumulated over time to make the best of it. But I was wondering about your thoughts about switching careers and abandoning all this career capital I have accumulated.

So thank you and goodbye. - Well, Sebastian, I'm always a little bit nervous about starting from scratch with career capital because it's an ironclad law of the market is that skills acquired quickly produce modest amounts of income at most. So if there was just some web development course you could take for a few months and then be making a really good steady living, lots of people would take that course and it would price the market down again.

So there's this supply and demand tension in most marketplaces, which means you have to have a pretty hard one skill if you want a nice sustainable income from it. It's not always true, but it typically is true. So I would be wary about just saying enough of the sound stuff.

I'm now gonna go become a web developer. Now this doesn't mean you can't start picking up that new skill, but I would do it on the side as I am trying to build a larger and more stable business in sound. I would see if it's possible to build on your existing career capital to perhaps get out of this mode of just, I'm a freelancer that does just this type of thing and hope people pick me and to build out a business that's a little bit more aggressive, a business that maybe is a little bit more niche, a business that has a good clear presence, a business that you are somewhat aggressively marketing.

This is what I would do at the same time. And so I don't know your field very well, but you know sound very well. You're doing location sound for films, but like for example, you could probably be a podcast sound engineer as well, which is something you can do remotely for people all over the world.

This is what I do. You send me your files. I master them, get them ready. I edit them, whatever. That could be really useful. You could be an in-person engineer to set up studios for people like podcast studios, like Joe is doing for us here or what have you.

But in other words, like finding niches that you could build into quickly 'cause you know about sound and sound equipment, building out clear businesses around it, being aggressive in your marketing and very good in your execution. You get back to people, you have processes. I mean, I would be doing that as a foundational piece to try to get that income more stable, to control your life a little bit more than just being a freelancer.

And then if you wanna pick up a skill on the side, do it at the same time concurrently and pull the Derek Sivers thing here that we talked about earlier in the episode. Don't switch over to web development until you're making the money already. I'm doing this on the side and I'm making a living off of it.

Okay, if I really wanna do that instead, now I'm happy to make that switch. And if I'm not, I know I shouldn't be making that switch yet. And then the final thing I would advise is combine. If you're gonna build up a new skill, find ways to bring that skill into the orbit of skills you already have to find a new hybrid combination.

Because then you are using the fact that you have a preexisting skill to raise that barrier to entry. So if you're doing web, maybe what you master is how to do web-based apps or projects for people in the sound space. Something that requires your existing network and connections to the sound space, your existing expertise.

So not just anyone who does a web development course can come in and compete for your same business. All right, so get more focused and ambitious about your work right now with your current capital. Two, if you're gonna build up a secondary skill, do it on the side. Definitely don't switch to that until you have evidence that it's making a lot, enough money for you for that switch to be safe.

And three, try to combine the new skill with your existing skills to get a unique hybrid that very few people have. That's often the best route to something that is very sustainable and lucrative and relatively non-competitive. All right, I think we have time for one more, Jesse. Do we have one more?

- Yep, we go. Another question here, it's about reading, which is a popular topic among your listeners. And she's reading quickly, but she also wants to be able to read deeply. - Not a fan of reading, not a fan. - You have your March books coming to an end.

- My, wait, what's coming to an end? - March books. - Oh, March books. Oh yeah, I finished the March books. - Oh, you're already, even with the busy time, like you've pressed read. - I finished, okay. I finished the five books in March, around mid-March, but I'm a little off the month boundary.

So like the, I was almost done with the book before March began. So like I got a freebie pretty quickly. But anyway, so I finished early because the Thomas Merton book's a beast. Because that 450 page book, I think in like standard modern print would be more like a 550, 600 page book.

So I'm throwing, and I'm busy. So I'm throwing two weeks at it in the second half of March. So I can finish that beast in April with time. I'm reading another book simultaneously, but so I have time in April to get the other four. So I'm reading that and another one simultaneously with the hopes that pretty early in the April, I can bring those to a close and then be off the ground running with only three books to go.

So. - Nice. - But still, my answer to this question is I'm not a fan of reading. That's time you could be TikToking. You could be refining your TikToks. You could be quitting your job to make a full-time living on TikTok. Just trust that that's gonna work. So it's not a good idea in general.

It could strain your eyes. If you strain your eyes, how are you gonna be able to see TikToks? Oh my, all right, we should get to the question. Here we go. - Hi, Cal. My name is Renee and I'm calling in from Melbourne, Australia. I have a three week vacation before starting my job as a junior lawyer.

I'm investing this time into my hobby, which is reading books. And I just picked up the "Lord of the Rings" trilogy for the first time. I read books quickly and widely, but often not very deeply. So I get the gist of the book or the author's main argument, but do not always appreciate their particular intricacies or nuances.

Do you find it hard to read deeply when you're also reading quickly? I know you aim for five books a month. Could you please provide some tips on how to do both for various benefits like memory retention, synthesis, and the generation of new unique ideas? Thanks very much. - Well, Renee, you can't do deep and quick at the same time.

So I think that's true. But what I would say is, and this is how I do the five books a month, different books require different levels of depth. And so some books are gonna be much faster to read than others, which is why I do a pretty careful balance.

So like right now, we just talked about it in the last question, I'm reading Thomas Merton's "Seven Story Mountain." It's a beast of a book in terms of length, but it's not a book that requires really slow reading because it's not conceptual, it's memoir. He's a very good writer and you could just get lost into his world and he can move very fast through that.

On the other hand, if you read a book that's more, it's given an argument, even like an intellectual argument, that might take longer. And I'll slow down with a book like that. Or what's often happens is if I'm reading a modern nonfiction idea book, I'm putting the accelerator off and on.

So there'll be a section where I'm like, I don't really care, I get your gist, I don't care about this and I go fast. Then I'm like, ooh, now you're treading water that is interesting to me. There's real depth underneath your legs here. And then I'm gonna slow way down and try to get that just right.

Then speed back up again when it gets back to something really interesting. So again, some books require depth, some passages of books require depth, others don't. And so I'll mix all them together to give my mind a variety of different things. So the fastest books, the fastest books are either fun novels or lightweight idea books, sort of nonfiction books that you might buy in the airport.

I like reading those occasionally. And you can read those fast, just shoot through. On the other end of the spectrum, I think it's like academic books where someone's really making an argument. And I'm more careful about how often I read those 'cause I know they're gonna take time. And then in between you have like really well-written literary novels, well-written memoir, nonfiction that has some good ideas and some filler.

And so you go the speed that the book demands. But in the end, what you really care about is not so much the count, not so much the pages, not so much the number of books. I mean, we like to joke around about the five books. And I think it's nice to have that particular number.

But what really matters is the experience itself, that you're giving the book in front of you the attention the book in front of you actually demands. So some take more, some take less. If you're reading one of my books, I would recommend six months because what you wanna do is savor, savor the language like a fine wine, the carefully crafted sentences, go show them to people, tell people about sentences you liked.

I mean, so my books, I would say six months, six months per book. I'm talking six months of a sabbatical. So you're giving this full time, six months full time attention. But for other books, you could probably go, you could probably go a little bit quicker. All right, so speaking about going quick, Jesse, we're at the hour mark.

So we should probably wrap this up. Thank you everyone who sent in your questions. I should probably remind people how to do that. It's go to calnewport.com/podcast for the instructions. That'll tell you how to do the voice questions. That'll tell you how to do the written questions. We're pretty international today, Jesse.

I don't know if this is the voice messages in general, 10 more international, or I just don't realize that the written questions are international, but this was a pretty, like a United Nations of deep life advice today. - Yeah, the audience is from all over. - Yeah, that's always good to see.

It's always good to see. So anyways, thanks for sending those questions, calnewport.com/podcast to find out how to submit on your own. If you like what you heard, you will like what you see. YouTube.com/calnewportmedia for YouTube videos of full episodes that every individual question that I do has its own clip.

You'll also like what you read at my newsletter, calnewport.com to subscribe to my usually weekly newsletter, though I've been a little bit tardy during this busy period. We'll be back Monday. And until then, as always, stay deep. (upbeat music) (upbeat music)