Dream. Believe. Do. Interview #25: Be your own Medici

It’s one thing to say, “I’m going to travel one day” and another to not only travel, but pick up every four months and move to a new country. Colin Wright left his promising corporate career seven years ago, packed his bag, hit the road and created a way to sustain his new lifestyle as he travels. I caught up with him in Wichita, Kansas, of all places.

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Colin: I guess you could say what started out the story of… this version of Colin because there’s been many versions. But this version is my adult life, I guess, from age 24 onward where everything changed was when I was out in LA running a branding studio and working with great big clients and running a… or living a lifestyle that was very traditionally successful; successful according to the metrics that a lot of people consider. So professional prestige. I had a lot of great big clients. People respected the way that things were going.

Dennis: Making good coin.

Colin: Making good coin. The work ethic was there. I was barely sleeping and that’s something that a lot of people respect in a lot of different fields. When you torture yourself a little bit more than everybody else is willing to do and I had all of that. My girlfriend at the time and I were living together in this townhouse near the beach and we were kind of the center of our social circle. And we’d go out “networking” two or three times a week which means drinking with people and hoping one of them becomes your client. It was that type of lifestyle.

It was kind of what I had wanted when I first moved out to LA was that type of go-getter, ambitious - recklessly ambitious, to a certain degree - type of lifestyle.

It all came to a head, actually, shortly before my 24th birthday when my girlfriend and I realized that we hadn’t seen each other really. We lived together but we hadn’t really seen each other for weeks because she had her business, I had my business. We were both so busy.

When we went to sleep… We’re in the same bed but maybe there for a couple of hours. Both of us too exhausted to even say hello to each other. So we decided to take a trip. We took a vacation, which was the first vacation that we had taken together.

Dennis: Right.

Colin: Because we just didn’t have the time or the energy to even think about it. We felt like we’d fall behind. For me, at this point, even then, you know, coming into my mid-20s, I still told myself that it was vitally important that I travel. Travel was like this goal of mine for most of my life.

Dennis: Had you traveled before?

Colin: No, not really. I’d been in a couple of places in the US. I’ve been out to New York. I lived mostly in Northern California and Missouri. But beyond that, I hadn’t. But I told myself travel was important because I loved reading. I was very much a pursuer of knowledge. I could tell, even there, that there were certain things I was missing out on. There’s some things that you just don’t write about or you can’t write about in such a way that it conveys the actual data that you’re trying to get from a real life experience.

Dennis: Very true.

Colin: I was aware of this but I was telling myself… I was goading myself forward in this lifestyle by saying, “You know what you’ll do. You’ll earn a million dollars and then you’ll retire young and then you’ll go travel.” That’s point A to point B; that’s the way I was going.

Dennis: That’s the typical model.

Colin: Exactly. That’s what you’re supposed to do. That was kind of the monomyth archetype at the time. The hero’s journey is that you go out to California and you make a million dollars while you’re in your 20s and then you retire and then you go travel and do it the way you’re supposed to do it.

It’s a very respectable type of path. People are really interested in that. They think it’s very cool. Older people respect it because you’re working so hard. Younger people respect it because you’re upsetting the system and disrupting the industries, blah, blah, blah. And so there was a lot of that momentum behind that lifestyle as well where you can’t just say… It’s very difficult to step back from it at any point to take a look at what you’re doing and why you’re doing it because there’s so much momentum.

Dennis: It’s almost like a drug, really. You get in that mode, right?

Colin: Yeah, exactly. So I had no reason to, until we took a trip up to the exotic land of Canada. First time I’d left the country, my passport was blank up until that point. And on the way back down, we stopped in this little bar in Seattle. We stayed overnight in Seattle and we’re in this like little underground converted bakery, hipster bar where it was like locally sourced organic cocktails and like a Latin jazz fusion band on the other side of the room playing.

Dennis: Of course.

Colin: My girlfriend, she leans over, and kind of just whispers in my ear, “You know, I think I want to move to Seattle.” And I, without thinking, just kind of lean over to her and say, “You know, I think I want to leave the country.” We turned toward each other and we just stare - don’t say anything, just stare - for what seemed to like a very long time because both of us, I think - discussing it later, I know - but, at the time, it seemed very clear that we were thinking the same thing that, “Oh God, I think we just broke up!”

Dennis: Without saying it.

Colin: Without saying it. And kind of what came out over the course of the rest of that night and the next couple of days driving back down to LA was that both of us were starting to realize that the way we were living our lives was not aligned with what we actually wanted to be doing. We had told ourselves that what we were doing was going to get us to where we wanted to be but she was an actor. Like she was a stage actor and she was working… running this business that was intended to allow her to do more stage acting. She wasn’t stage acting. I was a guy who wanted to travel and I was doing something that was intended to get me to a point where I could travel someday.

Dennis: But you weren’t traveling.

Colin: But I wasn’t traveling. And we both kind of realized, “Oh my God! We’re in our 20s. Let’s say we work another decade and both of us accomplish our goals, we still don’t get our 20s back. Let’s say it takes longer than that, which it usually does, we won’t get our 30s back either.”

We both knew, just from experience, we could always make more money. If I really need to, if I spend everything I’ve got, if I make some life mistake and I end up with nothing, I know how to earn money. Worst-case scenario, I take a job somewhere at something I don’t particularly enjoy, work my ass off, get back to where I am. But I can’t get more time no matter how hard I work.

Dennis: Very true.

Colin: That’s the one absolute finite resource that I was trading for something that actually wasn’t important. Something that I just thought might… that I might be able to trade for what I found to be important at some point.

And so the next day, after arriving back in LA - I was 24 now - I started a blog, which is what you do when you don’t know what you’re doing or how to get there. I started Exile Lifestyle. And my girlfriend and I decided on the way back that we entered into our relationship very rationally. We didn’t want to end up hating each other. We didn’t want to have a messy breakup. We had all kinds of agreements that if things went sideways, here’s the way that we’ll do it. We’ll stay friends, we’ll do this, we’ll do this.

We recognized that this was kind of a turning point where if we stayed together for the kids - the kids being our social network for our lifestyle that we were living and the businesses that we were running - if we stayed together for that, we wouldn’t be doing ourselves, or what we were trying to do, any justice. So we set a deadline four months in the future. At which point, we would have a break-up party and we would celebrate a wonderful relationship that had reached its logical end point and then go our separate ways.

Dennis: That’s so mature.

Colin: We had no idea if it was going to work because we hadn’t heard of anybody doing this before. It seemed perfect because we still care about each other today. To this day, when I go out to LA, I still visit her. She’s a great friend. She’s a wonderful person. I don’t know if we’d still feel that way about each other if we would have stuck with it just for the sake of sticking with it.

Dennis: Right.

Colin: To us, that made the most sense because it was a great relationship. There was nothing at all wrong with the relationship other than it being the wrong branch off of the trunk of the tree to get us to where we want to be; to be on the proper branch, toward the proper goal. We were lucky that we recognized it at that point before we got in even deeper, before that gravity of the situation became even more intense and the momentum was even hardcore and hard to pull away from.

But in the time in between, in those four months that we have, we both kind of figured out what we wanted to do with ourselves and what does “next” look like. We’ve never given ourselves the chance to consider what we actually want. What does that actually look like? How might we actually do that? How can we pay the bills? Both of us, obviously, going down different routes to figure this out.

For me the blog helped a lot because it allowed me, kind of in public, a way to sort out what I was feeling about this. The path I was taking. The experiments that I was running to try to figure out what made sense. I discovered minimalism, though that’s not what we were calling it back then because there wasn’t really minimalism blogs except for Leo Babauta’s blog. Basically that was just like the one. There weren’t many blogs back then. He had a great big blog.

Simplifying, stripping down to the essentials, focusing on what’s important and spending more of your time, energy, and resources - including money - on that core important stuff. This is something I kind of had to figure out. And then I learned what other people were calling it and then I started writing about it and it became a part of what I wrote about on the blog. At the time, it was very much like blindly wandering through a new environment and the environment was up in my brain.

Dennis: Right.

Colin: A space that I hadn’t really taken the time to explore.

Dennis: But in that four months, you were still running your agency work?

Colin: I was. Yeah. I kind of intended… I had this inkling that I could continue to do what I was doing just from the road. Because what I was doing was brand work and so some of it was actually building the logos and the style guides and the websites and such. But a lot of it was consultation. A lot of it was helping big companies and startups and stuff figure out their story; figure out how to tell that story and what components they’ll need to do that properly.

And that, in particular, the consulting stuff, I felt I could do from the road because it required fewer in-person meetings and such. That turned out not to be the case or at least not easily. I found that out later when I was in New Zealand. When I was 20 time zones ahead of most of my clients and the Internet, at the time there, was still dial-up in most cases.

Dennis: Oh my!

Colin: So I couldn’t send graphics or have a Skype call. So it was nearly impossible. But that was beneficial in a way too. That’s what goaded me toward becoming a writer professionally. At that point, I had never written a book for money before. I kind of realized that the impetus was there and that I needed to figure out a way to produce stuff that would allow me to maybe put it online. Maybe sell stuff continuously even when I’m not providing the service directly. So even when I’m not hands-on doing something, when I’m not in a place where I can connect to the Internet. I can still earn a living.

Dennis: Right. Because when you abandoned the agency, you thought you could take the agency on the road.

Colin: Right.

Dennis: New Zealand was your first stop then?

Colin: Second stop after Argentina.

Dennis: Argentina first, okay.

Colin: Yeah.

Dennis: So you picked up from LA, moved to Argentina for how long?

Colin: Four months.

Dennis: Okay.

Colin: Yeah.

Dennis: And then after four months?

Colin: New Zealand for four months.

Dennis: Right. During that time, you’re trying to run the agency.

Colin: Yeah. And so I handed off about half of my clients to other people who I knew that would take good care of them and continued to do the ones that were less hands on; that didn’t need me to show up at the boardroom and explain everything that I could explain over a Skype call. It was a lot of smaller clients but it was enough because my lifestyle…

Traveling full-time actually costs less than living in a townhouse on the west side of LA. My rent itself cost more than my entire lifestyle today. So I knew I wouldn’t need as much money. I still wanted money. Like I’m not allergic to money but I wanted to be sure that I had a realistic baseline and I was earning more than enough for that baseline.

And very fortunately, before I left, too, I was able to pay off all of my debt and I was able to ensure that I had some buffer funds in the bank so that I could make some of the expensive mistakes that I would no doubt make since I hadn’t travelled before, really.

Dennis: So you have some clients for a while which gave you some income.

Colin: Yeah.

Dennis: And then you started writing to create a new source of income that would support the lifestyle?

Colin: The writing actually started out as kind of a marketing thing where the blog and the first couple of books I put out, I put out for free and gave them away as a way to draw people in. The idea was that then the blog would help me generate leads for my consulting and for the agency stuff.

Dennis: That’s logical. Sure.

Colin: Yeah, yeah. It made sense. I didn’t want to make money directly from the blog. I don’t like advertisements on sites. So I tried to “do unto others” when it comes to the web and I didn’t want to do a bunch of pop-ups and market in that gimmicky way. Instead I had the blog, people came to know me, and then therefore they would think of me perhaps when they were looking for that type of work. That ended up segueing over to the books as a profession when I realized that the service thing was not going to fly with the type of lifestyle that I was living.

Dennis: Dial-up in New Zealand is not conducive to…





Colin: Oh my God! It was so slow. Even Starbucks, you had to pay like $10 at Starbucks to use their Wi-Fi and it was slower than what I had back when I was a kid.

Dennis: Unbelievable!

Dennis: Unbelievable!

Colin: It’s better now, thankfully.

Dennis: Not that much. It’s a little bit better.

Colin:  You can actually find high speed though and it’s free in a lot of cases. It’s changed a lot in the last like five or six years. Yeah.

Dennis: Right. That’s crazy.

Okay, so you started Exile Lifestyle; you started your blog and then how did you make the decision to go to Argentina?

Colin: I didn’t know where to go because I’d never traveled internationally, except for that quick drive up to Vancouver with my girlfriend at the time. Because of that - and also, I thought it would be a fun way to involve my audience - mostly because I have no idea where to go, I had my readers vote on what country I would move to. Just thinking, you know, “This will be fun.” It will randomize it for me, essentially, but it will give people the incentive to participate.

It’s a fun kind of gimmick like traveling the world, move to a new country every four months or so and your readers vote on where you go. And it seemed like a really easy story to tell. It’s something that differentiates from other people who are just traveling. But it’s also something that fit because my philosophy - what I suspected and, thankfully what’s turned out to be true - is that I could find the interesting and I could find the good and valuable and interesting to me, at least, anywhere I went. And therefore I didn’t really have anything to worry about.

If people sent me to a place that wasn’t Paris, you know - that wasn’t the type of place you’d think to go - I would still find the value there. And probably even more than I would at the incredibly touristy locations because it’s new, it’s different. You have to look a little bit harder. You have to learn a little bit more.

For me that’s what I was interested in learning anyway. I didn’t want the postcard version of a place. I wanted to see how locals lived. Go to the grocery store, rent an apartment. Live there rather than just pass through.

Dennis: Right. And not be a tourist but become part of the fabric as much as you can.

Colin: As much as feasible. It’s feasible to different degrees depending on where you go but as much as feasible.

Yeah, I mean I wanted to actually have an apartment where actual people live. Not in like the whitewashed part of town where it’s all McDonald’s and Starbucks. I wanted to be in situations where nobody spoke English and where I stood out like a sore thumb because I’m the biggest idiot in the room anywhere I go to; I don’t know what the smallest child knows. Because in those situations, it’s like going back to Kindergarten. Everything’s new and it’s a relatively flat learning curve. You can pick up a lot in a very short period of time because it’s all incredibly simple stuff but all completely new to me.

Dennis: True.

Colin: That was the experience that I wanted. Not like the big, ground-shaping, epic reporting type of journalism that you might expect but just like the simple everyday things that show you the foundation and show you the underpinnings of a given society. And then you can kind of grow upon that.

Dennis: Such as?

Colin: So, little stupid things. I get so excited about little stupid things.

In Argentina, people pay their taxes at the grocery store. You go to the check out line, you have your little tax form. You go in and you check out and pay your taxes just like you pay for milk.

Dennis: Interesting!

Colin: Stupid little… No one would ever think to write that in a book. It’s so mundane and yet it tells you a whole lot about how the economic situation works there and how Disco, which was the big grocery store in Buenos Aires at the time, how that fits in with the government. There’s all kinds of little connections that you can draw and figure out how these things cross-pollinate.

And then you can slowly, over time, build up a really broad, detailed awareness of things in a way that you can’t… I mean you could do but it’d be more difficult to do if you start from the top down and say, “Here’s my encyclopedic knowledge of this place. Now I’m going to try to learn all the little detailed things that make that up.” I was trying to start from bottom down and learn the simple ground level things that everybody who lives there knows and then build on top of that.

Dennis: Oh, interesting. Interesting.

So you started in Argentina, you went on to New Zealand. How many countries have you lived in now?

Colin: Like a dozen? I mean lived in for like four months or more, I want to say 11 or 12. I break it up. In between the four months, typically, I’ll do a couple of months either like road tripping, South America, or throughout the US, or doing train tours around Europe or whatever random thing kind of comes to mind that seems interesting.

And then a couple of times too. I’ve lived in Reykjavik three times. I lived there once - I was voted to go to Iceland - and then I went back twice. I was dating a girl off and on over the years, who lived in Reykjavik. And so we would get together periodically and play house and…

[both laugh]

Colin: Lived in Reykjavik during the winter and summer solstices.

Dennis: Oh really?

Colin: Yeah, yeah.

Dennis: That’s okay.

Colin: It’s a lovely city.

Dennis: I’ve only been to the airport years ago.

Colin: Oh, yeah. The airport’s not much.

Dennis: No airport’s a great deal. No. All airports are the same. Doesn’t count. Doesn’t count.

So you continue this lifestyle. How long are you going to do this, you think? Any idea?

Colin: I don’t know. My usual answer is until I find something better because to me this is every day.

This isn’t really an exaggeration, especially not on average, but like every day seems a little bit better than the last. I’m having so much fun. And this allows me to do exactly the things that I want to do and pursue every weird curiosity that I have and pick up every little hobby and skill and body of knowledge.

I’ve created all these little energy sources for that type of thing. Some of them business-wise so that I can continue to pay the rent but then some of them just experimental processes and methods for conducting projects to learn about music theory or to learn to play the piano. And to fit those into my life in such a way that I’m able to do it and focus on it the same way that I might have focused on stuff that I didn’t find particularly enjoyable or enlightening before.

The travel thing: I’ve been remixing a lot lately. And right now we’re sitting here in Wichita, Kansas, which is a weird extrapolation of my typical means of living. But I realized that after a little over seven years of doing the same thing - seven years that I did four months - a new country every four months, give or take. Little adventures in between. I realized that, at that point, what scared me the most - what seemed the most unfamiliar and weird and uncomfortable to me - was the idea of having to buy furniture. And the idea of having to go to the US, to a place where everything is so familiar, in a way, and live there for a relatively extended period of time - a year - that to me seemed like ages.

Living in the US seemed almost too easy. Like very friction-free compared to going to a place where you have to learn the language and learn the cultural mores and learn what foods are which and learn how to… which container is milk and which one is rat poison when you go to the grocery store. There’s little frictions and effort that you have to put in every day for simple things and to go to a place where that’s not the case, that, to me, seemed very interesting and scary.

I was at the premier for this movie that my business partner’s put out, The Minimalism Documentary, in New York. A reader of mine came up after the movie and asked me, “What’s the most exotic place you’ve ever been?” I kind of jokingly said, “Wichita, Kansas.”

Because I’d come here when my family moved from the Bay Area in California to Missouri when I was a kid. We had relatives just outside of Wichita. And we came out to visit. I was little 9-year old Colin. And the only thing to do in this little town was go to Walmart and buy ammo and then go out to a field and shoot at bottles. That, to me, was the most exotic, crazy thing I’d ever experienced in my entire life. And looking back, I realized that I still had not experienced that same thing.

I was joking about Wichita because most people in the US… the whole Midwest to them is just like this blurry, beige, boring…

Dennis: It’s like oatmeal. Right.

Colin: Yeah. It’s like not exciting in their perception. But to me, I realized that I’d spent so much time doing things that are exciting in that way where it’s like incredibly foreign and difficult, that what might be challenging and interesting now, today, would be to go to a place that a lot of people consider to be beige and boring. And go there and live find what’s interesting and see what life is like living in that way which is bizarre because, for me, this is something that’s...

Me having an apartment and buying my own furniture for the first time in seven years, and having to buy a car for the first time in seven years? So exotic and bizarre and interesting to me. And everything is new because I was a completely different person the last time I’d done all these things. So I didn’t even know what I liked in terms of furniture. I didn’t know what I needed in terms of car. And so I had to kind of do that process of self-discovery.

So this process now has been valuable enough that I’m going to do another year in the US. This time I had my reader’s vote on which state I would go to and they voted for Tennessee. After that, I’m not sure. I miss traveling internationally and there’s not enough speaking gigs coming in right now to keep me going back and forth quite enough that I’ll probably head back overseas. I’m not sure exactly what shape that travel will look like yet but I’m kind of allowing things to go as they will go and then basing those future plans on what happens.

Dennis: That’s interesting.

This whole lifestyle shift, going from the high-power job with the stress but the benefits that come with it; benefits: income, status and so forth and your social circles and whatnot. Now you’re on your own and you’re popping around the world to different points, 12, 13 different places around the globe. Back in the States where life is easy, as one who lived abroad for several years I can tell you, it’s very easy living in US regardless of where you are. What’s been the biggest challenge with this lifestyle of yours that you’ve chosen?

Colin: Part of it, I think… I mean there’s a lot of things that are little challenges. Like little silly challenges like the aforementioned buying furniture. I’m so accustomed… For seven years, I’ve only owned what I can literally carry on my back. So carry-on luggage has been the extent of my…

Dennis: Carry-on?

Colin: Yes. The extent of my real estate has been a laptop bag and a duffle bag for the past seven years. And so having anything above and beyond that is stressful for me.

Dennis: Why is it stressful? In what way? The responsibility or…

Colin: Partially that. I…

Dennis: Or it’s an anchor?

Colin: I like focusing. Like really, really hardcore focusing on the stuff that I’m doing at any given moment and being able to completely throw myself into something. Whether that’s writing a book or producing a podcast or learning a new skill or whatnot, I like to be able to set things up so that I know exactly what I’m doing. I don’t have too many distractions.

And owning a bunch of additional stuff feels too much like my past life, right? Just I had such - I had like eight computers for some reason - I just had so much stuff that I wasn’t using that I started to feel like Pharaoh hoarding his wealth so that the peasants couldn’t have it. So anytime I have stuff that I’m not using, it stresses me out and I feel like I need to give it to someone who will actually use it. Get it out of the hands of this person who is just hoarding it; to sit and gather dust.

That, philosophically, is kind of important to me at this point and makes me feel uncomfortable. But I feel great and I feel energized and very light and free anytime I have exactly the tools I need and nothing more than that. Then I don’t feel… It’s not a physical burden, at this point, but it still feels psychologically the same as if I was carrying all that extra stuff on my back. So little challenges like that. Like that’s a silly mundane thing but surprisingly big psychologically.

Dennis: I get on how difficult that is.

Colin: Yeah. Yeah. A lot of other things as well.

Self-perception is probably one of the biggest ones, too, where if you do something long enough, and especially if you do it in public and you become known to some people as like this guy who travels and then you go to live in Wichita, Kansas for a year, people are like, “So what’s going on here? Have you given up? Are you dropping out? Are you punking out on us?” There’s like that external side of it where you want to be sure that you tell the story correctly to make sure that people understand.

Not so much like if people stop following you or unsubscribe or something that’s going to happen regardless of what you do. There’s always going to be that. That’s cool. But if people don’t get that it’s an adventure, whether or not it takes place in Paris or Wichita, that you can grow and seek out self-growth whether it’s your own hometown or someplace far away. I wanted to make sure I got that story right.

And I also wanted to make sure that me, like looking inward, I was able to self-define really accurately and to make sure I knew exactly why this appealed to me so much and what I was trying to get out of it.

And the first couple of months that I was here, in particular, I spent a whole lot of time just deep diving into that to try to figure out how do I best spend this time? Like should I take a bunch of trips and just like have a home base and still travel a lot? Or should I like road trip around the US? I was thinking about doing that.

Eventually, I came to the conclusion that some of that would be kind of ruining the point. I wanted to see what a different lifestyle was like, at a different pace in a slightly different way. That would be kind of like trying to cram a different lifestyle. Trying to cram like a round peg into a square whole and trying to make… blend the two in an imperfect way. But that was really, really important. And something I wasn’t quite sure at first why I wanted to do this and why it seems so appealing to me.

Dennis: Do you have an answer?

Colin: Well, yeah. I mean now it is trying to challenge ceilings that I find myself with. Anytime I find myself with something where I’m like, “No, you can’t do that. That’s not correct,” or, “That is scary,” or whatnot. I almost, immediately, feel like I have to break that ceiling otherwise…

It’s almost like looking up into the sky and how terrifying would it be if the sky is like lowering above you. And if you do a lot of self-work and try to figure out what you believe and what you care about, then it’s very possible that you can limit yourself in that way. And so then your entire life becomes walled in and ceilinged in because you put these boundaries around yourself and say, “I will never do that. I can’t do that. I’m a guy who travels therefore I cannot live in a place that’s comfortable and cozy because then probably I won’t be able to grow. Probably I won’t have those stresses.”

And then you define yourself in terms of being somebody who is dependent on outside stimuli to grow. That was not somebody that I wanted to be. I didn’t want to feel like I had to keep moving constantly in order to iterate and to be the person that I wanted to be and to be happy. I didn’t want to feel like novelty was a requisite in order to have all of that.

Dennis: So what have you learned? You’ve been here now for close to a year.

Colin: Getting there. Yeah, a couple of months away.

Well, I’ve learned that… Actually, I enjoy this pace too. I don’t know what a melding would look like. I’ve been thinking a lot about that, like what happens after Tennessee because, frankly, I enjoy the hell out of traveling frequently.

Dennis: I get that.

Colin: But I’ve also been loving aspects of this. There is something very satisfying about being able to dig in and put down roots to a certain degree but also create structure and rituals. That’s something that I haven’t allowed myself to do very much while traveling because you never know what infrastructure you’ll have when you arrive at a new place. And so if your workout routine becomes dependent on certain piece of equipment and then you go to a new place and that’s not available.

I used to run a whole lot but in Kolkata, there’s no place to do that. You can’t do it socially. And all the roads are destroyed and it’s too crowded anyways. I found myself without a workout routine for several months because I was so dependent on that one way of doing things.

Dennis: Right.

Colin: My whole life was centered around portability. Now, I’m realizing that there’s certain things that I enjoy that are not portable and that I do much better when they’re not portable. One, being able to accept that and it not feeling like a clash of something fundamental about who I am. Me, as a person, does not need to be portable. That’s just one thing that I can do and one direction that I can go.

But then it’s also allowing myself to look at all these other things that I’ve ignored for a time. All of these things that require a kitchen or that require that you have certain equipment that can’t fit into a bag. I’m allowing myself to consider that stuff and not seeing it as off the table because it won’t fit in my bag. It’s something that I could consider. I would just have to reshape things a bit. And that’s been super valuable.

Dennis: A second bag.

[both laugh]

Colin: Exactly. I just have to bring one of those motorcycle trailers and haul it behind me.

Dennis: Thinking about four months in a given country and then trying to move on from there. I mean so much of it’s so new; you’re talking the language, the culture, the basics of daily life. And four months, in my mind, is just enough to scratch the surface in some respects and you’re on to the next thing whether it’s a tour, a travel tour about or whatever or moving on to another country.

You mentioned now you’ve taken up piano and guitar and so forth. You have time to focus and how you’ve set some structure and some routine and some discipline that enables you to focus on some new activities. You can’t do that easily, changing countries every four months and how do you keep up with practicing the piano or…

Colin: Yeah. I mean in addition to just the equipment. There’s so many things changing around you all the time. And, frankly, part of it, too, is that there’s so many opportunities and so many things changing around you that if you do not leave yourself open and flexible - like if you’re not malleable and you’re traveling - you’re missing out on most of what’s happening around you and most opportunities that come your way.

If I had any routines that said every morning you have to do this and if you don’t, you’re going to be off all day because you’re still accustomed to doing that, I mean half of what I was able to do, the first part of my day, I would have never gotten around to.

And maybe that’s an opportunity where you meet a stranger. They invite you out to some adventure outside of town. Maybe that’s… Trying out a different routine because they have the call to prayer every morning so you start waking up at a different time like at 5AM instead of your usual 7AM. You have to be really, really reshapeable to travel well, I think, in a lot of cases.

And being able to do that is super valuable and being able to MacGyver your way out of any situation, that’s super important too. That’s something that gets trained into you. You roll with the punches no matter what happens.

But I found myself starting to - not exactly look down on - but ignore the value of, I think something more structured and regular and routine. There’s value to both of those extremes. I was not allowing myself to consider that other side because it didn’t seem something that was possible anyway so I didn’t want to torment myself with that. And I kind of have - if I let it come out - there’s a slight OCD side to my habits and routines. So finding the balance between those things never seemed feasible, especially from the road or even particularly desirable.

But now, being able to explore both sides of that and find a healthy middle point where I’m still leaving myself open to opportunities and trying new things all the time, but also allowing myself to benefit from some of these structures and experiment a whole lot with different things that could maybe be portable at some point. But even if they’re not allowing myself to investigate that, that’s been valuable.

Dennis: Nice.

You’ve seen a lot. You traveled the world many times and all these different countries, different places in the US and you’ve had this full time career. You’ve got this unique career, if I may call it that. It’s full time. It’s unconventional, I guess, is the best word.

Colin: It’s generous to call it a career probably.

[both laugh]

Dennis: It’s a career, man! Look, you’re making it work, right? You’re able to sustain this lifestyle. You’re making money from speaking and writing and so forth. Power to you! A lot of jealous people, out there - including me - for making that happen.

Colin: I can’t believe it worked. I’m not wealthy. It’s not something that’s achieved that type of prestige. I mean maybe someday - there’s a lot of opportunities all the time. Some that I’ve passed on because they just haven’t fit with my overall philosophy and some that just have not emerged. But it is structured so that my basics are covered.

I make more than I need. My needs are very small. I don’t really have a lot of fundamental things that I have to pay for, thankfully. Most of the things that I love doing that I would do whether or not I was making money are things that I am able to make money from. That’s a very fortunate position to be in even if it’s not something that generates that million dollars that I thought I’d have by now back in my former life.

Dennis: What are some lessons you’ve learned along the way? Any insights?

Colin: Gosh, let’s see.

Dennis: That are transferrable to other people.

Colin: Yeah. You know, there’s something that was really pervasive back in LA and something that I find in a lot of otherwise really great people - people who were very ambitious and interested and intelligent and generally friendly - is that as soon as money comes into it or business comes into it then they become total sociopaths. There’s that, “It’s just business, nothing personal” type of attitude that people take - and that was so pervasive even with generally good people; and that we convince ourselves that the business space is a different space.

But what I’ve found - I mean at least in my experience and a lot of other people who I know and respect - if you treat people well and like do it even when you don’t have to and do it even if it costs you a little bit of something to do it, then, generally, you come out on top.

That’s partially… I’m not spiritual. You could call it like a karmic type of thing but I think it’s kind of, in general, that if you treat people well then they will wish you well. And if it’s in their power, they will do well by you as well. They, at the very least, will not go out of their way to hurt you if they can, whereas if you do people wrong and take the short term gain then you might make an enemy that then comes back to bite you. I don’t know if these people have never seen a movie or never read a book. The mistake that you make at the beginning comes back to bite you in the end.

But if you just do well by people and treat people like human beings then that’s good in life and it’s something that’s really great for traveling. Meeting new people, just not being a jerk and being generally friendly; being an addition to any place you find yourself, adding something of value.

And even then if you’re taking something away too, if you’re adding more than you’re taking away, then generally you’ll be welcome pretty much everywhere. You’ll be a good addition, a valuable addition to just about anything. At bare minimum you’re not sucking dry whatever group of people or business or society you happen to find yourself in. That, to me, has been like a really big picture thing that, for some reason, it’s not obvious. It wasn’t obvious to me either. I tried to do it out in LA, but that was just like compared to the other people that I knew so it wasn’t much of a focus. That’s a big deal.

I’ve been reading through all my old blog posts and going through and adding updates to them so I’ve been criticizing like my blog posts from years ago. There’s a term in there that I really like that I forgot about but “becoming your own Medici” where like…

The Medici were the Venetian - they had a pope in the family - they were very popular back in the day. Like in the heyday of Venice and they funded like Michelangelo and Donatello and a lot of the big artists back in the day. They were the sponsors, the patrons of these artists. And to me, I think, it’s vitally important that you see yourself as your own Medici. That you are able to bootstrap whatever it is that you’re passionate about and that means two things:

One, not losing your passion and recognizing that there’s an unlimited number of passions out there waiting for you to discover and cultivate them and you just have to be willing to follow your curiosity to find them. But then, two, a fundamental understanding of how to make enough money to pay for a roof over your head, to pay for money, or to pay for food on the table - whatever it is that you need - your base level requirements need to be covered.

And if you can do that, if you could figure out a way to iterate or to build your own business, or to even just work your way up in a career path. That, even if it is not your passion, if you can look at that as funding your passion as bagging groceries at the grocery store is not a sexy job but it more than pays for itself. If you’re able to pay the bills with that and use that then to free up a bunch of time that you can spend on your painting, or on your photography or on your writing, whatever it is that you’re really passionate about.

Dennis: I love it!

Colin: You don’t have to make money to directly necessarily off of your passion. It’s enough that you are able to spend a decent amount of time out of your day on that thing and focusing on that rather than trying to be the next big whatever. You don’t have to be a painter who’s selling their paintings for hundreds of thousands of dollars to be a great painter or to get something out of painting. You could be a terrible painter if we’re looking at it in terms of the business of painting. But if you enjoy it, that is worth funding. And if you see yourself as your own funder, then it allows you to kind of reorganize moneymaking capabilities and what your day looks like and prioritize accordingly.

Dennis: Amen! No, seriously, that’s so, so true and I love the phrase. I love the phrase, “Be your own Medici.” That’s classic. That’s classic. Thanks, man!

Colin: My pleasure.

Dennis: That’s great.

How can people get a hold of you? Or follow you, track you.

Colin: Yeah. My blog is exilelifestyle.com. My author page is colin.io. My podcast is called “Let’s Know Things”. And then I’m on pretty much every social network @colinismyname.

Dennis: Excellent. Thanks again.

Colin: My pleasure.


Dennis Hodges
Dennis Hodges


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