IN-DEPTH: The Art of Non-Conformity (w/ Chris Guillebeau)

In this episode of IN-DEPTH, Cal is joined by Chris Guillebeau, the author of the new book, TIME ANXIETY, and creator of the beloved Art of Non-Conformity blog and World Domination Summit annual conferences. Cal and Chris reminisce about their old days as early advice bloggers and dive into his new ideas about re-thinking our relationship with time. Video from today’s episode: youtube.com/calnewportmedia INTERVIEW: The Art of Non-Conformity (w/ Chris Guillebeau) [03:50] Links:https://www.calnewport.com/slow Sponsors:https://www.donedaily.com Thanks to Jesse Miller for production, Jay Kerstens for the intro music, Kieron Rees for the theme music, and Mark Miles for mastering. Learn more about your ad choices. Visit podcastchoices.com/adchoices

Speaker names marked ? are inferred from speaking time and the show’s known hosts — they are not voice-verified.

• 0:05Cal Newport?

  I'm Cal Newport and this is In Depth, a semi-regular series in which I talk to interesting people about the quest to cultivate a deep life. I'm excited about today's guest. It is the author Chris Guboe. He has a new book out called Time Anxiety: The Illusion of Urgency and a Better Way to Live. So clearly, this book topic is one that you know I'm going to be interested in, and we have a good conversation about it. But I was also excited to have Chris on the show because he's a blast from the past for me. We intersect strongly back in that early stage of my career, the 2000s, when I was blogging. I'd written my

• 0:49Cal Newport?

  first student books and I had the Study Hacks blog, and I knew Chris from back in that world. So we sort of go back and relive a little bit what that early stage of new media was like, where blogs reigned supreme. We talk about these fantastic conferences that Chris organized called the World Domination Summit, including this famous one within sort of our circles. I think it was the 2011 or 2012 World Domination Summit. You can find my video of me talking about So Good They Can't Ignore You. It's online, but it's this like 800-person venue, and it brought together all of these different people at early stages in their career that would go on to do really interesting things. So you know, I was there talking. Brené Brown was there as well. That was like one of a couple

• 1:33Cal Newport?

  different... There's a period there I was doing multiple different stuff with Brené. Gretchen Rubin, I think, was there. Susan Cain from Quiet was there. It was just like this really interesting period of where people are coming together. That's where I met the minimalist for the first time. Like, they were just coming up, and it was all this energy at this one place. So it was... We had a lot of interesting discussions, not just about his new book, Time Anxiety, which is great, you should check it out, but also about what was that world like? That world of online ideas like in that pre-social media age? In some sense, it was utopian, and there's other parts about it that was actually like much harder than is today. So we pulled it all apart there, and I don't know, it was just cool to see Chris again. It really reminds me of just being back at like my office at

• 2:17Cal Newport?

  MIT, writing my Study Hacks blog post. A simpler time, but an interesting time. So it's a cool conversation with multiple different angles I think you are going to like. The conversation is brought to us without interruption. We have a presenting sponsor today that is allowing us to hear this full conversation without interruption. That presenting sponsor is Done Daily, an online coaching platform that will help you break free from the noise of shallow tasks and focus on the deep, meaningful work that really matters. With Done Daily, you're not just getting to coach, you're getting a proven productivity system with expert guidance. You'll build your quarterly plan, lay out your weekly plan, and organize your daily plan to stay on top of what matters most. It's designed to keep you locked in on deep, meaningful work while

• 3:01Cal Newport?

  steering clear of the distractions that slow you down. That productivity philosophy there should sound familiar, though I'm not, you know, a partner of, or it's not my company. I know the people at Done Daily because they also do My Body Tutor. I've known them forever and they have this fantastic online coaching program for health and fitness. So I was happy when they said, "Hey, we want to use some of your productivity ideas from your podcast. We want those to be the ideas our coaches are helping to instill." And so I was happy to hear that they were doing that. Thing is a fantastic way to get some accountability on implementing the type of productivity ideas I talk about on my show. So it's a sponsor I'm happy to have. DoneDaily.com to find out more. And thank you to Done Daily for allowing us to present the following interview

• 3:43Cal Newport?

  with Chris Groo, without interruption. So with no further ado, let's get to my chat with Chris.

• 3:51Cal Newport?

  All right. Well, Chris, it's great to see you again. It's funny to think when we first met each other, this type of technology did not exist. I'm excited, of course, about the new book, Time Anxiety. This hits on a lot of my sweet spots, my listeners know. We're going to talk about time management, productivity, how it intersects with purpose, how it intersects with psychology, how it intersects with our quest to feel, you know, depth and meaning. But I'm hoping to start by going back memory lane a little bit because I think there's an interesting story here about the evolution of the internet and technology and just kind of an interesting guy.

• 4:25Cal Newport?

  I'm going to mention how I remember you coming onto my radar and then I'm going to flip it and see what the real story was, you know, from your perspective. So if we're going to play the Wayne's World Back in Time transition music, we're going to go back to that, that first decade of the 2000s,

• 4:41Cal Newport?

  Was when there is these glory days for us millennials where blogs were the medium for independent media, that you would have these WordPress blogs and it would be weekly or daily and people would read them through RSS readers, it'd be on Google Reader or something like this, reading them. And I had my blog, Study Hacks, that was based off of my student advice books. And then you sort of showed up on the scene a couple of years into it. And what I remember is you had this manifesto, the World Domination Manifesto, you had a very good looking website. And I remember I was thinking like, oh, you could look that professional. And you were like, interesting. I think you were in the middle

• 5:24Cal Newport?

  of your travel to every country in the world. And it was just like a boom, like you were a presence within a few months. What is your memory from your perspective? What was going on when you entered into this world of Web 2 back in those days?

• 5:42Speaker 01

  What was going on back then? It was an interesting time. It was a really fun time. You know, I'm always like skeptical of nostalgia and looking back, but I do look back fondly on that time. And I remember that a lot of things just seemed easy, for lack of a better word, in terms of, oh, it's not that hard to like, set up a website or a blog on WordPress. And I can't take credit for how it looked. You know, I found a wonderful designer named Reese Spickerman. I reached out to her and I was like, hey, I've got this project I want to write about. It's a little bit about going to every country in the world, but it's broader than that. I want to call it the art of non-conformity.

• 6:26Speaker 01

  So she helped me kind of get going with an initial design for that. And then there were people like you, like Gretchen Rubin, Leo Babauta, JD Roth, others, you know, who were all like mutual friends now, had known each other for years. And I looked up to them, to you guys. And I was like, oh, what, it's interesting, what? You know, everybody else has done. I wonder if it's too late, you know, for me to do something in this space, but I'll try, you know, and the going to every country in the world thing like I had been doing it for a while as a personal quest. It wasn't like this is my, you know, marketing campaign, but I did think of it as an interesting anchor, you know, to like, okay, this is a, you know, I want to write about life, work and travel, which is super broad, you know, it's like the opposite of the conventional

• 7:08Speaker 01

  wisdom about like, choose this, you know, very specific niche. And so since I want to write about life, work and travel under the lens of non-conformity, it's helpful to have like, oh, and I'm going to every country in the world as part of, in part of this. So that's, that's kind of how it came to be. And I remember reaching out to lots of people and just saying, hey, I'm, I got this thing. And a lot of people were kind enough to like link to it. And that was like a currency back then, right? I mean, it still is to some degree, but I think back then it was like, oh, if people are like linking up your, your blog, um, and that's very valuable. Um, and you were kind, you know, to write a post about me and the manifesto and, you know, things kind of transpired from there for, for both of us. And we ended up hosting an event that you

• 7:48Speaker 01

  came and spoke at, and you were obviously like taking off and going in different directions as well. But that's kind of how it started for me.

• 7:55Cal Newport?

  That event, the events you used to run, we, we've talked about them on the show before. I guess that came a little bit later, like the 2010, the World Domination Summit that you ran. I've talked about it on the show nostalgically before with people because I don't think this exists anymore, but my memory, those, those, that first one I went to, A, like the crowd there was really interesting. It was, I remember Brene Brown was there, Gretchen was there, Susan Cain was there. Um, yeah, J D Roth was there. He was nervous. I remember that it's because you got, you got big crowds. Those were, those were big crowds. Like there, there felt like something was happening. I remember I was hanging out with like Manish Sethi and Ben Casnuka and we were, uh, it was, it was a

• 8:39Cal Newport?

  Something was happening and it was coming out of the world of the internet. And it was an interesting energy that's not really there anymore, I guess. Like that idea of like, we would all get together in the same place with like 800 people. And you would do crazy things, like when you had the hundred dollar startup. That you're like, we're going to give everyone a hundred, a hundred dollars. Except for there's a thousand people there. And I remember like being backstage, you're like, oh my God, we just came back from the bank with a hundred thousand dollars. Wrapped up. There was an interesting energy at that time. What was going on? Here's the question I'm trying to understand. And maybe this is true of every generation and the current generation is feeling this now. And the past generation felt it as well. But, you know, in that period, I think as like old millennials and young Gen Xers.

• 9:22Cal Newport?

  There was really something in that post nine 11 world of like this online world was unlocking a lot of Tim Ferrissian, let's design our lives. Like, what do we want to do? You know, I'm not super interested in the conformist path. It wasn't that it was back to land radicalness, but there was really a sense in the air. There was such an energy, you were doing this. Leo for sure was doing this when he left, when he left his, when he left his job and paid off his debt with Zen Habits, his ebook he wrote, right? I mean, it was like an interesting time where people were looking for meaning in life. And they weren't looking for big wins.

• 10:03Cal Newport?

  They weren't looking for, you know, I want to be famous or I want to be rich.

• 10:09Speaker 01

  Right.

• 10:09Cal Newport?

  What was your read of like, what was happening in our world at our time that made these type of these blogs successful?

• 10:16Speaker 01

  You know, it's like on the, the search for purpose and meaning. You know, to get to like the skepticism about nostalgia. I, I want to be careful not to like overstate that, right? But I do think there was something to do with the mediums and how people connected that were quite different. In the sense that it was possible to kind of know everyone, or at least know of everyone. And I think that's a, that's a key difference. And yeah, there were like events like WDS where people ended up coming together. You know, I always saw like whatever role I had in it as being like an amplifier rather than a catalyst. Like this was just happening, right? And like, we were able to gather that in some way and that was fun. Whereas now, like, everything is so disparate and so segmented and.

• 11:02Speaker 01

  So yes, people are chasing, you know, virality and fame and wealth through becoming a professional influencer, but it's not only that. It's more like, you know, there are so many, there, you know, how many 15 year olds are there with a million plus followers, you know, on networks like TikTok? And it's not just 15. There are people doing all kinds of things and, and we've never heard of them, you know, like it used to be that everybody could hear of everyone in a certain space. And now, you know, it's like there's thousands of, or tens of thousands of spaces. There's a lot, there's so much more connection and such a lack of connection at the same time. But I think people are still searching for purpose and meaning, you know, I don't think that has changed.

• 11:45Cal Newport?

  Yeah. I mean, it's interesting that back then, at least in our space, you knew when someone new arrived. Like we knew when you arrived. Like it just, the link got passed around. I remember at your event, one of your events was when like the minimalist arrived. And I was like, oh yeah, okay, I'm looking at you. They weren't even on the main stage. They were doing something on the, you remember you had like the side rooms and stuff like that. And I remember looking at their site and I was like, this is, this is good. Like they're good. They've arrived. And they just were. And then like I became for everyone, I became friends with them. We knew them. Like that was, that was the world now. And yeah, that's funny to think about today. You know, it's not like, hey, everyone, guess what? There's someone new on TikTok. All right. Like, have you seen

• 12:27Cal Newport?

  him yet? Let's, nice to meet you. Like, okay, let's, let's, let's have a phone call. I mean, I wonder, was our audience very, maybe it was just small relatively speaking. I never really thought about it, but maybe all told, we were in more of a niche than we thought. But I felt like there was just a lot of niches like that going on back then. It would be run around web two and it was slower and more personal, I guess.

• 12:49Speaker 01

  I don't, I don't, I think the audience of creators was certainly much smaller. Right? I don't know if the audience of consumers, you know, I mean, to just kind of make a little binary there. I think maybe that has something to do with it. Right? Cause like, how many personal development, broadly speaking, blogs were there that were, you know, read by like a decent number of people at the height of that time? I would say probably like 50 to 100, maybe. And like you could be like, At least have a surface understanding or, you know, knowledge of most of them. Whereas if you pick any sort of category now, how many people are doing it? It's like thousands, right? And they're doing it in lots of different ways and in different forms. And everything is short form video and it just comes and goes.

• 13:31Speaker 01

  And then there weren't, they also weren't, there also weren't algorithms, you know, back then, at least, you know, it wasn't algorithmically driven content, the way that that, that, you know, the world works now. That was a big thing.

• 13:43Cal Newport?

  So you and I stayed with a strategy that not everyone did. Like you and I, part of what unifies us is that we've kept writing books.

• 13:51Speaker 01

  Yeah.

• 13:51Cal Newport?

  And, you know, you've continued to write books and have written a fair number. I continue to write books. I think our book counts are relatively similar. What's your thinking behind that? Why, why have you stuck with books?

• 14:02Speaker 01

  Oh, I don't, you know, I don't know that it's a strategic decision. It's not like, I'm like, let me look at all the mediums and kind of see what is best. It's, I mean, there probably is a certain, I mean, complacency would put like a negative tilt on it, but it's more like, I'm comfortable with, I like this. This is a medium that I know and appreciate. And maybe the audience for it is shrinking in some ways. So I need to think about other mediums and such, but I still like that medium and feel comfortable with it. I still have ideas for books. I still think there are things that can be best explored in like a long form concept. But who knows? Maybe I'm, you know, it's like, I think it's fair to always say like, maybe I'm just kind of set in my ways with that.

• 14:46Speaker 01

  And like, if I were starting over now, would I, would I have the same beliefs? I don't know. What do you, what do you think about it? I mean, why have you stuck with books?

• 14:53Cal Newport?

  I mean, I think there's two reasons. One, I like the form. I mean, I just think it's, it is a incomparable form that you can capture multiple years of thinking and you can crystallize it into a really legible product where someone can go inside the mind and really come out with like a new crystallization of knowledge. I don't know. I'm a sucker for that format. I think it's hard. It's hard for anything else to match it. It's also, the financial question's an interesting one. I think books are pretty winner take all.

• 15:29Cal Newport?

  You know, if the, after deep work took off, it's also a good financial proposition. But I can't say that's the way I was thinking when I was writing, you know, how to become a high school superstar.

• 15:41Speaker 01

  Sure.

• 15:42Cal Newport?

  That was not the, that was not the goal. So it's, it's an interesting, it's an interesting medium. I also feel like it gives us a foundation, a little bit of an anchor in a royal sea of new media, where anyone can show up and try to go for attention. I mean, what happened with, I lost track of everyone. I feel like in 2014, like what's, it's somewhere around there where, and I chalked it up at the time. I was like, I don't know. Like I moved, I started my professorship. I had a kid and like, maybe that's what it was. But I was still blogging. So it felt like something changed, like that world of blog base with real world meetups. I mean, I was at WDS or whatever. It would have been like 2011, 2012. That was like a big part when I was writing So Good They Can't Ignore You.

• 16:29Cal Newport?

  But by the time I was writing Deep Work, that world, that world had felt like it collapsed. Like I didn't know that world anymore. And what was I spending a lot of my time doing then was going on podcasts. So like, what did it look like from your, your end? I think you had a bigger thing going on in that world. When did things change?

• 16:48Speaker 01

  I think there was definitely like a slow, I was going to say disintegration. Maybe it's more of a splintering of people just kind of, you know, going off into their own things. And then there all of a sudden were more things like we were just talking. It wasn't just about blogs. It was like all of a sudden there were more events. There were a lot of events that came out of WDS that ended up serving maybe more specific communities. And of course, you know, other events that had nothing to do with, with WDS. So I think a little bit of the splintering, then you have the new mediums, right? The podcasting and, you know, Instagram and everything that that inspired or led to. Comments, you know, on, I think blog comments used to be like a big thing, right? And like most blogs don't have comments now, or if they do, it's like not really like the main feature.

• 17:33Speaker 01

  You know, now there's this rule of like, don't read the comments, right? Like reading the comments is not going to get you anywhere. Like there's no value in it. You know, at least that's the perception. So yeah, I don't know. I mean, like I'm doing a book tour right now, and even though I do very much, you know, believe in writing books. I want to write another book, you know, I'm happy with this one. I am doing like the book tour. I do notice like there's not a lot of people coming out to a lot of these events and I miss that. Like I wish it were different, but I also I can't just force it. It has to like, things tend to work best when it's like you're doing something that you know, you have some skill at. Hopefully you have some message that's worth sharing, but then there's also like demand for it. You don't have to generate the demand. And I think

• 18:17Speaker 01

  right now, there's not a whole lot of demand, you know, to come out to meetups and smaller events, at least not, you know, certainly not what it once was. So I've got something I have to think about.

• 18:28Cal Newport?

  No, that's interesting. So then what is, what's like at the core of your business right now? If, if, if, pen down like, oh, what, what do you do for a living? Which of the pieces of the different, because I know you speak and you write and you have a daily podcast and you still write the Ardon Conformity, which I appreciate that's you still write it weekly. How do you think about it now?

• 18:49Speaker 01

  Yeah, I do break it up a little bit in terms of what makes money and what I'm the most excited to do. And like, it's always nice when there's like perfect convergence there. But I would say right now, like the podcast is like the primary financial model. And the podcast is something I started seven years ago and I've done it every day since then. So that's, you know, remarkable in some ways, but also I think it's good to evolve, you know, in other ways and do different things. So I'm not, you know, as passionate about, I don't put as much time into that, but it provides a disproportionate, you know, financial benefit compared to some of the other things. So then, you know, the books, I have the Substack newsletter and the Substack newsletter has a paid component, but I really

• 19:30Speaker 01

  don't push it very much. You know, it's very, it's very like, all the content is free. I don't have paywalls. So it's more just like, if you'd like to support it, that would be great, you know, and some people do. But my understanding in talking with people who do like the paid newsletters is like, nothing converts more than a paywall. You know, like if you really want to like go that route, that's, that's how you do it, you know, no amount of begging or, you know, incentivizing, you know, compares to like that break in the article that forces people. And I just, I don't, I'm writing more about mental health and neurodivergence. I just feel like I don't, I don't know, there's something weird about that I don't like. So.

• 20:03Cal Newport?

  Yeah, you have to lose, you have to lose a lot of audience to, to make money off of, off a paywall.

• 20:08Speaker 01

  Yeah.

• 20:09Cal Newport?

  How, so I could never figure out back in the day when blogs were the main thing, I could never figure out how to make a living off it. Like that was the one, I think downside of that period in my mind was. There was great community, but it was very hard to monetize in a reasonable way. Like web to RSS driven, at least for a non-super business minded person, you know, like myself. How did you make that work back in like 2009 or like in those early days? So like I could never figure it out.

• 20:41Speaker 01

  Well, it's interesting you say that because I feel it's it's hard. It's a lot harder now than it was then.

• 20:46Cal Newport?

  So how are you, how are you making money back then?

• 20:49Speaker 01

  Back then I created products. I created, the blog is like there for free. And this completely, this, this came about completely organically. When I noticed people were asking me the same kinds of questions over and over. Cause I was writing about going to every country in the world. And I would occasionally have some posts about, oh, here's how I booked, you know, my around the world plane ticket. For example.

• 21:09Cal Newport?

  Oh, I remember that product. Yeah, like travel, it was like advanced travel advice was one of them.

• 21:15Speaker 01

  Exactly. I kind of geeked out on that. And I was like, well, you know, this is not really the main purpose of my blog to like go into like, here's all the frequent flyer hacks and tips and itineraries and things. But maybe people want to know about this, right? And so I created like the first ever digital product I sold was called like Discount Airfare Report, which is like the most unsexy, you know, non-marketing title. And it sold for like $10 or $15 or something. And I, it was like the opposite of a sales process. And when I put it up on a post, because I felt so like insecure about selling something. It was like, if you really, really want it, you know, like here's how you, you know, but you know, like a hundred people bought it or something. And I was like, well, that's interesting, you know, like maybe there's something to this.

• 21:55Speaker 01

  And so then I did start building out like other resources and, you know, okay, here's how I have worked for myself. Like here's some entrepreneurship guides and some other travel guides and things. So I did that for a number of years and that worked really well. Like I never like scaled it or turned it into like a proper company. It was always a lifestyle business, but from a blogging perspective, it worked really well. And obviously people still have courses and things now, but I think that world has also changed quite a bit.

• 22:20Cal Newport?

  That's, that's right. So that's the model. Yeah, you have a very popular blog and then you would have information products. It was just like, oh, you're interested in this bit. Let's dive deeper. Yeah, see, that's what I didn't figure out till too late. I started doing some online courses, but that was 2014. That was actually very successful, though. So you're

• 22:39Speaker 01

  right. I was gonna say, your topics, sorry to interrupt, I was gonna say the topics you were writing, especially the earlier topics, that's very, you know, specific with a huge recurring market, you know, and obviously people who are willing to pay at least a small amount of money, or probably more, but, you know, you could sell those at scale.

• 22:54Cal Newport?

  Do you remember?

• 22:55Speaker 01

  I'm surprised you didn't do that.

• 22:56Cal Newport?

  Well, I just, I don't know. It didn't occur to me. It, I, yeah, so I'm thinking about, why did not occur to me? I was writing books, but not, you know, for great amounts of money. I mean, you know, I was also just doing the, trying to become a professor. I was in grad school.

• 23:09Speaker 01

  That took some of your time.

• 23:10Cal Newport?

  It took a little bit of time. Not that I was making much money being a grad student, but I do remember, though, I feel like the first person, the first two people to try this was when Ramit Sethi did The Guide to Kicking Ass. Do you remember that?

• 23:24Speaker 01

  Yeah, I do remember that. I remember when he sold that, like an ebook or something.

• 23:27Cal Newport?

  Five dollars. Yeah.

• 23:28Speaker 01

  Right. He's done, he's done pretty well with that. So obviously, that's an example of like, here's, here's how it started, how it started, how it's going. I mean, he dealt, he went straight into that and went really deep and, you know, started selling courses for thousands of dollars and, you know.

• 23:42Cal Newport?

  Yeah, yeah, that's right. But it started with that. It was five dollars. He was nervous about it. And then Leo, Zindadun, ZTD. I remember that. Yeah, Zindadun. And he was, I remember that was kind of the hero, was when he, he sold that ebook and paid off his debt, and then they moved to San Francisco. And I remember that, reading that and being like, wow, this is someone. And also, like, Tim Ferriss, it was like, Tim Ferriss came along and had Lifestyle Design. But it, so that was really big, but it was kind of unclear how to do it. Like, the examples in the original version of the book were like, I don't know, I'm supposed to sell striped shirts. Like, it was, people weren't quite sure what to do. And then some of the bloggers, we figured out, like, actually, we have, like, audiences.

• 24:26Cal Newport?

  And, yeah, what a time. So, yeah, informational products. That was the way. I find today, so the thing, here's how I see it. Tell me if this makes sense. I see it as, this is very, like, nostalgic tinched glasses. This is probably not going to match with everyone's experience. There was kind of a golden, there's something kind of nice and nostalgic about the era of blogs, because there's a lot of community, and it was non-algorithmic, and you could, it was a nice period. And then, like, social media kind of sullied the party. This was sort of my take on it. I mean, I didn't use social media, but I just saw it fragmented that world. And content began to chase the algorithm and it became a different beast, right? I mean, our stuff reads as so earnest, but it was authentic in a way because yeah, we weren't chasing an algorithm. We were like building a relationship.

• 25:09Cal Newport?

  But I feel of all the new technologies, the one that has sort of best captured what we had back then is podcasting because it's, it's not algorithmic. It's relationship centric, like you build over time a relationship with the audience and it's more, it feels like it's more directly monetizable than blogs were. You could sell something else, but like podcasting, there's like a built in mechanism to convert an audience of just to have some ads. And they actually pay at a level that means if like a show is doing well enough, you can make, you know, you can make a living off of it. So I feel like there's a bit of a renaissance of that same energy that there was back then. It's not as connected. That's the only problem. It's a little bit more like you're in front of your microphone all by yourself, but I

• 25:54Cal Newport?

  do feel like I know a lot of podcasters, but that feels, that has some of that same vibe where you're connected to a person, not like surfing content. Has that been your experience with podcasting?

• 26:04Speaker 01

  I think it's a little different. I think, I mean, I think everything you just said is true and correct. And, um, you know, podcasting has, you know, the discoverability problem, you know, which has never really been solved. I'm not sure how it will, maybe with podcasting going more on YouTube. Perhaps that will, but then that also has other changes with now. Okay, now it's more video based and it's less passive, you know, consumption. You know, you can go out and go on your run and listen to a podcast, but it's also such a different learning style. You know, some people are natural auditory learners or enjoying that content and others would prefer to read. So it's a, that is a big shift. I think there is certainly a community, right?

• 26:47Speaker 01

  It's like, I know different people doing shows and we all go on each other's show and that can be fun and such, but I do think it's a little bit different. You know, I think it's like, if you're starting from. Like if you were first asking me like, how did I get started? How did you get started? I'm not sure that the model would work the same way, right? Because you got started by writing this certain content and then other people would find it and link to it and such. So how would that work in the world of podcasting? You know, it doesn't quite work as well. Obviously, people are able to like start from nothing and then build up. But I tend to think more like rather than being relationship focused, I think they they are more algorithmic focused and they probably should be just look at it like from like the naked perspective of what actually works. You know, if you if you don't have a lot of relationships with people

• 27:32Speaker 01

  who are known, quote unquote, then it probably is smart to like pay attention to the algorithm of them and build your business that way. And that in some ways is sad, but I think that's how it is.

• 27:43Cal Newport?

  I think you're I think you're right about the fact that it's a much it's a much narrower, there's a much narrower number of opportunities too, right? So it's there probably was more opportunities with web two writing than with modern podcasting. So it's easy to say if you have a show going well, but that's sort of like saying in the early days of CNN. Like, oh, this is great. Like suddenly with cable news, there's, you know, 30 new slots for TV shows where they used to just been 10 TV shows. And if you were Wolf Blitzer or something, you're like, this is great. Like, I didn't really have a space in the world of where it was just Walter Cronkite. But now there's, you know, 30 new shows and it's it's great. And but you're right, like for most people like, okay, yes, there it opened up some more opportunities. But it's still super narrow.

• 28:27Cal Newport?

  And because I think you're right about the discoverability, like what we were doing in those early blogs wouldn't make for a good podcast yet.

• 28:34Speaker 01

  Right.

• 28:34Cal Newport?

  Because there's a lot of authenticity, there's a lot of like talking about, man, there's so that world was so personal, I like that world. What you were doing, what the the minimalist were doing. Not the minimalist specifically, but the minimalist movement, like Josh Allen and Courtney and everyone else doing that. I mean, there was a lot of people were talking about their lives, right? It was more professional, which is doesn't play in podcast land. I'm just thinking out loud now. But yeah, no, you can't just have a podcast where you're sort of here's what I'm thinking about and here's what's going on, or you some wisdom. You're right, it has to have. Something and you probably have to have a pre-established platform like a successful book or be a B-list celebrity or something like that. Oh, you're kind of talking me out of it here, Chris, though I, I am enjoying it.

• 29:18Speaker 01

  I'm enjoying it too. I'm just thinking about it from the perspective, as you say, of people coming into that, this world, right? And not that like every one of your listeners wants to do that, but yeah, I do, I do often think like how things have changed and how, how we have to cater our content or not, or if we choose not to, then are we going to be excluded, right? If we choose not to like play by the rules of, you know, the social media or the algorithm or whatever, and we haven't even talked about AI, of course, you know, things are changing so much. And then I also don't want to be like, oh, well, you know, back in my day, right? You know, like, you know, I'm always wary of that. I do think like we have to, you know, learn new things and adapt to new things.

• 30:00Cal Newport?

  I mean, it was pretty, this just seems to be the, the reality of new media forms is there, there always seems to be a misguided notion in a reality, right? So the misguided notion is because this new form is available to everyone, that we're going to have like almost everyone will be able to have an audience. And then the reality would always be, okay, yes, we've democratized who gets access to the printing press, but still only the interesting brochures are going to get read. And like this was, this was the, the blog reality. Uh, remember this was like a big joke back then. It was like, everyone has a blog and

• 30:39Cal Newport?

  no one cares what your blog about your favorite pizza or whatever. And so it made it available for everyone to try blogging, but like only certain stuff work. And like, we found the certain niche that worked and there is a voice that worked. But, uh, for every like one of us, there's probably lots of people who gave up and podcasting is even more restrictive.

• 31:01Speaker 01

  You know, the thing I thought I meant to say this before on your last comment was like about Wolf Blitzer. I, you know, so Wolf went from, there was, there was a few channels and then now there's 30. Okay. So that's one thing. Or maybe there's even like 300 or something. But I think the difference is, you know, if we like extrapolate, it's like back in the day of the 2008, 2010, whatever the timeframe is, okay, that was closer to 30 or maybe to 300. And now that what is the number, you know, it's not quite infinity, but it's a huge, massive number. So it is, I think it is harder to stand out regardless of platform or medium and message.

• 31:37Cal Newport?

  Yeah, or but I might flip it around to say like, channels are the slots for having a good audience, right? Like, like, in other words, they're like blogs came along and now almost anyone could produce a blog, but like, most of them were never read by anybody. But there were, in the end, more things that had audiences than before blogs, you know, blogs like ours. We didn't have an audience before then, but it was still pretty small. The people who had, you know, six-figure audience numbers plus, right? It was it was bigger than it was in the age of Time Magazine and New York Times. But that's what I meant by like, network TV going to cable. There was like, more slots for people to have big

• 32:19Cal Newport?

  audiences. But like, most people still don't, you know, get a show. And I think the good I look, I look at it sometimes from like, from the consumer of information's perspective. That's great. Like, the shift to cable was great. Like, great, there's more options now. And now there's like, all in addition to watching like, Three's Company, now you have, you know, Mad Men and Sons of Man. Like, there's different interests. There's more of a variety of shows, and it's great. But it didn't mean like, most people get shows. Same thing with podcasting. I think social media tricked people. My theory is, at least in the original incarnation, I wrote, this is the way I wrote about it in Deep Work, is like, in the original incarnation, I feel like Facebook was a reaction to blogs being hard. Like, so many people tried, you know, would start a blog and no one would

• 33:03Cal Newport?

  read it, because it was really hard to get people to read blogs. Because who cared, right? Unless you had the right voice, in the right place, and the right links going on. And Facebook came along, and basically, what I think they were offering for their first five years was, we'll, we'll make it feel like you have an audience. So you can pub the web, web two is too brutal. Yeah, sure, you all have access, but it's a brutal experience. You start your blog, stop blogging, and no one cares. And that's brutal. So here's what's gonna happen on Facebook. You'll be writing stuff, and most of it'll be in main. But there's gonna be this, we're gonna connect you up to people who know you, and there's gonna be this social contract that they'll look in like your stuff, and you'll do that for them. And you will get to like, Have that feeling of there's an audience that cares what I'm doing. And I really think

• 33:44Cal Newport?

  that was the original appeal of something like Facebook was we'll give you a simulation of what it feels like the, you know, to have an audience. And that was immensely popular. And people said, well, that's where I want to be. And the people creating like the really interesting content are like, I'll create it over there because everyone's on there because they're also getting this tickle back. Then that went away. And I think now like most social media is just pure, just pure diversion. Right? So they kind of have got rid of that sales pitch of like, hey, people care what you have to say, and you're gonna have followers. And like, most people are like, no, just Tik Tok right into my brain. And I don't, you know, I don't care. But I, that, that was always my theory is that it was like the simulacrum of audience. And that was reacting to a real problem is that

• 34:27Cal Newport?

  there was only so many slots for like, art of non-conformities or study hacks. But on Facebook, everyone could feel like, oh, yeah, people are poking me, or whatever it was.

• 34:34Speaker 01

  Yeah, until it changed, until, until in shitification, right?

• 34:39Cal Newport?

  Yeah. And then they said, actually, you know what? Now that everyone's on here, yeah, and should listen to it. Now everyone's on here, we can get rid of that. We don't need to attract people to this anymore. We seem to look at it. And what's better than making people, make you feel like people are looking at your stuff is just like, putting stuff that is incredibly engaging. Yeah. Yeah. So, yeah, interesting. All right. We figured, we figured out all of media.

• 35:02Speaker 01

  So podcasts are very helpful, as you were saying.

• 35:04Cal Newport?

  Yeah, I think so.

• 35:06Speaker 01

  We've solved that problem.

• 35:07Cal Newport?

  We've solved that problem. Yeah, Chris and I have solved that problem by podcast. What happened to you with social media? Did you, how did you have to adapt to that?

• 35:14Speaker 01

  Oh, I feel so conflicted about it, Cal. Very ambivalent in the sense, I got, maybe I wish I'd taken a hard line like you. Or I wish I had gotten really good at it, you know? I don't know. I feel like I kind of like, split the difference. And that's not a great path to success in most media. But I also, the ambivalence is also partly just...

• 35:39Speaker 01

  Based on my own enjoyment slash aversion to it because sometimes I really like it and sometimes it's fun and I'm like, oh, okay, I'm going to get into this. I'm going to try to try to actually be more strategic about post strategic consistent about posting. But then I'll stop, you know, I think for whatever reason, I was always really disciplined in some things, you know, like going to every country in the world, or I have a podcast streak or other things, but I have failed consistently at applying that discipline to social media and I don't quite know why. But yeah, so I go back and forth of like, I'm going to post for a while, or I'm just going to stop posting everywhere for months and months.

• 36:17Cal Newport?

  If you had started, how many years later would this have been? 10 years later than when you did? Your original visiting every country hook would have been supernatural YouTube like series, right? Like it probably, if someone was doing that right now, I think it would have crushed in that medium probably. I mean, it's super visual. It has drama, right? I mean, some of those countries like Iraq and like you had some of these like really Afghanistan, these things were like you would land the airplane or go into like northern Iraq to the Kurdistan that would have to count or like, that's how you would have done it today, I guess. And it would have been more expensive. You would have had that good

• 37:02Cal Newport?

  camera, you have a camera guy and editing or whatever, but.

• 37:05Speaker 01

  Yeah, I'm so glad I'm not doing it today. I'm so glad I did it when I did for several reasons. I think one, there are some places that are fundamentally more dangerous now than there were then. But also even if we like leave that discussion out, just to focus on the like the sharing of it and the media of it. Yeah, I would need to be video and you have to like create some sense of drama and intrigue. And a lot of the country visits that I did, it really was about the goal. It was about the quest. I was not a great travel writer. I discovered that pretty early on, you know, there are other people that write really engaging, you know, travel pieces about all the conversations they have and the food and, you know, culture and lifestyle and that's great. I enjoy reading those things, but I was much better at writing about process.

• 37:49Speaker 01

  And so, does that make for as good of a YouTube? I think it just may, I would imagine like every comment would be, what is this? You know, like, this is not exciting.

• 37:59Cal Newport?

  You on a spreadsheet trying to figure out your layovers.

• 38:03Cal Newport?

  Yeah, that would be, yeah, you're right. You would have to have the very peppy, high energy. That's what it would have to be. Yeah, that's what have to be, have to be today. All right. So let's talk time. Time anxiety. This, my, my listeners are not surprised that I like this book. If you pick it up, you'll see I blurbed it with enthusiasm. This intersection of these ideas about our time and how we manage it and notions of productivity. Those intersections with our psychology, with our anxieties, with our, you know, sense of purpose and meaning and how they conflict and support each other. This has been a thread I've been pulling on for a while. You know, to me it fascinates. We had Oliver Berkman on here earlier in the year.

• 38:45Cal Newport?

  I think this book is a great compliment because it's, it's looking at similar issues and coming at it from your own, your own angle. Let's start with, I, I like how you define, like, when you think about time anxiety, I think you're putting your finger on something that's important. So how do you usually pitch that?

• 39:04Speaker 01

  I put it as a series of statements, you know, like if we were to like break it down, we could say, okay, time anxiety is like the fear of running out of time while simultaneously feeling uncertain over how to spend the time that we have. You know, so it's like this existential question of, you know, time is running out, which is true because it ultimately is. But also the, the constant pressure of, over how do we fill the time that we, that we do have and desire is, is limitless, right? There's always more things that we, that we want to do. And so what is the answer to that? And you, you know, provided a lot of different answers and responses to that question in different ways, you know, through your work, which I admire.

• 39:48Speaker 01

  And I think a key, maybe a similarity or something we very much agree on is like the, the answer is not to just get better at, at doing things like it can't, like, that's important in life, you know, to be efficient and effective and to learn various skills and such. But you know, that is a means to an end. That's a means to like, you know, doing more of what's important to you and living a purposeful life as opposed to being like the the main thing. But I would say also, maybe rather than just like that that definition, you know, I began the book with this series of statements. I forget exactly how they're phrased, but it's like, there's, there's something I should be doing right now, but I don't know what it is. And that is something I did this really extensive survey with a lot of people and

• 40:33Speaker 01

  multiple people used almost those exact same words like independently. I feel like I should be doing something, but I can't figure it out. And this is a recurring problem for me. This is like the biggest problem in my life. Some people even said, and I never knew there was a name for it, or like some sort of basket, or you know, way to like think about it. And it's, it's just a low grade sense of angst, you know, that not everybody, but as of all the books I've done, probably the most universal in terms of when I talk to people, I'm like, what are you working on? Before the book came out, it was like, oh, this concept about time anxiety. And so many people would say, I have that, like, I've never heard that, but I, but I have that. So I think it's just a sense of

• 41:15Speaker 01

  what, what do we do? And we're kind of assaulted, you know, with so many different options, some of which are good and some of which are not. But how do we manage any of them?

• 41:23Cal Newport?

  One of the things that's interesting to me about the book, and I want to ask you like a precise question about this, especially in part one of the book, there's quite a lot of advice that is, is aimed at like, concrete things to do around your time and schedule to to help with the time anxiety, right? And some of it is about reducing things that's on the plate. So what I'm going to do is I'm going to go through, I'll take two things off of my schedule, just to see what that's like, or the brick in the tank, let me just protect parts of the schedule. And some of it is very just basic organizational, right? I'm going to, let me just take like one thing and do it right now. This is actually a break

• 42:08Cal Newport?

  from the way other writers from like, the last five years or so have have come at sort of maybe a similar feeling, right? So there's this other approach to a similar feeling of, I feel like there's always something I should be doing. This other approach is just to say, That feeling is wrong. It's constructed. It's imposed upon you by X, Y, and Z. And there's truth to all the things that impose it. But the right response to it is like, you can just ignore that or chill out or just do less things. Whereas, you know, you're coming in saying like, what's, we need to actually, I think it's much more of like a psychological astuteness. We need to work on that anxiety. So there's like little things you can start doing that's going to make that feel better.

• 42:46Cal Newport?

  Like, I want you to feel better, more so than I want to make some sort of lart, like a value judgment about like where ideas come from or this or that. And so you're simultaneously in your book saying, hey, if you just go down a route of endless systems and efficiency, like the guy you profile early on anonymously, that every six months would change what productivity system he was talking about. Like, how could the best system change every three months? If you go down that route, there'd be madness. But just to say, yeah, we should just like proudly do nothing. Like, well, that's also, you're going to have all that anxiety is still there. You haven't solved that problem. So how do you think about the difference? And I asked Oliver about the same thing. How do you think about the difference between being like overly systemed,

• 43:28Cal Newport?

  but also needing like a baseline of systems and ideas can help reduce anxiety and kind of keep your life sane? Too much can make it worse. None at all can make it anxiety ridden as well. So how do you think about, like you use different terminology? How do you know like enough organization is enough? How do you know when you're tipping into becoming obsessed? To me, this is like the, the key question of productivity right now.

• 43:52Speaker 01

  That's very interesting. Well, I think I wrote the book differently first. Like, I first wrote the book maybe more traditionally. You know, I think it had like 12 chapters as opposed to 26. I didn't have like the practices or the activities that I added at the end. And, you know, that was like draft one or two. And you always hope that it's going to be, oh, that's great. I'm going to tidy it up a little bit. But, you know, I realized it actually wasn't quite there. And I have to give a lot of credit to my editor, Leah Travers. She did a really wonderful job in helping me think about how to construct it in a way that's a little bit more neurodivergent friendly perhaps. Or if people don't prefer that term, just in a sense of like, what do I do right now?

• 44:34Speaker 01

  You know, and I think Oliver Berkman's book is great, you know, philosophically. I think he deals with that and it kind of defines the problem really well. And he also has solutions. I don't say it's not solutions based. But I really wanted, I was like, okay, what's, what's my space? Like, how am I carving up any sort of lane here for me? And I thought, well, Before people can deal with any of perhaps what they see as the bigger problems of life or time or work, or how do we, you know, construct or find that balance, as you said, the ideal reader, at least a common reader of this book, is going to be pretty stressed out. They're going to be distressed, you know? And I've actually always thought about that. My readers are discontented in some way, right? They're actually, and I don't

• 45:16Speaker 01

  mean to say they're unhappy, they're just dissatisfied. Like, they want something more from life, whatever, you know, whether it's the things we were talking about previously or in this situation, they're struggling with with time, broadly speaking. So when you're in that place, you need relief, like, you need relief. And you need, you need to somehow begin to feel better, and then you can make better decisions. And so I think trying to front load some of those things that you mentioned already about taking things off of your calendar and putting a brick in an inbox, and maybe also just paying attention to what you, paying attention to what you want to do more of and what you want to do less of. And I think if you just start doing that, if people, you know, spend their time and notice how they are spending their time without constructing any great system or

• 46:01Speaker 01

  using new tools, they naturally begin making decisions differently. And maybe then is the time, like, okay, maybe there's, there's something else that I can introduce here, I can add to my palette or my toolbox, per se. But I think if we don't deal with the distress people have, then they don't really believe that there is any sort of relief in sight.

• 46:21Cal Newport?

  I thought it was really innovative that you're integrating also third wave psychotherapy, in particular, like cognitive behavioral therapy. That hit me as I read it, like, well, of course, this is related. Like, a lot of issues we have around time and workload management, there's really like a psychological component to that. Like, of course, we should be thinking about, these type of tools should be just as important, actually, as to-do list format. What, what, what led you to that? Like, what's your thinking behind bringing in, like, let's point out ruminations, let's name them, let's make sure, you know, that's, I was like, yes, this makes so much sense. Why is this not in every book?

• 46:57Speaker 01

  Yeah, right, right. What led me to it? Probably some of my own experience of learning about neurodivergence and ADHD for me in particular, some of my own experience, like going to therapy for the first time, probably seven or eight years ago, in which like you think you're pretty smart and you've had lots of life experience and you go to like a few therapy sessions, you're like, oh, actually, there's a lot more I can learn about myself very quickly, you know, even if you don't want to go to therapy for the rest of your life. I think it's very, very helpful for people. So some of that. And then maybe drawing upon like, you know, I didn't, I didn't go as nearly as far as you have in academia, but like I had a master's degree and I had an undergrad in sociology and I really liked social psychology. And so I have a little background in that, understanding

• 47:40Speaker 01

  of research methods. And so like, put that together was like, let me, let's, let's try to ground this, you know, in a certain degree of like evidence-based research, which leads naturally, I think, to thinking about executive functions and, you know, cognitive distortions and, you know, many things from there.

• 47:58Cal Newport?

  And this comes up, it came up, I would say, in the aftermath of my last book, where I was talking about workload, which, because, you know, I was always coming from a frame, I'm an engineering type. So my frame was often like, this isn't a really smart way of doing things. This is a bad use of your brain. This is making you unhappy. So reduce this. But it was like relatively engineering. And when I was talking about workload and workload management, I had what I thought was like a pretty crystal clear technical case for having too many things on your plate. You know, this was, this was inefficient, right? It was going to stress you out. The administrative overhead was going to overwhelm you. There's like an optimal number of things to be working on. It's probably much less than you think. And the feedback I kept getting, including, by the way, in like a conversation

• 48:40Cal Newport?

  I had yesterday, a pre-interview for something I'm doing, it was a psychological response where people, people had

• 48:49Cal Newport?

  The distorted thought in their head that I never say no to anything. And this is why people like me. And if I start saying no to things, this is going to be a real problem. And like, people are really paying attention. And this is, and I was like, wait, this is classic cognitive distortion. I was like, well, of course, of course, you're saying no to things. So what are the chances that all of the work that people are throwing at you randomly just happens to exactly feel like 55 hours or whatever it is, right? Like, it just happens to feel like a kind of overloaded, but like tractable work week. Like, what are the chances? If we really just said yes to everything, we should have people working, you know, working themselves to death and people doing 120 hours a week, being hospitalized.

• 49:32Cal Newport?

  But that's a real coincidence that it's never 30 and it's never 60. Like, oh, that's interesting. Like, of course, you're saying no to things. So what we're really talking about is like saying no to a few more things. And no one's going to notice the difference between that. They don't have a chart, right? They don't have a graph or whatever. But that was classic. I was like, oh, it's a cognitive distortion. You've distorted the reality to you've forgotten all the times you are saying no. They'd be like, I always say yes. And if I start saying no, that's going to be a real problem. And then you're predicting the future in a catastrophic way that like, when I first say no to people, my boss is sitting there with a must, you know, twirling the mustache with a cigar like, I thought this was day would come. I've been waiting for it and gets out the big you're fired stamp or whatever. That's all psychology. It's distortion. Yeah. So I was like, what are we talking about?

• 50:17Speaker 01

  Leads to, well, it's a distortion that leads to an operating principle, right? So it's not just like this internal thing because it leads you then to your behavior. So that I have this distortion that I must do, I must say yes to everything because everyone is watching me. So there's actually two different things there, but you know, together it leads to this operating principle of therefore I must do this, which is then going to contribute to a certain amount of demise in your, in your life. You know, first of all, you're not going to be able to do everything well. And that's going to cause you stress because you are a person who wants to do things well and like to do things with excellence. But good luck, you know, doing that when you're saying yes, you know, to everything.

• 50:58Speaker 01

  Um, and then, you know, you're going to inevitably prioritize other people's, you know, preferences and requests, demands um, over your own. Um, it's, it's going to lead to all sorts of negative outcomes, but you know, trace to this operating principle, which is based on this cognitive distortion, you know, as you, you correctly labeled it. And so, you know, what's a different way to think about like, what's a different rule you can create? Like, I have a section in the book about time rules. I think you've written about this in different ways, too. It's like, what, what, you, what are the time rules that you have for yourself? And maybe you haven't actually sat down and said, these are my time rules, like, but you have internalized, you know, beliefs about time and, and work and behavior and response. Um, and maybe it's time to rewrite those a little bit and see if your life is better.

• 51:44Cal Newport?

  That, you know, I applied a lot of this to myself when I was reading the book. And so maybe you can help me here. So here's what I, here's what I discovered. Like, here was a, a, a time rule that had become a principle for me that I, that I think is a problem. I, I've created this rule that says basically, um, if you're doing something at a high level, then you can't stop doing that. Right? If it's something that you're doing at a high level that like, a lot of people would want to do that and would be like, really happy to have made it there, then how could you stop doing that? So my issue is not saying no to things. I say no to things all the time, but it's the number of like, major things I'm doing. I know it, I, I know it's too much probably. And it's, I, it's probably preventing

• 52:25Cal Newport?

  me from being like excellent and, and either it's, it's, you know, writing academia, podcasting, you know, um, there's journalism. So it's like, yeah, but in all four of those areas, my rule is like, well, how could you walk away from, you don't walk away from a full professorship. You don't walk away from a, a, a contract position at the New Yorker.

• 52:50Cal Newport?

  You don't walk away from, you know, podcasting is the medium of the future and you have something that's really working and it's lucrative. Like, how can you walk away from that? How can you walk away from book writing? You can't walk away from that either because like, you know, you've had a good, a successful run there. And so then I'm just stuck. Because because of that rule, I'm just stuck. But that's too many things. I should be doing two things, not four, or one thing's not four.

• 53:13Speaker 01

  Right. And then there's some, the fifth thing is going to come along, whatever the next, you know, thing is, or platform or medium, and then you're probably not going to have space for that. Or you're going to make space for it somehow, but then something has to go. So, I don't know, I always think it's good to evaluate it based on more than one criteria or metric. So that, you know, just because you're really good at something, I mean, not to be like, super reductive, but if we go to like, follow your passion, like, are you, are you still passionate about it, right? Like, are you, I mean, maybe you are just as passionate and you're just as good at, you know, all four things. But I tend to think like, that there's a time in which you're more excited about something and then you stop being as excited about it. And, and then if you're not getting better, it's like, somebody said something to me

• 53:58Speaker 01

  once about how, it sounds kind of like, you know, the so good, they can't ignore you thing, but it was, if you're not getting better at something, you're getting worse at it. And I've thought about that a lot. I'm like, oh, there's probably a lot of things that I'm just kind of coasting at. And maybe that's fine for a while, but if I'm really not improving at it, maybe that's actually a thing that I should give up. It doesn't matter that I have the contract position, or whatever the status is, or the money, or the, you know, the perceived value. I mean, isn't, ultimately, isn't life more exciting when we're kind of pursuing something new, or maybe it's not new, but it still feels new to us, or different, or challenging in some way, especially for those of us who have, like, the ability to choose. I mean, that, I think, is like, the most precious gift, right?

• 54:41Speaker 01

  The ability to like, forge a path that could be, you know, a number of different ways. So if we just kind of get stuck and keep doing the same thing, and I have this conversation with myself, like, if I'm just doing the same thing, am I really, like, am I, you know, maxim, not, it's not so much maximizing opportunity, because that's not possible, but it's like, something to do with potential, I think.

• 55:01Cal Newport?

  Yeah. It's funny you mentioned follow your passion, because I remember- I gave that talk at one of your events and it was before that my book had come out about that being bad advice and I still remember the turn that came in the talk. I was like, and it's bad advice. And the guy, my memory, there was like an audible gasp. That was an audience that was like all on board with passion.

• 55:22Speaker 01

  It was great that you came to balance that. That was really good because we had, I always told people, like, the ideal WDS talk is inspiration with substance. Inspiration with substance, you know? So we do want people to feel inspired. You have to make an emotional connection, but hopefully there's some depth to it, you know, as well.

• 55:37Cal Newport?

  Yeah, no, and I think I turned the audience around at the time, but

• 55:39Speaker 01

  You did. You simplified that.

• 55:41Cal Newport?

  But then, but then I did, Brene Brown had the audience dancing. So I was like, all right, that's a different.

• 55:46Speaker 01

  Well, she started with that. It's hard to, it's hard to follow Brene.

• 55:49Cal Newport?

  Hard to follow. That was the, that's how that works. Okay, I like, I like that advice.

• 55:56Cal Newport?

  I think a lot of what you write about dovetails with my idea of lifestyle centric planning. This idea of like, well, what ultimately are you working? What matters? Like, what's the goal? Like, well, what make, what determines how you, your experience of life is actually just like the day to day stuff that's happening in your life. Like, that is what, like, what type of, the, the rhythm of your work, where you live, who's around you, the footprint, different types of work has in your life, what other things are going on? Like, these are the things that define your subjective experience of your life. And really, there's nothing else that you can work with more effectively than like, what is my daily life like? Okay, now what I'm doing are like levers I can pull in, you know, trying to get there,

• 56:37Cal Newport?

  which is like a very different way of thinking than I think the, the specific of the job will matters, or it's gonna, that's gonna make all the difference. And if like, the job matches a passion, then, then you'll be happy. Or if you can just have this one aspect of your right life, like, I want to live on a houseboat. If I could just make that happen, everything will be better. And it's like, well, maybe, but what about all the other parts of your life? Do you like where the houseboat is? Like, what type of people live around there? Like, what type of work are you doing? Do you have to commute two hours into a city from your houseboat because the city's not near the water? Like, you know, and what's that make your day to day life? And it seems like when you're, when you're confronting time anxiety, it's a sense I get from the book, you, you, you need to know what it is that does matter. Like, well, this is what I'm going for, and I'm kind of getting this. So it's okay that I'm not doing six more things right now. Because

• 57:22Cal Newport?

  actually, what I'm doing right now is pretty compatible. With a vision of a life well-lived, there's some notion of knowing that's ultimately what matters.

• 57:34Speaker 01

  Uh huh.

• 57:34Cal Newport?

  Yeah, more so than any metric or quantity or something like that.

• 57:38Speaker 01

  I think most people, if they ask themselves that question, what matters? And even like, what matters to me right now? I feel like most people will have an intuitive answer. And maybe that's a clue, right? Like especially when you're in that place of like, oh, I have like, I have the four different things and maybe it should be two. Like what matters to me right now? And then what do we do with that? And something Gretchen says that I like, I think about a lot. Um, I don't know if she originated this, but she probably did because she's Gretchen. Um, she said, uh, you know, what we do every day matters more than what we do once in a while. Um, and if we think about our day to day, there are levers. As you said, there are things that we can do.

• 58:21Speaker 01

  Like, I think the core principle of any sort of self-improvement, you know, for lack of a better word, is that, okay, a lot of stuff is outside of our control. Um, we have to accept that first of all, but then like there is this limited sphere of autonomy and control and influence that we have. And it is important, I think, to think about, think about that and what do we do? You know, with that limited sphere. Um, whether we have free will or not, that's another conversation, but like, um, what are some things we can do to be better? Like, how can we be better tomorrow than we are today? Or at least better today than, than yesterday? And hopefully that's going to make life better for other people too. But all, you know, um, starting with, with ourselves.

• 59:03Cal Newport?

  How do you use tools to prevent chaos in like your schedule and obligations? Without falling into the tools becoming the whole point?

• 59:15Speaker 01

  How do I use tools? To avoid the chaos without the tools becoming the points.

• 59:22Cal Newport?

  Right. The premise being if you had no time management tools of any type,

• 59:25Speaker 01

  Sure.

• 59:26Cal Newport?

  life would be pretty stressful. Yeah.

• 59:28Speaker 01

  Right.

• 59:28Cal Newport?

  But we also don't want to be the guy who has a new AI powered, you know, automatic language model enhanced time management productivity expert agent tool, you know, that they build each month or something.

• 59:40Speaker 01

  Right, right. I don't know. I guess like, maybe it's need based, you know, or solution. What do you need to have? It's funny, I was just talking with this guy Jeremy Kaplan. He writes this newsletter called Wonder Tools and he writes all about tools. And I actually like, I get his newsletter and I'm like, every week he's got like five or six new tools that he's writing about. And it's, it's fun. It's interesting and enjoyable. But I do notice sometimes I'm like, oh, this is a cool thing. Maybe I should try this or sign up for a trial with this. And then I look and I'm like, what would I, what do I really need this for? You know? Like, what, what actually is this solving for, for in my life? It's actually just additive. Okay. So I don't need this. Right. So I think maybe that's like, okay, it's helpful to have a calendar because that tells me certain dates and times and things, you know?

• 1:00:23Speaker 01

  It's helpful to have, you know, some sort of, of tool for tracking to do's and, and project notes and outlines and such. There are various options for that, you know?

• 1:00:34Speaker 01

  It's helpful to have, you know, a few other things, but I guess what is, what is actually meeting a need versus creating just more to keep up with or more to manage? Maybe that's some of it.

• 1:00:43Cal Newport?

  I love that idea. Yeah. What problem is this solving? Is there a simpler way to solve it? Yeah.

• 1:00:48Speaker 01

  Yeah, maybe those products are solving problems for somebody else, you know? Maybe somebody else has that specific, you know, specific need, but for me, not necessarily.

• 1:00:57Cal Newport?

  I think this became a thing in the productivity software space, especially more aimed at businesses than individuals. But they really sold this idea that this tail wagging the dog, this, this complicated tool. Just trust us. If you're using this tool somehow, you'll just will be more productive. So you're not working backwards from here's something I do every day. I'm having a hard time with blank and I need assistance to help me do blank. It's like, I don't even know how this tool works, but the videos are slick and it's complicated. And I just bet if we had that tool, things would be better and like there'd be dragons, right? And when people go the other way and say, what are my actual needs? How do I solve it? The problem is for the productivity software industry is often the answer is a free digital calendar, like a document, like a text file.

• 1:01:42Speaker 01

  Right.

• 1:01:42Cal Newport?

  You know? And like a pretty good, a pretty smart way to organize some folders on your Mac. Like that's 90% of the way there. And there's no real magic in it. It's like, yeah, I can write stuff down in here. I have a calendar and I have folders for different projects I'm working on. And I can put like Word documents in them. That's often all you need.

• 1:02:04Speaker 01

  Yeah, maybe another criteria is like, how much of a learning, learning process is this? Like, is it actually a project of its own to learn how to use this thing? And so if you're in certain technical fields, right? If you've never, you know, if you learned you need to use like film editing tools or something. Okay, maybe that's, that is a project that's worth investing in because you're upgrading your skills. Okay, but for productivity tools, you know, or across the time management industrial complex, I don't think that they should be a project, you know, to, to learn. It should be pretty intuitive and simple and you can jump right in and know if it's going to help you or not.

• 1:02:38Cal Newport?

  Yeah, I think complexity gives you the illusion that the more complex, complicated is, the more you'll believe there could be a big result. And because it just makes it more believable. Like, oh, this is going to take a long time to learn. So I'm more willing to believe that it's going to have a huge impact once I do it, which of course is not the reality. That's another person from our era, Merlin Mann. That was, I mean, he wasn't really in our circles, but he was definitely of that era. I interviewed him more recently for a thing, a New Yorker thing. But he was also very much of that era. It was like productivity was very personal, it's very Gen X-y, like sort of self-deprecating and had a bit of a, you know, there's a certain like video store geek vibe to it or whatever. Also from that era.

• 1:03:20Speaker 01

  That's a great way to put it.

• 1:03:21Cal Newport?

  Yeah. And he gave up on all that. He was, he was like, this is interesting. I wrote a whole story called The Rise and Fall of Getting Things Done. And it like kind of talked about.

• 1:03:29Speaker 01

  I have not read that. It's in The New Yorker. I need to go check it out. I read The New Yorker every week. Must have missed that one.

• 1:03:33Cal Newport?

  Merlin's, Merlin's story is, is definitely an interesting one. Okay, well, I know I've taken you over time, but this has been, this is fascinating. So we've, we've solved two things here. First of all, we've, we've understood like the past and future of new media. So, you know, you're welcome, audience.

• 1:03:47Speaker 01

  That's right.

• 1:03:48Cal Newport?

  We ended up with like, it's harder than you think. There's less slots than you think. Social media tricked you. There's no spots left in podcasting and blogs are dead. This is pretty grim.

• 1:03:56Speaker 01

  That's great.

• 1:03:58Cal Newport?

  But then I think we got some good insight into, yeah, when it comes to, we're thinking about time, time management, its role in our lives. This is. There's a psychological aspect to this as well. There's like an anxiety that we need to resolve, that we need relief requires concrete steps as much as it does is like mindset change, which is, which is what I really like about that book. I'm still processing the ideas. I still have a lot of need for a lot of the ideas, but I'm glad this one's out there. Definitely one of the more practical, I think, entries into this like new space. We have a new name for this space, but.

• 1:04:31Speaker 01

  That's true. I feel like you should coin the name. I mean.

• 1:04:34Cal Newport?

  Well, I coined slow productivity, but that's.

• 1:04:36Speaker 01

  That's right. You did. That's a book itself, you know, so.

• 1:04:39Cal Newport?

  The book itself. Yeah. Elliot Dall had feel-good productivity. So like there's different, different names are, are, are being coined, but I think, I think we're on to something. I think you're definitely on to something. It was great catching up. It was great having that blast from the past. I miss those times where things were simpler back then, but there's cool stuff going on now. Where can people, beyond just looking for the book, Time Anxiety, is The Art of Nonconformity still the best website to go to to find everything, Chris?

• 1:05:14Speaker 01

  I'm doing more of my writing at.

• 1:05:15Cal Newport?

  Oh, you have your own. And it's your name.com now, isn't it?

• 1:05:18Speaker 01

  Yeah, but nobody can spell that, ChrisGillevault.com. So you go to EuropeMentalHealth.com, that's my Substack. But yeah, the original site is there at Chris Gillevault. Or for those who do use social media, it's 193countries on Instagram and Chris Gillevault everywhere else.

• 1:05:34Cal Newport?

  Yeah. And the podcast name is The Side Hustle Morning.

• 1:05:39Speaker 01

  Side Hustle School.

• 1:05:39Cal Newport?

  School.

• 1:05:40Speaker 01

  Side Hustle School.

• 1:05:41Cal Newport?

  And that's been daily. Is that right? You're, you're a madman.

• 1:05:44Speaker 01

  Yeah, every day. I haven't missed a day.

• 1:05:47Cal Newport?

  You're a madman. I love it. All right.

• 1:05:48Speaker 01

  Thank you.

• 1:05:49Cal Newport?

  Well, Chris, always a pleasure. Thanks for, thanks for joining the show.

• 1:05:52Speaker 01

  Thanks, Cal.

• 1:05:54Cal Newport?

  All right. So there was my conversation with Chris Gubrow. That was a great blast from the past, but we also covered some really, I think, interesting topics about time and anxiety. I like how, Chris, like one of the things he's carving out that came out of that interview is thinking about different types of neural diversity and how that overlaps with things like time management or productivity. I think that's something he's really good on. So there's like a lot of interesting angles in his work on time there. But also it's just cool to remember that time of blogging. I gotta go back. It makes me just want to go back and. Write my three blog posts a week back in the simple days. Mondays was Monday Masterclass. That's what I called my Monday blog post. It'd be some sort of study advice and there'd be a case study in there and usually something that was a link. I mean, I just had a lot of free time back then.

• 1:06:38Cal Newport?

  I was also writing books and papers and dissertations and oh, those were the days. So Chris, thanks for giving me that blast back in the past. Hope everyone enjoyed this conversation. We'll be back with a normal episode of the podcast as always on Monday and thank you for listening.

• 1:06:58Cal Newport?

  Hi, it's Cal here. One more thing before you go. If you like the Deep Questions Podcast, you will love my email newsletter, which you can sign up for at calnewport.com. Each week I send out a new essay about the theory or practice of living deeply. I've been writing this newsletter since 2007 and over 70,000 subscribers get it sent to their inboxes each week. So if you are serious about resisting the forces of distraction and shallowness that afflict our world, you gotta sign up for my newsletter at calnewport.com and get some deep wisdom delivered to your inbox each week.