In-DEPTH: The Art of Non-Conformity  ## Metadata - Author: [[Deep Questions with Cal Newport]] - Full Title: In-DEPTH: The Art of Non-Conformity - Category: #podcasts - URL: https://share.snipd.com/episode/d81f8a7d-dab0-4eb0-8cbf-ffc999e0ad7e ## Document Notes ## Highlights - **Chris's Blogging Genesis** - Chris Guillebeau entered the blog world with a professional site anchored in his quest to visit every country. - He leveraged existing communities and link sharing to grow his presence in the early 2000s blogging era. Transcript: Cal Newport Read them through RSS readers. It'd be on Google reader or something like this, reading them. And I, 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 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? Chris Guillebeau What was going on back then? It was an interesting time. It was a really fun time. I'm always skeptical of nostalgia and looking back, but I do look back fondly on ([Time 0:04:55](https://share.snipd.com/snip/9533d751-2c90-4dae-9b66-3a40a8101fcf)) - **Close-knit Early Blog Community** - Early 2000s blogging connected a smaller, more intimate group, making it easier to know and elevate peers. - This closeness fostered unique community energy unseen in today's fragmented social media landscape. Transcript: Cal Newport Rich right what was your read of like what was happening in our world at our time that made these type of these blogs successful? Chris Guillebeau You know, it's like on the search for purpose and meaning, you know, to get to like the skepticism about nostalgia, 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 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 so yes, people are chasing, you know, morality and fame and wealth through becoming a professional influencer. But it's not only that, it's more like, you know, there's so many, 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 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. Yeah. Cal Newport 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 that. You had, 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 ([Time 0:10:08](https://share.snipd.com/snip/30b05c4a-6edb-49d4-acca-ebcbce17775d)) - **Books as Enduring Medium** - Books provide a lasting, deep medium that captures years of thinking and crystallizes knowledge. - They also offer financial opportunities that occasional online formats like blogs lack, despite changing media landscapes. Transcript: Chris Guillebeau Know, it wasn't algorithmically driven content the way that the world works now. I think that was a big thing. Cal 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. 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 have you stuck with books? Chris Guillebeau Oh, 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, I think it's fair to always say like maybe I'm just kind of set in my ways with that. And like if I were starting over now, would I have the same beliefs? I don't know. What do you think about it? I mean, why have you stuck with books? Cal Newport I mean, I think there's two reasons. Um, 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 is an interesting one. I think books are pretty winner take all. 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. 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 sort of anyone can show up and and try to go for attention i mean what happened with i lost Track of everyone i feel like in 2014 like what's the it's somewhere around there where and i 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 um yeah 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 podcast so like what did it look like from your your end I think you had a bigger thing Chris Guillebeau Going on in that world when did things change 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 WDS. So I think a little bit of the splintering, then you have the new mediums, right? The podcasting and Instagram and everything that that inspired or led to. Comments. I think blog comments used to be a big thing, right? And most blogs don't have comments now. Or if they do, it's like, not really like the main feature. 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, I'm happy with this one. The book tour, I do notice there's not a lot of people coming out to a lot of these events. And I miss that. I wish it were different. ([Time 0:13:37](https://share.snipd.com/snip/15a5df01-d63e-4877-89e4-b395eeb36639)) - **Monetize via Digital Products** - Create digital products based on repetitive audience questions to monetize a free blog. - This approach can create a sustainable lifestyle business and engage your community effectively. Transcript: Chris Guillebeau Figure it out. 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. So how are you, how are you making money back then? Back then I created products. I created, the, you know, the blog is like there for free. And this completely, this, this came about completely organically. Um, 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 round the world plane ticket, for example. Oh, I remember that product. Cal Newport Yeah, like travel. It was like advanced travel advice was one of them. Chris Guillebeau 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 know, but you know, like 100 people bought it or something. And I was like, well, that's interesting. Maybe there's something to this. And so then I did start building out other resources. And okay, here's how I've worked for myself. Here's some entrepreneurship guides and some other travel guides and things. And so I did that for a number of years. And that worked really well. I never 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. Cal Newport That's right. So that's the model. Yeah, you have very popular blog and then you would have information products that was just like, oh, you're interested in this bit. ([Time 0:20:40](https://share.snipd.com/snip/c67ba83f-bd1e-43aa-87a7-991c57227675)) - **Podcasting's Relationship Renaissance** - Podcasting revives relationship-driven media connecting creators with audiences beyond algorithms. - Unlike social media, podcasts build deep ties and support more direct monetization through ads or sponsorships. Transcript: Cal Newport 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 uh 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. 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 non-algorithmic. It's relationship-centric. Like you build over time a relationship with the audience. And 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 to just have some ads. And they actually pay at a level that means if like a show is doing well enough, 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 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 ([Time 0:24:40](https://share.snipd.com/snip/32ccc40e-c4e0-4c06-bbe7-24c33728f5b7)) - **Understanding Time Anxiety** - Time anxiety stems from fear of running out of time and uncertainty about how to use it well. - The problem is universal and linked to the overwhelming number of choices and pressures we face daily. Transcript: Cal Newport 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 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 at FastHV, I had Oliver Berkman on here earlier in the year. I think this book is a great compliment because it's looking at similar issues and coming at it from your own your own angle let's start with 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 I pitch it as a series of statements you know like if we were to like break Chris Guillebeau 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. So it's like this existential question of time is running out, which is true because it ultimately is, but also the constant pressure over how do we fill the time that we do have. And desire is limitless, right? There's always more things that we want to do. And so what is the answer to that? And you've provided a lot of different answers and responses to that question in different ways through your work, which I admire. And I think a key, maybe a similarity or something we very much agree on is like the answer is not to just get better at doing things. That's important in life to be efficient and effective and to learn various skills and such. But that is a means to an end. That's a means to doing more of what's important to you and living a purposeful life as opposed to being like 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 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 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 just a low grade sense of angst, you know, that not everybody, but as of all the books I've done, it's 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 have that. So I think it's just a sense of what do we do? ([Time 0:38:20](https://share.snipd.com/snip/2e9017b2-1b97-414c-b1e5-3ef0e2d75146)) - **Relieve Distress First** - Start time management by relieving distress with small practical steps like removing tasks or protecting schedule blocks. - Once calm, you can gradually add tools or systems to maintain control and reduce anxiety. Transcript: Cal Newport Question of productivity right now. Chris Guillebeau That's very interesting. Well, I think I wrote the book differently first. I first wrote the book maybe more traditionally. 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 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? And I think Oliver Berkman's book is great philosophically. I think he deals with that and it kind of defines the problem really well. And he also has solutions. I don't mean to say it's not solutions based, but I really want it. I was like, okay, 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 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. And I've actually always thought about that. My readers are discontented in some way, right? They're actually, and I don't 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 time, broadly Speaking. So when you're in that place, you need relief, like you need relief and 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 spend their time and notice how they are spending their time without constructing any great system or using new tools, they naturally Begin making decisions differently. And maybe then is the time like, oh, okay, maybe there's something else that I can introduce here or I can add to my palate 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. Cal Newport I thought it was really innovative that you're ([Time 0:43:50](https://share.snipd.com/snip/2d6beccb-b88e-4a52-aa21-b7bab0310ae7)) - **Psychology Behind Time Anxiety** - Cognitive behavioral therapy concepts can reveal how distorted thoughts worsen time anxiety and decision-making. - Recognizing these distortions helps rewrite harmful time rules and improve personal boundaries and stress management. Transcript: Chris Guillebeau Sort of relief in sight. Cal 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 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's make sure, you know, that's, I was like, yes, this makes so much sense. Why is this not in every book? Chris Guillebeau Yeah, right, right. What led me to 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 go you're pretty smart and you've had lots of life experience and you go to a few therapy sessions, you're like, oh, actually, there's A lot more I can learn about myself very quickly. 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, I didn't go nearly as far as you have in academia, but I had a master's degree and I had an undergrad in sociology and I really liked social psychology. 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. Cal 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 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 I had yesterday, a pre-interview for something I'm doing, it was a psychological response where people, People had 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 people are really paying attention. And I was like, wait, this is classic cognitive distortion. I was like, well, of course you're saying no to things. Like 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. 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. 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 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 it gets out the big you're fired stamp or whatever. That's all psychology. It's distortions. Yeah. So I was like, what a way to talk about it. Chris Guillebeau Leads to it. Well, it's a distortion that leads to an operating principle, ([Time 0:46:20](https://share.snipd.com/snip/f037d38a-5227-492c-ae2f-3b9beec4e85f)) - **Keep Productivity Tools Simple** - Use only tools that address your specific needs to avoid complexity and overwhelm. - Simple calendars, to-do lists, and project folders often suffice for effective time and task management. Transcript: Chris Guillebeau How do I use tools to avoid the chaos without the tools becoming the points? Cal Newport Right. The premise being if you had no time management tools of any type, life would be pretty stressful. Yeah. 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, know, that they build each Month or something. Chris Guillebeau 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 it. 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 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 do I really need this for? What actually is this solving for in my life? This is 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, it's helpful to have, you know, some sort of tool for tracking to-dos and project notes and outlines and such. There are various options for that, you know. It's helpful to have, you know, a few other things. But I guess what is actually meeting a need versus creating just more to keep up with or more to manage? Maybe that's some of it. Cal Newport I love that idea. Yeah. What problem is this solving? Is there a simpler way to solve it? Chris Guillebeau 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. I think this became a thing in the productivity software space, especially more aimed at businesses than individuals. Cal Newport But they really sold this idea that this tail wagging a dog, 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 a system 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, 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. Chris Guillebeau Yeah, maybe another criteria ([Time 0:59:15](https://share.snipd.com/snip/a9caa370-669d-46c9-92a0-8c9f25578bab)) - **Avoid Overcomplicating Productivity** - Avoid complex productivity tools that require learning projects unless essential for your work skillset. - Prioritize intuitive, minimal systems that solve your specific productivity problems without adding overhead. Transcript: Chris Guillebeau How do I use tools to avoid the chaos without the tools becoming the points? Cal Newport Right. The premise being if you had no time management tools of any type, life would be pretty stressful. Yeah. 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, know, that they build each Month or something. Chris Guillebeau 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 it. 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 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 do I really need this for? What actually is this solving for in my life? This is 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, it's helpful to have, you know, some sort of tool for tracking to-dos and project notes and outlines and such. There are various options for that, you know. It's helpful to have, you know, a few other things. But I guess what is actually meeting a need versus creating just more to keep up with or more to manage? Maybe that's some of it. Cal Newport I love that idea. Yeah. What problem is this solving? Is there a simpler way to solve it? Chris Guillebeau 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. I think this became a thing in the productivity software space, especially more aimed at businesses than individuals. Cal Newport But they really sold this idea that this tail wagging a dog, 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 a system 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, 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. Chris Guillebeau Yeah, maybe another criteria is like, how much of a 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 ([Time 0:59:15](https://share.snipd.com/snip/66e9e67c-7929-4716-9bd2-e0488afefb57))