Many people go out on their own in pursuit of the perfect lifestyle. Of course, “perfect” is entirely subjective.
Maybe it’s to become a digital nomad and travel the world. For others, it’s the freedom to work from home and be closer to family. And still others are chasing audacious goals and world domination.
All is well and good until you find that your business is now running you instead of the other way around. It happens all too often, and all too easily.
Today’s episode is all about refocusing on your priorities, and getting back on the path to your perfect life. Our guest is David Kadavy, who like a lot of Unemployable types has multiple sources of income that have allowed him to relocate to South America and live the unconventional life he desires.
The Show Notes
It’s Your Duty to Design the Life You Want
David Kadavy: I’m David Kadavy, I wrote a book called Design for Hackers, I host a podcast called Love Your Work, and I am hopelessly unemployable.
Voiceover: Welcome to Unemployable, the show for people who can get a job, they’re just not inclined to take one, and that’s putting it gently. In addition to this podcast, thousands of freelancers and entrepreneurs give actionable advice and other valuable resources from the weekly Unemployable email newsletter. Join us by registering for our free Profit Pillars course, or choose to sign up for the newsletter only at no charge. Simply head over to Unemployable.com and take your business and lifestyle to the next level. That’s Unemployable.com.
Brian Clark: Many people go out on their own in pursuit of the perfect lifestyle. Of course, perfect is entirely subjective. Maybe it’s to become a digital nomad and travel the world. For others, it’s the freedom to work from home and be closer to family. Still others are chasing audacious goals and world domination. All is well and good until you find that your business is now running you, instead of the other way around. It happens all too often and all too easily. I’m Brian Clark, and this is Unemployable.
If you’re enjoying this show, make sure to leave a rating or review over at iTunes. You can hop over there directly by going to Unemployable.com/iTunes. Today’s episode is all about refocusing on your priorities and getting back on the path to your perfect life. Our guest is David Kadavy, who, like a lot of unemployable types, has multiple sources of income that have allowed him to relocate to South America and live the unconventional life he desires. David, thanks for being here, man.
David Kadavy: Thank you so much for having me. It’s an honor to be on this podcast. When I saw the name of Unemployable, I was so jealous.
Brian Clark: Yeah, it does have a unique resonance with those of us who respond to that title.
David Kadavy: That’s the perfect criteria for a good name, I think, is that some people might see it and think, “Why do you want to be unemployable? Then somebody like me sees it and it’s like, “Oh, yes. Exactly. Oh my gosh, I am so unemployable.
Brian Clark: Yeah, and I get that a lot. It’s clear that some people see it and it just goes right over their head or they think it’s being literal. But that’s okay, because I’m not looking to talk to those people.
David Kadavy: Yeah, that’s positioning right there. That’s what that’s called.
Brian Clark: Let’s talk a little bit about how you get here. First of all, I know you’ve written a very popular book. You’ve got a very popular podcast. What’s paying the bills these days?
David Kadavy: Probably primarily — and I say probably because I don’t pay great attention to that sort of thing — but primarily my online courses that are related to my book, Design for Hackers. So I have a course called D4H Video that teaches the underpinnings of visual design, the framework behind it. I have another course, believe it or not, that’s entirely about whitespace, if you could possibly think about anything more obscure. Yeah, I think that’s probably the majority of my revenue.
Also, a little bit of podcast sponsorships, some Amazon affiliate stuff through — I’ve got a reading list for books that I read and then also blog posts that recommend books. Then, freelance writing every once in a while. Book royalties. I’ve got quite a mix of things. I also have remnants of passive revenue streams that I created in the past that helped me write Design for Hackers and do this entrepreneur thing.
Brian Clark: A consummate unemployable type. That’s exactly how it should be. “I got money coming from everywhere, I don’t know.” Of course, the online courses are a favorite of mine, even though we moved more into software. It’s still …
David Kadavy: Yeah, good move.
Brian Clark: Yeah, well, you know. Some days you go, “I could create a course myself. Now I am dependent on an entire organization — which is a good thing most of the time. When I saw that you had moved to Columbia full-time and I read about your thoughts on that … There’s still some romanticism to the solo who makes it out there and lives a life they want to. I definitely want to talk about that in a minute. Let’s go back a little bit. Where did this journey really begin? Before you wrote the book, or did it go back a little bit further than that?
When He Got the Entrepreneurial Bug
David Kadavy: Yeah, I think it’s really way before I wrote the book. I guess I really started to get the bug sometime after college. I was like 23 years old. I had a $13.50 an hour job as a graphic designer at an architecture firm in Omaha, Nebraska where I grew up. I didn’t want to be in Omaha, Nebraska, and I was trying to fit into the template of “get the job.” My boss would come to my desk every day and ask me, “When are you going to buy a house? My friends would parrot, “It’s the best investment you could make. It never made sense to me, and I didn’t really have people around me who necessarily agreed with that.
One day I started a blog. The first blog post is terrible. The entire blog post is about how I had wanted to start a blog and I was afraid to, and here I was doing it. Through that blog, I started blogging about what I was learning about web design and some random things here and there as well. Eventually I got discovered by a crazy entrepreneur in Silicon Valley who moved me out to California, and I started the design department at two different startups in Silicon Valley over the course of a few years. Then, eventually that ended and I started working on my own things. I invested in learning. I did my own DIY MBA by cashing out some stock that I had bought and giving myself a year to mess around.
Then eventually, after years of experimentation and moving back to the Midwest — moving to Chicago so I could have more space to think, cheaper rent, and everything. Get away from the Silicon Valley noise. Eventually I wrote some popular blog posts. That’s how I ended up getting the book deal for Design for Hackers. That, at least, gets us to that point, which was maybe 5 years ago.
Brian Clark: Yeah, I love the way you originally started blogging. Everyone thinks that they have to be an uber authority out of the gate. No, really it’s just a mechanism for, as you said, “Sharing what I’m learning.” You’re two steps ahead of your own audience, but that’s all it takes if you’re generous with what you’ve learned.
David Kadavy: Yeah, I definitely agree with that. A lot of it is useful, because if you just learned something or if you’re in the process of learning something, you at least remember what it’s like to not know that thing. You remember what it’s like to have the new thoughts enter your brain. If you’re an expert on something … A lot of people say, “Oh, I’m not an expert on anything. I’ll tell them, “Do you know how to tie your shoes? There’s a lot of people who don’t know how to tie their shoes. You could write an article about tying your shoes. Which is to say, there all sorts of things that you take for granted that you know, but then there’s also things that you are learning now which you can teach other people and write about the process as it’s going.
I think that may be what holds people back, or what makes them uncomfortable in that sometimes. They are afraid of putting on a posture of authority. They picture themselves taking that posture and not being qualified for it. To that, I just say, “Be open about that. It’s like, “Okay, here’s what I know. Here’s what I did and here’s what worked. I think this is what happened. That’s a start.
Brian Clark: Yeah, it’s interesting reflecting back when I first started Copyblogger. A couple of things. I was a good copywriter, but once you start trying to teach it to someone else you find that your own knowledge goes to a whole other level. I didn’t realize at the time, but there are psychological studies that show the best way to retain information — say for example, from a book — is not to read the book over and over again or not even to take copious notes. Try to explain it to someone else and your own understanding accelerates. That’s one thing.
The other thing at the time of starting Copyblogger was — all I did was attribute everything I knew to the people I learned it from. Sometimes you don’t see that anymore. Have you ever had the wonderful experience of having your ideas recycled without attribution? It happens to everyone. It’s too bad, because I think those people shouldn’t fear revealing who has taught them, motivated them, and inspired them.
David Kadavy: Yeah, definitely. You are the curator siphoning through this information, and you might think that because you’re interested in a particular topic that, “Oh, everybody already knows this.” It’s just like the tying your shoes thing. But you can state very obvious things and you can introduce people to ideas from other thinkers and mix things up together, and really blow people’s minds that way.
Brian Clark: Yeah, absolutely.
David Kadavy: To me, that’s the greatest reward of being somebody who creates writing or audio content, or whatever is consumed by others.
How David’s Obsessions Led to Podcasting
Brian Clark: Yep. You’re essentially, I guess you would say, an information entrepreneur at this point. Everything from books to courses. Content is your life, let’s put it that way. Tell me about starting the podcast, because it’s about 50 episodes in if I’m not mistaken.
David Kadavy: You’re absolutely right, the 50th episode is coming out tomorrow.
Brian Clark: Was it really just, “everyone’s doing a podcast these days, I need to do one?” Or were you drawn, especially topically, to the love of work? That’s important to you, I would take it.
David Kadavy: Yeah. I guess from a Freudian standpoint, I’ve only begun to realize why I named it that and why that is so important to me. Perhaps it has something to do with the fact that my father worked for the same insurance company for 37 straight years. That was fantastic, but I don’t think that he loved his work. He never talked about it. Whenever he noticed that I had a passion for anything, he seemed confused about that, that I could be passionate about my work.
He came from a different generation. There’s no telling whether — if I had the same forces applying upon me — I would have done something that I didn’t find particularly satisfying or not. That was my reaction to probably speaking to that 23-year-old version of me, who was sitting at that cubicle at the architecture firm and wondering what was the point of all of this.
As far as the impetus for starting the podcast, I was already listening to a lot of podcasts. I listen to a ton of podcasts, listen to a ton of audio. I do a lot of cooking at home, and it’s something that you can do really easily. Or, when I was living in Chicago, riding on the subway or something like that. It was always an activity that was really easy to do. It just became this point where … I listened to great podcasts like James Altucher and Tim Ferriss and stuff. Eventually I just felt like there was something that I wanted that was different. I wanted to have different conversations.
I didn’t want to have conversations about optimization. That would be how I would categorize a lot of Tim Ferriss’s stuff. I’m not obsessed with peak performance. I’m not obsessed with being the best, necessarily. I’m obsessed with the contours of an individual’s personality and experiences, and how that all drives them into doing the thing that only they can do. I wanted to curate guests and talk to them about those things. Ride those contours and digest them. And make them accessible to others for others to see — or hear, I guess.
Brian Clark: Yeah. The way you describe that, and the person you kicked off the show with — Jason Fried of Basecamp, formerly 37signals — he almost epitomizes what you just said.
David Kadavy: He does. It was such a thrill to have him be the first guest on the show. That interview continues to encompass everything that the show is pretty much supposed to be about, and it’s the most popular — most downloaded episode for sure.
His Unusual Strategy for Booking Guests
Brian Clark: Yeah. Another thing I’ve noticed, is you have some of the — I’ll call the usual suspects — that we all tend to talk to at one point or another if you’re in this space and doing a podcast. But you also have some pretty eclectic guests. Some guests I thought, “Wow, how did he get her or him? Talk about your procedure for reaching out to potential guests.
David Kadavy: Yeah. Especially in the beginning, it was really about feeling a burning curiosity or a sense of love for seeing the way that somebody approaches what they do and the way that they approach their life. With somebody like Jason Fried — just the contrarianism I admired. I was mystified by his ability to say things that were counterintuitive and that perhaps weren’t going to be popular and to not be scared of that, which is something that I think that I’ve been scared of in the past and continue to struggle with.
As an example, somebody who many people probably haven’t heard of is Paul Bennett from Context Travel who sailed around the world while running his business with three children. That was through friends and stuff. That was somebody who I just randomly met through friends while on a trip and was like, “Wow, if I ever have a podcast this is exactly the type of person that I want to interview, because he’s really lived life by his own rules. He dreamed about something and then somehow made it a reality.” That’s something that I’ve struggled with myself so much in the past. The kid who was sitting in the cubicle at the architecture firm and who wanted to leave his town. Why didn’t he? Because he was scared.
In that case I was like, “What is the architecture of getting from that scared point to getting to the point where you do chase these aspirations? In the beginning it was really just strict curiosity. Now I have to put a little bit more effort into the curiosity, but I definitely don’t … I try very hard to not force it too much. I’m a big reader, so I am always looking out for new books to read, and the podcast makes it a great excuse to look for new books to read. I then write about some of those books on my book recommendation list, so that synergizes well. Really, it’s always been about following my curiosity.
Everything that I’ve ever done has been about satisfying my curiosity and this feeling that I can’t shake of wanting to know everything about a particular topic and dig into it. When it comes time to choose a guest, I have to find that curiosity in myself first about, “What is it about this person that is a lesson that I can teach other people?” That’s the beginning of it. Then I try to get them on the show. I brainstorm a trajectory for the interview and then do the interview, and then I listen to it several times to try to find the lessons and find the theme.
Brian Clark: Yeah, it’s interesting. Speaking of themes, a big theme of Unemployable — it’s a little bit different than the narrative you would get out of Silicon Valley or the traditional startup world — it’s more about doing what you want. Having the freedom — whether it be intellectual, geographic, or being able to do work you actually love, which you mentioned earlier. Earlier generations — work wasn’t about what you loved, it was your duty for your family or to yourself, whatever the case may be.
In a sense, you’re living an unconventional life. I think that’s what we’re all talking about here. As opposed to, “Raise money and cash out,” and this and that and the other, it’s more about, “How do I craft a life — which includes business, obviously — that I love? Or at least affords me enough freedom to do what I love.”
The Virtue of Living Outside North America
Brian Clark: I want to shift gears a little bit, because I think the thing that inspired me to ask you to be on the show was a recent piece you did about why you moved to Columbia. I guess it was the virtue of living outside of North America. It really caught my attention, and I thought it would resonate with people. Talk a little bit about the decision and some of your ideas about how beneficial that can be to someone who can do that.
David Kadavy: Sure. To start off, I don’t want to sound like I’m — I need to say the word right — proselytizing or anything. The article is called “Yes, You Can Leave the North America Bubble.” I’m not saying that you should, it’s just that I know that there are people who think about doing things and don’t. I want to speak to those people who do consider that and who maybe don’t take the action, because of fear or fear of judgment from others, even. Things like that.
I guess the main reason why I think there’s a good opportunity for a lot of people to live outside the United States is just because it’s easier than ever. I can run my business. I can run a popular podcast from my closet here and interview people like James Altucher, Dan Ariely, Laura Roeder, Steve Case, and Ryan Holiday. The list goes on and on. The people that I’ve talked to from my closet in Columbia. All this is possible because of all the wonderful technological progress that we’ve made — much of it from Silicon Valley — over the past couple of decades.
I think that there is a little bit of a status quo bias that people have. I think there’s a lot of people in Silicon Valley who are working there who, maybe they expect the next 20 years to be like the last 20 years. It was a different set of problems. And they were, to me, big, important problems. Problems of connecting people. When I was living in Omaha, Nebraska as a kid, I remember consciously thinking to myself like, “Oh my god, why do I have to hang out with the people who live in my neighborhood? This makes no sense, I don’t have anything in common with these people. I remember fantasizing that there was this other world out there where people were like me. And the Internet made that possible, for me to connect with people who were like-minded.
If it wasn’t for that, I would continue to be an outsider in my hometown. I think that those were really important problems that were solved. And they were seemingly, relatively low-hanging fruit. I think, “Hey, why don’t we celebrate that?” Sure, maybe there’s a few things to be innovated still, but why don’t we look at what we’ve accomplished and look at what is now possible that wasn’t possible, and take advantage of that and go live a life on the edge of possibility? I think that was really the thing that I was trying to get across and hopefully inspire a few people to do with that article.
Brian Clark: Why did you choose Columbia in particular?
David Kadavy: It’s a little bit of a long story. The first winter after I wrote Design for Hackers, which was … That winter that I wrote that book was just miserable. It was snowpocalypse in Chicago, and writing a book is very painful and everything. I thought I would treat myself the next year and go to Buenos Aires for the winter. I did that. It was great. And the next logical choice for a place to go was Medellín, Columbia.
Then I continued to go to Medellín every winter for a few winters, and it started to make a lot of sense. It started to feel more like my home then Chicago did. I saw that the cost of living was cheap, I really liked the laid-back culture, and I saw that I could really set up a life where I could prioritize following my own curiosity — much of it through the Internet. I liked the challenge of living in a different country. I met a woman, and it started to look like, “Well, okay, I should be pursuing this as well. A lot of different things happened. It was really not a planned thing. By the time I actually went back to Chicago and sold all my stuff and moved here, in my heart it was really already my home. It was a slow-motion leap.
Brian Clark: Yeah, a lot of people choose strategically, especially when there is existing ex-pat communities like Belize, Costa Rica, or Panama. I think some people hear Columbia, and all of a sudden they’re in an episode of Narcos or something. It must feel essentially very comfortable to you.
David Kadavy: Yeah, it does feel really comfortable to me. I don’t know. Maybe I’m just a little bit ignorant or something to some of Columbia’s past. I’ve learned some of those things better. It is South America, there is crime. I’ve had an attempted mugging happen to me before. It’s not a utopia as far as that goes, but then again, neither is Chicago.
Brian Clark: Yeah, one could argue Chicago is more dangerous than Columbia at this point.
David Kadavy: Yeah. I’m sure statistically it’s probably very different. In Chicago I would go for a walk at night in my neighborhood and maybe even cut through a park, but I wouldn’t do that here in Columbia. Maybe it was a bad idea to do that in Chicago, but when I did that in Columbia, that was when I did learn my lesson.
Brian Clark: Yeah. I think the irony of this conversation at this point is that we are recording this before the U.S. election, but the episode is airing on November 8th. There may be a lot of people listening with a keen interest on how to at least leave the United States. I don’t want to get too much into that, but it’s definitely been crazy. Did American culture in any way …
You talk about finding the status quo silly, and a lot of us feel that way. We realize that we do things out of cultural norms and whatnot. A lot of us have spent our whole life breaking those to a certain extent, and maybe even feeling bad about it. I know I used to until I realized there’s nothing wrong with me and this is actually the best positive attribute, I think, at least when it comes to making a living and supporting my family.
Being an entrepreneur has been the best thing that’s ever happened to me. But at the beginning I thought something was wrong with me because I didn’t like practicing the law. I had it good compared to a lot of people, and yet … It goes back to one of your original points, if you’re not happy with what you’re doing — given the gifts of technology and other changes that we’re experiencing — you’re almost shortchanging yourself for not living the life you want to live.
David Kadavy: Yeah, absolutely. I think it’s great that you did feel a little bit like something was wrong with you. Because there are some people who, just from the beginning — maybe their parents teach them or they are just very independently minded — and they don’t ever think twice about it. It’s hard to learn from those people because they didn’t have that change. Yeah, the way I see it, it’s your duty to live on the edge of your curiosity and on the edge of technological possibility. What did we make all this progress for if not to move our lives and our work further up Maslow’s hierarchy? We didn’t do it so that we could have tacos delivered to us by drones or something — which is cool and everything. But to me, it feels like a duty for myself.
Brian Clark: I love that. The duty to live the life you want. I couldn’t put it any better. I’ve been saying for quite a while, “This isn’t a dress rehearsal. What are you waiting for? This is it. Let’s do something here.” We do have more opportunity. I know not everyone has the freedom of being single or being childless, or able to just change careers. But more is possible than ever before. If you do have that capability and you’re still holding yourself back, then you really are violating your duty to yourself.
David Kadavy: Yeah. Again, I don’t want to proselytize, but it was easy for me. It became easy for me, at least. A lot of it is that none of my family lives in my hometown anymore, so it wasn’t like I was going to go back to some hometown that I totally loved. I had lived in San Francisco and I had lived in Chicago, and I’d spent a month or two in a bunch of other places around the world. I don’t have children, and I’ve built a business very much by design so that I would have some sort of independence. I’ve had a lot of lucky breaks along that way.
Sometimes it’s like we are a dog staring at a wall. We don’t realize that there’s a doggy door there yet, and that we just need to wake up and learn that we can go through it. That’s a difficult challenge, to sometimes separate the difference between that which you can’t do and that which is merely going to be a little bit challenging, or that which is going to be quite easy and we just don’t know because we haven’t tried.
Brian Clark: A lot of constraints are real, but most of them are in our heads. There is no doubt about it. David, thank you so much for your time today. Tell people where they can find you and look up some good stuff you got going on.
David Kadavy: I think a great place would be Twitter. I’m very active on Twitter. I also have a page on Facebook, if that’s your thing. Kadavy.net is my main blog, but I do the bulk of my thought experimentation over on Medium, which you can search for. Or just go to kadavy.net/medium, and that will take you right to my Medium profile.
Brian Clark: Excellent. Well, I really enjoyed talking to you. I think you’re doing it right. You’re living true according to yourself, and that’s a message that resonates with this audience. Thanks a lot.
David Kadavy: Thank you so much, it’s been great being on the show.
Brian Clark: All right, everyone. We revisit this theme over and over. We talk to real people doing it. They’re not talking about building unicorns or conquering the world, what they are doing is living a life that makes them happy. You know what? That’s not too bad. Start designing the life you want if you’re not living it yet. And as always, keep going.