Deep Questions with Cal Newport - Ep. 220: The Two Types of Ambition

Episode Date: November 1, 2022

Get your questions answered by Cal! Here’s the link: bit.ly/3U3sTvoDEEP DIVE: The Two Types of Ambition [4:36]- LIVE CALL: Escaping the “Second Control Tap” [28:10]- Can journaling make me a better writer? [53:26]- What’s an example of a keystone habit for building community? [56:03]- Can Cal give an example of a quarterly plan? [1:00:00]- How does Cal choose what books to read? [1:06:16]- What’s is Cal’s philosophy on caffeine? [1:15:12]- How can a teenager prepare to live deeply? [1:20:59]Thanks to our Sponsors:givingwhatwecan.org/deepmasterclass.com/deepeightsleep.com/deepzocdoc.com/deepThanks to Jesse Miller for production, Jay Kerstens for the intro music, and Mark Miles for mastering. Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

I'm Cal Newport, and this is Deep Questions. Episode 220. So if you're new to the program, it is where I answer questions for my audience about the theory and practice of working and living deeply in an increasingly distracted world. We're recording today on Halloween, which I think is exciting. Jesse thought it would be a good idea, producer Jesse, to wear a costume, which I, which I, encouraged. I think he went a little bit too far, though. I'll let you be the judge. If you're listening, you'll have to go look for the episode 220 video at YouTube.com slash Cal Newport Media to participate here. But you be the judge. I think Jesse went a little bit too far here. So I really got into the costume. So what do you think about that? I mean, it's pretty elaborate,

Jesse. What is a skeleton's favorite plant? I don't know. What? A bonsai. I mean, I think I have to fire you at this point. I think that's clear. All right, fair enough. Oh, my. All right, enough nonsense. Actually, I take it back. If you're listening, don't go to YouTube to watch this. This will be a waste of everyone's time. All right, while we get the real producer Jesse back into his seat, I got a couple announcements to make.

Look, we can even look what he, look what I've read, poor Jesse. I have on camera now. Oh my. I'll tell you, Jesse, before I do the announcements, this felt like a good idea when I was walking out of my house. As I got to the HQ, I began to have doubts and I'll tell you why. right next to our office in the HQ is a legitimate documentary video production company. And we're talking about a company that does serious issue-based documentaries. Now, they know who I am.

Like, they know my books, but I think they're confused why I have an office. And in their minds, it's probably some sort of weird, you know, grown man's clubhouse. And I just was having this thought as I was walking down the street carrying a fluorescent skeleton that if they see me right now, I'm not going to be disabusing them of their impression of what's going on in here. So fortunately, I did avoid them, avoided our super, did run into my neighbor carrying the skeleton, but yeah, could be worse. For those not watching, it's good to know that the skeleton is, you know, probably five feet

tall. It is a big. Yeah, yeah, we take it seriously. We take it seriously. Our Halloween decorations have a lot of skeletons in them. So we got a good show. So there's two blocks of questions coming up early in the first block. We have our very first live caller.

Jesse had promised us by the end of October. This episode has been recorded on the last day of October. So that's exciting. So we'll actually have me talking live with a caller going back and forth about their issue. Also, I have a good deep dive I want to get into. Before we get all that, a couple quick announcements. First, I want to mention the live event. Come see Jesse and I live Monday, November 14th at 7 p.m. at the East City Bookshop here in Washington, D.C. That's on Capitol Hill. There is a book of it. My friend David Sacks has a new book out called The Future is Analog and I'll be moderating a conversation with him. So sort of like me interviewing David. But I haven't really done or been to an event just for my readers and listeners since pre-pandemic. So if you're in the DC,

area, come by November 14th, 7 p.m. East City Bookshop. Other reminder, submit your questions. There's a link right in the show notes to do so. You go right to a survey. You fill in the questions. If you're interested in doing the question live, you can also put your email address there at the end. While we're still early in this new survey, it's your best chance to get your question on a show. So definitely go submit your questions. All right, well, that's our news for now. Now let's get rolling right away with today's deep dive. I'm calling it the two types of ambition. Now, this deep dive is based off of an article I posted to my newsletter at calnewport.com

just a few days ago. So the original title of the article, and I have it on my screen here for those who are watching instead of just listening, the original title of the article was on Michael Crichton's busy ambition. It's from October 28th. So the motivation for this article, which I want to pick a part in our deep dive today, was actually coming across a profile of Crichton

in the New York Times archives from 1970. And I have this on the page now, on the screen if you're watching, a profile that's titled for Michael Crichton, Medicine is for writing. There's also a picture of a young Michael Crichton there. So what struck me when I read this profile recently was the busyness of Michael Crichton at this very early stage of his career. So let me set the scene for you.

This is the scene that I opened the article with. All right. It's Michael Crichton, his last year at Harvard Medical School. He's 26 years old. He goes to the dean of the medical school and he says, I don't think I'm going to practice medicine. I've figured this out. but what I do want to do is publish a non-fiction book about hospital life, and in particular the hospital in Boston where he was doing his intern rounds.

And he asked, can I, instead of doing some of the normal whatever work you would do during your final semester, can I instead go around the hospital and gather research for my book? And here's the actual quote I have here from this article, which was written one year after this occurred. He said, why should I spend the last half of my last year at medical school learning to read electrocardiograms when I never intended to practice? All right. He says this to the dean of Harvard Medical School. The dean replies paternalistically, Michael, I don't think you realize how hard it is to write a book. Right.

So he's trying to warn this young kid. Like, you can't just, like, go walk around the hospital and gather some notes. This is when Crichton did his mic drop and revealed to the dean of Harvard Medical School that he had all. already published four books during his first three years at medical school. He had been doing so under the pen name, John Lang, L-A-N-G-E. Not only had he written those four books, but he had multiple other projects in action, not just this nonfiction book idea, which he had already started, by the way, but his first two, I would say, serious publication efforts. His first four books are pot boilers. I've read them. You can buy them. They reissued them under Michael

Criton's original name. They're Clive Custler, James Bond-style thrillers with some techno flavor added in. But he was also, by this final year of his med school, deep underway with some more serious books, the first being a case of need, which he published under a pseudonym as well. But it was really the first thriller he wrote that got medicine more deeply involved. This would win that next year. it would win an Edgar Award for Best Mystery Novel of the Year. It's a hard award to win.

He also was working on the Adronoma Strain. First book he would publish under his own name and, of course, would be a big breakout bestseller. It's what really started his fame in the literary world, became a big movie back in the 70s. He had all this stuff already going on when he went to talk to the med school dean. So by the time you get to a year later when this New York Times profile is written, you see that this is a one-man multimedia operation. So in addition to all of those projects going on, he somehow

has two more pop boilers he writes under his pseudonym by 1970. So somehow he adds two more books unrelated to a case of need, unrelated to the Adronomus Stream. He also, by this point, was working on what would become the terminal man, his second

techno-thriller written under his own name. It was called something different. In the profile, they're still calling it to a sympathetic man. Like the sympathetic nervous system. but Terminal Man is much better. He revealed that he was already intent on directing the movie for the Terminal Man. So he was concurrently writing a screenplay. He was also traveling to Hollywood every week on what he called,

and I'm highlighting this here, a skills building gambit. So he was going to Hollywood. He's trying to pick up because he wanted to be a director as well. And so he was going to Hollywood a couple days a week. So this was the year after he left medical school. so he had this sort of half-hearted postdoc at the Salk Institute in La Jolla. La J-O-L-L-A. Hoyia.

Hoya, is it La J-O-L-A? Yeah. Okay. Which is not far from L-A, I guess. Yeah, yeah. So he was going back and forth community. It's like San Diego area. Yep.

All this stuff was going on. 27 years old, all this was going out at the same time. The New York Times profile called his career hyperactive. And it is. Can you imagine that? I mean, I do a fair amount of things. That's crazy. The amount of things he had going on.

So all these different projects he was juggling at the same time. Oh, and by the way, he also published a novel with his brother under a pseudonym between 1969 and 70 as well. An experimental novel about drug dealing where they would pass the manuscript back and forth. And he would write an entire draft and then his brother would edit an entire draft. All this stuff's going on. So busy guy. I compared him in this article, let's say apples to apples, another really successful fiction writer, John Grisham.

John Grisham's younger. He really got his start in the early 90s, whereas we have Crichton getting his start in the early 70s, but whatever, same idea. And there was a period in the 90s where they were competing back and forth, not just for the biggest book sales, Grisham and Cretton for a period in the 90s there were in a huge war on movie rights. They were breaking records for movie deals and, Their agents would say things like, I want whatever Crichton got for his last book plus $1.

Like they were trying to one up each other. All right. So what's John Grisham story? So John Grisham in the 1980s is a lawyer, small town Mississippi lawyer. He runs for and also wins a seat in the Mississippi state legislature. So he's a Democrat state legislature and a small town lawyer doing both of those things. State legislator is a part-time job. And he decides he wants to write a book.

He gets an idea for a book from a case that he wasn't trying but was observing, and he gets this idea for a book. And he tells his wife, I want to try to write a legal thriller. And she said, okay, but do two in a row. So that way, you know, maybe one of the ideas doesn't work. You have two shots at it right away. And if both of those ideas don't work, then you know that maybe that's not for you. So he does this. It's hard.

It takes him longer than it takes Christen. I have the numbers in here, but I think it was something like three years. because he's writing in between these two jobs. And you can find him in some interviews talking about, oh, I have my notepad while I was waiting for meetings. I was waiting for a legislative session to begin at scribble notes. But I found a really definitive interview where he said, this is the secret.

I woke up at five and I wrote every morning. And it was really hard. And I was often really tired. And it wasn't like all that fun. And that was the only way to really make progress. And it still took him three years to write the first book. He started the second book. the day after he finished the first.

Good thing he did that because the first book, the time to kill, he had a hard time finding a publisher when it came out. Small first printing did nothing disappeared. But he had already basically finished his second book by that point. So he was like, I might as well. This time, his second book, which is the firm, his agent leaked bootleg copies of the manuscript to movie producers. So before they had even sold the book,

book, Paramount came in and said, we'll pay you $600,000 for the movie rights for the firm. So then once the publishing industry heard that Paramount had paid $600,000, they're going to do a big movie, which they eventually did with Gene Hackman and Tom Cruise, double-day snapped up the book rights for a lot of money. That book got a lot of coverage, went on to sell a lot. The number I quote in the article is 7 million copies. I couldn't really source that well. It might be less than that. But anyways, it sold a lot of copies instead of his whole career. This is where, and I say in the article, Grisham's path diverges from Crichton.

Grisham does not look at the buffet of appealing opportunities that is generated by his initial success and say, let's start feasting. He does something very different. He says, I now have the leverage and money needed to simplify my life in a way I couldn't before. stops practicing law, leaves the legislature, based on the advice he heard from a bookseller, that all the big fiction names published once a year, he said, that's what I'm going to do. One book a year. That's what matters, especially in the beginning. I need a book every year to solidify my audience.

And he basically retreated into just a writing routine of one book per year. And I have some of the details of it because he's talked about this before. Here's how he eventually perfected this, I would call it almost. monastic writing routine. He starts writing on January 1st. He works three hours a day, five days a week. He used to write in their Oxford,

and he moved to Charlottesville, Virginia. They have a farm. He has an outbuilding on that farm that they renovated for him to write. No internet connection there. First thing in the day, three hours. He basically writes till lunchtime, five days a week, not on the weekends.

That rhythm has him finished the first draft usually by March. the editing begins. He wants to have the manuscript completely locked in by July. Starts in January, six months later, done with the manuscript.

Now that's it for writing until the next January. Now, he'll think and do research about what his next book is going to do at his own pace. He will do clearly publicity. He usually does fall releases. So when that book comes out in the fall,

he'll do publicity, but he's not a big publicity guy. He does limited tours. He'll do the big shows and interviews and then retreats again. back to his farm. And that's kind of it. He doesn't do these other projects.

He doesn't want to direct. He doesn't want to do 17 different types of books like Crichton was doing. He wasn't trying to establish a production company or get involved in television. They would sell the movie rights to his books, but that was about it. 15 hours a week, six months out of the year. The rest of his energy goes to other things. When he had younger kids, he was really into Little League baseball. And so he built, it's not, he doesn't want, it's not officially associated with Little League, but a youth baseball complex.

Five really great fields. They started their own youth baseball league. He was the commissioner of the league. He loves baseball. He loves coaching. He thinks it's great, you know, for kids. I know he's heavily involved in, you know, political fundraising as well. It just has other stuff that he does.

So I found an article. I can't, I can't excavate this anymore. But I remember finding this and reading this, and I wrote about this somewhere. I can't find where. So I can't find the original source, but you'll have to take me at my word for this. At some point, this was an article from probably the last 10 or 15 years. His longtime assistant retired, and he realized, according to this article, I found, that he didn't need to hire a replacement because there's no work for her to do. I mean, his agent has his number.

His editor has his number. They know his routine. He's not involved in a lot of projects. He's not involved in a lot of schemes. So there was nothing for the SSent that even organized. He writes from January to March, edits from March to July, does a one-week publicity tour in the fall.

So anyways, very different than Crichton. Crichton says, I now have success. I want to go do lots of different things. Grisham says, I have success. I want to simplify my life. So what I did in this piece and what I want to do right here is try to put names to these two different approaches to ambition.

So what I write in the article is the first model exemplified by Crichton is what I call type 1. It craves activities and feasts at the buffet of appealing opportunities that success creates. The other model, exemplified by Grisham, is what I call type 2. It craves simplicity and autonomy and sees success as a source of leverage to reduce stressful obligations. Medical school wasn't sufficiently stimulating for Crichton. Life as a lawyer was too hectic for Grisham.

They therefore reacted to their success in much different ways when it respectively arrived. Now my argument is this is a spectrum, but most people fall towards one end of the spectrum or the other, the type 1, Crichton end, or the type 2, Grisham end. And that it's important to understand where you fall on the spectrum because it will have a big impact on not only how you plan your professional or aspirational endeavors, but how you react to successes when they come. If you don't have this figured out, you can end up in a mismatch situation. If you're a Grisham that allows the pressure of your success to push you into a bunch of Crichton-style projects, you're not going to be happy. If you're a Crichton and you use your first book taking off to move to the middle of the woods, I can finally now live in the house and Maine overlooking the water. You might be bored. You might be depressed.

You say, I've just isolated up here. This doesn't make me happy. So understanding where you fall, I think, is important. and that was the call I made in that article, recognizing those are two very different types, and they're both valid, I think is in itself very validating for people. So when you're doing something like lifestyle-centric career planning,

you have some clarity. So the final question is, where do I fall? Well, in the article I was really clear, Grisham is what resonates with me. I got some pushback, though. People say you say Grisham resonates with you, but your life looks more critoney to us from the outside.

I think that's a very good point. And I guess what I would say is that I'm aspirationally Grisham. I mean, to me, being able to work autonomously on a hard project on my own terms and my own timings to disappear for a while and just come back into the public eye occasionally, that really resonates. When I read that profile of Christen, it stressed me out, made me anxious. So I think I resonate more times Grisham. Now, it looks like I'm doing a lot, and partially that's true.

I'm probably a little bit more on the Crichton spectrum than where I need to end up. But partly it's an illusion because I do things sequentially. I work on things a little bit at a time. This is classic slow productivity, a little bit of time,

but with great focus, do that long enough and things begin to pile up, but I'm not necessarily working on all those things at the same time. I think the podcast newsletter video portion of my empire makes my activity seem really multiplied.

But as Jesse will attest, this is a half-dust. venture for me. So the way I see all of this, like what you're hearing right now is, unlike Grisham, I'm a Web 2.0 guy. I grew up with the internet. So I do like to be able to connect directly with my readers and listeners. To me, that's really important, but I keep it confined. And so I just have a burst each week of let's do a bunch of stuff to connect with our readers, but it's confined. It's not a lot of ongoing projects that are eating up a lot of my time throughout the week. So if you put that aside, it's basically writing in CS.

And if I had to pick an ideal, where would I be when I sell, you know, seven million copies of the firm or whatever my equivalent is? Honestly, to me, an ideal would be I'm always writing, I'm always thinking sequentially, though, one thing at a time. You know, I'm finishing this book chapter, then I'm writing this New Yorker piece, then I'm writing this academic article, then I'm writing a couple more book chapters with a half day every week where we do this nonsense so that I'm not just living in a cave. To me, that would be great. And I'd be happy with that. I don't need to be directing or whatever the equivalent is of all of Crichton's busyness. So anyways, type one, type two, know where you are. Use that knowledge to help direct how you approach both your ambitions and your successes.

And I think it'll make people a lot happier. Do you think Crichton still like that? Well, he's dead. So he's the ultimate. Oh, right. I was thinking, yeah. Yeah. Yeah.

So Crichton died in 2008, maybe. Cancer. Yeah. He's older. By the way, I'm always surprised by how old he was. Well, we talked about this before on the show, but you read his first book under his own name, The Adronomus Drain, which again, read so modern.

You think this book was from the 90s. And yet in the book, no one's landed on the moon yet. So that's a long career. So when he first started writing these things, there were no personal computers. We hadn't landed on the moon yet, you know, because he was born in 1942. Yeah.

I was getting confused with money. ball. Oh, Michael Lewis. Yeah. Yeah. Yeah. I wonder what his deal is. He, so he has a podcast with his, his buddy Gladwell's network. Mm-hmm. He writes, usually he's always working on a book. I thought he had a, one of these sort of visiting, like, professorship things at Tulane. Yeah. For a while. I mean, I know that's what Isaacson's doing. I think Meacham is doing that. A lot of these writers, like these sort of that generation of came out of magazine. Yeah, they're in their 60s. Pulitzer winning writers. A lot of them have these positions at universities. But, yeah, I think Lewis is a good example. You know, I think he's just like, I just want to write.

Yeah, I know both. The whole time I was just thinking about Lewis for some reason. I don't know why. Yeah, well, I should go down that radical too. All right, so we're almost to our very first live call. I first want to mention a sponsor. Actually, two sponsors that I'm very excited about because this is just coming straight out of my own life.

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under the comforts. So, I mean, eight sleep has basically ruined me for travel. Because I really notice it now. I'm like, man, I miss my eight sleep.

It would be pretty eccentric to bring it with me, though, Jesse. It's a, because there's, you know, it's, you have this big mattress cover and this cool,

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Eighthleep.com slash deep to get that $150 savings. Eight sleep currently ships within the USA, Canada, the UK, select countries, in the EU and Australia. We have a new sponsor today. Again, something that I have been using for a long time before they sponsored the show. And that is Masterclass. Masterclass is where you can learn

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Go to masterclass.com slash deep now. That's masterclass. Dot com slash deep for 15% off masterclass. All right. We're going to start our first question block with a something we've been excited about for a while now. A live caller. So I can actually talk to someone back and forth.

We have video on the live caller too. So if you're a YouTube listener, YouTube.com slash counterfeit media, you can actually see both of us on the screen. Our first live caller is Spiros, who has questions about lifestyle-centric career planning and concerns about falling into the second control trap with his current career that may be going too well, and because of that, it is steering him,

the pressures of that, or perhaps steering him away from a deeper life. All right, so let's go to our phone line and talk with Spiros. All right, we have our next caller here. Spiros, thank you for calling into the Deep Questions podcast. Now, for what I understand, you actually have a case study you want to share with us of some of the principles I talk about actually put into action. Yep, exactly. Yeah.

So what I would like to do is I would like to talk about how I've been applying so good they can't ignore you since I read it like a long time ago, actually. But then I feel like I kind of messed up somewhere along the way. So after I kind of summarize, I would like us to go into kind of like, where did I go wrong? and where do I go from here? Sounds good. All right. So I moved to the US from Greece in 2012, like literally 10 years ago, to do a PhD in robotics.

And I read your book a couple of years later, so in 2014. And I was like, whoa, okay, I see what I'm supposed to do. So I started applying it first to research, but then I got the opportunity to participate in the 2015 DARPA Robotics Challenge. So then I started applying the principles to robotics software as opposed to just robotics research. That went pretty well. I got really into kind of like the more the software side of robotics. I decided to take a little of absence to join a robotic startup, ended up dropping out of the PhD program with a master's. Did really well in that startup. I was the first software engineer.

I hired the team eventually. Followed the startup to Austin, Texas in 2016. Then moved to San Francisco in 2017 to work for another robotic startup. Again, did really well, got promoted, got to travel to Hong Kong and China for manufacturing purposes. And now since 2018, I've been working for one of the top three, perhaps the top self-driving car company here in San Francisco. Again, I've been doing really well. I've gotten very high performance reviews. I've gotten promoted.

I'm on track to get promoted again. I'm considered very reliable, high performer, all of the good stuff you would expect from somebody following these principles. I have tons of options. I don't mean to like sound. I don't mean to brag, but like I get so much recruiter email these days that it's almost like spam. So I do have options. Now the reason, now this is where this is turning from a case study more to the question. I feel like to put it in terms of your book, I think I fell for the second control trap.

I think I got too excited about the performance and the promotions and the compensation and the recognition that I've kind of become too busy. I have too many responsibilities. I'm too busy. My compensation is too good to ignore, if you will. So that's kind of what I would like to focus, the question part. Excellent. Excellent. Well, let me first. I'm going to back you up to the beginning of your case study just for the edification of our audience. I want to go back to you as a PhD student. You read so good they can't ignore you. Now, you glossed over a little bit. Oh, I put those principles in the play and started becoming very successful in my studies. studies, let's go back and try to make that concrete. So, like, can you identify what did you start doing that, let's say, other students in your cohort who weren't as successful or you, the password yourself, weren't doing? Let's try to do some differential analysis here, because I'm curious in this beginning point first, and then we'll get to you now. Yeah, yeah, for sure. So because of your own case study in the book, you were also a PhD student,

eventually a postdoc, et cetera. I was like, oh, I'm just going to do exactly what Carl talks about here. Carl talks about, you know, getting a very fundamental research paper and kind of like going deep into the research paper trying to understand the proofs, trying to understand the results. So that's something that I did. I scheduled some time every week to go through either fundamental papers in my field.

So I was in formal methods in robotics, which is like formal verification, formal synthesis. Anyway. So I was By the way, I'm happy to geek out with you about that. We can talk about your improvers and we would lose all of our audience.

But just let you know, you should know I'm restraining myself right now. I'm tiptoeing around it on purpose, yeah, because this can be a rabbit hole, yeah. So that's one thing that I remember very distinctly doing. Then once I got the opportunity, though, to participate in the DARPA Robotics Challenge, I was like, okay, I can apply this here as well. So then it shifted from like reading research papers as my deliberate practice, let's say, to learning C++, learning Python, which are like some fundamental languages for for this kind of thing, and then something called the robot operating system,

which is like a middleware for robotics applications. So I knew that these things existed, and I knew some programming, of course, already. But I was like, okay, these are the three fundamental things I need to know if I want to write robotic software and get the robot to actually do something. By the way, we got to work like my team for the DARPA Robotics challenge, go to work with those like Atlas humanoid robots from Boston Dynamics. So, yeah, pretty crazy platform to be working on. also terrifying but yeah go on yeah and so that's another way I applied that so like I was for example

I remember very distinctly scheduling blocks at the very beginning of my day like before I even went to into the you know the grad student cubicles or whatever like I would let's say go to a coffee soap or something like that and I would spend like let's say two hours just going through tutorials you know writing code you know just deliberate practice okay so just to clarify for for the The first thing you did was it's hard to understand these fundamental papers. Having that knowledge will be useful. Quick follow up here because I get this question a lot. How did you actually structure the reading of hard papers without a formal forcing function?

Like, I need this for a project I'm working on. You just had a system, a quota. How did you do that? Yeah. So the way I motivated myself was that, hey, I'm seeing that I'm having a hard time with like the very formal aspect of writing. So I was able to write research papers, but they were kind of like, they weren't going very deep on the math, on the proof side of things. So I was like, okay, I'm going to motivate myself by saying that by understanding the fundamental

papers and how this proofs work, I will be able to do that myself eventually. Then in terms of like how I structured that, I think it was something like, you know, kick off a note in Evernote, you know, pick one of these papers and then schedule time within the week. You know, as a grad student, I, you know, you have, like, I kind of like, reminisce about flexibility I had in my schedule as a grad student. And so I was scheduling that like, yeah. Once a month, at least once a month, I have a moment where I just insanely nostalgic for that.

But anyways, go on. Yeah, yeah. And so I was, if I recall correctly, this was like eight years ago at this point. I was scheduling time like on a weekly basis to make sure I get in at least a couple of hours. So this kind of like go over the paper. And then the other thing I was doing, which I think you also mentioned in the book, is when I was reading like paper, around what I was writing, like papers I wanted to reference,

I wanted to cite in my own paper, I wouldn't just like, you know, skim through them or read them and then forget about them on a pile. I would actually take notes, like in a, I would take digital, I would take notes on the paper and digital notes, and I would kind of sketch out what this paper is trying to do

and how it, you know, proves the results. Yeah. Right. Well, okay, so just to summarize that before we jump now to the current moment, just to summarize that for the listener,

What Spiros is doing here, which is straight out of so good they can't ignore you, is identifying the thing that is actually valuable in the field where you are, not what you want that answer to be, not what matches how you want your day to go, but what is actually valuable. So first off for him, that was understanding how to do this more fundamental theoretical work. And then later on, okay, understanding how to use all the different programming language tools that are relevant to the DARPA robotics challenge. so I can be as useful as possible. And in both cases, what you did, which I think is right, is said, okay, that's the reality of what matters. What do I actually have to do to learn that? Oh, it's hard. I have to read these hard papers.

And, you know, I'm in the same place. Theoretical computer science is the same as early in your grad student career. Understanding papers is how you advance. Understanding papers is incredibly hard. And those two things are true at the same time. And it was a big differentiating factor when I was coming up, those who would wrangle papers and those who would just look for what's easy. So I think that's a great example of the principles in action. And it worked.

Okay, so it worked too well. So now we jump ahead. You're suffering from the second control trap. So for people who haven't read that book, the first control trap is trying to get a lot of autonomy in your career before you built up the skills to actually justify it. That's where you are 23 and you quit the start your nonprofit that's going to change the world. But you don't know what you're doing. The second control trap is when you get a new. enough leverage and skills and power into marketplace to actually have control of your career

is exactly when all of the pressure in the marketplace is going to be to stay, to move up to the next level, to take the higher salary. So it's when you're most able to be autonomous is when it's hardest. And that's what you're hitting now. So why don't you explain to us a little bit more, what is your job like now? What is your day to day like now? Is it managerial? Is it technical?

Let's get a sense of where you are. Yeah. So my title is staff software engineer. So it sounds like I'm a software engineer, like I'm writing code every day, but I'm not actually writing code every day because at a certain level in the individual contributor, like career ladder, as we call it, you kind of like fork into different archetypes. So there is the software engineer archetype, and this is the person that, like, writes really good code. There is the domain expert archetype. This is the person who has like, you know, three PhDs in convex optimization or, you know, machine learning or whatever. So domain expert. And then there is the archetype that I think I better fit into, which is kind of like high-level tech list.

is what we call it. And so this is the person who is able to kind of understand how the system works end to end and kind of, you know, coordinate this team with this other team and this other person over here and get this, you know, other subsystem to do the right thing. And then you get the entire project or the entire effort to do the right thing just by understanding the system end to end and leading the integration effort. So to put it more concretely, I do everything from, you know, analyzing kind of like metrics to see kind of like where we have, you know, gaps, writing project proposals, writing design documents.

And then once we kind of move into the execution part of the project, I'm usually maybe, maybe I'm running some meetings or not, depending on whether we have a program manager support or not. I'm coordinating all of these different individuals, you know, software engineers, systems engineers, test engineers, sometimes operations teams that are like, you know, handling the self driving cars on the road. So what's a day look like? is how much of it is slack and email how much of it that's that's exactly what i you hit the nail on the head it's very much uh you know hyperactive hive mind modes uh all the way like i have to fight really hard just to block out like two hours at the beginning of my day and maybe if i'm lucky will actually you know get to actually do do deep work in those two hours like today i'm on call for example so like for all i know once my own call you know shift starts i will be

completely derailed by like an issue coming in on pager duty. There is a lot of activity on Slack. I've done all sorts of tips and tricks, applying some of the stuff from your books and your podcast to minimize that. I only check email, like I try to check only once a day. I once experimented with going a week without taking work email, and nothing terribly happened. So I'm very much in time to keep doing that again.

Yeah. But like email is okay. Slack is where most of the hyperactive high mind is kind of like operating. There are lots of meetings. It got much worse, you know, during the lockdowns. I'm sure I'm sure others are saying the same. Like it's like sometimes I feel like, you know, when am I supposed to like use the restroom and like make coffee? Like there is no time between these meetings. So there's a lot of that. Yeah, exactly. There is a lot of that. Yeah. Like I, one of the things I talk to with my manager the most often is like, hey, I need to we need to figure out a way from it. I need to carve out time to do proactive work as opposed to waiting for a problem to arise

and then doing reactive work and then fixing the problem. Like, the reactive work, part of the problem is that reactive work is actually gets recognized a lot. So there is like, it's really hard to motivate proactive work when there is tons of reactive work to do and it gets recognized too. so that's one size. Right. But why do you care about it being recognized?

Who? Wow, I was not expecting that question. When I say recognized, I mean, okay, there is a recognition in terms of like, you know, like performance reviews and stuff, but there is also the like doing what the company, the business thinks is most, you know, valuable, you know, right now, this quarter, this month, you know, this year, whatever. And it's often the case that what, you know, the business priorities are to deal with their, with the reactive problems. They are not to go and, you know, do proactive work.

Yeah. All right. Well, I'm going to give a two-part answer here. And I'm going to be terse because the second part of this answer is something that's probably going to take you weeks of actual thinking to do right. So you'll have to check back in. I'm going to give you a short-term, a short-term thing to try and a long-term thing to consider. The short-term thing to try is I think this might be a good. set up for a deep to shallow work ratio conversation with your manager. So I talk about this

some in deep work, but then got a lot of feedback from people after that book came out about this particular strategy working well. So it's pretty well road tested. And it's where you have a conversation like the type you're already having with your manager, but it's a little more quantitative, right? You say, okay, this is what deep work is. This is what like reactive work is. You're in a tech company in San Francisco, so they probably know the term already. And you say, say what ratio of this sort of reactive shallow to deep proactive do you think is optimal for my position? Like what ratio of those two is going to produce the most value net for the organization? So we've got to get a number on it.

And when you have to get quantitative about it, they're not going to come back with the answer. I want you to do 100% reactive shallow, right? Because you have this other value. You have this training. You can produce new things. So when you get a number that they agree to, this often leads to the dissolving of ossification in business culture. So it lets let loose a lot of innovations. They might say, okay, maybe it should be 50-50.

So what we're going to do is, you know, mornings an hour for you to do proactive work. No calls start tell you're not on call till the afternoon. We tell the whole team, don't expect responses. That's just an example. I don't know your exact situation. It might be, you know, Tuesdays and Fridays. you work from not at the office and maybe from somewhere else and you're just doing proactive. The quantitative nature of that really makes a difference and the positive orientation makes a difference.

So it's you coming to your manager saying, how do I produce more for the company? Not you coming to the manager and saying, I'm fed up with you slacking me all the time. You know, you're terrible. The latter conversation doesn't go well. The former conversation I have report after report of that working. this is a short-term solution. Try that, see how it helps. And that might be it.

My long-term solution, I'm going to ask that you probably are at a good point. And let me actually ask you, how old are you if you don't mind sharing? Yeah, I'm 34. Okay, so you're in this sort of heart of the millennial generation approaching middle age. It's a perfect time to start thinking through these questions of, okay, let me step back. How are things going in my life? What reconfigurations are looming on the horizon? And it's a good time to go through a serious lifestyle-centric career planning exercise where you really look out, I would look at 40 and 50 as age targets.

And like we talk about on the show, have this really clear vision of all aspects of your life in an ideal world at that point, not just work, but where you live, what you're doing with your time, who you're around, see it, smell, it, taste it, we like to say. Get that vision for 40, get that vision for 50. and then look backwards and say, how do I get there? And in answering that question, you may end up saying, okay, my current career trajectory, that's fine. I just have to do the steep to shallow work ratio, maybe do a lateral move at some point into more, you know, you could maybe figure it out. Or you might end up with an answer. You say, I have a lot of skills. I am an ML robotics expert engineer.

Okay, why don't I take that out for a spin and I can actually maybe do something drastically different? I'm on contract. I work six months out of the year. I live on Vancouver Island. You know, I mean, you could, you have a lot of flexibility. So short term, I would do that ratio conversation. Long term, I would say, let's, let's go through that exercise in detail and just see where it leads you. And don't be afraid if it leads you to, I'm more or less close.

I see to make some tweaks. Or if it leads you to, you know, I'm about to buy a ranch outside of Austin. You know, it could lead you in a lot of different directions to be open to all of that. How does those as a one-two punch? does that sound as a potential way forward. I'm glad the conversation went there because I kind of anticipated this and I've already like I've already done the first draft of what you just described knowing that it was all right.

Tell us. Yeah. It could come up. Should I actually go into it? Yeah. Okay. Give us to give us the brief summary of the ideal lifestyle picture you're playing with. So the brief summary is that I want so I'm originally from Greece, right?

So I want to, I want to get to a point where I can I can spend more or less every summer in Greece. Working, not working doesn't really matter. spend about six months out of the year in the US and then spent another quarter just working from somewhere else. Other things I want to be doing, I want to be able to be near the water. I love swimming, I love water sports and whatnot, so I want to be able to do that. I want to start writing.

I wrote a few blog posts and articles back in grad school, and I really enjoyed that, but I gave that up later on to focus on my career. so I want to get back into writing. Maybe eventually, actually write a book. We'll see about that. I'm currently single, so eventually I want to be able to meet somebody. Now I feel like I'm so busy or so exhausted that I don't even like make enough time in my schedule for dating. So I definitely want to, you know, the connection bucket is suffering essentially to put it in deep life terms.

Other things in there. Finally, you mentioned Austin. It's actually Austin is on that roadmap because I figured that. If I were to move to Austin, which is central time, but I work Pacific time hours, then I get two extra hours in the morning when I still have energy and willpower to do things like deep work, to do things like riding before I engage with the hyperactive hive mind. So Austin is actually on the trajectory, potentially. Well, okay.

I mean, it sounds like to me you're heading down the path towards changing your career situation. If that lifestyle sounds like either a greatly reconfigured job at your current employer or a different setup altogether that's maybe more freelancer contractor-based. Is that a scary thought for you or is that where you've led yourself already? Exactly. You're spot on again. What is scary is I don't want to, in my attempt to escape the second control trap, I don't want to accidentally veer all the way to the first control track.

Because it'd be easy to say, you know, screw all this. I have enough money in the bank to last me, you know, X many years. I'm just going to quit. I'm just going to say, you know, screw Silicon Valley. I'm going to go to, you know, Mexico and work on my book or whatever. But then I would be probably falling for the first control trap if I go so extreme. So the scary challenge is bridging the gap between like where I am right now and kind of this vision for my, for when I'm 40 or when I'm 50. Yeah.

Well, okay, this is great. So in the first answer, I got to give some generic advice about deep to shallow ratios. a first step and lifestyle center career planning. Now we get an example of lifestyle center career planning. So I can give you a piece of advanced advice

that goes to lifestyle center career planning implementation. And you're spot on about you don't want to fall back into the first control trap. You're not going to be happy

if you say I'm going to go to rent the house and Cabo and just work on my book. That'll last a month before, you know, you start to get antsy. So what I'm always looking

for in this situation is concrete exemplars. I'll often talk about the rule of three. So you want to find a real person who has your background, who has a professional setup that resonates. Hey, that works. Okay, here's how they did it. Oh, they're a contractor that works on this type of ML project or whatever. Like, it's concrete.

This is someone, and it's a job that they do. It's a six-month-a-year job. It's a flexible enough job. They take summers off. They go up to New England in the summer. So real people doing with your skill set what you want to do. Rule of three is if you want to be really secure, find three different people doing something like that. So now you know it's not a one-off.

It's actually a viable path. But have a specific target that you're working backwards from. This guy, her and him did this setup with my type of skill set. How do I move there? I mean, I will say I'm doing that in some of my own lifestyle-centric midlife career planning I've been doing. I don't share a lot of details about exactly what. I'm thinking about because there's a lot of stakeholders involved, but this has been my approach, is what I'm seeking is examples. I am seeking people with similar backgrounds who have already

figured out a configuration that seems to work. That's how I think you can avoid the first career trap. I think you're there right now, the seeking stage. Go seek out these examples. Meet the people. Also, by the way, say, can I call you? Can I take you out for coffee if they're local? People are happy to share details of their experience and get concrete with them. How did you make this change? What are the hard parts? What advice do you have? I don't know if you ever took.

You probably didn't. But in that top performer course I did with Scott Young, we talked a lot about this, this journalistic approach to career development. I know of that course, but I haven't taken it no yet. We have students actually go through this. It's like you're writing an article on how this specific type of job transition works. You're out there doing research, gathering real information, always concrete, always like this is something that people are actually doing. doing. And I think you were ready to start looking for those exemplars, which is also an exciting part of the process, because you get all the aspiration without actually having to yet do anything

to scary. So, you know, good for you. I think you're in the fun part. But I would, no reason why you can't start just trying to find people right now who come out of your background, who have a setup where they, they work eight months a year, they work six months a year, their location independent. I'm sure they're out there in your field. There may be an academic affiliation. There may be a nonprofit affiliation, maybe they're a fellow at the Open AI, whatever, and there's so many options out there for your field. I think you're ready to start looking for concrete examples. This makes a lot of sense and really resonates. Yeah. You've mentioned this before, but I never, you know, pieced it together. You're right. Yeah, that's what I need to do. Excellent. Well,

Spiros, keep me posted. I want to know what you end up doing. And maybe I'll follow up and we'll share that with the audience. But in the meantime, you know, thanks for the case study, thanks for the questions. and also an excuse for me to go through a lot of different advice. So I find that useful as well. Yeah. So good luck for you. Thanks very much. Thank you, Kalianzzi.

Bye. All right. So there we go. Our first live call, I enjoyed that. We have more of those to come. So stay tuned. And if you have feedback, of course, you can always send us notes to Jesse at calduport.com. All right.

So let's move on now with some written questions. Let's see. Jesse, do you have the written questions you get to? Now we've got kind of a culture shock here. We've just talked to someone live and now we're going to written questions, but we do it all on here. All right, what's our first written question of the day? First question is from Philip. He says, you got started by blogging, but what are your thoughts about using private journaling or building creativity or even a writing career?

So what are your thoughts for using journaling to, you know, build that? Well, so, Philip, my thought on becoming a better writer is the best way to do this is to write, but in particular to write for audiences where there's feedback. So you have some sort of feedback function that is going to apply pressure to your craft that try to improve it. So that could mean writing for editing. There could be an editor that needs to either accept or reject your piece, and if it's not good enough, they'll reject it. Or they've commissioned the piece, but they're going to be editing it. and you have that feedback in your mind of if this is not good,

they're going to be disappointed. There's going to be a lot of work to do. I want to impress them. It can also mean writing for an online audience if you have other metrics to look at, such as it could be views or clicks. It could be more the direct feedback you get from your readers, the comments they leave, the emails they send you, was this thing clicking or not?

Did this if you're a tech writer get picked up on Hacker News and do well? How is the subscribers to my email list doing? So you can get online metrics now as well, but what you want is writing for an audience with feedback. It's that stretch to want to optimize or improve that feedback function that you get better. That's where you get the deliberate practice effect. Writing to a private journal is not going to generate that. So as a source of making you a better writer, writing your private journal is not going to directly improve your craft. There are other benefits to it.

I see here in the elaboration of your question, you mentioned that the book, The Artist Way talks about private journaling as a way to increase creativity. And that might be the case. If you're a novelist, doing private journaling on ideas might surface more random combinations and connections of ideas in your mind and help you pull out more grist for the creative mill. So I could believe that if you're a nonfiction like idea writer, I think taking notes on thoughts you have, different theories or connections between ideas, you don't want to lose

that. So having a place to take notes, that could help us. well. So my summary is as grist for material, that material, then yeah, private journaling could help. I don't, but it could help. For making you a better writer, you have to write for people who care and you have to care about how they feel about what you're writing. That's what's going to push you to improve. All right, what's our next question? All right. Next question is from Alessandro, a 24-year-old from Italy. What are some examples of Keystone Habits for the community bucket?

You know, I've got this question a few times. Really brief review for those who are new to the show. One of the methods we talk about on here for developing what we call the deep life is to divide your life into these different categories that we call buckets that cover different aspects of what's important for you. And the method we often propose is you start with a keystone habit in each of these buckets. Just something you do every day to signal to yourself that you take each of these parts of your life seriously to single self-efficacy to yourself. am able to do things that's not required or mandatory just because I think it's important. And then step two is you rotate from bucket to bucket and spend a month or two on each overhauling that part of your life.

All right. Alessandro is saying, and I've heard this again from multiple people, the community bucket. So the bucket where it's you sacrificing non-trivial time and intention on behalf of other people or people who are important to you, it's not always obvious. What's a daily habit to do there? In the same way that it might be more obvious for craft, it might be something like, I do an hour of deep work every morning, or for Constitution. It might be, I walked in thousand steps a day.

What's the equivalent for a community? I wrote down three ideas here, just to get you thinking, Alessandro. Write text or call someone you know every day. You know, it could just be, hey, a friend. I was thinking about you. You thought my things was interesting, calling your parents as you're driving home from work, seeing what's going on with the sibling. but just in this discipline, if I take a little time out of every day just to keep touches on different people in my life, see what's going on.

Idea number two, perhaps there's an online community that you're involved in that's very important to you, people that share a certain interest or a philosophical or theological orientation or they're involved in a niche hobby, whatever it is, right? But maybe you have an online community, hopefully that doesn't exist in a massive public mind-warping social media platform. Hopefully this is in something that's more controlled and niche and more of a long-tail social media type environment. And maybe you do something every day on that community. You post something or another type of useful effort. You do 20 minutes of moderation on their forum, whatever it is, whatever helps keep that community up and running. So you feel connected to that online community. You're giving it energy every day.

Idea three, I talk about this in deep work, something, whatever your equivalent is of data, daily Torah study. I thought this was a really cool example from my book deep work. In the Orthodox Jewish community, there's this tradition of, you read Torah every morning. There's a

page a day. There's a way to break this up, so it's a page a day. Page means that there's a scroll, but whatever. It's, you know, one reading per day. And there's a tradition where you do it with a partner. I'll probably say the word wrong. Shavrusa. Khrufra.

Abusa. I'm not saying that right probably. But what they do is it's usually early in the morning before people have to get to work and you have a partner and you sit there and you study a page of Torah every morning. There we go. That's just an example or whatever the equivalent is in your faith community of every day doing something with someone else. There's a bunch of us in the same room. Connects you to that community. All right.

Those are examples Alessandro, but that's the type of thing. It doesn't have to be major, but it's not trivial. It's tractable. It might take some sacrifice some days, but you can almost always get this done. But it's not over the top. It's not I have to spend four hours a day hosting a live event or something like that. So those are the type of keystone habits I have in mind for the community bucket. All right.

What do we got next, Jesse? Next is from JP, a 43-year-old from Montreal. And he's looking for a deep dive with concrete examples of a template of a quarterly plan. I like this. Let's stay nuts and bolts. All right. So background here.

I'm a big proponent of multi-scale planning. So you have a quarterly or semester plan that you look at each week when you build your weekly plan. You look at your weekly plan each day when you build your daily time block plan. So you're controlling your time and energy on multiple different scales. That's what allows you to take advantage and mold your time optimally at different types of levels. You need all three of those levels in there. There's a lot of variety for what people put into these quarterly or semester plans. To prepare for this, I went and just looked at mine

before we went on the air today. I maintain two, one for my professional life and one for my life outside of work. And the thing that struck me about my professional life on when I was looking at it, my plan for the fall, the semester we're in or quarter we're in right now, is it's pretty pretty brief. Honestly, like a normal weekly plan will have more text in it than my plan for the entire fall semester. I mean, so when I was looking at it, basically, it was, there's three things in there. And I'm talking sentences with a few bullet points under them for each. So there is Georgetown academic work. It's at least so many things to say here. Like this is, I'm working on these two academic papers and, you know, there's a administrative type thing I'm working on.

The details don't matter, but just boom, boom, boom, right? Writing. It's not that complicated. This is where I want to be, like I'm writing my book. I'm working on my book, slow productivity. This is where I want to be by then this semester. Here are some miles. So I broke it out month by month milestones for the semester.

That's there. Then I'm doing some New Yorker stuff. and I know what's coming up, and I have a couple notes there on how I want to interleave it. All right, that's it. And then for, I always call it the online empire, but the media company, the podcast, video, and newsletter, we have things, just to have some things we're working on. I have some bullet points to remind me of, like, the objectives, like, where do I want to be by the end of the fall? We're talking about, it doesn't take up a whole page, my Google Doc. If you printed it, it could fit on one page.

All right. So these aren't essays. it's not complicated pros. It's not Gant charts. It's not spreadsheets full of different milestones. It's like get three chapters done and get this article done in between and make sure you look into the possibility of shifting, like for the summer doing X. Like we're talking about that level of detail. It seems like that's not enough information to help, but it makes all the difference in the world because now you have that in mind when you're doing your weekly plan.

You're like, well, okay, if I'm going to finish this chapter by the end of this month, then this week, I really, Tuesday of this week, I need to maybe take that over for writing because the Thursday and Friday are busy. This little bit of information unlocks a large volume of decision guidance about all this other stuff that happens in your life at smaller scales. All right. So, so JP, it does not have to be complicated. In fact, the higher scale you go, the simpler these things get, because you're talking to such a big granularity, you can only get so many things done when you're talking about pretty big objectives. So these things get simpler.

Don't overthink it. Don't overwrite. Don't over detail it. You're just giving your energy for the next few months some guides, the roughly guide it down. Trust your weekly daily habit and then focus that. So with your personal quarterly plan, is that just kind of keeping an eye on things outside of your time blocking for the day? Because you do that outside of work. Yeah.

So that'll have objectives and goals. So like let's say you have new objectives fitness-wise or something. like that like that would be on there um it's like health and fitness stuff would be in there a lot of family stuff you know the you know we want to do what's coming up this you know this fall well we got a bunch of birthdays you know the fall is always complicated for our family because we have Halloween which we have high holy days yes so then Halloween really kicks off the busyness because we take Halloween seriously and then I have a son has a birthday the week after Halloween then we have Thanksgiving and then another son has a birthday right after that.

Then you get into the whole holiday season. It's like we're constantly buying gifts. We're constantly doing decorations. And so just having a reminder of that, I might pull back on other things. The winner, I typically will have like some more ambitious plans for the kids. Like, okay,

we're going to set this up. We're going to learn how to do this. We're going to have these projects, you know, because the winters are otherwise dark and less crowded. So all that type of stuff goes in there. So for the technicalities of when you look at your, quarterly and you're doing your weekly plan

like every day in the time block that that's outside the time blocking for your working hours, right? Most of the time. Yeah. Yeah. So, I mean, sometimes it's not, right? I mean, personal stuff, if it happens during my work hours, it'll be, it'll be integrating the time block plan. It's also a very effective way, by

the way to make progress on like annoying personal things. Like, I got to do the family budget or I got to go, you know, we're doing financial planning stuff right now. Like, I got up some insurance. I have to change the

retirement deductions or whatever from like Georgetown. And like that's actually a good thing to maybe capture. Here's an hour on Wednesday from two to three. Use time block energy for that stuff. So I'll often like grab those things inside it.

But yeah, for the evenings, it'll be, it's the beginning of the week. I'm looking at my strategic plan. I'm looking at my personal plan for the semester. I see like, oh, we are, where one of our objectives for January is to get to this new milestone with our Maker Lab. So like, okay, I'm looking at my week. Why don't I choose an evening this week that we can go here?

And then that'll go into my weekly plan. Like, yeah, Tuesday after pickup from the bus stop, let's go straight to the Maker Lab or whatever. Yeah. Yep. So there's the nuts and bolts. All right. What I got next? All right.

Next question is from Jay. How do you choose what book to read next? Good question, Jay. There's two main ways that books come onto my radar of things I need to read. It's either functional, so I need it for research. Maybe I'm working on an article or I'm working on a book chapter and I need to read something because I need to know that information. So there's functional ways that things come onto my list of things to read. Everything else is inspirational. That looks interesting. Let's get that and read that as soon as possible after I get it. So it's sort of like spontaneous or functional or inspirational and functional. So I just looked here. I have four books I bought four books in the last week. So I thought I would just go through those and I'll, for each, let you know what the motivation was.

These are four books. I'll probably read these all within the next three or four weeks. That'd be the idea. So I bought First Man by James Hanson. It's a biography of Neil Armstrong. It's because I was watching Damon, Damien Chazel's movie First Man, which, by the way, is underrated.

I think he's a fantastic movie, especially if you can watch it on a good screen with a good sound system. I don't want to geek out about, you know, his use of 16 millimeter film and the cockpits. And there's like a lot of really interesting decisions he makes. It's Ryan Gosling and Claire Foy

from the Crown, whatever. So I was watching this movie, which is great. And the guy, I want to write, I want to read the book. It's based off of it. So that was just inspiration. Yeah, let's do that. this. Karen Armstrong's new book, Sacred Nature. I love Karen Armstrong's work. I talk about the case for

God and the history of God a lot on this podcast. He has a new book out about the ways that people have found sacredness and nature throughout history. I mean, of course, I'm on board for that type of thing. I saw that just mentioned in the New Yorkers Roundup of the Best Books of the Year so far. Boom, just ordered that. Short book,

I'll read in a few days. I'm very excited for that. I also bought Superintelligence by Nick Bostrum. This is an AI ethics type book. It's for an article. So that's more like homework. I'm reading a chapter every morning of that. And then there's 15 chapters. So I'm reading a chapter every morning as a baseline. And then I'm going to throw in here and there extra sessions to read a couple more chapters

here and there so I can get it done within 10 days. It would be nice. And then I also just bought right before I came here John Meacham's new Lincoln biography. I am a big, I'm a Lincoln fan. I read a lot of Lincoln stuff, but I'm particularly excited about Meacham's new biography for a lot of reasons. I read a great review of it

in the Washington Post book world this weekend. And so that's on its way. That's a big book. I'll find time to read it. I want to get that done in November if I can as well. So there you go. It's a mix of inspiration and functionality. And if I get inspired, I buy it.

I want to get into that book before the inspiration dies down. When you're reading enough, you can get through a lot of books. So on a given month, how many books do you read? Or how many books do you buy? Sorry. I mean, five.

So last week you bought a lot of your quota. Yeah. Yeah, I have all I need for the next month. But sometimes I, I mean, sometimes I'm buying books. I'm not going to read the whole thing, but I need like this chapter and that chapter for an article or book research. Like, that's worth 25 bucks to me. Yeah.

If I can get a good example out of something. But, yeah, I bought a lot of my quote in a big burst. And then you take trips to the library too every once in all too, right? Yeah, and we have Little Free Libraries in my town. They're really big. My town is really big on these Little Free Libraries are everywhere. And I get a lot of good books out of those. It's just to take a book, leave a book type system.

Are those on the side of the road? Yeah. Okay, I've seen them. They look like mailboxes. Yeah. I walk by one. Yeah, I mean, this is like Willie Wonka's factory for me, for my personality, is this town. is like just wander around and just pick up free books from these like well-educated

people's like their professors, little free libraries and just walk around and just like pick up free books and when you're done picking up free books, go to like one of our mini coffee shops that just sort of like sit and drink coffee and read and it's a cool town. It's a good match for me. So I should stop promoting it because we don't want too many more people to move here. It's getting expensive. So yeah, do not move here. Helps your house value though.

does help the house value. It's a cool town. It's quaint. It has a lot of books and good coffee shops. That's all good. Infested with werewolves. So just, you know, caveat emptier. Otherwise, great.

Good books, good coffee. You may have your flesh be devoured by a lithon trope. So you've got to balance that out. All right, we got another good block of questions here. Let me just take a quick break to talk about another sponsor that makes this show possible. And that's our good friends at Zoc, Doc. Doc doc is a free app that shows you doctors who are patient reviewed, take your insurance, and are available when you need them.

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How do I find a dentist? I could ask a few people and then try to get on the phone with them, or you could go to Zoc Doc. Here's a dentist in my area. Let me read the reviews. Let me see if they take my insurance. Let me sign up right there on the website. This makes a lot of sense.

I currently have two doctors in my life that use Zock, Doc, my dentist and my primary care physician. That makes things really easy. I really like how I can fill out paperwork online. I don't have to do it on the clipboard when I get there. So I am a fan of Zoc Doc because of, all of those features, and also because I like reading out their URL. ZockDoc.com, my favorite URL to read.

So go to Zock.com slash deep and download the ZockDoc doc app for free. Then you can start your search for a top rated doctor today. Many available within 24 hours. That's ZOC, doc.com slash deep, Zock.com slash deep. Say it three times fast and they'll give you $100,000. This is where I have to do the advertiser disclaimer voice and say $100,000 prize, not guaranteed. One other sponsor I want to talk about. This one I'm excited about. It's called Giving What We Can. This was co-founded, if it sounds familiar. It's co-founded by William McCaskill, the effective altruist philosopher at Oxford, who did 80,000 hours, which we talked about on the show as well. So he has this co-founded, this new group, which I'm, which I, which I, I'm excited about called giving what we can.

So this helps you answer the key question of which charity should I give to, which charity is going to be most effective in spending my money. This is what giving what we can where it enters a picture because they've done this research for you. Founded by William McCaskill and another philosopher named Toby Ord. Its goal was to try to figure out their goal is to try to figure out how to help others give as effectively as possible. So that's why giving what we can takes your ability to do good in the world seriously.

Searches for evidence back, donation opportunities to help you maximize positive impact. The recommendations are backed by tens of thousands of hours of research by expert charity evaluators and grant makers. So you can be confident that your donation translates into real world impact. Otherwise, look, you see a slick website. I don't know. You see a bumper sticker. You're like, hey, why not? Why don't I give to this charity?

What is this, you know, over here? It's the Deep Work HQ skeleton fund or something like that. And then you realize I just gave $100,000 to this charity so that Cal and Jesse can do nonsense with skeletons in their ad, in their HQ or something like this, right? You don't want to make that mistake, but you also don't have hundreds of hours to research and detail how effective charities actually are at converting money to good. So you go to giving what we can. They've done the research for you. now you can put not only your money to use, but put it to use as effectively as possible. So over 20,000 donors worldwide right now trust giving what we can.

You should join their group. Go to giving what we can.org slash deep to maximize the impact of your donations this giving season. That's giving what we can.org slash deep. Don't forget to slash deep. That's how they know you came from us. All right. Well, I think we have time. Let's do a couple more questions, Jesse.

What do we got? All right. Sounds good. Question from Aaron, a 30-year-old from Boston. Cal has alluded to sleep issues and often mentions caffeine consumption. Bevco, except for her stuff like that, the coffee shops around Tacoma Park. I'm curious about his philosophy on caffeine. Well, first of all, Aaron, I don't know where you get this idea that I drink a lot of caffeine.

For those who are watching or listening instead of watching, you will see what is one of the world's largest coffee cups in my hand. Not as big as a coffee cup from the HBO show, Veep, the chief of staff's coffee cup. But this one is actually branded from our ad agency that does all our podcast ads. I think this is their way of trying to keep me sharp so we can we can sell more ads. Here's my caffeine philosophy. A, I drink a lot of it. So here's the backstory.

I got started drinking coffee in high school. So I went to high school at a public school in Mercer County, New Jersey. which is the county that includes Princeton, New Jersey. And I blew through, this is not going to surprise people, but I blew through all of the available computer science instruction. By the time I was a sophomore, I took the AP course when I was a sophomore, got a five. I was sort of like out of computer science stuff to do.

And they had an agreement with Princeton University that they could send students from the high school who were sort of bored in certain topics to Princeton, tuition free to take some courses at Princeton. So in high school, I started taking. the computer science sequence at Princeton. And I would stop at the Tiger Mart on Route 31 and pick up flavored coffee in those cheap styrofoam cups. And so early on, I built an association between coffee and intellectual work.

By the time I got to MIT, that got much worse. The theory group at MIT is fueled by coffee. They have these giant crafts and professional brewers, the things you see in Starbucks, like the really big brewing machines up on a big stand. and I was often tasked. I was the person who would brew it. A lot of Pete's coffee. I drink a lot of coffee in MIT. And so that's just been a part of I associate coffee with doing intellectual work.

I do cut back. So my philosophy is I don't drink after 130 or so. It is 127. So by the time we finished taping the show, it's why I literally have this with me because it'll be too late to drink coffee after taping the show is over. I try not to drink after one or so, but I don't really limit what I do before them. I probably drink a lot too much, but stopping at one seems to prevent it from really affecting my sleep right now. So there we go.

Coffee is like a liquid manifestation of my type one ambition. The type one piece of my ambition to reference the beginning of today's show that sort of like, let's get things done, it's sort of manifested in my coffee. I probably should drink like three cups max in the morning to be done with it. I should do that. I don't. But I honestly think the key to doing that is having. It's all somatic. I need a alternative ritual to associate with doing deep work.

I mean, that's what this serves. And so there we go. That's everything you need to know, Aaron, about Cal and coffee. You always drink it black, right? Always drink it black, because that's what I learned. I like cheap flavored coffee because it's what I associate with being in that lecture hall at Princeton. And, you know, it was the first exposure to like, oh, I see. This is what college level, and that's sort of a weed out class, too.

I was like, okay, I see what like college level work is like. It's much more mathematically demanding. It moves much faster. So I just have these associations from that. I have family members who are real coffee snobs and roast their beans and, you know, carefully extract one drop at a time from a, you know, a bag made out of the wings of a certain type of moth or whatever. And for me, I was like, I don't care. I'm drinking right now Trader Joe's Pumpkin Spice, harvest whatever holiday coffee.

I just associate that acidic cheapness with time to think. And you never drink tea? That's what I do when I need the deep work after 130. I'll drink herbal tea because you get half of the associations. It's bitter and it's hot. And that actually works pretty well. That'll work pretty well. You're probably way more controlled about nutrition.

What's your coffee philosophy? No caffeine? No, I drink coffee. Well, you had a coffee cup when you came in here today. Yeah. Yeah. I like to have cream with it, but. ideally I would drink it black

but sometimes when I treat myself I put cream in it I was listening to someone somewhere which is not a very useful description all I know is was on a podcast and it was within the last month that's all I can locate it and he was saying

like full fat cream and coffee is like much better than butter or other types of things because there's something about the way the fat is encapsulated in dairy that works well with the coffee and blah, blah, blah, metabolism, blah, blah, blah, something, something is like you get energy out of it and it doesn't just store the fat away.

But if you have other sources of fat and coffee, because I guess the keto people or the paleo people put like butter in their coffee, actually it's not so good. Like that, it becomes, it's not as good. Like that just gets sucked right into cells to be stored or something. So he was a big proponent. Whoever this guy was, some of the. guy I heard some time on something was a really big believer in just like full cream full fat cream heavy cream like there's actually much better for you got it yeah well with that type of detail

about who he is and his credentials I don't see how you could not listen to this advice some guy on something I heard it sometime I think he ran a heavy cream factory let's do one more question what we got okay questions from Kman do you have any recommendations for my 16 year old son who is now reading your books and listen to your podcast. He would like to create multiple streams of income and enjoy a deeply satisfying life. Let us know we'll be listening. Well, I mean, first of all, good for your son. Let that be the underlying piece of this answer is just to have someone at that age who is thinking so intentionally about their life is like a superpower. When you're 35 and thinking really intentional about your life, it's like welcome to the club.

Like everyone at that point is starting to think through like, oh, what works for me, what doesn't, how should I organize my efforts, what I want to do. At 16, almost no one's doing that. Or if you're doing that, they're doing it in a very simplistic formalism, like the millennial obsession with following your passion, like some notion of like, well, there's one job I'm meant to do. And my job is to figure out what that is. Very few people your age are thinking so systematically. So that by itself is going to yield lots of benefits, irregardless of any particular advice I now give you going forward. Now, let me provide you, I took some notes on this.

I was looking at this question before. So I want to try to provide some off relatively rough advice for you, as someone who was young, to lay a foundation of support of sorts that will support a deep life as you enter adulthood. Now, the main thing I want to say to set up this foundation before we get to these specifics is be wary about getting too specific right now at your age at 16 about what your sort of post-schooling adult life is going to be like in terms of specific sources of income, etc. It's very difficult as a 16-year-old, for example, to get 23, what your life's going to be like at 23 to get those details right. because you're not you're not you don't have knowledge yet of what you're going to be exposed to you and what opportunities are going to be open to you so this is really the right time to be much more laying a foundation for being able to take advantage of opportunities and build this lifestyle when the time comes as you enter adulthood so i would say don't worry about the specifics yet let's work on you right now to make you into a deep life generation machine so that you four or five years from now is going to be well suited to start crafting you right now to make you to make you into a deep life generation machine so that you four or five years from now is going to be well suited to start crafting a really cool life. So here's a few things I wrote down. Number one, be 10 times more organized

and intentional about your academic work than everyone else you know. Most students are terrible at study strategies. Most students are terrible at time management as a student. If you are not, you can reduce the amount of time it requires for you to perform your schoolwork at a certain level by a factor of three or four. It really is almost like a magic trick. I learned from experience. You start treating your student life like a job, like a 35-year-old would treat their job, and it becomes significantly easier. Its footprint on your life becomes significantly easier.

The amount of stress it causes will reduce down to very little, and you will be able to perform academically at the very height of your potential without grinding it out, without overloading or overburdening yourself. So, you know, I wrote a book about this, how to become a straight-A student. That's for college kids. I wrote another book called How to Be a High School Superstar. If you look at the part one playbook for that book, I adapt a lot of those study and time management advice from college to the high school context.

So you might find value in both of those. So the straight-A student book and the part one playbook from How to Become a High School superstar. The story I always tell is I was a reasonable student my first year of college. At the end of the first year of college, I got serious about, my academic strategies. I started treating the problem of how do you do well as a student like an entrepreneur would treat the problem of how do I learn how to market. How do I find the new audience? Because I'd run a business. I was used to that way of thinking. I brought that way of thinking to my academic work. And I jumped from a good student, B plus A minus student, to

four O's starting my sophomore fall every single quarter until I graduated except for one A minus in my senior spring. You ended up graduating with a 3.95 GPA. If I had done this one quarter earlier, I probably would have been to valedictorian in my class at Dartmouth. I did not get smarter between the summer of my freshman year or my sophomore year. What made me unique is I was one of the only people on that campus to start experimenting with what's the right way to take notes, what's the right way to study for a

math test, what's the right way to study for an art history test. How can I manage my time so I don't have to ever work past 8 p.m.? It was much easier than you would think. All right. So be 10 times more organized and tension about your academic work. Number two, introduce some discipline into your life. So you get used to the idea of having a disciplined life. There's things that are important but hard and you're willing to do that work over time

and see the results in the long term. You probably should have some sort of physical discipline. So some sort of sports or training, something that you do that will put you in better health or shaped and just sort of the average person you know who's not a serious athlete. You should have some sort of mental discipline in there built around the reading of hard physical books. I'd probably recommend that above all else for someone your age, that you have some sort of systematic program of study involving real books that you read. You have set times you put aside. Have two or three things like this just so you have a self-image as someone who is disciplined.

And again, the details don't matter because you just need to, when the time comes, you know, when you're 24 or whatever, the time comes for, your discipline is going to unlock something awesome. You want to already have that tool sharpened. All right. Number three, be very wary of video games, the social media. Your time is very valuable right now because you get leveraged.

Interesting moves or developments or opportunities you unlock when you're young have the maximum amount of time to actually earn experiential interest and start generating really cool things. So don't waste your teenage years, your early 20s, your college years, don't waste 40% of your discretionary

time in college duty. Don't waste 40% of your time on TikTok. Maybe that's okay for some people, but I can tell right now that this is a kid who is awesome. At it, he's on it, he's listening to deep questions, he's reading my books, he's intentional, he's already

thinking about multiple income streams. So be very wary of those devices. Be the guy who's weird about like, yeah, I just don't really use my phone. Let that be your thing. All right. Number four, expose yourself to bulk positive randomness. That's a term that comes from my longtime friend Ben Kastnoka, who wrote about that in his memoir of being a teenage entrepreneur prodigy.

So like starting companies in his teenage years, the startup of you is what that book is called. And he talks about this a lot. Expose yourself to lots of interesting stuff all the time to see what clicks, what sticks, what ends up resonating and holding your attention the next day the next week. Go hear speakers, read interesting things, go to interesting documentaries, go to conventions, you know, expose yourself to bulk positive randomness. This is how you get

eventually something really interesting clicking in your life. And now to pull from my book, how to become a high school superstar, once there is something that catches your attention that you're pursuing, you want to pursue what I call the failed simulation effect, which is you want to get to a place with that activity if you're a young person where people say, I have no idea how he did that. And the way you generate that effect, which is incredibly powerful and opens up all these interesting opportunities, is you just keep leveraging up. You do one thing that's kind of explainable.

You use that to get access to the next thing. You use that to get access to the third thing. That third thing, you use access to get to the fourth thing. And by the time you get to that fourth thing, that might be interviewing Supreme Court Justices for my podcast as a 17-year-old. that thing seems like I have no idea how a 17-year-old does that, but if you look the three steps before, that started with you, you know,

being exposed to a court reporter at a whatever, an internship, yes, the path makes sense, but not when you see the final thing. Maybe that's a confusing explanation. I have a whole chapter about this in my book. I also wrote about this, interestingly enough, for Tim Ferriss's blog, way back in the day when I first met Tim.

So it's on there somewhere. We're talking 2007, 2008, probably. I wrote an article for Tim. Dot blog, back when that was his main online platform, about the failed simulation effect. So you can actually find my article on his blog. I'd probably just search for my name and tim.com. Or something like that.

But anyways, you expose yourself to interesting stuff. When something clicks, you keep going, keep going, keep going. The first six months you're working on something, it's interesting to you, but not to the outside. world. You get to a year plus six months and you might be at a place now with that interest where people have no idea how you did that at your age and that's when really cool opportunities open up. Number five, study character and leadership. Expose yourself to examples of people who live with great character who act as great leaders even during difficult times. Read biographies,

read profiles, watch documentaries, maybe if they have a social media presence, so maybe like a jaco-willink type if that resonates. Maybe you're listening to his podcast and the military professionals he has on the Tales of Valor. Whatever it is that resonates, you want to be imprinting young,

a real affiliation or affinity for character and leadership, especially during difficult times. That is going to be a North Star or a guiding, through all sorts of different ups and downs and competing pressures and diversions you're going to experience the next, let's say, 10 years of your life. Now is the time to start building up those examples.

And number six, serve people. One way or the other, be doing that now. And it's just setting the habit of, and it could just be volunteering. It could be this is this cause. Or online, I go and I help. I'm in this community just to help these people. Whatever it is, you also want that imprinted into your soul at a young age that serve other people because that's what you need to fall back on when the other pursuit you have isn't going

well. This company failed and I lost this job and I really am feeling down on myself because I had these ambitions that I was going to be Michael Crichton at 27 and instead I'm at, you know, I'm getting to that age and I'm short on money and my plans didn't work. You fall back on helping others. Well, you know what? Let me just put that energy to helping others while I also am trying to figure myself out. the more you can fall back on how can I serve or help other people, the more emotional and psychological resilience you're going to have for all the ups and downs that are going to come. So what's going to prevent you from ending up instead, 26, and bitter and on Twitter and just mad and yelling at people and medicated seven ways to Sunday and just not even sure what to do with your life, you'll end up maybe like an ideological groupie for some weird whatever. and just be miserable. You don't want to be there.

So falling back on serving others as a default is that buffer, is that protection. Be useful to the world. Be useful to others. Let that also be a guiding light. All right. So those are my six pieces of advice, but good for you for thinking about this stuff at such a young age. You do these things. You're going to be a rock star.

You're going to be a rock star in college. You're going to come out of college and be living a life that you are going to have full control on the reins of this life. And when you start doing lifestyle-centric career planning seriously, but you really should wait until a little bit later in college to do so, you are going to have options. And whatever comes out of those initial lifestyle-centric career planning exercises, you're going to be able to shape your life there.

They have a deep life and a useful life. So I'm glad you asked that question. That's my advice. And that is also all the time we have. So thank you everyone who sent in your questions. Click the link in the description if you want to submit your own. We're looking for questions. please submit. We're also looking for people to do live calls. You can do that at that same link.

You can express your interest. We'll be back next week with the new episode. And until then, as always, stay deep.