Dirtbag Rich Interview with David Six



David Six is a 40-something-year-old software developer, Triple Crown thru-hiker, and lifelong travel addict who has spent the last two decades figuring out how to work as little as possible while hiking, biking, and exploring the world. (@walkacrossoregon)

David breaks down how he built a life that lets him disappear into the wilderness for months at a time without running out of money. He explains how he went from high school drop-out to self-taught programmer, how he co-founded a ticket sales software company that now funds his adventures, and why he sometimes mails himself a laptop just to keep his business running while on trail. Unlike most thru-hikers, who treat long-distance hiking as a one-time adventure, David turned it into an ongoing way of life, balancing the need for income with his desire to spend as much time as possible moving through the world under his own power.

We discuss what draws people to thru-hiking, why long hikes feel like time travel, and the transition shock that hits hard when the journey is over. David reflects on his anti-authority streak, his deep-seated resistance to full-time work, and why, despite having a near-perfect job setup, he still resents it. He also shares how he and his wife (a nurse) use travel hacking and careful planning to fund their adventures, including multiple round-the-world trips.

Finally, David talks about his next big project: walking across the entire state of Oregon, from the Pacific Coast to the Idaho border, in the middle of winter.

Full transcript: dirtbagrich.com/david

Recorded in November 2024.

AI Notes

This is an AI-generated summary and transcript. Typos and mistakes exist! 

Summary

David Six, a self-described ‘triple crowner’ in the through-hiking world, discusses his experiences hiking the Appalachian Trail, Pacific Crest Trail, and Continental Divide Trail over a period of 24 years. He explains the concept of through-hiking, describing it as a series of hikes from town to town, with periodic stops for resupply and rest. David shares his unique approach of mailing himself a laptop to work remotely during his hikes, allowing him to maintain his lifestyle. He discusses the transformative nature of long-distance hiking, its impact on time perception, and how it has shaped his life. David also talks about his transition into a digital nomad lifestyle, starting around 2006-2007, before it became a popular trend. He describes his unconventional path into IT, starting a ticket sales company with a friend, and how this led to his current work arrangement that allows for extensive travel and hiking. David shares his experiences of world travel with his wife, including their creative use of credit card sign-up bonuses to fund a round-the-world trip. He discusses the challenges and rewards of balancing work, travel, and personal life, and his plans for future adventures, including a walk across Oregon.

Chapters

Introduction to David Six and his hiking experiences

 David Six introduces himself as a ‘triple crowner’ in the through-hiking world, having completed the Appalachian Trail, Pacific Crest Trail, and Continental Divide Trail over 24 years. He shares his longest period without a shower (19 days) during a trip to Africa that included climbing Kilimanjaro and going on a safari.

00:02:08 Explanation of through-hiking and trail life

 David explains the concept of through-hiking as a series of hikes from town to town, describing the routine of starting with food from town, hiking and camping along the trail, and then resupplying in the next town. He mentions his unique approach of mailing himself a laptop to work remotely during his hikes.

00:04:37 Motivations for through-hiking and its impact

 David discusses the reasons people undertake through-hikes, often as transitional events in life. He explains how the intensity and immediacy of the experience affects time perception and can be transformative. David shares how through-hiking has become an ongoing part of his lifestyle.

00:11:47 David’s journey into IT and remote work

 David describes his unconventional path into IT, starting with dropping out of high school and finding tech jobs in the late 90s. He explains how he started a ticket sales company with a friend, which eventually led to his current work arrangement allowing for extensive travel and hiking.

00:56:08 World travel experiences and creative financing

 David shares his experiences of world travel with his wife, including their round-the-world trips in 2014 and 2017. He describes their approach to travel, emphasizing overland journeys and local experiences. David also explains how he creatively used credit card sign-up bonuses to fund their 2017 trip.

01:06:06 Balancing work, travel, and personal life

 David discusses the challenges and rewards of balancing his work in IT with his passion for travel and hiking. He talks about his wife’s career as a nurse and how they’ve managed to save money and buy a home while still maintaining their adventurous lifestyle.

01:09:03 Future plans and closing thoughts

 David shares his plans for a future project of walking across Oregon, from the Pacific Coast to the Idaho border. He discusses how this project will be another experiment in balancing work and travel. The conversation concludes with David expressing gratitude for the life he’s been able to create.

Transcript

Blake Boles 00:00

David Six, welcome to Dirtbag Rich. 

 

David Six 00:03

Hi. 

 

Blake Boles 00:05

What is the longest you’ve gone without taking a shower? 

 

David Six 00:08

I believe it’s 19 days. 

 

Blake Boles 00:12

And was that recently, just while you were at home? Cause you… 

 

David Six 00:15

No, that was on a trip that I was in Africa and went up Kilimanjaro and went on a safari and my lodging was just a little not the nicest lodging and access to water and showers was limited a lot of camping and probably that was a mistake. 

 

Blake Boles 00:42

Interesting. I was hoping this question would lead you into discussing long trails, but we are going to get to your world travels and your your overland travel. But let me redirect you. Tell me about some of the long walks that you’ve been on, in which apparently you showered more frequently than every 19 days. 

 

David Six 01:02

So, I am what is known in the through hiking world as a triple crowner. And that means that in North America, I have hiked the Appalachian Trail, the Pacific Crest Trail, and the Continental Divide Trail. 

 

David Six 01:17

There’s also a bunch of other hikes that I’ve done that are shorter or sections I’ve also done some bike touring and things like that. But yeah, that was a process that I did over a period of 24 years in sections where most people go out and hike one whole trail in a single year in a single season say they take, you know, three to six months to do a trail. 

 

David Six 01:41

For me, it would be going out anywhere from a weekend at a time to a month or two at a time. 

 

Blake Boles 01:50

For people who don’t know anything about these long trails, maybe they’ve heard the names before, just tell us a bit more about them and what it’s like to hike them, what constraints you’re working with, and then maybe why people do this in the first place. 

 

David Six 02:08

Yeah, so the way to think about a long hike like that is that it’s really just a series of hikes from town to town. And so for example, if you’re on the Pacific Crest Trail, and you’re in Oregon, maybe you’re hiking starting from in one section up by Mount Hood. 

 

David Six 02:31

And so you start out with food that you’ve brought from town. And then you hike up around the side of Mount Hood camping each night along the way, camping in the back country. So that means putting up a tent at the side of the trail, not necessarily anything that you might recognize as a designated campground or anything. 

 

David Six 02:52

And then reaching a road crossing or hiking out from a trail at the end. In this case, that would be in the Columbia River Gorge at the bottom of the gorge. And then going into town again, hopefully getting a shower again, maybe a night in a motel, and buying some food again, or picking up a food drop from a post office. 

 

David Six 03:13

And then, you know, when you’re ready heading out for the next section again, in my case, my kind of routine is that I usually take off a day or half a day a week. And in hiking jargon world, that would be called a zero day. 

 

David Six 03:29

That’s a day that you don’t hike at all or a narrow day, which is a day where you hike a really short day because you’re going into or out of town. In my case, what I do that’s unusual or what I’ve done that’s unusual is that I sometimes mail myself a laptop. 

 

David Six 03:47

And that’s because I work remotely. And I need to be available to fix any issues that arise. And so that means working in town when oftentimes my friends are going to the bar or relaxing or whatever. 

 

David Six 04:04

But that’s sort of the compromise that I have to have to make my lifestyle work. 

 

Blake Boles 04:10

And now why do people walk these trails in general? So you can speak for yourself and for the greater through hiking community. What’s the appeal to being out there for three or four or five months? And as you said, it’s, it’s not this continuous hike that some people think it is you’re stopping, you’re pausing, and you have these zero days. 

 

Blake Boles 04:31

Um, but still, why do you do it? It’s a bit psychopathic, right? 

 

David Six 04:37

It’s definitely a bit masochistic. Thank you, better word. Yeah, I think broadly kind of zooming out and looking at the community, it’s something where it’s oftentimes a transition event for people. And it’s generally, a through hike is generally something that someone does in one year. 

 

David Six 04:58

And I would say most of the community does one, maybe two through hikes, and it’s not really normal to do more than that. You gotta be a chronic weirdo or have some kind of special lifestyle accommodation to do more than that, because the average through hiker, the way that this works for them is that they save up money and then quit their job, move out of their housing. 

 

David Six 05:23

It’s a big transition kind of event. So oftentimes it lines up with somebody who’s in college, somebody who just retired, somebody who just went through a divorce. These are sort of the normal contexts for Americans to have this kind of a thing. 

 

David Six 05:41

And so the why for them often is that they’re going through a change already, and this is something that’s gonna be transformative for them. And in my case, it was something that’s been really transformative for me, but in an ongoing way. 

 

David Six 05:56

And I really look for that. Like one of the things about it that’s different from the other kinds of activities that you might do or other kinds of travel that you might do, is it’s so physically intense and it’s in environments that are so, that are so involving and so engaging and so immediate. 

 

David Six 06:18

You’re really living in the moment out there that it definitely affects your time perception. And so it sort of stretches out the perception of time. And in doing that, you’re having a new experience, you’re encountering a lot of new things, a lot of change day to day. 

 

David Six 06:36

You have this time perception of extended time. So if I go on a month long hike, honestly at the end, it feels like relative to my home life, that three to six months has passed. And in a weird way, it’s almost like time travel, like it creates a feeling of life extension in doing that. 

 

David Six 06:58

Where the just sort of normal day to day routine of a normal home life is one where, because there aren’t new experiences, at least for me, it’s kind of like, well, what did I even eat that day? What went on that day? 

 

David Six 07:11

It’s kind of blurs together. 

 

Blake Boles 07:14

It makes me think of special relativity. If you travel near the speed of light or you travel near an extremely massive object like a black hole, then your clock actually slows down relevant to maybe a carbon copy that you have back in a stationary object like an earth. 

 

David Six 07:36

And actually, I’ll say for most people, it’s so transformative that it creates challenges once they’re done, once they finish the hike, because they go home, they don’t feel that way anymore. They don’t feel that intensity and immediacy of their lives. 

 

David Six 07:52

And then they struggle to do the things that they did before to go back to having a normal life. And so for me, as with a lot of other folks in the community, I just never really fully went back to having a normal life after my first long hike. 

 

Blake Boles 08:10

This is why I wanted to talk to you, David, because there’s a lot of people who have done long distance hikes out there, but as you said, it’s often a one time thing or maybe you get, you’re lucky, you get to do it twice and it’s transition and you go back into something that then feels more normal and stable. 

 

Blake Boles 08:25

But you have found a way to really integrate long distance hiking into your life for multiple decades and not just wilderness hiking, but foreign travel and bike touring, all sorts of adventures. And maybe you’re doing something a bit different, like mailing yourself a laptop and do it, you know, smash the keyboard a bit while everyone else is kicking back on their zero day. 

 

Blake Boles 08:49

But it sounds like you really have found this sustainable long-term balance between time spent in nature and wilderness and outdoors and travel, and then also having a long-term foundation of financial stability and not worrying like, what’s my next job going to be? 

 

Blake Boles 09:10

Am I painting too rosy a picture? Is this actually what your life is like? 

 

David Six 09:16

There’s been a lot of times when I thought that it wasn’t going to continue as such or like that, uh-oh, this is finally, you know, finally, I’m going to get to a situation where I won’t be able to travel as much, but I’ve just been really lucky and really, that’s the way that I’ve always thought about it because it wasn’t, it wasn’t a deliberate process to get here. 

 

David Six 09:37

It was incremental, you know, basically the root of this is that I was living in DC. That’s where I’d grown up and, uh, working for a company that I’d helped start, uh, you know, small company, um, with a friend and he moved away. 

 

David Six 09:54

He moved to Florida and then suddenly I realized, oh, you know, maybe I don’t need to be in DC anymore. And then that sort of opened up the door to, well, my income’s not going to change. So maybe if I change my location to some place that’s less expensive, even if it’s just a temporary place, then maybe it opens up more things that I could do. 

 

Blake Boles 10:17

You’ve told me that you were a digital nomad before it became cool to be a digital nomad because you started around 2006, 2007. Uh, yeah. So when Tim Ferriss published the four hour work week, you were, you were not deeply impressed or, or shocked. 

 

David Six 10:35

No, I remember I remember skimming it and thinking like, yeah, yeah, yeah, that’s what I do. Like, in my case, the thing that’s different, I think, from a lot of other people that do what I do in terms of work is just that we completed most of the development on the project. 

 

David Six 10:52

You know, and we’ve had we’ve had term periods where the intensity of development will increase again for a while. But most of the code was written, I’d say the last big round of coding was probably, you know, eight, nine years ago. 

 

David Six 11:09

And so since then, it’s mostly maintenance and dealing with emergencies. And so that means that, yeah, there’s weeks when I work 20 hours, but there’s also weeks when maybe I just work a couple hours, maybe four hours. 

 

Blake Boles 11:23

All right, let’s, let’s back it up. Just like explaining through hiking to people, because at this point, it sounds like you just found a, a lantern that you can rub and a genie comes out and that genie gives you money. 

 

Blake Boles 11:34

Uh, how did your, tell me about starting this tech company with a friend. I mean, what’s the actual product or service and then how did your role evolve within that? 

 

David Six 11:47

So I had an unconventional path into IT. I dropped out of high school and was already doing a little bit of sort of contracting work in high school, contracting with the school system, helping build computers for teachers and things like that, and being a teaching assistant with some of the IT programs. 

 

David Six 12:13

And that was mostly all self-taught stuff. And then I was lucky to stumble into a couple great jobs. I was a teenager. It was the end of the 90s. And first I found a job at a tech firm where I was just kind of doing hardware stuff. 

 

David Six 12:32

And then that company started doing layoffs at some point when we lost a big contract. And I managed to find another tech job from that, learned programming there. And then while working there, we ran some web development user groups or community meetings where developers would get together and discuss new things that they were doing or problems that they were having. 

 

David Six 12:59

And I didn’t know this, but at one of those meetings, my then boss, my previous boss, had made me a door prize, which meant that somebody coming to the meeting was going to draw this drawing and get a training session with me. 

 

David Six 13:20

And that training session was with my now boss. I went out, gave him a session, showed him the web development stuff that I do because I’m a web software guy. And he basically concluded, well, I’m not going to be able to do this, so I just want to hire you. 

 

David Six 13:39

And initially, I said, I’m not sure if that’s a good idea because I was used to having a normal job, used to having a 40-hour workweek steady income. And I was worried that starting a company with him was going to be too disruptive with my income. 

 

David Six 13:59

But that summer, I went on a long hike, and I think it was about three and a half weeks. And the whole time I was on the hike, I was thinking, I really don’t want to go back to this regular kind of 40-hour-a-week desk job. 

 

David Six 14:15

I really should start this company. So I came back, and we decided to start the company. He was working in the music business. He’s a musician. And he realized that he was tech-savvy enough, and a lot of the venues and artists that he worked with were asking him to do kind of IT stuff. 

 

David Six 14:40

And one of them really wanted to do ticket sales. And so he decided to start this ticket sales company. And he knew he couldn’t do all the development himself. So he was hiring me to be a partner on that. 

 

Blake Boles 14:56

Okay, so you just created an entire ticket sales web platform. Yes, single handedly platform. 

 

David Six 15:05

Um, so I brought on a friend, somebody that I knew actually, this is going to date me, but through live journal, um, exactly, exactly. One of the early social media websites. Uh, I had a friend who was a pen pal and he was up in Canada and I invited him to come down. 

 

David Six 15:25

So, he came and stayed in my boss’s house and did a bunch of the development with me at that time, kind of working for cheap and, and, and getting a good reference on his resume, um, as we were starting things. 

 

David Six 15:40

Um, and we’ve brought on some other contractors, some other people that are remote, um, worked with some folks in India. Um, that’s all kind of fun. 

 

Blake Boles 15:51

And at what point were you able to, to walk away from being heavily time invested in this company and essentially be a, become a consultant to the, the company that you helped create. 

 

David Six 16:04

I’m going to introduce one more character in this, which is starting in 2004, I started working for a retail chain, a travel and outdoor store. And part of that was that working for them a certain number of hours meant that I could get health insurance. 

 

David Six 16:25

And I was able to transfer within that company when I moved out West in 2007 and keep my health insurance going. And this was a company that would allow me to take kind of leaves of absence. So I could take unpaid leave, say, three, four, or five days here or there without much of a fuss. 

 

David Six 16:49

And once a year, I was allowed to take a leave of absence because I had a good relationship with my bosses. So I could take up to 12 weeks off. And usually for me, that meant I would take the whole 12 weeks off. 

 

David Six 17:02

And in that time, then I would go and do a big adventure and remote work off and on when I was doing it. The first big one that I tried to do after moving out West was a bike tour where I bicycled from New Mexico from outside of Albuquerque up to Michigan. 

 

David Six 17:22

And that time, I actually did not bring a laptop with me. In hindsight, I kind of wish I had. And believe it or not, I would go to internet cafes or to FedEx office, Kinko’s type places, or to libraries and get online and actually remotely log into a server and then make fixes for my boss. 

 

David Six 17:51

And this is over a period of time. Yeah, yeah, yeah. It’s also long enough ago that I used just like free state highway maps to navigate. I had no GPS, I had no smartphone, and I had a CD player like listening to CDs while I was biking. 

 

David Six 18:08

So yeah, it’s ancient history. 

 

Blake Boles 18:10

You are an original gangster. 

 

David Six 18:14

Um, but yeah, that, that gave me a chance to kind of iterate and practice what it would be like to, uh, try to travel while also working. And at the end of it, my boss was kind of frustrated and I realized like, you know, this isn’t, this isn’t productive enough. 

 

David Six 18:29

And so the following year I hiked the Colorado trail. So I hiked 500 miles across Colorado. And what I tried that year was hiking with, uh, friends and having two cars and always leaving a laptop in one of the cars and then going into town and doing work, taking a couple of days off in between sections. 

 

David Six 18:50

Um, that was a pain in the butt because sometimes in Colorado that meant eight hours of driving at the end of a week, just shuttling the cars around again. Um, and that really kind of disrupted the hiking experience for me too much. 

 

David Six 19:07

And that’s kind of how I got back to this idea of mailing the laptop, which I had done a couple of times before that. 

 

Blake Boles 19:14

Okay. Let me see if I got your equation, uh, your, your financial, your, your work and employment equation down here. So you’d be working for the outdoor retailer. Uh, was that part time or full time? 

 

David Six 19:27

That was part time. 

 

Blake Boles 19:30

to get health insurance and other benefits. 

 

David Six 19:33

Initially, I’ll back it up just to say that before I left DC, because DC was expensive. I was actually contracting for my previous job, doing teaching sessions. I was working for the startup, which wasn’t earning that much money yet. 

 

David Six 19:48

And then I was also working for this outdoor retail company. And so I was really working six days a week. And now I look back and it’s like, that was insane. That was not sustainable. And then once I moved to New Mexico, it was more like 20 to 25 hours a week doing outdoor retail. 

 

David Six 20:06

And then, say, 10 to 20 hours a week doing development. 

 

Blake Boles 20:12

And just to fast forward, what is it now? 

 

David Six 20:15

Lately, so I left the outdoor retail company in 2013. And so I’ve just been focused on my software work since then. And it really kind of is seasonal, it sort of ebbs and flows with emergencies that arise. 

 

David Six 20:34

You know, sometimes we’ve had some security issues, and then it’s been an emergency. And then I’m working, I’d say I’m rarely working more than 30 hours a week. And in the past week, I think I worked about eight to 10 hours. 

 

Blake Boles 20:48

Okay, so it started out with part-time at the outdoor retailer, giving you, uh, as much time off as you, as you want. And also some health insurance. Well, at the same time working on these, these tech consulting or teaching side projects, eventually the tech stuff became enough of a sustainable, substantial income that I assume you just were able to purchase health insurance on like the open market. 

 

David Six 21:16

Well, that’s the other thing that happened. Without getting too political, Obamacare was passed and that meant that there was state marketplace healthcare exchanges. And I had previously tried to buy a private healthcare plan and actually was turned down, which was bizarre. 

 

David Six 21:36

But hey, that’s the United States. But once the state marketplace plans were out, then I could buy that plan. Then I no longer needed the outdoor retail job for my health insurance. 

 

Blake Boles 21:48

Got it. So now here we are and you’re working something like 10 to 20 hours a week depending on on which fires need to be put out. 

 

David Six 21:58

Yeah, and over the summer while hiking, it was really more like four to eight hours a week. 

 

Blake Boles 22:03

Okay. Yeah. Okay. Very cool, David. I am curious about your relationship to your work now that we know the details because I get the feeling that you don’t derive a lot of like purpose or meaning like you don’t feel like you’re saving the world in some way with the tech work that you’re doing. 

 

Blake Boles 22:24

Correct me if I’m wrong. 

 

David Six 22:27

Yeah, I mean, this is a ticket sales company. The product is useful for people, but it’s not that I’m passionate about ticket sales. Honestly, to confess this, we sell tickets for events. I’ve never been to a single one of our events. 

 

David Six 22:44

I do like going to shows, but it’s just not usually what I’m interested in. And I like tech work. I find software development, when it’s magic, it’s kind of like play, where think of like messing with a Rubik’s Cube where you’re sort of flipping around the pieces and trying to figure out a problem. 

 

David Six 23:12

And when it’s good, you can even get into kind of a state of flow where you’re really not thinking about your other concerns and whatnot. But the longer I’ve been in that business, the less and less that happens. 

 

David Six 23:28

And the more my driving thing is always what I’m planning or what activity I’m on. I’m somebody who’s generally looking to the future. And so I’m thinking about what’s the next hike? What’s the next trip? 

 

David Six 23:44

And then also my identity is definitely tied to my interpersonal relationships. I’m married. I’m super lucky. My wife’s great. And she’s really supportive in me. She was always clear that she wanted me to finish the Triple Crown. 

 

David Six 24:03

And so she’s part of that anchor of my identity that maybe other people might get more in their work. 

 

Blake Boles 24:10

Mm-hmm. You have previously told me that your sort of default setting is to hate any job 

 

David Six 24:19

I feel like, I think this is the term I use with you before there’s kind of a hedonic equilibrium, which is to say like, I think people have maybe like an internal self-concept around this that they sort of revert to this. 

 

David Six 24:32

And I feel like there’s some part of me which just like has a little bit of resentment of authority and I kind of can’t help that. And that was one of the things that probably led me to having this kind of different kind of life. 

 

David Six 24:48

And so I think my job situation objectively is fantastic, but that doesn’t mean that it doesn’t stress me out or that I don’t really get cranky about it. I take it for granted, but you know, push comes to shove, it’s definitely something that I’ve intentionally continued to cultivate. 

 

Blake Boles 25:12

Uh, this intrinsic dislike of authority, is this also the root cause for you leaving school in your, your final year of high school? Can you tell me more about that? 

 

David Six 25:23

No, I would say that for me felt like, I don’t know, I think there was like, this is really old, this is stuff that I saw when I was a little kid, but I think in there was an episode of I Love Lucy and also an episode of the show Laverne and Shirley, which nobody under age, you know, 35 has probably even heard of, but where there’s this conveyor belt going down and they have these jobs where they have to, 

 

David Six 25:51

you know, do something on a conveyor belt, grab things, change things. And in both situations in both shows, they’re getting completely overwhelmed and everything’s going wrong and then they’re going to lose their job. 

 

David Six 26:01

And that’s kind of how I felt about my high school experience, which is like all these assignments are getting thrown at me. And once I start to figure out what’s going on and get my head around something, then we’ve jumped into the next thing and just this sort of conveyor belt of scores and grades on things. 

 

David Six 26:24

And if I need more help on something, I don’t necessarily get time for it. And it’s just not the way that I operate. It didn’t work for me. It felt a little bit too much like a, like a factory system. 

 

Blake Boles 26:39

I feel like I’m putting my hat on from my previous podcast off drill learning now, but I want to dig in a little bit more. Did you, did you kind of drop out impulsively, like without a plan? You’re like, I just can’t handle this anymore. 

 

Blake Boles 26:52

Were you aware of, of homeschooling or unschooling or alternative schools? Uh, did you like go to the library and realize that you can get your GED and you can still have a normal life and everything will be okay. 

 

David Six 27:06

That’s a great question. I was kind of early to all of that. And so the internet was pretty limited still for me at that time. This is like the end of the 90s. And so I’ll say I’ve always been a little bit ADD. 

 

David Six 27:23

I can remember being a little kid, being in elementary school and having some big project that I was supposed to be working on for weeks at a time. And then I’m just staying up all night doing the project the night before it’s due. 

 

David Six 27:38

Because it was hard for me to break it down into smaller pieces and do it gradually over time. And then the other thing is I’m kind of a night owl. I’m not great with alarm clocks. And high school specifically was set up so that we were getting up pretty early. 

 

David Six 27:56

At my school at that time, it was getting up like 6 AM or before 6 AM. And so I was just sleep deprived all the time. So I’m not at my best to begin with. And I just sort of was gradually showing up less and less. 

 

David Six 28:18

I think my GPA started to suffer. And the one thing that I did have that I really enjoyed was a lot of extracurricular activities, like involved in tons of different programs at the school. And my GPA got low enough that I was no longer eligible for those programs. 

 

David Six 28:35

And then that just made me feel kind of depressed about the whole thing. And then eventually I think my parents got a letter that I had been absent more than 25% of the time. And then just finally was just not going. 

 

David Six 28:52

And then they got a letter saying that I’d basically been dropped out by virtue of not showing up. And I remember going to a family counseling session where it was like, I don’t think my sister was there. 

 

David Six 29:10

I’ve got an older sister, but I think it was my parents and I. And the counselor was saying, you’ve got to get yourself together. You’ve got to get back to school. You can’t just get a GED. You’ve got to go and take classes for it. 

 

David Six 29:23

And I don’t think he knew me at all. And I don’t feel like I had a good voice to sort of express my needs at that time in that context. And ultimately, I was actually going back and forth to see a therapist where I would pass by a copy shop and chat with a guy until he offered me a job. 

 

David Six 29:46

And then the job at the copy shop meant that I met clients at the copy shop. And one of those clients was working at an IT firm. And that’s how I got the job at the IT firm. 

 

Blake Boles 29:57

If you didn’t drop out of school, you might have never ended up in the IT and dah dah dah dah dah. 

 

David Six 30:03

There’s absolutely a scenario where I just live in D.C. and have kids and am miserable. Like, that was at least a 50-60% chance. Not to say that kids would be misery, but just sort of like being anchored to things like an alarm clock. 

 

David Six 30:18

I could see, oh man, that would be awful for me. 

 

Blake Boles 30:23

And I think it’s funny that there are so many people who are labeled ADD or something similar by the school system who will then go on to like meticulously plan a long distance hike over five months. 

 

Blake Boles 30:36

And it’s so much about autonomy and sense of control more so than any lack of actual attentional capacity. 

 

David Six 30:46

I mean, for me, my experience of it is that it is a motivation problem. And the motivation problem is that it is harder for me than it appears to be for some other people, for me to motivate myself to do things that I hate doing. 

 

David Six 31:00

And so that drives my decisions. 

 

Blake Boles 31:04

Do you think that you’re unique in this way? Let’s just say, among the through hiking community, like the other outdoor fanatics who you’ve run into and befriended, do you feel like they’re similar to you in this personality, this anti-authority, and like, don’t tell me what to do personality trait? 

 

David Six 31:24

Yeah, but I think that it’s not just the anti-authority thing per se. It’s definitely a factor, but I think just to back it up a little bit, one of the things that I experienced growing up is that my father was always really busy with work and never got the amount of time off that he wanted and never felt like he had the resources or the willingness to spend the money to do the big adventures that he dreamed of. 

 

David Six 31:54

He always fantasized about visiting the Grand Canyon, and he’s still around. He’s retired, but my mom’s health isn’t great, and he’s never been to the Grand Canyon, and not for lack of me trying to twist his arm and to get him out there. 

 

David Six 32:12

Not really something my mom would be interested in, but I saw that his sort of dream fulfillment never really came. Growing up in D.C., I was a latchkey kid. My mom worked, my dad worked, for my dad sort of facilitating all of that and making that happen meant that he was often out of the house 10 hours a day, something like that, with commuting time. 

 

David Six 32:39

He’s a real workhorse. He is a real workhorse. I just saw it felt like he was disconnected from the kind of dreams that he had, the fantasies of the kinds of things he would want to see and do. I think that that is a big part of my psyche, that I feel like I’m living out some of his dreams in a way. 

 

Blake Boles 33:09

Yeah. Yeah. And you took a cue from this negative example of someone who’s working all the time busy. I mean, doing it for their family ostensibly and yeah, but never got to go to the Grand Canyon. It’s not that hard to go to the Grand Canyon. 

 

David Six 33:25

No, no, no, it shouldn’t be. But no, we grew up, you know, our finances weren’t great when I was little. And my dad joined the military to get out of upstate New York where we had lived. And he was just lucky. 

 

David Six 33:44

DC really had a rising economy, you know, had gone from being a really dangerous place to him being able to get promotion after promotion and rise up through the ranks to where once he retired, you know, things were really comfortable for them. 

 

David Six 34:01

They kind of had the baby boomer cliche of like buying a cheap house in the suburbs and fixing it up gradually over time and then having equity because of that. 

 

Blake Boles 34:13

So did you have positive examples that led you toward the kind of lifestyle that you’re leading now, uh, anyone in real life or books, movies, TV shows, other media? 

 

David Six 34:26

in kind of like, well, yeah, I think so. I mean, I started reading some travel books. I’ll say the one thing that I was lucky about is my grandfather, when I was 12, dragged me to Europe. And I say dragged, I was excited to go, but I didn’t fully understand what I was getting into. 

 

David Six 34:49

He was really into amateur photography. And so what he wanted me there to do was to carry his camera equipment and hand him lenses, but also to cook him dinner at least half the time. 

 

Blake Boles 35:03

a bag boy and a personal chef. 

 

David Six 35:05

Yeah. And so he’s also hard of hearing. And so he wanted me to liaise between him and the world in all these countries in Europe where he didn’t speak the language and I didn’t speak the language. And he wanted me to navigate train timetables and things like this. 

 

David Six 35:21

And it was kind of jumping into the deep end initially. And then I just sort of started to figure it all out. And this trip, there were two trips, two summers and each one was about a month long. And it gave me a window into this kind of extended travel and also a window into different kinds of lives. 

 

David Six 35:46

I mean, even just going to European country, you see examples around you of people who have a different kind of life, more balance, more time off, more prolonged vacations, especially something like taking August off. 

 

David Six 36:02

And then fast forward, I read a bunch of travel books. As I got a little older, I went back to Europe with a girlfriend when I was like 19 and spent a month over there, you know, twisted my boss’s arm at the time for unpaid leave and just had a rail pass and just sort of drifted around and spent a lot of time reading books and walking. 

 

David Six 36:28

But I didn’t really know what my kind of passion was in terms of travel yet. And then I think it was in 2000, I was out on a hike with a friend. And we can go in as much detail as you want on this particular story. 

 

David Six 36:45

But let’s just say, I wasn’t really much of a hiker then I didn’t really have any idea what I was doing. And I was out on the at the Appalachian Trail in Virginia and Shenandoah National Park. And during the day on this hike, this this very unprepared hike, my friend and I ran into a guy coming the other direction coming from the south. 

 

David Six 37:07

And I asked him where he was coming from. And he said, Georgia. And he was a thru hiker. And he was the first sort of one on one encounter with a thru hiker that I’ve had kind of doing the activity. He had a tiny little backpack, he stunk, he had a big beard. 

 

David Six 37:24

And he answered some of my questions and gave me just enough information that it was like, it was like this light bulb went off. And suddenly, there was nothing else I wanted to do. And that was a big transformation for me, because I had been the kind of like it vampire before that, where I was staying up all night programming and avoiding the sun and sleeping late. 

 

David Six 37:47

And this gave me something that I could connect with, that was totally different. And that made me feel healthier and made me feel better about my life and made me feel more optimistic about things. 

 

Blake Boles 38:02

Yeah, I feel like there’s so many parents who have these vampire kids often science and are just like, how do I convince this kid to, to go enjoy the outdoors and exercise and fresh air? And it’s funny, you need a moment like this, where essentially you, it’s like you’re in your own role playing game and you stumble into this, this other character and, and they somehow inspire or, or infect you. 

 

Blake Boles 38:30

And you can’t control this. You can’t, you know, this could have happened to you in Europe. You could have met someone else who inspired you in a different kind of way, but you happen to be hiking in Virginia, in Shenandoah, and you ran into the stinky through hiker. 

 

Blake Boles 38:44

Yeah, yeah. 

 

David Six 38:45

Well, I think I think looking back now, it does that kind of activity does fit with me in some ways that other things don’t fit as much. There’s something about a long term travel, long term outdoor travel, something that’s physical that gives you the kind of experience that you don’t get if you say fly to Denver, rent a car, drive up to Rocky Mountain National Park and go to Overlooks and hop out of the car and take pictures. 

 

David Six 39:20

That doesn’t pull you out of the sort of inertia of your home life enough to be transformative if you do that kind of travel. I’m not judging. For a lot of people, that’s what they really want to do. 

 

David Six 39:33

That’s what’s comfortable for them. For me, I realized the sort of exercise, the challenge of that, realizing that the abilities in my body, becoming more body aware was something that really made my life so much better. 

 

Blake Boles 39:52

And I think for a lot of people who I interview on this podcast, it’s this extended time in nature, but not just sitting around and observing nature, but moving through nature in a human powered way, you know, feet or pedals or something else, uh, that is the secret sauce because it changes your state of mind. 

 

Blake Boles 40:11

Can you speak to that a little bit? Like how your brain changes how you’re thinking or your emotions, um, how they’re different from when you’re back at home in the city, especially if you’re in like through hiker mode. 

 

Blake Boles 40:24

Yeah. 

 

David Six 40:25

Yes. So I feel like I essentially have kind of two identities. I have the identity of David, who, you know, has responsibilities at home, and who, you know, enjoys being at home in Portland, Oregon and the city. 

 

David Six 40:42

You know, I have a dog and I have spent a lot of time walking him and I spent a lot of time going around to restaurants and doing things in town with my wife. But then I have the persona of 6-2 and 6-2 is my trail name in the trail world. 

 

David Six 40:59

When I put on my hiking gear, when I get my backpack on, when I get the clothes on, I sort of become 6-2 again, I kind of become the persona. I think there’s an underrated thing with the costume, which is to say, like, you know, if you’re a firefighter and you put on your firefighting gear, you become the firefighter. 

 

David Six 41:23

If you’re a soldier, you put on your uniform, you become the soldier. And I think this, for me, is the same way that, like, something about getting into the gear, getting everything together and breaking free of kind of the normal home life routine is something where I adopt a different mindset in doing that. 

 

David Six 41:45

Where I know I’m going to face challenges, but I have enough experience with the hikes that I know that there are things that I’m going to be able to overcome. And in doing that sort of on a day-to-day basis while I’m out there, it changes my outlook on life. 

 

David Six 42:02

You know, it makes me feel more optimistic about what’s possible. It makes me feel more motivated to take on positive changes in my life. It makes some of the things that seem tough, you know, on a gloomy winter period, then they don’t seem like a big deal anymore. 

 

David Six 42:20

It puts things into perspective. 

 

Blake Boles 42:24

Let me put my cynic hat on and say, are you just reflecting the, the serotonin or other happy drugs that are coursing through your head through endurance sports, and also are you just an escapist who’s out there in, in nature? 

 

Blake Boles 42:42

And it’s not something many other people can really practically do. And you’re just avoiding the messiness and the problems of the world by being out, uh, hiking for weeks and weeks, months and months. 

 

David Six 42:53

I think for your first point, absolutely, it’s the chemicals. But if you’re a runner, that’s got to be a big part of the reason why you run. And lots of people, I think, who have more normal kind of nine to five existences end up taking medications to try to get the same sort of chemicals, the same sort of feeling. 

 

David Six 43:18

People definitely take drugs to feel a certain way. In my case, nothing else that I’ve experienced makes me feel the way that I do, say, three weeks into a hike. The problem is that’s a big commitment. 

 

David Six 43:34

You’ve got to get two or three weeks into a hike before you really deeply start to feel that feeling. And for the second part, I think initially it was escapism, but now it’s just my life. I’m not running away from something anymore. 

 

David Six 43:56

I’m running towards the things that I like to do. 

 

Blake Boles 43:59

You found your hedonic equilibrium. Yeah. 

 

David Six 44:03

I mean, I will say I don’t, I think listening to this so far, somebody might think, okay, I grab my backpack, I grab my shoes, I hop in the car, I go out and head out on the trail and I’m, you know, immediately grinning and loving it, but most of my hikes are solo or with my dog around here, like most of my kind of off-season hikes, and most of the time I start out and I feel sluggish, and I feel that inertia of like, 

 

David Six 44:34

oh, this is hard, I don’t want to do this, am I really going to go out for six hours and do this, and I have to just sort of like put my head down and hike for two or three hours, and then that inertia goes away, and then I feel that optimism come back into my life. 

 

Blake Boles 44:52

Hmm. And just so I don’t forget your trail name 6-2. Can you just tell people what it means and where you got it or who gave it to you? 

 

David Six 45:01

Yeah, I wish I had a great back story for this. But I was starting out as a hiker, you know, after that initial thing of meeting the through hiker back in 2000. I started out section hiking. And at the time, I was working a 40 hour a week job. 

 

David Six 45:19

And so initially, I was just going out on day hikes and going out on the weekend, twisting people’s arms to go out to the trail with me. And on the Appalachian Trail, there are shelters all along the trail, which are basically these sort of three sided open front, some people would call them like a lean to it’s kind of like a log cabin, but with no front on it. 

 

David Six 45:45

And inside, generally, there are these spiral bound ruled notebooks, which are trail registers or trail journals. And the way that they’ve been used going back, you know, more than 50 years is that as hikers roll through, they’ll write down the date, and then they’ll write down kind of whatever they want in in the journal. 

 

David Six 46:07

And so one of the ways that I was exposed to the kind of AT hiking culture early on was seeing these journals and seeing the beautiful things people would write in them, or, you know, people having a bad day writing lame things in there. 

 

David Six 46:21

And but everything was signed with people’s trail names. And I was very self conscious of being a section hiker and not being a thru hiker. And I wasn’t having you kind of generally the way you get a trail name on a thru hike is like it’s a social thing. 

 

David Six 46:37

Like you do something silly or something silly happens, or there’s something unusual about you. And people notice it, and a name gets given to you. And that’s, ideally, that’s the way that it happens. 

 

David Six 46:50

But because I was coming at this as a section hiker, I just kind of had to write something in the book. And there’s nothing about the name 62 that means anything other than other than the fact that I’m six feet two inches tall. 

 

David Six 47:06

It was a handle that I had used in chat rooms in the 90s, like as a teenager. And I don’t even know how I came up with it. 

 

Blake Boles 47:17

So it’s just your nerdy tech online chat room handle translated into the hiking world well 

 

David Six 47:25

And then like 20 plus years of feeling unsatisfying with that story of the name, but also, you know, I’ve used it for so long that it’s like, no, that’s that’s, you know, part of my identity. There have been years when people have given me temporary trail names that have stuck for like a season. 

 

David Six 47:44

I was hiking in Virginia and I went to a hiker get together called Trail Days. And this is like basically like a big party with a parade in the town of Damascus, Virginia. And there was a what they call a trail angel, which is like somebody that is in the community helping out hikers, but isn’t necessarily hiking, who is talking with some of us and putting people up in her house. 

 

David Six 48:09

And she took pictures of me and a friend and my friend’s name is John. And somehow she misunderstood. And she had posted a picture of me online on the Appalachian Trail community that said John six colon two, like, like as if this was like a biblical thing. 

 

David Six 48:25

And I just thought that was hilarious. So that season I used John six two with a colon as my trail name because I thought that that was cute. Yeah. 

 

Blake Boles 48:39

I want to hear a bit more about your wife, who you mentioned, and I know that you two have done some serious travels together, so tell me how you’ve met and where you’ve been. 

 

David Six 48:51

So I’ll say I am divorced, which is I met somebody when I lived in DC. We got married. We moved to New Mexico together. And then we got divorced in 2012. And I felt that kind of like through-hiker kind of transition feeling of like, I need to shake up my whole life because of this divorce and get a fresh start. 

 

David Six 49:17

And so I moved away from New Mexico and I moved to Eugene, Oregon. And I had an early 90s Japanese economy car at the time. And I packed my stuff up to the ceiling of the car, had a rooftop bag on the car, had a bike rack on the back, had the trunk fall, and showed up in Eugene not really knowing anybody. 

 

David Six 49:43

But I had gone on the old school dating website, OKCupid, in advance of that. And so I was already talking with a few people in Eugene before I got there. And actually, it was kind of nice because it meant that it wasn’t just dating. 

 

David Six 50:00

It was also, I don’t know anybody in this town. And I don’t know how the town is laid out or what are good places to eat or what are good bars or whatever. So I sort of was cheating with the dating initially, which is like I’d meet people and I’d be like, they’d be like, where do you want to go? 

 

David Six 50:16

And it’d be like, I don’t know anything. And so I got introductions. People introduced me to their friends. I got to see kind of the places in town to go. But on the very first day, I met Deanna, my now wife. 

 

David Six 50:32

And what was funny was for the first month, we both kind of dated other people and continued to go on dates. But we’d still get back together, meet up and kind of discuss how our other dates were going. 

 

Blake Boles 50:46

That’s perfect. Yeah 

 

David Six 50:49

Really funny. And initially, I was sleeping in a yurt that I was that I’d gotten through Airbnb in somebody’s backyard, which is just incredibly Oregon. And she helped me go and look at rooms for rent and apartments. 

 

David Six 51:07

And I moved into a room with a couple of people. And it was fantastic. And it’s a good thing that I moved there when I did. It was like, I think the end of September, because I didn’t yet fully appreciate how intense the Oregon winters can get. 

 

David Six 51:30

And I think that year, we had a stint where it was like 30 days of temperatures staying below 40 all the time and rain every day. And, you know, what Seattleites might call the big dark, where like, you know, it’s not weather that makes you want to go hiking. 

 

David Six 51:48

And so it’s harder to connect with those kinds of exercise activities unless you’re into skiing or something like that. So the good news was I was falling in love with her. And that helped me manage the fact that the weather was awful. 

 

Blake Boles 52:07

And at what point did you decide to start doing some travels together? And she was fairly well traveled already before she met you, right? 

 

David Six 52:17

She so she had grown up, you know, with even less money in her family than I had. But she was always curious about the world, you know, she’s Mexican American. And so she had one foot, knowing about the kind of cultural experiences of her family in Mexico, and then knowing about her family experiences here in the US. 

 

David Six 52:45

And I think that that made her curious about other cultures and other people. And then I think by high school, she was voted most likely to go around the world in her yearbook. And she, you know, worked low paying odd jobs at stores and things like that. 

 

David Six 53:04

I think she worked at a like little gas station up in the mountains in Oregon for a while, and saved up her money until she could take herself on a trip to Europe. And she bought like one of those like gap year kind of youth bus tours where she was piled together with a bunch of other young people. 

 

David Six 53:26

And she says like she got like three marriage proposals while she was out there by people from different countries. And she came back and went to the U of O in Eugene, University of Oregon, and met a guy there. 

 

David Six 53:43

And he was really into travel in Latin America. And he twisted her arm to come with her on a trip in South America. So she had traveled around in Peru and Ecuador and Bolivia. And so yeah, she’d had a taste. 

 

David Six 53:59

And so by the time we met, most of my travel had been in Europe, but I also had taken a trip to Mexico and a trip to the Bahamas. But I had spent enough time looking at guidebooks, and like Lonely Planets and reading travel logs, that I kind of had this sense that there was this other world out there that was different from the way that I’d say your average sort of normal suburbanite in the US thinks about international travel. 

 

David Six 54:33

There’s places that aren’t Paris. There’s things that aren’t going to take a beach vacation because you’re exhausted from your job, that there was a kind of travel that was independent travel that was self-organized that could be really rewarding. 

 

David Six 54:49

And so once I realized that she and I were serious about each other, I said, we need to have this conversation. I need to ask you something. And she was horrified because she thought I was going to propose. 

 

David Six 55:04

And I said, no, no, I’m going to do this round the world trip in two years. I’m already starting to plan it. And I just want to let you know, if we’re going to be together, I would want you to come with me. 

 

David Six 55:18

And I’m willing to pay for everything. But this might not work out if that’s not something you’re interested in doing. And she was like, oh, yeah, of course. Absolutely. I want to do that. 

 

Blake Boles 55:30

Mmm, green flag. 

 

David Six 55:33

Yeah, exactly, exactly. So I actually got an inflatable globe. And we just started like looking at the map and looking at around the world and looking at the places and guidebooks and thinking about what that would mean. 

 

David Six 55:50

And I figured out pretty quickly that there were sort of a limited number of sort of normal paths that people follow for around the world trip, if they’re trying to do more overland. I read a bunch of Paul Thoreau books, for one. 

 

David Six 56:08

I saw the documentary series Long Way Around, the motorcycle series with Ewan McGregor and Charlie Borman. And so these were kind of specific inspirations. But one thing was I wanted to do this in a kind of thru-hiker style. 

 

David Six 56:28

So I really wanted us to pack light and to use local travel as much as possible, not flying, not hiring guides to solve all our problems. For one thing, I didn’t have the money to do a lot of those kinds of things. 

 

David Six 56:46

And so we ultimately did that trip in 2014, 10 years ago. And we basically took a train across the US, and then flew to Iceland, and then flew to Paris, and then traveled by train up to Amsterdam, went out to the North Sea, and then we’re able to do an overland trip where we didn’t fly all the way from Amsterdam to Hong Kong. 

 

David Six 57:15

And between those two points, we traveled through Turkey and the Caucasus and Central Asia and Western China. And it was that same kind of transformative experience of a thru-hike, even though it wasn’t thru-hiking, because it still had an immediacy. 

 

David Six 57:33

It was still tons of new experiences. It was still sort of physically intense. And actually, that’s my 

 

Blake Boles 57:40

bit of dirt bag type travel. You were hitchhiking also. 

 

David Six 57:43

There was hitchhiking. There was meeting lots of other travelers along the way, you know, I’m still good friends with a couple of the people that I met that were just sort of following the same course. 

 

David Six 57:56

Yeah, I mean, Central Asia is off the beaten path enough that there’s regions where unless you, you know, hire a big company to take care of everything for you and plan everything for you, you’re just going to get into adventures because that’s how the local people live in that region. 

 

Blake Boles 58:17

And I want to make sure that we touch upon your financial situation kind of as a combined married unit because it fluctuated for a while. You guys were not living on much income. She was in school and now things are a bit different. 

 

Blake Boles 58:33

So tell me how this works for both of you together. 

 

David Six 58:37

Yeah, so she when I met was unemployed. But she managed to do it in a way that was graceful. Like I was impressed. Like she lived in a rental house with a nice backyard and a big shade tree up front. 

 

David Six 58:50

And I was thinking like, this doesn’t make any sense. You know, there’s some part of my brain inside, which is still this like East Coast person and has this like, more rigid view of like, people’s lifestyles and professions and things like this. 

 

David Six 59:04

So I think I was a little underprepared for Eugene and the fact that like, people definitely live different kinds of lifestyles there, especially back then when housing was cheaper. And she was interested in becoming a nurse, but she worked through a lot of different odd jobs. 

 

David Six 59:23

I think she had a like a contracting registering voters at that time. She had been a nanny in the past. She had a degree in anthropology, which wasn’t necessarily leading to the kind of career outcomes she wanted. 

 

David Six 59:38

And so she started by being a nursing assistant and started going to school initially at the community college to get her prerequisites. And then she was lucky that kind of her hard work and her her good attitude and good connections led her to get into OHSU, which is the big kind of medical school research university up here in Portland. 

 

David Six 01:00:10

And so we moved up to Portland at a time when, you know, Portland was already on the expensive side. And at the time, I think my pre tax income was around $50,000 a year. And because I’m self employed, I pay business taxes. 

 

David Six 01:00:31

So I do get to take some deductions, but it means that my net income is less than, you know, a regular job at that income. And she was kind of working summers. She took a retail job one year, which actually she loved, because even though the pay was low, it was very chill. 

 

David Six 01:00:50

But she was working through nursing school and doing that. And so I kind of intentionally designed some of our travel and trips around nursing school. So we did another round the world trip in 2017. As she was kind of just starting out with nursing school at OHSU. 

 

David Six 01:01:13

So she had the summer off. And part of the plan with that was that I had seen other people traveling in 2014 who were like bloggers or who had some kind of like unconventional approach to how they were financing their travel. 

 

David Six 01:01:34

I knew I could work remote and I also knew that my income was enough that if you’re in a place like India or you’re in a place like Southeast Asia, it puts your income way above normal local folks and so it can facilitate a lot of travel. 

 

David Six 01:01:53

But always with the US, the airfare thing is a big thing. Like it’s expensive to get from LA or San Francisco to you know a place like Singapore or Australia most of the time. Likewise, for most of the traveling life that I’ve had even going from the east coast to Europe is was relatively expensive. 

 

David Six 01:02:15

It’s better now than it used to be. There’s more discount carriers but I was seeing what other people were doing and one of the things other people were doing were signing up for credit cards, signing up for travel credit cards and so I decided in 2017 to attempt to go all the way around the world with all of my airfare financed through credit card sign-ups and it took two years of planning and picking out the exact right credit cards to sign up for. 

 

David Six 01:02:46

If you’re not in this world, if you’re not a Reddit kind of person, I think that this probably sounds crazy or like that it would wreck your credit or could be a problem but the sort of basic rules for me were I have to make sure that this is something where I can meet an initial spend requirement. 

 

David Six 01:03:05

You know most of the cards will say you get this amount of airfare, this amount of points if you spend a certain amount of money in a certain period of time and I was only going to do that with the knowledge that I would be able to completely pay off the credit card. 

 

David Six 01:03:21

As soon as you’re carrying a balance on cards and paying a high interest rate it’s going to negate the sign-up bonuses. Exactly. It’s a casino. American finance is a casino and so I’m trying to beat the house in signing up for these cards and I pulled it off. 

 

David Six 01:03:40

I was able to fund all of my airfare and some of my wife’s airfare around the world with lots of stops. 2017 was going from the US, flying to Europe, spending a few days with jet lag in Europe and I went out ahead of her and went to the Caucasus to visit a friend that I had met in 2017 and also to see another friend in Amsterdam and then my wife came later because she had down in Namibia, traveled around southern and east Africa over land over a couple months and then a trip to India and then she went home via Japan and I went to southeast Asia. 

 

David Six 01:04:22

It was a bunch of flights and it also took some finagling to figure out how to fund some of the exotic ones. One of the things was like the chase card, chase sapphire card. That gives you points and so I could use those points to book with an international airline. 

 

David Six 01:04:45

Again, this is just one of those things where I had kind of a geeky goal that I wanted to see if I could pull this off and was satisfying to actually do it. 

 

Blake Boles 01:04:55

I mean, it’s pretty incredible just to say I traveled around the world, uh, just using credit card promotions, spending stuff and spending money on stuff. I was already going to spend money on in order to get these promotions. 

 

David Six 01:05:10

That’s the key. One of the things for me is I’m self-employed. And so one of the things that I can do to spend money on a credit card is I can use a credit card to pay my quarterly tax bills. And in doing that, that means I have a certain amount of minimum spend every quarter as I pay my taxes. 

 

David Six 01:05:28

You do pay a fee to do that, but the signup bonuses are better than the fee. 

 

Blake Boles 01:05:32

Okay, so that trip, which brought you to Africa, is what allowed you to go for 19 days without showering. Full circle. 

 

David Six 01:05:45

Actually, no. That was my second Africa trip. The first Africa trip was Kilimanjaro and that was 2006. Yeah. 

 

Blake Boles 01:05:51

Just to put a bow on the story of you and your wife, so now she is a nurse, she’s making quite a bit more money and this has enabled you to do things like buy your own place in Portland. Is that right? 

 

David Six 01:06:06

She she perfectly had terrible timing, which is that she graduated from nursing school in 2019, and then we got married right after she graduated. And we took another around the world trip in 2019. And we got back to the US not knowing where we were going to live, not knowing where she was going to work because it was going to be her first nursing job. 

 

David Six 01:06:32

We had all of our stuff in storage. And we kind of snowed it around for a while. She did over 100 job applications before she found the right job. And that ended up being in New Mexico. And so she started that job February of 2020. 

 

David Six 01:06:50

No, exactly, exactly. The thing that I’ll say, though, that was lucky for us was that suddenly she was getting a good income. And also, we couldn’t really go out to eat. And we couldn’t really do much traveling, we pretty much stayed in state in New Mexico. 

 

David Six 01:07:11

And that meant that finally, we were saving money, finally able to set aside some money. And so I was able to radically save that year almost at like a fire level, if you know the financial independence retire early kind of movement. 

 

Blake Boles 01:07:30

highest savings rate. 

 

David Six 01:07:31

extremely high savings rate and that led directly to me realizing for the first time in my life that like oh maybe we could actually buy a place you know even if it wasn’t something that we intended to live in full-time long term you know even if it was something that maybe would get rented out or where we’d have a roommate because I was just worried that in the long term there was going to be some time what if I was disabled and it was hard to travel I didn’t want to feel like I was still trapped kind of renting you know getting to the age where the first digit in your age is a four and then you look at 30-year mortgages it’s like huh this could be a problem 

 

Blake Boles 01:08:17

Well, it sounds like you figured out some things very early in life, David, and then some things like home ownership are coming a bit later, but all in all, it adds up to a pretty incredible life. And it’s wonderful that you and your wife can do these kinds of adventures and not work full time. 

 

David Six 01:08:43

Yeah, we’re super lucky. Yeah, she works three days a week, three 10 hour shifts, and she can kind of move those days around. So she’s still able to travel sometimes, you know, five days in a normal work week. 

 

Blake Boles 01:08:55

For anyone who wants to find out more about your adventures, do you have any public place where people can follow you? 

 

David Six 01:09:03

Yeah, so I’m intending to kind of do a little more with this, but I have an Instagram profile called Walk Across Oregon, No Spaces. So just Walk Across Oregon. And that is around the fact that my next big kind of outdoor project next year is going to be walking from the Pacific Coast in Oregon through the mountains, through Portland, across the desert, out to Hell’s Canyon on the Idaho border, and then into Idaho. 

 

David Six 01:09:39

And again, this is another experiment in finding a balance between work and home life and the kind of travel that I like to do. So it’ll be something that I’ll be doing part-time, but I’m hoping to start in February. 

 

David Six 01:09:54

And I don’t know how well you know the Oregon climate, but it should be pretty exciting. February on the coast is not a dry and sunny time. 

 

Blake Boles 01:10:07

And keep your laptop well protected from the elements. Yes, yes. And finally, I think we should thank our mutual friend and friend of the podcast, Tim Mathis, for connecting us because you also appeared in his book, The Dirtbag’s Guide to Life. 

 

David Six 01:10:25

Yeah, he and I and Angel also all keep kind of bumping into each other. We’re talking about maybe going to Egypt at the end of next year. 

 

Blake Boles 01:10:35

together. Fantastic. Yeah. Uh, David six. Thanks so much for coming on dirt bag, rich. 

 

David Six 01:10:43

Wow, thanks for having me. I really appreciate it.