#124 Can You Ever "Make It" While Self-Employed - David Kadavy on Doing Work You Love, Self-Publishing, Traveling & Perspective, Mini-Lives & Living as An Expat

[00:59] Paul: Welcome to The Pathless Path. I'm Paul Millerd, and in this podcast, we examine the invisible scripts that run our lives and dare to imagine new stories for work and life. Today I am talking with David Kadavy. I'm super pumped for this conversation. I feel like you, David, are somebody that has landed on some wisdom that I needed earlier and have sort of created your own Pathless Path world as well with your own terms, your own writing, you're publishing books and figuring it out as you go and helpfully sharing that with other people. I love this from your about section.

You say, I think we're in a creative age where we humans have to be productive through ideas instead of basic procedural or even knowledge work. I love that. It's such a, like, going after like a much more aspirational idea of like what is possible in today's world. So we're going to explore that today. You've written several books, Mind Management, Not Time Management, The Hard to Start, Design for Hackers, a bunch of those. You've done all sorts of experiments.

You have some awesome terms I want to start using and sharing with people too. Welcome to the podcast, David.

[02:16] David Kadavy: Paul, thank you so much for having me. This is an honor.

[02:20] Paul: I am pumped to be the first person getting to experience your incredible new video setup. Um, we can dive into how we think about like tech and all that, but question I start with all my guests: what are the stories and scripts you grew up with around what you were supposed to be doing as an adult?

[02:46] David Kadavy: Oh, lots of them. I think I'm still discovering some of them because they're kind of— they're visible, right? You don't notice them. I think definitely it was to do well in school, to get a job, to be financially secure. I think that was probably a good one. Um, but, uh, a lot of those were stifling and sort of went against what felt natural to me, I guess.

Uh, I wanted to express myself creatively, and that was supported, but there wasn't really good examples around me of, of role models, people to follow, uh, to to do that. I, I wasn't surrounded by people who were entrepreneurs or who had their own businesses really, or who did anything, uh, original or interesting. They just were sort of middle-class people with secure jobs in Middle America. And those were the scripts that I was surrounded by, and those were the ones that I had to notice and then deprogram myself of to go down the path of a creative career.

[04:06] Paul: That was one of the big challenges for me. I grew up mostly around full-time workers, and there was this sort of like collective wisdom of like, well, what else would you possibly do? Uh, part of my challenge of leaving to do my own path is I just didn't have any stories of people that, uh, were taking different paths. Did you grow up with anyone that stood out who you were curious about or you looked at?

[04:30] David Kadavy: Not really. I mean, there's a story I tell at the beginning of The Hard to Start of one person who did something kind of unique. He was a kid who lived in my neighborhood who was several years older than me, and he had like a— maybe started a number of different businesses, but one of them was like snow removal. So he had this truck and he had this snowplow, and I remember asking him about that business and how, like, oh, you go and clear the snow from this parking lot at this grocery store? Like, how did you get them as a customer? How did you know how to repair this old truck that you bought?

And how did you know how to attach a snowplow to it and stuff? And it was actually kind of a frustrating conversation because he's just sort of shrugging, like, oh, you know, I just did it. I just figured it out. And that to me was just unreal that you would try to do something. And, and that nobody has shown you how to do it. Even though, you know, today we would have YouTube and they could— there's probably 1,000 videos about how to start a snow removal business on, on YouTube or, or how to attach a snowplow to a truck or something.

But in the '90s, you know, I don't know how you learned how to do that stuff. You just sort of had to figure that out. So that was at least one person who I remember that visceral feeling of speaking to and just kind of being like, you just figured it out. And how, how you just seem so different from what I was used to.

[06:15] Paul: You did graphic design in college. Was that something you entered planning And doing— and at the time, did you see that as sort of a— were you like a black sheep in the college world of picking something like that? Because I know it was not a very obvious thing to be doing in that time.

[06:32] David Kadavy: Yeah, we're talking, you know, late '90s, early 2000s. It wasn't a super obvious thing. It was before it became like cool or maybe even lucrative to be a designer. And I sort of stumbled into it because that invisible script of, you know, get a job, secure a job, was there. But I also really, really loved to draw. I loved art.

And I sort of thought, well, okay, this is something where I get to draw a lot and I'll have a better chance of getting a job than if I were to get, say, a fine arts degree. I didn't really know necessarily what it was. I think the first college that I went to, it was called Visual Communications and Design. Another common term for it at the time was commercial art, which is a term you'd like never hear anymore.

[07:30] Paul: That's not inspiring.

[07:31] David Kadavy: No, no, not at all, right? And then sort of stumbled into it that way. And then when I transferred colleges and it was, you know, BFA in graphic design, I had at that point started to fall in love with it and fall in love with the visual communication aspects of it and with typography. And I did have to take a fair amount of drawing classes to end up completing that major. That's funny, I hardly ever draw anything anymore.

[08:04] Paul: Is that— are you sad about that, or is that something you miss?

[08:08] David Kadavy: Um, actually, over my shoulder, people who are watching on, on video, is, um, a drawing or a poster by, uh, my, I guess, creativity partner, my mastermind partner that I talk to every 2 weeks, Phil Thompson from Wonder City Studio. And I do remember just even a few years ago being over at his house while he was just drawing all— we were both working and he was just drawing all day. He just like draws these cool illustrations of architecture around Chicago, amongst many other things. And I do remember feeling like a little tinge of jealousy over the fact that he was drawing all day. And I, you know, when I feel something like that, I certainly ask myself, okay, well, is there something that I need to incorporate into the work that I do? That can help me satisfy whatever sort of feeling of envy or FOMO that I have in watching that.

And I think I like went and got a few drawing supplies and did a little bit of drawing and did a little bit of watercolor and stuff. And I don't currently feel a need to be drawing a lot. I certainly get to design my book covers and design my book interiors. And I draw little stick figures sometimes for my blog posts and stuff, but I don't feel really compelled to do any really detailed illustration like I used to, fortunately, because if I did, then I would probably be unhappy.

[09:50] Paul: Yeah, I love that. What was the impact of studying abroad in college?

[09:56] David Kadavy: Oh, that was massive. I got the opportunity to take a semester abroad in Rome, and I actually didn't want to go. I was somebody who I remember in high school telling a friend one time, I have no desire to ever go to Europe. I don't ever want to go.

[10:19] Paul: This was me too. This is such an— I sense this is like a middle-class sort of statement. Stance, which is like, ah, what do we need abroad? America's perfect.

[10:30] David Kadavy: Well, I think honestly, for me, I think I would just didn't want to be on a plane that long. Ah, yeah, I just hated the idea of being on a plane for like 8 hours. I was mildly afraid of flying. Like more afraid of airsickness, probably than I was of flying. I just like after watching too many movies, I just thought like if you went on a plane, you automatically like had to barf into a barf bag or something. And I just didn't want that to ever happen.

I think that was deep down what it was about, which is probably kind of strange. But, you know, I just had enough people, I think, say like, oh my gosh, like, you've got to go, that I went ahead and did go. And it just busted Pandora's box wide open because it as soon as I saw how different the life was there, it wasn't just the realization of what the life was like, say, in Rome, Italy. It was just the realization that, well, if life is this different here, that means life is probably different yet again in every other place. And here I am, 21 years old or so, and thinking, oh my gosh, Like every— my entire mental model of the world, those were the words that I used. My entire mental model of the world needs to be completely redesigned, but I can't do that without lots of information.

And so I'm going to have to find that information through exploring. And so then that has been the last 20 years or so. And, you know, I recently bought a house for the first time, so I feel like I've got— I've started to get a pretty confident idea of what I think the world is and what I want out of it. And I think a lot of that started with a study abroad. And it sort of reminds me of a letter that I read from Thomas Jefferson to his uncle— or sorry, to his nephew. And there's a whole collection of letters that he wrote to his nephew.

And I think One of them said something like, if you're going to travel, you have to do it early in life because it's extremely disorienting to do it later in life because, because of how it's going to be so mind-expanding. And, you know, 21 or so is certainly not late in life, but I wish I might have Tried something earlier, sooner, you know, done a, been an exchange student in high school or something like that. But that was the furthest thing from my mind when I was that age.

[13:20] Paul: See, I'm thinking that with you, I didn't really. So I was listening to your podcast. You had this podcast about mini lives, which we'll dive into, and I love it. You started off, I hate vacations. Right. And I was like, oh wow.

Some— I totally like me too. Right. I don't like the rushed nature of it. I never feel like I get to settle into like a certain mode. I never feel like I'm actually living in a different place. And when I was 32, um, I had done a couple test trips the year before, but when I was 32 was the first time I moved abroad and I experienced a lot of what you talked about.

In that idea, which is that we're so dumb. We think we know who we are, and then we go live in another place and all our habits and behaviors change. And it's like this portal of like figuring— it's a humbling device, but it's also a magical portal to like, oh my gosh, you can live in so many different ways. And I had the same reaction. It was like, What was I doing? I should have done this earlier.

And it was very disorienting. And the past, like, 5+ years have really been me trying to, like, figure all this stuff out. Um, and now try to figure out life.

[14:42] David Kadavy: Yeah. And I have gotten to live in a lot of different places and spend a month or longer in a number of different places. And you're absolutely right. You think that you know yourself. And then you end up in this other place and all of a sudden, uh, you know, it depends who you are. Some of us are more malleable than others, but certainly myself, if I go to a different culture, or at least when I was younger, if I went to a different culture, I would behave differently.

And like, when you start to, uh, well, well, so if you're in New York, uh, and you're walking down the street, You're just— everybody's in your way, and you know, you just kind of want to— you just kind of want to just like yell at them or like get them— you're like, well, why are you standing right in front of me right now? Like, oh, because you're waiting for the light that I should be waiting for, or something like that. And it's just that kind of, um, the way that the rhythm of life there interacts with something innate about the human nervous system in general, maybe not everybody's, but at least mine, causes that sort of agitation.

Whereas if you're in Medellín, which I live outside of now, and you spend some time there, after a while you kind of fall into this very relaxed rhythm where you're going to just sort of take things as they come, um, in part because you just— if you do try to control things and have things happen quickly and according to some type of schedule like we're used to in the United States, you're just going to go completely insane, um, because it's not going to happen. And, and it turns out to be really wonderful, is a really wonderful rhythm of life. And And so what I found through my travels over the years, not just travels, because like travels is like you could go spend a day somewhere and that's considered travel.

[16:51] Paul: But I mean, yeah, tell us about the mini life.

[16:54] David Kadavy: Yeah. Spending time in existing. Well, yeah. What I say at the beginning of that article is like, yeah, I hate, I don't like travel so much. I don't like to be in a place for a short period of time and you know, you've got to get certain things done, you've got to see certain things. I enjoy the experience of being there long enough to develop my own routines, to figure out what I would be like if I lived in, in this place.

I think that a lot of people fantasize about, oh, what if I lived in New York, or what if I moved to Seattle, or whatever, and they never get a chance to do it. And then it sort of becomes this thing that you imagine what life could be like, and you're never going to find out. And since you will never find out, then you can tell yourself that the life that you have would be fixed if you could have this thing. It's almost like being in an unhappy relationship and fantasizing about, about somebody else who you don't even know, your celebrity crush or something like that. And that just like makes you less happy in that relationship because you're never going to find out what it's like with your celebrity crush. And so it's sort of protective in that way.

But, you know, I've gone and I spent a month in Brooklyn, I spent a month in Manhattan, and I got to see what I am like and what it's like to live there to some extent. And yeah, you know, I don't fantasize about living in New York anymore. I'm happy not to. And it's an interesting process because When you do that over and over again, you see yourself change where you think that you have certain personality characteristics. You think that maybe the culture in a certain place is a certain way. And then you really get to find out through that process what is true to some extent.

So for example, I was living in Chicago a lot when I was taking trips to South America for a couple months at a time. And I'd go to South America and I'd be kind of go, go, go. I want things convenient. I want things now. And then I would get into that South American rhythm where, you know, lo que pasa, no pasa nada. You know, whatever happens is fine.

Si Dios quiere.

[19:42] Paul: Colombian.

[19:43] David Kadavy: And, um, and you get a little relaxed, and then you come back to Chicago and you see like how pissed off and grumpy people are. And it's almost like you're watching, uh, animals in a, uh, in an aquarium or a cage or something like that, until slowly you find yourself becoming just like that. And maybe you're able to retain like some little bit of it. And maybe through repetition, you're able to figure out how to hold on to the aspects of the personality that you would like to have, uh, in some firm way where even if you are in a different situation, uh, that you can be more like the person who you'd like to be.

[20:30] Paul: Yeah, I love that. That like when I'm in Asia, I eat more fruit and like silly things like that just because it's super available, delicious, and everywhere, right? Versus the US, I end up cooking more and the food's not very good here.

[20:45] David Kadavy: Yeah. And a lot of times you think something like, oh, an arepa. I've never had an arepa before. And like, oh my gosh, we don't have this in Chicago. Yeah, you do. You go back to Chicago, you're like, oh, look up arepas.

[20:57] Paul: You just never eat it though.

[20:59] David Kadavy: And now you know where to get them. And then now you have this new thing that's a part of your life in the place where you are. that you call home, or that is your home base. And, uh, it's, it's sort of a forcing function that opens up your eyes to things that were right under your nose.

[21:17] Paul: What was the first, uh, moment in your cubicle, 2004 in Nebraska, where you were like, this life is probably not going to keep going this way?

[21:32] David Kadavy: Well, I don't know when I knew it was not going to keep going that way, but I certainly remember thinking, maybe this isn't how life is supposed to be. It was probably one of these 8:00 AM arriving at work. I've been up all night because my girlfriend was yelling at me on the phone all night, just like terribly. Toxic relationship and having no sleep and, and then, you know, being told what to do in that cubicle and having things that I would rather be doing and realizing, gosh, this is— I just need to reach out in some way because I was in Nebraska. I didn't want to be there. I tried after college to go somewhere else.

And it wasn't a great job market, wasn't a great time to be a graphic design degree holder. People weren't falling all over themselves to fly you out to some other cities to interview because there were plenty of other fresh graduates there. I didn't feel like I could just move to one of these places. Practically, maybe I could have, Maybe I could have figured it out. It's hard to get an apartment if you don't have a job, but it's hard to get a, a job if you don't live in a, in a place. Um, and so especially then, yeah.

And I, and I do remember, but I certainly didn't want to be back in Omaha, but I do remember sort of exploring what was there. And I did find there was, you know, there was a creative scene there. There was a nice graphic design AIGA chapter there that I spent a lot of time with, and it was actually turned out to be a great experience. I worked with the American Institute of Architects on a number of things, the local chapter there, and it was actually turned out to be a pretty good few years creatively in that I could really dabble in a lot of different things. And then when there was this amazing music scene, uh, there that was kind of, uh, maybe the, the, the golden age of indie music, um, and bands like, uh, Bright Eyes are from Omaha. And then there was a whole other scene with the label Saddle Creek that, uh, that Bright Eyes was in.

And there were these great shows and stuff. So there was a creative community there, and I started to see some of that. And I do remember one of the, um, one of the guys who I guess worked at Saddle Creek, which I didn't even understand how a record company would actually be a business. I think it would just be like, oh, some folks who get together and play music, and then I don't know where these CDs come from. How is that like— do they know? They just like— how do they record that?

I don't know. Was that actually a business? They make money doing that? Um, Don't they have to work at insurance companies or something? I remember seeing that and seeing the website, actually the personal website of one of the designers at Saddle Creek, and he would do all these weird experiments on there and stuff. And then I also was reading blogs from people in San Francisco, web developers, and Douglas Bowman from— who ended up designing at Google and Twitter.

Reading these blogs and Merlin Mann, 43 Folders, writing about getting things done. And I thought, well, gosh, these people have these websites. I guess I could just, I have a website, you know, anybody in the world could view whatever it was that I had to create. So first I created on Kadavy.net this little Flash toolbox. Flash, I don't know if anybody remembers that. Sort of dating myself.

[25:30] Paul: Oh yeah.

[25:31] David Kadavy: But, uh, I remember it was this animation thing, writing ActionScript and making these little toys and putting it up on my website. And then eventually I said, well, I want to be able to write something on here. I want one of these blogs. But I was very intimidated by the blogs that I saw. They all had this cool calendar widget and they all had these beautiful designs. And I, you know, I just didn't know how you would do something like that?

It's like the snowplow. Like, how, how do you put a snowplow on a truck? How do you make a blog? Well, there was blogger.com, it turned out. So I went to blogger.com, like, oh, this is cool, I can just do this, like, right now. And so I remember telling myself, okay, like, don't get, don't get stuck in the details here, just get one blog post out, just get one, just set it up, get one blog post.

I put like 10 Dave Kadavy's blog, just picked a theme and wrote roughly 130 words saying, all right, I don't know why I'm doing this, but I don't want to get paralyzed by my perfectionism here. So I'm just going to barf this thing out and clean it up later. I think this is someplace where I might experiment with web design and things like that. And I think that was, that was the beginning, uh, right there. And I, that was, I believe I was still at my desk after a long evening, uh, at work. And when I wrote that blog post, and, uh, within a year I had a job in Silicon Valley, and it was in part thanks to that blog that I started with that, you know, sort of whim of let's just get one blog post out here.

[27:21] Paul: Yeah. What— when did you shift to self-employment?

[27:29] David Kadavy: Uh, July 17th, 2007.

[27:32] Paul: I was working at a startup in San Francisco and you just celebrated your 15th year. Congrats.

[27:40] David Kadavy: I did. Thank you. Yes, I did. Yeah, and there's actually a— I believe you might have shared even the article about that.

[27:50] Paul: Yeah, the making it one.

[27:52] David Kadavy: Yeah, yeah. Uh, yeah, July 17th.

[27:54] Paul: Let's definitely, let's definitely talk about that, but, uh, feel free to answer the question first.

[27:59] David Kadavy: Sure. Yeah, yeah, July 17, 2007. Um, my boss came to my desk and, uh, said, hey, um, "Can you come talk to me?" And I followed her down the hallway and she had this manila envelope in her hand and I sort of thought like, "Hmm, I wonder what's in that envelope." And she sat me down, she said, "I need to terminate your employment." Whatever. I didn't ask a lot of questions about why or anything like that, but I was very unhappy in that job at that point in time. And I didn't have the guts to quit. But the moment that I was fired, I knew that I was never going to work for somebody else again.

So, wow, I got up, I thanked my boss. I literally said, thank you very much. "July 17th, 2007, this will be a very special day in my life." And I didn't say, "This is the last day I work for somebody, you suck," or something like that. But yeah, I thanked her and collected my stuff, had some lunch with a couple of colleagues to say goodbye, and descended into the Powell Street BART station and returned to the Mission. And, and then the next day was just nothing but vastness and trying to figure out how to fill that up with something interesting that would also pay the bills.

[29:38] Paul: Yeah. How did those first months feel? For me, it was— I sort of orchestrated my exit, but I sort of under-anticipated the vastness. It's a great way to put it. I had the intense feeling that I needed to make money immediately. I also had the overwhelming, like, feeling that I need to figure out my entire life.

And I also had immense excitement. How are you feeling at the time?

[30:11] David Kadavy: The first few weeks, the most memorable sensation was sort of just like looking at my arms and touching them and acknowledging that I still existed despite the fact that I did not have a job. That's kind of how deep that programming was, that, you know, you have to have a job. My dad, my dad had the same job for 37 years.

[30:45] Paul: So same here, very steady.

[30:48] David Kadavy: Okay, yeah, very steady. There, people don't change jobs. People definitely do not, uh, get fired. And people, if they get fired, they certainly go and look for another job. And so I had no plans to look for another job. And so I— and part of the reason maybe I think that I was unhappy at the job was that I had a decent retirement savings.

I was 28 years old. I had bought Google and Apple stock. You know, here's, here's where some of the luck works into the equation. I had like $130,000.

[31:26] Paul: Um, you know, this is 2007.

[31:30] David Kadavy: Yeah. So, and I, uh, but I would look at that in the, in the poor portfolio. And I think like I had accrued a lot of that because during that time when I was in the cubicle in Nebraska, I was eating these 80-cent banquet meals every single day. I'd be in the break room and somebody'd walk through like, hey, Academy, what do you— oh, Salisbury steak today. It's like, am I in office space right now? I want to shoot myself.

[32:04] Paul: So, um, similar experiences.

[32:07] David Kadavy: Yeah. And I was just piling it all into as much of it as I could into my retirement. Cause that was also a part of the programming was, you know, you invest. And I think that was good. I just think that I had different ideas of what I wanted to do with that investment. Cause I was thinking, oh yeah, I'm investing for retirement.

But I was also thinking like, oh, and investing for freedom someday. And, and so I had that $130,000. I'm like, what is this for? Like, I, you know, obviously, I, you know, you want to have millions or something when you retire, and you're gonna get old and all that stuff. It's very hard to imagine when you're 28. But also, it was like, well, what am I just gonna be miserable for the next few decades and then enjoy it?

And like, what's the point? And I think that knowing that that money was there and knowing that I didn't need to have the paycheck, um, you know, great problem to have. Uh, I think that sort of helped manifest some of my misery perhaps. And so as soon as I was on my own, I cashed out $40,000. I thought about, I thought about it a little bit. Like I saw my roommate was filling out applications to go to business school.

And I thought, do I want to go to business school? And like, what kind of path is that? Okay, you go, maybe you learn some things, but you're going for the connections so you can go like get a high-paying job at some Fortune 500 company or something. But like, I don't want that. So if, if he's going to go spend, you know, six figures for this degree, like, why can't I spend $40,000 for a year and call it my tuition. A year of freedom.

I love that. A year of, okay, you don't have to try to make a cent, just try to make it worth getting out of bed. Uh, try to reconnect with that feeling that I had when I was alone in my room by myself drawing, and the hours were melting by. Not that— didn't mean I need to be drawing. It just meant that I needed to feel that way. And so that became my first metric, was curiosity.

Because that first morning you wake up, you could do anything. It's vastness, and it's intimidating in a way because it's a little bit like if you were, you know, Maybe you had a few too many drinks and you're in a bar parking lot and there's this big giant who you've decided to pick a fight with and your buddies are holding you back and you're sure, oh, you know, if they would let me go, I would show this guy what I got. You know, I think a lot of us think, oh, if I had the freedom to spend 6 months in a cabin or, you know, have the time to do the things I want to, well, heck, I would do it. And once you have that opportunity in front of you, I mean, it's very intimidating because now you're going to get your face bashed in, you know, or yeah, right. You better prove it or you're going to get your face bashed in. So that— those were the main sensations.

In the beginning.

[35:42] Paul: Wow, this is so powerful. I love that reflection about seeing if you exist because this is one of the central themes I explore in my book is that we've sort of flattened our idea of work as having a full-time job. And I quoted this sociologist, André Gorz, who says the way you prove membership in today's society is by having a job, right? It doesn't matter that you work. It matters that you work in the proper way with the right credentials. Right.

And this, this was really intense for me after I left my job because I didn't expect that I would feel like I didn't exist anymore in this society. But that was very powerful and hard. So it's, it's cool to hear that somebody— and I wonder if it's like just we have such similar backgrounds. I mean, my dad worked at the same company for 41 years and like, yeah. I didn't really know what it would be like when I stepped into that new territory. But yeah, it's wild.

[36:48] David Kadavy: There was that lack of identity. But there was also— I also felt when I worked for other people, if I didn't feel totally engaged in it, if I wasn't totally into it, then more of the things that I was curious about on the side, my side projects would start bubbling up. So there You know, if you were to go through my blog and see the consistency of my posts, you'd see, you know, for a few months posting relatively regularly and then just nothing for 6 or 7 months. Well, then nothing meant that I was engaged in the work that I was doing, that I felt some sense of meaning in it.

And so once it became— anytime— once a job became, uh, Once I started to not feel engaged in a job, then it started to feel like wearing a straitjacket or something and just really wanting to fight out of it because why am I wasting my time changing the paper on this printer when I could be doing the thing that I want to do? And that was aggravating to me.

[37:55] Paul: So many people have the case of once they find these small little side projects, and I think it's often a mistake to think you need to make money from these. It's really just something that's a portal to make you feel alive. And then it's not overwork that often burns people out. It's the disconnection from working on anything that you think matters, which sort of brings me to, um, your podcast title, uh, which I love. So can you share, uh, how you landed on that?

[38:26] David Kadavy: Yeah. So the podcast is called Love Your Work. Uh, you You know, in some ways it's a great title in that when I put it in the subject line of an email that goes to a potential guest, I think that it grabs their attention. But I think it's also very much not what people expect when they think that they're gonna listen to a podcast about love your work. I think they're thinking more about employee engagement at human resources and Fortune 500 company or something.

[38:54] Paul: Well, in the last 10 years, a lot of these terms have sort of been co-opted by like what I call culture PR. Right? And they're trying to sell people this idea of loving your work. But like, often when I meet people like you, I know you're talking about something deeper. Like, and if you spend more than 30 seconds reading any of your stuff or listening to your podcasts, you think, oh, he's talking about this deeper sort of like connected state. And yeah, one thing I've been writing about is like, this state exists.

Knowing that this state like we should want to seek it out, right? When was the first time you sort of stumbled upon that state in your own work?

[39:37] David Kadavy: Um, I mean, I think it was during that period after that, when I gave myself that year to explore whatever I wanted. And I ended up just going to a different cafe in San Francisco. I met this developer on Craigslist, we each tried to get each other to be co-founders in one another's companies, but What we ended up doing was just going to a different cafe every day and we'd work on all these different projects that we had in mind and like working on like a dozen of them at a time. And we'd spend like all day in cafes, like from the morning until like the last cafe closes. Then like walking home at night, feeling like, wow, I didn't make any money at all, but I feel great. Um, but I do hope that I make some money at some point.

Uh, and, uh, there was a point in time, uh, when I did finally seize upon a project that I really wanted to have succeed. I would— and, um, it was when everybody was— there was a gold rush for Facebook apps. Facebook was apparently to get on open up their API and let developers develop on it, and that didn't really work out. But I had this idea for this Facebook app, and I decided to shift my schedule, uh, so that I would work from 8 PM to 4 AM, and then I would sleep from 4 AM to noon, and then I'd have, you know, my 8 hours or so in the afternoon, in the evening, and then I would be working, and then I could then focus and concentrate. Um, and I worked on the specs for this app because it wasn't a developer, so that I could hire a developer.

And I just, I just tried to make like the most detailed, gorgeous, well-thought-out spec document that I possibly could, because one of the things that I had felt working for other people was this sense of rush. The sense of like, let's get this done, we don't have the budget to spend time on this and to do this right and to think this through, or, you know, kind of backhanded compliments like, oh, you're very methodical. I just wanted to do it my way and do a thing that I thought was good and that I felt proud of, whether it worked or not. I certainly thought it was going to work, but I certainly got the value out of just that satisfaction of doing a good job. Because in a way, it felt like nobody gave me a chance to do a good job, and I gave myself that chance.

And then lo and behold, I went and showed the spec document to developers, and, you know, they were just— I just remember showing to some friends, and they were just gushing about it. They're like, this is the best spec document I've ever seen, which is like, sounds very nerdy, but it felt very good to feel like I had done a good job with that.

[42:50] Paul: I wanted to read something you wrote about this past summer. You just mentioned it before about making it. 15 years as a creator. I'll never make it in parentheses. And you quoted yourself from 5 years prior in your 10-year reflection, which was Um, take it from me, a 10-year veteran self-employed creator. If you are looking for security or reassurance, I do not recommend this line of work.

Second on that one. Um, however, if you are burning with curiosity, if your heart and intuition lead you to do things that don't make sense, well then you don't really have a choice in the matter, do you? And I sort of sense this too, that like I don't really have a choice and this is hard to articulate. What do you mean by that? And what does it feel like to be burning with curiosity?

[43:42] David Kadavy: Well, I mean, that quote came from a post that I had written, like you said, for my 10 years, where here I was, I had moved from San Francisco to Chicago, which felt like a step down. And then I had moved from Chicago to Colombia. I was living in a third world country to where I still, still live, uh, in the pursuit of this thing of being able to do the work that I wanted to do, of being able to explore my creativity and find what was there. And here I was in Colombia, and I was kind of just barely getting by in this third world country. And I'm saying to myself, well, it's July 17th, 2017 now. You know, you think that it's going to take a while, but when it's been 10 years, you think, well, it's time to have a really serious conversation with myself here.

Like, did I make a huge mistake? I can't even— and I think part of the reason why I even asked myself that question, because obviously practically I could just, you know, go get a job or something like that, but that seemed like not an option. And also I had, you know, to go back to working as, say, like a web designer or something, I mean, it would take a little bit of training to get back to being able to do that job after years and years of creating and being a writer instead. And so I did sit down and, and like had that conversation with myself and reminisced about where I had been, about where I was, about what I thought was going to work and how I thought it was going to work out, what did work out, and the situation that I found myself in, which was a scary one, which was that I didn't really see how this was going to work.

And so that's where you feel like you don't have a choice, is that you can look at all the rational reasons why this isn't going to work or why you can't do this, but you still want to keep going. And it's a feeling that I had from the beginning. I do remember having drinks with a friend once shortly after going on my own. And she said, you know, you'll get a job within 6 months. And I looked at her and I said, I would rather be dead. And I could imagine myself like face down in a gutter.

I don't know why I come up with that situation, but I think about like, you know, ending up like Edgar Allan Poe or something where you're just like, okay, some guy who's dead in the gutter. And, you know, that's dramatic or whatever. That's how I felt. And so I think that's what that sensation is, is that you can rationally go through the whole thing and say like, okay, this is— you've tried for 10 years, man. You've spent a bunch of your retirement savings and and moved from places that had opportunities and, you know, cut off relationships or made a lot of sacrifices for this thing. And where is this going?

So that was the question I was asking myself, and the answer was Well, I just have to keep going.

[47:34] Paul: Yeah. And it's such a, I think it's a hard thing. And I imagine you had people seeing you, probably fans of your writing and stuff, or kind of like, oh, David's this big deal and you're still trying to like figure it out, make it. And I was excited.

[47:52] David Kadavy: It's funny. I remember, I just remember getting a comment on that because that, That blog post, I felt it was an extremely vulnerable writing process. It was a very serious conversation with myself. I mean, I think right before I wrote that paragraph, I stopped and cried, which is not something I do often. And because I realized, oh my gosh, I'm very scared, but I feel like I have to keep going. And I just sort of hit publish on that.

And I didn't do any of the normal, oh, I'm going to choose tags for it or put it, submit it to this publication or send it to my email list. I just sort of hit publish and said, okay, I'm a writer. As uncomfortable as it is for me to put these feelings out there, this is my job. And so I'm going to do that. And I did it. And then it just sort of like, you know, nothing, nothing, nothing, nothing for a while.

And then it became like one of the most popular things I've ever written. And I remember getting one of the comments on there. It was just from some, you know, from some online marketing douche or something who was all like, oh yeah, you know, you really, about what tactics I used in it or something. It was like, oh, and aimed at, uh, at online writers too. And it's like, this, this person has no idea what it's like to, to actually feel something for their work. This was, was my conclusion.

[49:37] Paul: Yeah, that, that tension is so hard, and I have so much respect for the people that went before me. I just think it was literally way harder to make money doing the kind of things we're doing before I took the leap in 2017. There was just way more, like, even things like publishing books. Amazon makes it so easy now. It was a mess 10 years ago. I've, I've no friends who have done it.

And like, they're explaining it to me. It's like, oh my gosh. Or even getting a podcast up in 2015 was still sort of non-trivial.

[50:13] David Kadavy: Well, that's a very, that's a very positive attitude, I think, to have about it. I think it's also, it's very easy to feel like the land grab is over and that the opportunities have dried up. So that's, I think that's a very positive way to look at it, is that it was perhaps harder before than it is now. I don't know, it might be the opposite.

[50:34] Paul: Yeah, I mean, I mean, it's, it's always hard to know in the moment. But in your case, the past few years you have had some financial payoff. How does that feel?

[50:46] David Kadavy: Great. So, so great. I mean, it's just, um, I had this vision when I started on this path of just being myself for a living, of the sort of natural desires and natural, comfortable actions, just money coming from those things. And, uh, you know, it was a step-by-step process. I did do a lot of building of passive revenue streams that were awesome income but that weren't core to me, uh, But the— that was the ultimate goal, was to be myself for a living, to have whatever it is that I am curious about result in some kind of product that is useful to people. And, you know, Design for Hackers, my first book in 2010, was a taste of that.

Um, but it was really only in the last few years, uh, or sorry, 2011 was when Design Practice came out. 2010 was when I got the book deal. But it's been only in the last few years that I'm starting to see in my income reports that I share on my blog where, wow, this money is really coming from something that was core to me, such as my latest book, Mind Management, Not Time Management, which was something that I conceived of as I was writing Design for Hackers, and then 10 years later, uh, had explored the concepts enough and written the book and had it out there to have that be something that's like bringing in money that is, you know, affecting people. Um, and it's enough to get by in Colombia. And to live decently. And I bought a house.

Um, it's awesome. And in a way, but in a way it feels like, um, like a revelation of a truth, you know, like this thing that, that had this sense of inevitability to it. Like this is when you have a vision for something And you have no logical reason to believe that vision. And you watch over very many years it come to fruition. For me, it's usually not like this feeling of elation. It's this feeling of like contentment of like, yes, okay, this is truth in some way.

[53:43] Paul: I love that so much. I, I've had a somewhat similar experience. This is the first year I've really made money from the stuff that lights me up. Yeah, I've more or less sort of like, I do online courses and coaching and workshops with corporations using some of my past skills, but I basically using that to like write for free about work for 5 to 7 years. And, uh, The book, making money from the book, it's like, yeah, I mean, I think similarly it just made me like want to cry because it felt like true. Like, it was like, ah, I did well.

And yeah, I didn't sacrifice anything. I— this flowed out of me in such a true and powerful way. And I sort of took it as like permission to like lean more into that and not be afraid.

[54:41] David Kadavy: Um, yeah, that really resonates with me. I think when you say, oh, that makes you want to cry, but it's for me, it's like I want to but can't, you know. It's like if I could have imagined the moment long ago, it would have made me cry, right? But like, now I'm in it, it's just It's just nice.

[55:02] Paul: It's kind of just, yeah, it, it's weird. I'm sure people ask you this too. What's it, what's it like publishing a book? And I don't know, it just sort of feels sort of, yeah, it's like nice. It doesn't feel like anything. Do you have a similar experience?

It's just very hard to describe. I don't have the words.

[55:27] David Kadavy: I've been thinking about this a lot, about what it's like to ship in general. And the best analogy I think I could think of is, is like being in the schoolyard and telling your crush how you feel, which is something that I would get up every morning and be like, oh, today I'm going to tell her. And it would never ever happen. And The reason why you don't, you're afraid to say it is because one, there's no external signal telling you that what you are going to offer is going to be reciprocated necessarily. Like when you're shipping something, when you're telling somebody who doesn't know how you feel, how you feel, yet it's something that you feel very truthfully, um, and you feel it very truthfully. The external world has nothing to validate it.

And when it comes to creative work, whatever it is that you have to offer is, is nothing like anything anybody's ever seen. I love this story about Jackson Pollock, where I guess he was out in his studio and he called his partner or wife in and and said, is this a painting? Like, not is it a good painting, like, is this a painting? You can imagine him feeling that way because the work that Jackson Pollock did was so unlike anything anybody had ever seen or done. And that's what it feels like to put something into the world that is very personal and is very that comes from the heart because it comes from your unique experiences. Nobody is like you.

And so this thing that you've created is unlike anything that you've seen out in the world. Like maybe you have some vague examples, but there's really, there's only one thing like it and there's no external validation going on there. So you're really making this leap of faith. Of putting it out there and saying like, okay, look, I know, I know, I'm, I know I'm flawed. I know this could be better, but here's how I feel. And you might laugh in my face, and I'm afraid that you will, but I can't hold this in any longer.

So I think that's what it feels like.

[58:02] Paul: I think people's, the, or the origin of the question too, I think assumes this sort of way the world works as you do things for other things, right? You do things for the payoff, you do it for retirement, you do it for the promotion, right? And it becomes very hard unless you've experienced this state of like aliveness and connectedness in your work that you do just things for the sake of itself, right? And this sort of ties back to what you were saying about making it and what I thought was so powerful is that on this path, like there is no arrival. There's only like getting the right to continue to play and your environment's always changing. The incentives are always changing.

The things you can do are always changing, but really you're just trying to orient around things you can continue to do.

[58:55] David Kadavy: Yeah. I like to quote by, um, Walt Disney that I heard from Jeff Goins, something like, we don't make movies to make money. We make money to make movies. I'm not writing books to make money. I'm making money so I can write more books. So I've always, you know, I think that certainly there's the situation of being in poverty or starving or something where you just need money and who cares.

But after a certain point, it's a perversion of what money is supposed to be to make your pursuits entirely about how much money you're going to get paid to do something. Because money is supposed to be an expression of value. And so if the pursuit of money is an experience that is not valuable, Well, then what was the point?

[59:57] Paul: Yeah. And I love how you close that piece. You write, I'll quote you again. So after 15 years, I've made it as a creator, financially speaking, in a relatively minor way for now. But maybe the best part of making it is realizing you now have the privilege of feeling you haven't. So you can freely struggle to reach your destination only to do it again.

Are you excited about continuing on the journey?

[01:00:22] David Kadavy: Yeah. And as I've shared in that post, like there have been moments where, you know, after feeling like I've made it, reaching, you know, 6 figures in the self-publishing business, there have been moments where I've thought, oh, okay, like now what, what am I doing this for? And that's where, when you don't have that struggle there, you have to create some kind of struggle. And this has been a journey of continuing to create different struggles that hopefully get me deeper and deeper into exploration of who I am and what's important to me. And, um, and so now Uh, that's something that I find myself continually searching for. Uh, say, you know, as I'm working on the next book or the next article or the next podcast episode, I'm asking myself, okay, do I even have to do this?

I don't. Okay, well then let's find a reason to want to.

[01:01:36] Paul: I love that. Do you think more people should consider self-publishing their own books?

[01:01:42] David Kadavy: I personally think this is probably not a— this is probably an unpopular opinion. I think everybody should publish a book. I think, uh, you know, I think you could go on kdp.amazon.com right now with like a 500-word document and upload it and you would have the same real estate as War and Peace. Now, I don't think necessarily that we need to have millions and millions of 500-word books out there, but I wish that more people would do that just so they could just see how easy it actually is and see that it's something that they could do. And they can go— you can unpublish it when you're done. You can put it under a different name if you want or whatever.

Just going through that process I think shows you that it's possible.

[01:02:32] Paul: I don't think I realized this until I actually published my book and I published the paperback in it. I didn't realize it would actually just go live immediately. Like I was expecting to do a presale. And then I think I realized the power of it. I was like, oh wow, this was incredibly simple. Um, and I, I think I wrote the book at the right time, but it's really opened my imagination to— yeah, you could do other smaller books and put them out there and do all sorts of stuff.

[01:03:06] David Kadavy: Yeah, I think that a very common criticism of a lot of books these days is, oh, this was a 250-page blog post. I think more likely, instead of being a blog post, it probably should have been a 30-page book. I've had very long blog posts I've written which I just go ahead and publish also as a Kindle book or even on other platforms as well. And people seem to enjoy reading the shorter reads that I have out as well. Some of them, some of them are hits.

[01:03:39] Paul: How, yeah, how have some of those done, like with Amazon? What have you learned about the platform?

[01:03:46] David Kadavy: I don't know what I've learned about the platform, but I have learned that writing the book has been— writing a book, getting a book out there, does not have to be a huge production, and it can be very, very surprising. I came to this realization when I was speaking with Seth Godin on episode 77 of my podcast, and that was when I was really struggling with whether I was going to self-publish or whether I was going to try to traditionally publish again. And that's where he said to me, you know, you just got to publish a book a week, which I think is an exaggeration. Uh, I don't— never did publish a book a week, but I got it because it's like, well, how do you— because even if you get a traditional publisher, who's going to be doing all the marketing? You are. How do you do that?

You do that by learning. And so you do that by publishing a book a week. And so I ended up publishing some short reads. And so one of them was How to Write a Book, and that has been surprising. I haven't— I've been very surprised at how much money I've made from that, how much people enjoy it, because it was something that felt very honest and natural to me to write. And in a way, it felt like, well, if something is this easy then it can't do that well.

Like you, you feel like if it's easy, then, then maybe that must mean it's, it's sloppy or something, but it hasn't, that hasn't been the case. I think there's just an honesty to that. Uh, and then also another big hit has been digital Zettelkasten, which I haven't been doing Zettelkasten for a super long time, but when I first discovered it, I realized, oh my gosh, this is what I've been looking for for years. And then everything that I found out there about this note-taking method, uh, it was extremely hard to digest. And so I wanted to understand it myself. And so I went through wading through it all and coming up with what I thought was the ideal setup for a digital Zettelkasten, because they're traditionally just cards, like almost like a card catalog.

And I put that out. Took me a couple months to write it. It's like 75 pages or so. And I'm getting foreign rights deals for it. So it got a Polish deal, got a Korean deal recently. Whereas Mind Management, Not Time Management, one of my magnum opus that took 10 years, has had just one foreign rights deal.

And it was a lot more work to write. It was a lot harder. So it's been just surprising. It's been interesting to watch the difference between maybe writing something that is specific and meant to solve a particular problem versus something where you are trying to offer some kind of new mental model or abstract concept to the world. I think the former is easier to get some sort of mediocre success with. I think the latter is much harder to get a mediocre success with, but I think the potential is greater.

And I think the world needs more of this, you know, coming up with your grand way of seeing things and offering it to people. Those are the types of books that I enjoy reading myself.

[01:07:21] Paul: These are probably like a couple selfish questions for me as a self-published author.

[01:07:25] David Kadavy: They should all be selfish questions.

[01:07:28] Paul: Well, I, so I, and hopefully this can help other people too, but, um, I published my book this year. I've had like minor success. Um, and I was excited stumbling upon your book because I think you were at a similar point, like, I've sold about on all platforms like 6,000 books probably in 10 months, which is pretty mind-blowing. And that's a whole lot. I'm sort of— yeah. And it sort of surprised me.

I had really no expectations, but I'm sort of thinking about like, okay, what do I do next? Like, what does year 2 of a self-published book look like?

[01:08:11] David Kadavy: For Mind Management, not Time Management, it's just been continuing to grow. That's one of those conceptual books. It's an offering of a new way of seeing things. And I love to see it snowball in that way where when you get signals like that, where it's clear that every dollar that you're spending on, say, advertising or every book that you're getting in the hand of of somebody else's resulting in more dollars, that is resulting in more sales to others, then you just have to find as many ways as you can to, um, to, to push it out there. I, I recently bought like even a Kirkus review, which is this thing that it's $375 or so, and the popular opinion is, well, self-published authors, you shouldn't waste your money on that. And there's certainly a lot better ways to spend $375 on a book early in its life.

But once it's been proven that— oh wow, there's something—

[01:09:08] Paul: Gray was telling me about this.

[01:09:10] David Kadavy: Oh yeah, Nick Gray, uh, got a starred review for his 2-hour cocktail party. Well-deserved starred review for it, by the way. And also was featured in Kirkus's magazine. Mine was featured in Kirkus's magazine. Don't have a starred review, but I have a positive one at least. And, um, yeah, Nick's is— at least it's early in his in the book's life.

But I mean, his book's going to be a huge hit. So it already is.

[01:09:37] Paul: Agreed. Shout out to Nick if you listen to this. Yeah. What have you, what have you found with Amazon advertising? I've put very little effort into that. I do some like automatic spending, but I was looking at your income chart today and I was like, I think I need to do this.

I'm probably leaving opportunity opportunity on the table.

[01:09:58] David Kadavy: Well, you're doing the automatic spending at least. That's, that's good, which I think is a very Pareto way to go about it because I have really gone down the rabbit hole of like trying to get the right keywords and trying to get the bid right, and you can drive yourself crazy with that. But the auto campaigns work pretty well. The biggest mistake I think you can make is just to not spend any money on ads, especially if your book is sitting there with zero reviews or something, which is certainly not for you. And I think that it's another one of these things that where the money psychology around it is, is odd because people will go spend $100,000 on an education, but then they put a book up on Amazon and then they try an Amazon ad and they spend $5 and haven't made a sale and they freak out. Like, well, you know, you're learning this thing.

So view it as tuition, like go ahead and lose lose $500 if you can, lose $1,000 if you can. You know, I go into some of these promotions like, like BookBub, for example. I recently did one where I said, okay, my goal is to lose $2,000. And that's a great way to learn what works and what doesn't. I mean, it's not just like willy-nilly and just throwing money at things. Just have some kind of hypothesis.

And put some money towards it, man, you know, I've had enough success that for me to lose $2,000 isn't gonna break the bank. It's part of the, you know, and ultimately I'm not losing $2,000, I'm making money. But I do think that you need to have a growth mindset about it, about the ads.

[01:11:39] Paul: Oh, definitely.

[01:11:41] David Kadavy: Being willing to purposefully try to lose some money in the pursuit of at least getting some impressions, getting some reviews, finding out if it passes the smell test of, of the audience and seeing what sort of signals you get. And that's one great thing about having various books out is that when you try something like that, you see like, wow, I'm really getting more from my ad dollars on this book than I am on this. Why is that? And that's how you learn.

[01:12:11] Paul: I love that. Yeah, it also gets to this point. I mean, there's sort of infinite opportunities the more bets you put out there. How have you managed just trying to figure out what to focus on? And given you have a little more financial wiggle room now, like, what do these next bets or opportunities or work experiments look like for you?

[01:12:31] David Kadavy: Yeah, I try to— I'm a big fan of Nassim Taleb's barbell strategy, which is essentially to have your sure bets that keep you in the game, that keep your income coming in, and then have wildcards where these like crazy ideas that you normally just sort of dismiss that you put out there and that give you some opportunity to be wildly lucky. And I think that something like Digital Zettelkasten was kind of that. It was a little bit of— it was more of a gray swan than a black swan, in that I knew it was a, it was a good SEO play, but it was also sort of like, this is crazy, how come nobody's done this? So I'll, I'll try it. Um, and it's something that I try to cultivate because I come from that sort of, um, risk-averse background. It's, it's sort of programmed into my organism in some way.

And so That's one thing that I— one way to practice that is, is like by doing really long meditation sessions. So I've done 60 hours in 60 days based on Naval Ravikant's recommendation of no effort meditation. And that has been— I've done that two different times, did 89 days, quit on purpose before 90, and then did 60 again. And now I'm just sort of doing an hour here and there. As much as I can. Um, and that's something where I have found if I take the time to just sit and think— one, you have to carve out a bunch of time so you do everything else faster.

Two, those ideas that you just sort of think of for a moment but then dismiss immediately start to take on more presence in your head, and you start to say to yourself, maybe I should do that Zettelkasten book even though I'm busy with this other stuff that is a sure bet. So that's what I'm often trying, trying to do. But I'm also trying to have fun with things. I recently advertised in Times Square and, yeah, turned that into a publicity stunt. Yeah, and that was, it was fun and it cost me some money. And, you know, it's fun to kind of say like, oh, let's spend $500 on, on this, just see what happens.

I love to I love to not know what's gonna happen.

[01:14:55] Paul: Yeah, I sense that's part of the joy of the path for people like us is like not fully knowing. And this is something people who are on traditional paths often have a hard time understanding is like, I like not knowing what I'm gonna be working on next year. That is a feature, not a bug. Um, but yeah, I, I love, um, how you're embracing your path. Like I wanna dive into more of your stuff. I feel like I still have some more ideas to remix.

And pick from you. But yeah, I appreciate everything you've been doing and keep sharing your work, keep going, and I'm rooting for you. Where else do you want to point people?