
Blake Boles is a 42-year-old writer, cycle tourist, trail runner, partner dancer, and California-born temporary European expat who leads international trips for self-directed teenagers and young adults. (blakeboles.com)
In this special episode, former guest Jenny Abegg interviews Blake about what he’s doing with his life, the Dirtbag Rich project, his early influences, and how he thinks about freedom, purpose, security, and more. Topics include:
- Freedom as βnot being available for servitudeβ
- His view of long-term security and alternative retirement plan
- What the hard moments look like in a life on the road
- His undying love for the Deutschland Ticket (an unlimited travel pass covering all forms of public transport in Germany)
- How much stuff he actually owns (and the rules he sets for himself around possessions)
- Finding stability through extensive planning (and Google Calendar), and security through extensive friendships (his friend buckets include: dance, outdoors, college, and two summer camp communities)
- Why getting older is mostly awesome
- Who Dirtbag Rich is actually written for (and why itβs not 40/50/60-year-olds)
- His allergy to most “lifestyle” books (see: The 4-Hour Workweek) and how he’s trying to do better
- The mysterious overlaps between unschooling, tiny houses, partner dance, love of wilderness, and the pursuit of dirtbag riches
- His biggest early influences: the Berkeley Student Cooperatives, Deer Crossing Camp, and Not Back to School Campβyin and yang
- The magic of working your ass off, surrounded by people you deeply respect, in a beautiful natural environment
- How pointless school experiences led him to a deeper search for purpose, which he found in off-trail backpacking, reading alternative education theory, and independent foreign travel
- The flywheel of total aliveness, curiosity, enthusiasm, and positivityβand how keeping the flywheel going became his purpose
- What idolizing a dirtbag hiker (and failing to hike the Pacific Crest Trail) taught him at age 22
- His money situation
- How his life is currently not working
And finally, if you stick around to the very end: Jenny & Blakeβs illicit scheme to create a “dark night of the dirtbag soul” OnlyFans.
Full transcript: dirtbagrich.com/blake
Recorded on May 21, 2025.
Transcript
This is an AI-generated transcript. Typos and mistakes exist!Β
Jenny Abegg (00:00)
Blake Boles, welcome to Dirtbag Rich.
Blake Boles (00:04)
Jenny, thanks so much for having me.
Jenny Abegg (00:05)
Well, thank you for having me. This is your podcast after all. β You interviewed me like, I don’t know, half a year ago or so. And after being interviewed by you, who I think you are an exceptional interviewer, I said to you, Blake, you’re so interesting. Why don’t you have somebody interview you for your podcast? And so here we are. And I said, well, I’ve never done this before, but I’m very curious about you. β
Blake Boles (00:27)
And I said, would you like to be that person?
And here we are.
Jenny Abegg (00:36)
So can you, I know people who listen to this probably know little tidbits about you, but can you just start by introducing yourself? Who are you? Where are you right now? What are we doing here?
Blake Boles (00:49)
I am Blake Boles. I’m 42. I am currently in my friend’s room in Leipzig, Germany. I was recently in Berlin at a four-day partner dance event. After we finish this call, I will go out and dance some more this evening in Leipzig. I’m living in Europe for two years right now on a residency permit that I scrounged up. And I’m originally from California.
and have spent most of my life in the US and in the Western US. β I definitely am a West Coast, best coast type of guy. Jenny don’t really feel that attached to the East or the South of the US, but the Western US, Rockies and West, definitely. That’s my home range.
Jenny Abegg (01:42)
What about Europe though? How does that fit in? What draws you to Europe? What are you doing there right now?
Blake Boles (01:47)
it’s just so magical. Just like taking a train or riding my bike across any city or rural area, anywhere in continental Europe, I just find extremely charming. And I’ve made lots of friends through the dance community here and I can do my work mostly remotely. Or if I run my trips for teenagers, I just leave and go do that and then I can come back.
It’s, it’s just a really high basic quality of living here. I don’t know if that means that I want to be here longer term. That’s an active question in my life. And, β it’s, it’s the people and the place and the public transportation. I got here today from Berlin on not one of the fastest trains, but a train that’s still pretty fast. And I was using this thing called the Deutschland ticket, which is now it’s 58 euros.
Jenny Abegg (02:26)
Mm-hmm.
Blake Boles (02:45)
A month so like bit more than 60 a month for unlimited public transportation in the entire country of germany jenny, β everything except the fast trains You can take the slow trains all levels of public transport locally and regionally so trams β subways Everywhere all up. It’s just this dream this traveler’s dream. Yeah. Yeah, definitely It’s a month-by-month subscription service, but when i’m hanging around germany and you can’t take your your
Jenny Abegg (02:53)
Wow, wow, that is insane.
Do the locals use it? Okay.
Blake Boles (03:14)
bike on the fast trains that easily anyway. And so if I’m biking around Germany and I have a Deutschland ticket, I can just go anywhere for slightly more than $60 a month. That is the dream. I am living a version of the dream.
Jenny Abegg (03:26)
That is totally insane.
Yeah, yeah. I remember when I was in my 20s, I traveled around Europe with a year rail pass. Do they still have those? Yeah, man. Do they just know how to do it better over there in some ways?
Blake Boles (03:34)
They still have them.
Well, it was all built when everything was denser and there was, you know, there are historical reasons for this. And that’s why I find it so charming. Aside from riding my bike on cobblestone, not so charming.
Jenny Abegg (03:52)
Yeah, I’m sure there’s some funny, funny accidents to talk about there. Before we started recording, you made, you were telling me about a dance retreat that you’re preparing to host in September and you had, said the line, I’m trying to manifest the world I want to live in. And I wrote that down because I thought that was a poignant line. And so I’m wondering in this moment, you’re
Blake Boles (03:58)
Ugh.
Jenny Abegg (04:19)
In Germany, you have a $60 a month transit pass, you have your bike, you’re dancing a lot. What is the world that you want to live in?
Blake Boles (04:31)
I recently read this book called on freedom and the author goes lots of different places trying to really break apart this word freedom. But one of the definitions that she gave, she quoted someone else on this was, β not being available for servitude. And I think that’s the kind of life that I’m living right now. And that I’ve been trying to live for, for most of my.
adult life. And so that touches on on work and paid work, not wanting to feel like I’m in some state of servitude when I when I make money and I earn my keep that touches on my beliefs about education and schooling and unschooling, which has been a lot of what I have been working on and working towards and trying to develop a body of thought around that. And and relationships too. I really value
friendships. I and I’ve learned this more and more over time. Just friendships represent this this perfect equality in my mind and no one is serving anyone else. It’s it’s full consent. Whatever this word consent means, it’s that friendship really feels like it embodies it. And I’ve just found it really easy to make friends in Europe and to go to these these dance weekends and to connect with people. The event that
Jenny Abegg (05:42)
Hmm. Hmm. Hmm. Hmm.
Blake Boles (06:00)
we were discussing is titled creme de la connection. And so this idea of human connection is really central to a lot of what I’ve been pursuing in life. And maybe I’ll stop right there. Maximal human connection.
Jenny Abegg (06:12)
Yeah, wow.
Yeah, but not freedom is not being available for servitude. I actually find that quite fascinating because I think of human relationships as being infused with servitude or like that there’s like some level of give and take and what you’re kind of sharing is that freedom is just having mutuality in all of the aspects of your life.
Blake Boles (06:32)
Hmm.
Jenny Abegg (06:40)
Like a mutual give and take maybe is what I’m hearing.
Blake Boles (06:42)
Yeah,
I guess it really depends on how we choose to define that word servitude and there can be joyous serving. I recently took a group of 13 teenagers who are mostly from the US to Greece and Turkey for six weeks with a good friend of mine, Dev Carey from Colorado as my co-leader. And that was a lot of work and a lot of stress and a good amount of anxiety. But it was joyous servitude.
Jenny Abegg (06:45)
Yeah.
Mm-hmm. So there was some giving. Yeah.
Hmm.
Blake Boles (07:10)
For sure.
And at the end of the day, I didn’t feel like I just took a bunch of rich kids on a vacation. I didn’t feel like, like, what did we just, did it even matter? No, I felt like I helped expand these, these teenagers worlds. β we gave them a lot of adventure challenges throughout the trip that I believe really expanded their, their, if we’re going to use jargon, you know, social, emotional skills. And, and I felt like it was, it was genuinely.
good work and therefore if that’s the form of servitude I’m going to do to make money and to spend my time, I’m very happily serving in that way.
Jenny Abegg (07:44)
Hmm.
Hmm, hmm. Okay, yeah, servitude that almost like gives back in a way. Is that what I’m picking up on? some.
Blake Boles (07:59)
Yeah,
I don’t know. I’ve mixed feelings about that phrase give back. It implies some sort of original theft. β But, β geez, we’re just getting right into it, aren’t we, Jenny?
Jenny Abegg (08:01)
Okay, yeah.
Okay.
Yeah.
Philosophy 101 with Blake Boles. β Okay, so you have this, β I don’t know what to call it, a framework, a worldview right now that β I hear you talk about a lot that includes three elements to it. Those elements are purposeful work, copious amounts of free time for whatever.
Blake Boles (08:12)
Hahaha
Jenny Abegg (08:37)
your whimsy brings you, whether it’s people or adventure or time outdoors or whatever, and low consumption, low environmental impact, low financial stress. β And I’m wondering how this feels. Sometimes when I think about you, I think I like have this mental picture of somebody walking a tightrope because it feels like it’s so easy and human nature to fall to either side. And I wonder,
if maintaining these three things, if you, do you feel like you’re constantly in balance? Do you feel like you’re constantly in tension, trying to maintain balance? How does your life feel in service to your worldview?
Blake Boles (09:19)
boy. Yeah, it is a tightrope walk. It is a slackline. I feel like slackline might be better than tightrope because tightropes are…
Jenny Abegg (09:32)
Why is that?
Blake Boles (09:34)
fairly rigid in a slackline. You’re undulating, you know, it’s swinging back and forth and your your leg is kind of trembling and you have to if you try to fight the swings then then you’re going to fall off. It’s going to eject you but you have to like let it it go back and forth and feel out of balance and then let it swing to the other side and feel out of balance in a different way. So
Jenny Abegg (09:37)
you
Hmm.
What does that feel like? is, like, I’m curious, I’ve always been curious about this with you. What do your hard moments look like?
Blake Boles (10:05)
Yeah.
You know, I got into personality typing pretty seriously back in my early twenties. And I, it was the Myers-Briggs, the MBTI. And I was introduced to this through deer crossing through the wilderness summer camp where I went as a kid and I went back to work as an adult was very important in my life. And in that system, I identified myself as an introvert.
Jenny Abegg (10:15)
Like are we talking like the Enneagram or the Myers-Briggs?
Mm-hmm.
Blake Boles (10:35)
And an introvert being someone who needs a lot of solo time to recharge. then throughout my twenties and thirties and having these discussions with people about personality, they’d say, you’re so clearly an extrovert. And I’d say, really? I still consider myself an introvert. They’re like, well, I certainly don’t see that. And so I think something that I’ve, I’ve long struggled with is, is this the
Jenny Abegg (10:48)
Mm-hmm.
Blake Boles (11:02)
finding a balance in this thing we call introversion and extroversion because I really do need to retreat into myself, into my own head. Writing is super satisfying for this, but I also just consume a lot of books and podcasts and watch movies. β Also within the framework of Myers-Briggs, β having like a one-on-one conversation with someone can be considered introversion.
Jenny Abegg (11:15)
Mm-hmm.
Hmm. Hmm.
Blake Boles (11:29)
Whereas going to
like a big concert, hanging out with a noisy group of friends, β jumping back and forth between lots of different conversations that would be more classic extraversion. And I am capable of that and I do enjoy it. like this Berlin dance weekend was a great example of it. Just like lots of different people, little interactions, jumping back and forth. But, β yeah, and this life that I’ve decided to have where I don’t have a permanent house or.
Jenny Abegg (11:39)
Mm-hmm.
Blake Boles (11:59)
apartment or if I do, I’m just renting it temporarily. But it’s really mostly life on the road and a life visiting people, making a lot of transitions, trying to recall details about other people’s lives and their relationships and what’s going on for them. And sometimes for me, having a sort of Groundhog Day like conversation where I’m talking about myself in the same way with someone today as I did two days ago because we’re catching up. I think that
Jenny Abegg (11:59)
Mm-hmm.
Yeah.
Hmm.
Blake Boles (12:29)
That is, that can burn me out and I need to, well, I just need to be careful to like remember my introverted self and to carve out space to retreat and to not have the, the possible social interactions, not do all the events. β so maybe I am functionally in extroverts now, but, β that’s not where I came from. So that’s a tension that I hold Jenny.
Jenny Abegg (12:33)
That is the hard.
Yeah. Yeah.
Interesting. Yeah. Yeah, and we’ve talked about you being an enneagram seven in the past Which I think I remember I feel like I’ve read all enneagram sevens are extroverts Which is probably a pretty large sweeping statement, but yeah pretty weedy β Just like logistically curious so when I think about people who travel all the time you think about living out of a backpack or out of a car, but it seems like you
Blake Boles (13:03)
Yes. Yes.
We’re getting into the weeds now, yeah.
Jenny Abegg (13:26)
give yourself a bit more stability than that? Like tell me about what, is there like a norm for how this looks for you? Like are you staying with a friend right now because that strikes me as having to be very social or do you get your own place when you travel?
Blake Boles (13:42)
Right now I’m in travel mode. I’ve been in travel mode since the beginning of 2025. But what that looks like is I rented a furnished house for a month with some dance friends, one from Poland and one from the UK in Valencia in January. And then I went to go β stay with a friend and her friends in Portugal for a week. And then with some old camp friends.
Jenny Abegg (13:55)
Hmm.
Blake Boles (14:08)
up in the UK for a period of maybe three or four days each. And then I went and took a group to Greece and Turkey and we were moving all over the place for six weeks. And so now I’m still in this mode. mean, downstairs in the courtyard of my friend’s apartment building here in Leipzig is my touring bicycle, which I purchased in Germany in 2020. And in the corner of this room here are two…
Jenny Abegg (14:17)
Wow. Wow.
Blake Boles (14:35)
panniers, two saddlebags, and then a duffel bag that connects to them. It sits on top of the back rack and then a little like book bag that I wear. And so all my stuff fits into these three carry-on, three or four carry-on size bags. And that’s yeah, my default existence here in Europe. β later this year I’ll rent an apartment and, β like I have one more bag of stuff chilling at a friend’s place in Vienna right now.
Jenny Abegg (14:36)
Mm-hmm.
No way.
Blake Boles (15:02)
And so I will have a bit more like winter clothing and like my yoga mat. But, fundamentally I’ve, I’ve chosen to, to not own more stuff than I can physically carry on my myself, β at this moment in life. But it hasn’t always looked like this, Jenny, like for a long time, I had a storage unit, like a five by five or five by 10 unit in, in South Lake Tahoe or Carson city nearby.
Jenny Abegg (15:06)
Mm-hmm. Mm-hmm.
Blake Boles (15:29)
And I would have a bunch of outdoor gear, backpacking gear in there. And I did have a car for most of my existence, either a Toyota 4Runner hand-me-down or a Subaru Forester. And my rule for myself then was only own as much stuff as fits inside your vehicle. Yeah. Yeah. It’s graceful. And so.
Jenny Abegg (15:37)
Hmm. Hmm.
Yeah, I’ve had that rule for myself before too. Yeah.
Blake Boles (15:55)
Yeah, I guess I’ve never been in a moment where I’ve had a lot of stuff. I’ve never owned a couch. I think I owned a mattress once for a year. I rent other people’s furniture. I pay off other people’s mortgages as a renter, I’m happy to do that. I fully embrace that. I don’t see it as some sort of failure to accrue equity because I don’t have my own place that I’m.
Jenny Abegg (15:56)
Yeah.
Yep, with your rent, yep.
Mm-hmm.
Blake Boles (16:23)
renting out to other people. You are very good at this. We talked about this in your interview. So yeah, that’s a bit of the logistical β situation.
Jenny Abegg (16:25)
As we…
Yeah,
you know, as you were talking, I’m thinking like, as I have gotten older, I feel like, like I’ve never been a stuffed person. I’ve lived, we’ve talked about this in vehicles and closets and, but as I’ve gotten older, you know, I like have a house and I have my things in it. And I find surprisingly a lot of stability in that. Like a lot of like the sense of home that I have here and like a groundedness that like, it really makes me feel.
safe in life to have a home and stuff. And I’m curious what it feels like to be you to just have four bags and a bike in Europe. And that’s all all the things that you own to your name. Where where do you think that you find stability?
Blake Boles (17:20)
Stability or security?
Jenny Abegg (17:22)
Yeah, I mean, maybe talk about both or what’s the difference between those for you.
Blake Boles (17:26)
Yeah,
OK. I’ll give you the quick answers. Stability, Google Calendar. Security, β relationships, which primarily means friendships. Yeah, tell me if you want me to expand.
Jenny Abegg (17:35)
Hmm. Mm-hmm. Mm-hmm.
Yeah.
Okay. Stability Google calendar. Okay. I think I understand that. And, I, and I think of you as a planner, like you’re not like a total fly by the seat of your pants kind of guy. you, you value stability. Yeah.
Blake Boles (17:47)
You
Yeah, definitely. No, no, that stresses me out. Yeah. Well,
I, I value, I need security too. I need to know that I’m going to be sleeping somewhere that’s comfortable and safe. β I, yeah, I definitely am not this like last minute, super spontaneous, β traveler who’s like, yeah, I’ll fly to your, your city or something. I have multiple months planned out in Google calendar. And even that is kind of progress for me. I think my.
Jenny Abegg (18:07)
Mm-hmm.
Yeah, yeah, right.
Blake Boles (18:24)
Some of my longer term friends have known me as the one who has the next year planned out. And if you ask me, what are you going to be doing on June 17th of next year? I could tell you where I’m going to be and likely what I would be doing. And so three months is actually feeling a bit more flexible. Yeah.
Jenny Abegg (18:33)
Mm-hmm.
Short for you.
Yeah. Yeah, it seems like as somebody who does value some stability, you’ve done a really good job at like making that happen in a non-traditional way. I’m curious, I wanna talk about your friendships. It just is like, β I’ve known you for like four or five years and we’re like, we’re not close friends, but we talk every now and then. Like you are very good at keeping in touch. And I imagine that that’s a really important skill for you.
Do you have lifers in your life? It seems like you also have a lot of people that come in and out. β If security lies in relationships for you, what do those relationships look like?
Blake Boles (19:17)
Yeah.
Let me describe some buckets. So Jenny, you are in the outdoors bucket. And I spent a lot of my life prioritizing doing stuff in the outdoors and being in cool mountain towns. And you came into my life through our mutual friend, β Hannah Hall. I also have the dance bucket, which is mostly fusion dance. Tango is how I started dancing. But I never really
Jenny Abegg (19:46)
Mm-hmm.
Blake Boles (19:54)
felt like a member of the tango dance community. I was just there to learn skills. β But the fusion dance world, to a small extent in the US and to a large extent in Europe, that’s another big bucket and a really satisfying and more recent one for me. But the lifers you’re referring to definitely come from three other buckets. One is college, β UC Berkeley, and I have a small group of
Jenny Abegg (20:16)
Hmm.
Blake Boles (20:21)
β it’s not a group like we all know each other, but like a small set of, of, of close friends from that time. And then it’s the two summer camps where I spent a lot of time working. And so it’s a lot of my coworkers from those camps, Deer Crossing camp in Northern California and not back to school camp, the one for unschoolers and self-directed learners, β that happens in Oregon and Vermont. And, β and just the years that I spent.
working alongside people there just brought me so close to some very specific people. And those are my lifelong friends where like, I know that they always have my back, you know, forever. You know, they are chosen family.
Jenny Abegg (20:58)
Mm-hmm.
And I imagine that most of them are in the States. Yeah. Yeah.
Blake Boles (21:07)
They are, yeah.
Jenny Abegg (21:12)
Yeah, yeah, how interesting to hear you say that β you find most of your security in your relationships and yet you are not the kind of person that is posted up in a small town and living there for 20 years. Your relationships are everywhere and not necessarily reliant on you, I would imagine, because of that.
Blake Boles (21:36)
Yeah. Yeah.
Jenny Abegg (21:37)
There’s an in
and out nature to your relationships.
Blake Boles (21:43)
There is, but the amount of upkeep or the amount of friction that’s encountered when I reconnect with an old friend, it feels pretty minimal. It really feels like we can drop right into the conversation that we’ve always had. So I don’t find that to be stressful. I know that other people do, but for me that just has never felt like a significant barrier.
Jenny Abegg (21:53)
Mm-hmm.
Mm-hmm.
Blake Boles (22:12)
You know, the newer relationships, know, people who I meet through dance, maybe people who I meet through the my more like professional connections in the world of education. Yeah, there’s, there’s a chance that something will flourish or die off because it’s still kind of newer. But yeah, the long standing ones. I feel extremely secure, Jenny, like that’s, that’s the bottom line. And, and when I think about
Jenny Abegg (22:37)
Yeah. Yeah.
Blake Boles (22:40)
Because I get asked this question a lot when I meet people. They’re like, so you don’t choose to live any one place in particular? My response is usually, if I chose to live most of my year in one place or multiple years in one place, I would be cutting out most of the important relationships in my life, or I’d be forcing them into digital-only interactions. so moving around is how I sustain.
Jenny Abegg (22:47)
Mm-hmm.
Mm-hmm. Mm-hmm. Mm-hmm. Mm-hmm. Yep. Yep.
Blake Boles (23:08)
the relationships, even if it’s infrequent face-to-face contact. And I want to keep moving my body as long as my body can move Jenny and moving doesn’t just mean going for runs or backpacking trips or something like it’s, it’s like traveling through the world and getting to live in Europe for a few years or getting to take a group of teens to, to Turkey or, β bouncing around. Yeah. Like I have the rest of my, my elderly adult life to.
Jenny Abegg (23:15)
Hmm. Yeah.
That is such a good point. Yeah.
Yeah.
Blake Boles (23:37)
be in one place and to cultivate
Jenny Abegg (23:38)
Yeah.
Blake Boles (23:39)
strong community in a single location. I don’t, I have done this just in fits and spurts. I’ve done this in South Lake Tahoe, California, more than any place else. But even there, it’s just been some long summers where I’ve rented my own place. One winter, it’s probably the closest thing that I have to a home. But even there, it’s, you people don’t expect that I’m going to be there.
every year. They’re kind of like, Blake, you’re here. That’s cool. I wasn’t expecting you.
Jenny Abegg (24:07)
Mm-hmm.
Yeah, and the idea of movement being a muscle that we need to continue to work in order to keep it functional, that makes so much sense to me. think the older we get, maybe the less we want to move and then the harder it becomes to move, whether it’s because you now own a couch that can’t fit into your car or it’s just easier to be home. that’s very, like that makes a lot of sense to me that you wanna keep that muscle strong.
Blake Boles (24:26)
Yeah.
Jenny Abegg (24:39)
Do you think that one day your life will look differently?
Blake Boles (24:45)
Certainly. mean, I’ve had issues with, um, with my back, with my lower back. Sometimes it just sort of goes out and I’m hobbled around like a, you know, old guy with a cane, uh, for some days or sometimes a couple of weeks. And, know, that is a, striking reminder that at some point this body is just going to stop being reliable. And so in my mind, like, this is my theory, Jenny, and maybe this is going to be proven foolish and immature and wrong.
Jenny Abegg (24:59)
Hmm.
Hmm.
Blake Boles (25:15)
over time, but my theory is that if I just continue cultivating strong relationships, then at some point when I no longer want or am able to continue traveling around so much, then I’ll just sort of survey the scene and see like who’s interested in having Blake as a housemate, right? I’m good at cooking and cleaning. Anyone? Anyone?
Jenny Abegg (25:29)
Mm-hmm.
Take your pick.
Wow. That’s awesome. Do you envision yourself being partnered later in your life? Is that a hope? Yeah, romantically partnered.
Blake Boles (25:51)
romantically partnered?
Yeah. Yeah, I do. That feels important to me. It’s been a focal point of my life for all of my adulthood.
Jenny Abegg (26:02)
Okay. Okay.
Blake Boles (26:04)
even though I have not ended up in many β longer term place based relationships. My longest was about four years with a lovely woman in North Carolina.
Jenny Abegg (26:16)
interesting. For some reason I thought you were gonna say in Europe, you dated a woman in North Carolina for four years. Was that a lot of long distance?
Blake Boles (26:24)
I was about half half. I think half the time it was more long distance and half the time I was in Asheville, North Carolina.
Jenny Abegg (26:31)
Did we, I don’t, have we talked about this? I lived in Nashville for like six months and I love it there. Oh, it’s such a great place. So cool that you got to live there. Yeah. Okay. I, as somebody who just turned 40, aging has been on my mind a lot. And I really, I didn’t plan on asking you this, but now that we’re talking about it, I’d love to hear your thoughts on what it’s, what it’s been like to get older. You’re 42. There’s the body stuff. I’m.
Blake Boles (26:33)
it doesn’t surprise me, Jenny. Yeah.
Jenny Abegg (27:00)
I’m kind of more curious about what it’s like to be in your brain and in your heart getting older. And if you even feel like you’re getting older, what’s your emotional mental age right now? β have you noticed it change over the last 10 years or so?
Blake Boles (27:13)
Hahaha
Okay, I’m not going to answer the emotional mental age question. I don’t think it makes sense to me. I, I, guess it’s all a big package deal, right? You, you, you have all these experiences. You meet all these different people. and you, you change and, and I feel like it’s almost like you’re asking like a split personality type question. It’s like, you have the idealism of a 25 year old, but the wisdom of a 30.
Jenny Abegg (27:24)
β tell me why.
Hmm.
Blake Boles (27:48)
five
or a 42 year old. It’s like, no, it’s all a package deal. And, just to answer your question, it feels awesome. And I feel like I’ve never had more, like a richer, like intellectual life. feel like I’ve never had a richer, um, social life. I’d say the transition from high school into college was, was a much bigger jump into like a rich social life. That was huge for me, but.
In terms of just like total number of satisfying social connections and even just this dance world in Europe, being able to show up and be β recognized and seen and valued and desired. It’s extremely high right now. I, I kind of marveled at, at my situation and my fortune these past weekends. Cause I also went to one dance weekend in Toulouse, France also two weeks ago and
And really there was so many great dancers there. And in years past, I would have been the person mostly sitting on the side and watching the great dancers and feeling kind of amazed, but also intimidated, a bit curious and anxious about how anyone ever becomes that person. And then in the past year or two, I’ve somehow ended up becoming that person where a dance ends and
There’s just immediately someone else who’s going to ask me to dance, who I’m going to ask to dance and they’re going to say yes. And we’re going to have amazing dances. And, and it, that’s it. Like the weekend is full until I’m completely exhausted. And, and that just feels great. Like it’s, I know you could like use a sociological term for like social capital or something, but, fundamentally just I’m.
Jenny Abegg (29:24)
Hmm.
Hmm.
Blake Boles (29:40)
I’m living a really great life and it’s mostly great because it’s rich in relationships, it’s rich in freedom and autonomy, in my relationship to money.
Yeah, just just that lower back thing. If I could pay money for that to never happen again. I think I would I’d give half my life savings for that to never happen again.
Jenny Abegg (29:56)
Yeah.
man, I can relate to the body stuff. β
So yeah, think the things that you just, the notes you just touched on, I think they define kind of dirtbag rich for you. β And this is again, that you kind of, your life embodies and that you wanna tell the world about. I’m curious, I’m curious, like as somebody, I hope you don’t take this the wrong way, but as somebody who comes from a religious background, speaking for myself,
I’m β sometimes wary of people telling me how to live. And you have found a way that works really, really well for you. I’m curious if you think it works really, really well for everyone. Who is it for? Who is it not for? Why do you, a lot of your work is centered around the idea of quote unquote preaching this message.
And I would just love to hear you talk about that. Like, why does it mean so much to you to tell people about it? β Who are you speaking to?
Blake Boles (31:23)
Hmm. Funny, just this morning in the past few mornings, I was working on the section of the Dirtbag Rich manuscript about finding purpose and especially β the disappearance of religion from modern life and how β extended time and endurance sports in the outdoors has replaced functional religion and community, the community provided by religion for many people. β
Jenny Abegg (31:38)
Hmm… Mm-hmm.
Yeah, wow.
Blake Boles (31:52)
I know that’s part of your story too. just, β yeah, a propose.
Jenny Abegg (31:53)
Mm-hmm. Wow, yeah. Mm-hmm.
Blake Boles (31:58)
I also have this mixed relationship to people telling me what to do in book form. On one hand, I’ve been a big lover of sort of lifestyle guidebooks. I, let’s see, probably the book Vagabonding by Rolf Potts.
Jenny Abegg (32:20)
Hmm.
Blake Boles (32:20)
which came out 2001, 2002, and I picked up shortly after it came out was, was a big one for me. And it’s like direct advice about how to travel long-term and how to travel differently and to not be a normal dumb tourist. And, β I picked up the four hour work week by Tim Ferriss shortly after it came out and I was very mesmerized by it, like many people were. And, and then pretty quickly.
Jenny Abegg (32:42)
Mm-hmm.
Blake Boles (32:51)
I saw all these gaping holes in his arguments and his life advice. And I realized that there’s a way to offer this kind of advice to other people in which the author is the one who has lived a certain way and is very enthusiastic about this way of living and wants to share it and share practical advice and
Jenny Abegg (33:19)
Mm-hmm.
Blake Boles (33:21)
inspire others. There’s a way to do this that I find more, reputable than, than the others or the word in my head is, is less smarmy. I love that word smarmy. Yes.
Jenny Abegg (33:31)
Yeah.
Smarmy.
You mentioned gaping holes. Do you mean misalignments between what is practiced and what is preached? what kind of was off-putting about some of that genre for you? What was smarmy?
Blake Boles (33:51)
Yeah. Yeah. I mean, there’s this whole like not acknowledging privilege side of things β that I think is pretty ubiquitous in the self-help β world. β Also in that book, The Four Hour Workweek, there was a lot of interesting ideas about rethinking retirement, about not trying to do everything yourself and outsourcing to other people.
about creating automated workflows using technology. But when it got down to like, how will you provide value to other people such that they will give you money? The author’s advice was create some information product that you sell online as like a PDF to rich people. And I was like, really? That’s your advice. Create and Tim Ferriss himself, the way that he
Jenny Abegg (34:18)
Hmm. Mm-hmm. Mm-hmm.
Mm-hmm.
Ugh.
Yeah.
Blake Boles (34:46)
kind of made this initial money enough. And that’s the thing he wrote about in the book was he created these like brain enhancing, like somehow legal drugs β that like helped you think more quickly. And it’s, you know, it’s sort of like some off-brand Ritalin or something. Yeah. Just like very like tech bro optimization culture. And then learned how to like drop ship it so that he doesn’t, you know, his
Jenny Abegg (35:04)
Yeah, wow.
Yeah, yeah.
Blake Boles (35:14)
subcontractors in India can just manage all the process and he can check in from Barbados or whatever, you know, in the middle of his windsurfing lesson. And, and that did not feel good to me. And I’ve noticed that kind of vibe in lots of books out there, this sort of blindness to where you come from. And there’s also blindness to what’s largely possible for other people. And so I’m, I’m trying to be really sensitive to this in this
Jenny Abegg (35:19)
Yeah. Mm-hmm.
Mm-hmm.
Blake Boles (35:42)
this book writing project, Jenny, without letting that sensitivity like completely handicap me and, not let me stand up for anything or, or really make a point because I like reading books that are, short and punchy and the author stands up for something and they, make a point and they stand by it. And so I’m trying to, I’m trying to walk the tightrope. I’m trying to walk this, the high line here, Jenny, and it’s challenging. It’s super, super challenging.
Jenny Abegg (35:51)
Great.
Yeah, totally. Do you think-
Are there, do you find yourself caveating? Do you think that like, do you think that what you’re proposing as a life well lived is kind of a blanket proposal for any human? Or do you think, who is it for?
Blake Boles (36:23)
No, no, absolutely not.
Yeah. This is a great question. And this is a question I’ve tackled in discussing unschooling and alternative education, self-directed learning. They’re like, is unschooling for everyone? And I’m like, no, it’s definitely not for everyone. Regular school is a better fit for most people. β And then all of sudden it gets into a bit of dicey territory. Are you suggesting that this is only for a privileged elite few? And I’m saying, no, this is for
Jenny Abegg (36:38)
Mm-hmm. Mm-hmm.
Hmm.
Blake Boles (36:53)
a certain kind of weird person. Okay. And like the unschooling stuff, it’s largely not practiced by super rich, super privileged people. know, their kids are going to Exeter and Andover and, and, you know, they’re staying up in those upper echelons so that they can maintain the connections that will perpetuate their wealth and privilege. β and so I think the dirtbag rich thing is for a certain subsection or like
Jenny Abegg (37:09)
Right.
Blake Boles (37:22)
niche subculture. And here’s what I’ve seen. It’s definitely biased towards people who have grown up with access to actual β wilderness that is accessible. And so not just wilderness, like there’s the wilderness in like the Himalaya, but a lot of it is just not accessible. There’s not trails, there’s not roads, there’s not campgrounds. It’s like you have to be a hardcore expedition person to go into that wilderness or, you know, the Balkans or something like there’s the wilderness, but it’s
Jenny Abegg (37:34)
Hmm.
Blake Boles (37:52)
It’s like a bit more scary wilderness. β In the Western US, due to all sorts of reasons of history, we just have super accessible wilderness. have public roads cutting through these giant deserts in the Great Basin. You can live in a place like β Squamish or Levensworth or South Lake Tahoe, Bishop, Mammoth, Joshua Tree, β Boulder, Durango.
Moab, like there are these little outposts there where you can actually have a life and this of course has to do with like the possibility of remote work also and the changing nature of how you can even make money. β and so there is this sort of historical and cultural alignment that, that, that connects with physical geography and place that that makes something like being a dirt bag climber or being
someone who is super into the outdoors or super into dance or an artist or a writer and you really want to prioritize this and you want to find a way to work β less and to focus on your passions. Yeah, this is definitely not something that can be genuinely offered to every single person β in the world. And I don’t think that that should be a precondition for writing a book about something or about promoting
Jenny Abegg (39:17)
Yeah. Yeah.
Blake Boles (39:19)
an idea and I’ve come to just really put up a wall there and to wholesale reject this argument that if something is not 100 % accessible to every single person in the world at this very moment, then you’re not allowed to write about it. It’s like, no, go away. You’re wrong.
Jenny Abegg (39:35)
Yeah,
totally. Yeah. Okay, I wanna dig into this because I find it really fascinating. I mean, here you are, you’re in a city in Europe. You are spending a lot of your time dancing. You read a of books. Like none of that has to do with like quote unquote physical wilderness. But the kind of like the tie that you’re drawing between growing up near wilderness leading to this way
of thinking this way of wanting to live. I read a recent blog post that you wrote that kind of compared European worldview and lifestyle to American worldview and lifestyle. And when I think about being an American, like versus being a European, one of the biggest things that stands out to me is that we have way more public land and way more wilderness. So we grow up, I’m just like verbally processing this all right now, but.
Can you speak more to this, all of the, can you take it from there? Okay.
Blake Boles (40:34)
Yeah. Yeah. Happy too. Yeah.
Yeah. I, I think that the, the phase of my life where I’m traveling around Europe and dancing necessarily needed to come after the outdoor exploration phase. And I haven’t fully fleshed this out yet, Jenny, but there is something about being presented with a trail head in which you can go left or right or straight, or you can not follow any of the trail signs.
And you can just cut your way through some granite shelves and bushwhacked through some manzanita. There’s something about that experience that is fundamental to, to this, this concept of, of, freedom and choice and this idea that, that I want to follow my passions. It’s somehow connected there. And maybe I should like get a psychologist and a historian on my research team or something, but.
Jenny Abegg (41:09)
You
Hmm.
Yeah.
Blake Boles (41:34)
β in my twenties, it was completely about accessing wilderness and imagining myself in the wild places of the Western U S and also places like the South Island of New Zealand or the Himalaya or maybe the Alps, but you know, the Alps, they’re not real wilderness. There’s their cell phone service everywhere. There’s, you know, cable cars taking you to restaurants on the top of some crag. So.
Jenny Abegg (41:56)
Great. Great.
Blake Boles (42:04)
It’s about this possibility to go off and explore and get lost and to perhaps suffer and die alone in the woods that I think is fundamental to this, this attitude that I’m trying to embody and describe and promote in the book. And I have no doubt that a lot of people who are, you know, my friends or family members, or think I’m a nice guy.
Jenny Abegg (42:12)
Hmm.
Blake Boles (42:30)
when I hand them the book, we’ll just kind of read a few pages and stare at me blankly. I need to find a way to connect with the people who will pick this up and be like, oh my gosh, this guy gets me. And so I’m thinking ahead already, Jenny, to like, okay, if I’m going to do a book tour, where would I go? And it’s going to be the outdoor Mecca spots of the greater Western, know, North America, US and Canada.
Jenny Abegg (42:43)
Hmm.
Mm-hmm. Mm-hmm. Mm-hmm. Mm-hmm.
Blake Boles (42:59)
And so I’ll go to Boulder, I’ll go to Moab, the places I listed previously, because that’s where these kind of people come. And of course, these people, most of them were not even born there. The people hanging out in Bishop, they’re born in Connecticut or Florida or Mexico or something. The people who are in Squamish, they’re coming from all over the world. The people down in El Chalten, Argentina, as you know, extremely, when I say extremely international, it’s still largely European, North American, Australia.
Jenny Abegg (43:10)
Right.
Mm-hmm.
Blake Boles (43:28)
New Zealand and maybe some more money parts of South America. β Yeah, these little nexus points, these meccas, that’s where my readership, I’m fully confident lies. And it is largely outdoor centric. I’m not sure how many people in my partner dance communities are going to vibe with this book. I’m not sure when I say artists and writers. β
Jenny Abegg (43:52)
Hmm.
Blake Boles (43:57)
You know, when I put out the call for interviews for this podcast, a lot of people who have freelance writing careers were very interested in talking about it and they feel very aligned with these principles. So there’s something there too. I don’t know where you, you encounter a nexus of freelance writers. You know, it’s pretty much online. β
Jenny Abegg (44:05)
Mm-hmm.
Mm-hmm.
And are those freelance writers influenced by wilderness? β
Blake Boles (44:21)
They are, they’re
people who in their free time that they’ve created in the flexible lives that they’ve created for themselves, they mostly spend it in nature. And these, these partner dancers, these fusion dancers who I hang out with in Europe, I will tell you 98 % of them are super into the outdoors and nature. And in the same way, I was mentioned in some article in some magazine some years ago, quoting me about unschooling and the quote that they use from the interview was like,
Jenny Abegg (44:26)
Yeah. Yeah.
Wow.
Blake Boles (44:49)
Anyone who’s into unschooling is also into tiny houses, which I stand by. And I think that there’s, I think there’s a lot of overlap between, β this thing called dirtbag rich. and just this general, like alternative lifestyle, low impact. you, you mentioned some of the keywords, key phrases earlier. There’s, know, high overlap with like concern for the environment and.
Jenny Abegg (44:54)
Hehehehe. Hehehehe.
Mm-hmm.
Blake Boles (45:19)
climate and not being wasteful and probably like the debt your dedication to recycling is probably extremely high. If you are going to read this book, even if you know that it’s kind of a sham and just symbolic.
Jenny Abegg (45:35)
I’d be really curious. I don’t know if we need to get into it here, but I’d be super curious to hear what kind of conversations you have with Europeans about the dirtbag rich concept, about your book, about your lifestyle. Do they get it? They’re into it.
Blake Boles (45:48)
They’re into it. Yeah.
Yeah, they’re into it. They’re curious. I believe they don’t have as much exposure to people who have really created their own businesses that really look different from other businesses. You’re a startup person, Jenny. You get together with some people who you trust and you come up with some ideas and you’re like, let’s just make this happen. Those people do exist in Europe too. It’s just there’s less of a culture of it. β
Jenny Abegg (46:17)
Yeah.
Blake Boles (46:18)
I think the fact that I grew up in the nineties in Northern California, adjacent to Silicon Valley, when the internet was becoming a thing is probably massively influential on me thinking the thoughts that I do and thinking that this kind of thing is possible. Yeah.
Jenny Abegg (46:24)
Mm-hmm.
Mm-hmm. Mm-hmm. Mm-hmm.
Yeah.
Let’s talk about your other influences. I’m curious. So our mutual friend Hannah Hall, I think is incredibly influenced by you and also by her time at Deer Creek Crossing, Deer Crossing? Deer Crossing. β And I’m wondering, were you always like this? What are your most important influencers in your early growing up years? How have you arrived here?
Blake Boles (46:45)
Dare Crossing Camp, yeah.
No, not always like this. think definitely more shy and bookish, β but still like genuinely like positive and happy and like positive affect that I think that’s largely genetic. And as I mentioned before, this transition from high school, which I never really felt like I fit into and didn’t have many friends and really focused on academics, being a good student.
Jenny Abegg (47:11)
Hmm.
Blake Boles (47:32)
Um, the transition into college was, was huge for me because all of a sudden I was around all the weirdos and the nerds that I dreamed I could be around. And I ended up living not in the dorms because the dorms were overcrowded. I lived in the student cooperative houses where, uh, rent was a lot lower, but you had to cook or clean or help manage the house in some way. It was much more messy and democratic and.
Jenny Abegg (47:49)
Hmm.
Blake Boles (48:00)
They threw incredible parties and, just getting thrown into that culture of those student cooperative houses. Cause I lived in a house with 125 people for three years. Yeah. It’s called Casa Zimbabwe. And it’s part of a network of, think, roughly 15 houses with about a thousand total students. And so you would not just hang out with the people in your massive house, but you hang out with people in other cooperative houses around the Berkeley campus as well. And that.
Jenny Abegg (48:11)
Yeah. Wow.
Mm-hmm.
Blake Boles (48:29)
That massively transformed my personality. think it made me more extroverted, more self-confident. I just had a lot to say and conversation flowed much more naturally for me compared to my social life in high school. I also spent a lot of time as a kid on computers and teaching myself like web coding and web design and getting β lost in like…
Jenny Abegg (48:34)
Mm-hmm.
Blake Boles (48:56)
internet relay chat, IRC, know, learning how to like pirate, you know, movies and, and software and just be like a little sort of like hacker kid. β so that was, β yeah, that was another big part of the foundation. But the camp that you mentioned, deer crossing, I went there as, β as a kid for four summers. So usually two weeks, one week, β one summer I did four weeks and.
Jenny Abegg (48:59)
Hmm.
Yeah.
Blake Boles (49:25)
There’s a lot to say it’s, it’s really like a wilderness camp, like off grid, many miles from the closest road, but it’s on a lake so you can boat in and the, the camp would have kind of normal outdoor sports and activities. learned how to windsurf, but there’s also kayaking, rock climbing, sailing, canoeing. β and at the end of every two week session, there would be a three day out trip. And usually you go backpacking or maybe canoe camping and.
Jenny Abegg (49:34)
Hmm.
Blake Boles (49:55)
It was a camp that was highly structured, yet at the same time, it gave you a lot of freedom and autonomy. most of what you did at that camp was chosen by you. And the most important part of that camp, by and large, was the director of the camp, Jim Wilton’s, who is this larger than life, Indiana Jones, tall, β powerful, booming voice, β natural authority.
Jenny Abegg (50:13)
Yeah.
Blake Boles (50:24)
type person and I looked up to him a lot as a kid, but I was really more focused on the pure social experience when I was a camper there too. And like the most important thing to me at age 12 and 13 and 15 when I went to that camp was like learning how to flirt. Like just like learning how to talk to girls in a way that maybe got a positive response and to kind of be playful. And I like had some of my first kisses there at the flagpole. That was definitely
Jenny Abegg (50:40)
Hehehehehe
Blake Boles (50:53)
high priority. But when I went back to work at the camp, when I was in college, that’s when like the big stuff happened. Getting to be, I mean, first of all, just for the whole dirt bag thing, just like living out of a tent for 10 weeks in the high Sierra and getting in and out of a cold water lake, teaching windsurfing and helping gas the generator and
Jenny Abegg (50:55)
Hmm
Blake Boles (51:18)
You know, food would be delivered by a Cisco truck and would be loaded into canoes and boated carefully, know, delicately, boated in and then hauled up just a lot of physical labor. β that was like this incredible somatic experience. I just, felt so good all the time. I woke up and I was full of energy and then I would get tired and I’d taken a nap and I’d be full of energy again. And it was not just being 21 years old.
Jenny Abegg (51:25)
Yeah, wow.
Mm-hmm.
Blake Boles (51:48)
It was the nature of the work and being outside and getting to be around this, like the energy of young people, the energy of the fellow staff who were all in their early to mid 20s β and under the sunshine and in the water. And the director, Jim, I got to know a lot better by working for him. And he’s just one of these guys, he’s kind of out of a…
out of a storybook these days. He’s like a real hard ass. Like he could be really difficult to work for with very high standards, very stringent. But when you did things right, when you met his standards, he was just turned into this playful teddy bear. And, and I ended up learning a ton from him. I ended up emulating a lot. He’s also a writer and he gives talks and does workshops for school groups in the Bay area, which is how he recruits kids for the camp.
Jenny Abegg (52:29)
Hmm.
Blake Boles (52:43)
And I decided like, I don’t want to be him, but I want to embody the best parts of him.
Jenny Abegg (52:51)
Yeah. Is
he the originator of the word Tanaki?
Blake Boles (52:55)
He is Tanaki,
the phrase I can’t spell it backwards and the story of the Tanaki monster, is mandatory storytelling for all campers, first time campers when they hike into camp. Yeah.
Jenny Abegg (53:09)
Yeah, he must be such an influential person because I know that Hannah seems to be also just like a result of spending a lot of time with Jim. Yeah.
Blake Boles (53:19)
Yeah. Yeah.
And Hannah actually went through the four week leadership program for teens, which I never went through. I only helped facilitate it later as an adult. β so she got the real, she really drank the Kool-Aid. Yeah. But a lot of my, a lot of my life or friends from, from deer crossing are the ones who went through that leadership program and then went back to work for Jim. And I met them there as coworkers.
Jenny Abegg (53:26)
Okay. Okay.
Yeah, yeah, the Tanaki monster Kool-Aid.
Cool.
Yeah. Yeah. I’ve worked, I worked a lot in summer camps too in my twenties. And there is something so special about living in community like that, having the same kind of like common goal as the people around you that’s like odd and off the grid and involves a lot of manual labor and a lot of time in nature that kind of like shows you a different way to live than like the live in a house with a couch and a bed and do the nine to five.
Blake Boles (54:11)
Yeah. Yeah.
Jenny Abegg (54:13)
Yeah, those experiences, they stick with us, don’t they? Yeah.
Blake Boles (54:17)
And it’s
glorious when you get that day off and you drive down the hill to Placerville or South Lake Tahoe and you rent a motel room and you get to sleep in a comfy bed and eat all this fantastic diverse food and you taste this freedom and you get to shave and have this 20 minute hot shower in the same way that you get back from a backpacking trip or a long run or a long rafting trip and you’re like, β civilization is so amazing.
Jenny Abegg (54:20)
Yeah. Mm-hmm. Mm-hmm. Mm-hmm.
my gosh,
Yeah.
Blake Boles (54:45)
but then it wears off so quickly that that joy of creature comforts. And you’re like, actually, what makes this so good is that I was working my ass off surrounded by people who I really like and respect in a beautiful natural environment. That is what makes creature comforts taste good. Therefore, yeah.
Jenny Abegg (54:49)
Mm-hmm. Mm-hmm.
Yes, yes. And I see,
I feel like you’re still doing that in many parts of your life. Like I think that like contrast is the spice of life. Like having these experiences that are hard or uncomfortable or extreme in some sort of way and then flipping the switch to like, to comfort and routine and then getting to go back. Like what an immense privilege really. And I think that.
Blake Boles (55:19)
Mm-hmm.
Jenny Abegg (55:35)
That flow is what draws me to climbing and running and other like type two things. But I feel like you’ve found a way to do that just in life. Like constantly switching things up so as to get that contrast. Does that feel like it drives you?
Blake Boles (55:40)
Yeah.
I think so. And I’m coming back to this analogy of like getting into the cold lake and then getting out and drying off in the sun and then doing it over and over again. And maybe, maybe if we have these sort of experiences as young people, we kind of, I don’t know, shape our, our, our bodies somehow, these kind of extreme, uh, feelings that we, we learn the far end of, of positive affect that, that we can, we can feel.
Jenny Abegg (55:58)
Mm-hmm.
Yeah.
Mm-hmm.
Mm-hmm. Mm-hmm.
Blake Boles (56:22)
And you could say that we get addicted to it, but whatever, if you’re going to get addicted to anything, that’s a pretty good thing to get addicted to. And, and then you have a choice, which is to either like try to forget that knowledge and say, no, that’s, it’s not possible to sustain that. Or I don’t know anyone else who lives this way. I, know, or relationships I’ve been singing high praise about relationships, but most people’s lives are just much more.
Jenny Abegg (56:24)
Mm-hmm. Mm-hmm. Mm-hmm.
Mm-hmm.
Blake Boles (56:53)
urban and creature comfort oriented. And so if you want to have relationships with people, like you need to go to those places where those people are. β so it is, it is well said. Yeah.
Jenny Abegg (57:01)
Yeah, it’s a blessing and a curse in some ways.
Yeah, to glimpse that way of living and that special set of emotions that you can have in an experience like summer camp or rock climbing or whatever. And then to kind of like live the rest of your life in search of that. Yeah, blessing and a curse, indeed.
Blake Boles (57:27)
I want to continue answering your question with one more important point here, Jenny, which is β right when I started becoming more of an administrator, like assistant director for deer crossing camp, I also started working at the other camp, not back to school camp. And this was like yin and yang. Not back to school camp was not this highly structured.
Jenny Abegg (57:30)
Yeah.
Mm-hmm.
Hmm.
Blake Boles (57:51)
super skills based, hardcore work from 7 a.m. until 10 30 p.m. every day type of place. It was like, hey Blake, what’s up? Nice to meet you. Let’s do an emotional check-in. Never once did an emotional check-in at Deer Crossing Camp, let me tell you. I was suddenly introduced to β nonviolent communication, to radical honesty, to this like slow flow.
Don’t push it. Don’t go too hard. It’s really a disservice to label this like a hippie or new age, even if there’s some overlap there. β but I met the other hero mentor of my life who’s Grace Llewellyn, who’s the founder of not back to school camp. And she wrote the book, the teenage liberation handbook subtitle, how to quit school and get a real life in education, which is one of the books that I read when I was getting into alternative education. And I was like, wow, totally electrified by it.
Jenny Abegg (58:34)
Hmm.
Blake Boles (58:50)
And then the last page of that book says, Hey, there’s a camp I started called not back to school camp. And I email her and she says, sure, come, come work for us for one session. And, and so there’s a number of years where I would work a full summer at deer crossing. And then by some sort of magic chemistry, like the day after deer crossing ended was the first day of staff training for not back to school camp.
Jenny Abegg (58:59)
Bye.
Blake Boles (59:18)
And so I would drive my butt 10 hours from South Lake Tahoe up to Eugene, Oregon. And, β and I’d go work for not back to school camp, which almost felt like a vacation to me because it was so chill and relaxed. then like, I needed to lead like three hour long workshops over the course of a 12 day session. And otherwise I can just sort of drift around and hang out with kids and other staff attend other people’s workshops, maybe play some games. And, but the idea was just come up and just show.
up and be your authentic self. Connect with the campers, connect with the staff, volunteer for some stuff every now and then, and that’s your job. so just the working environment is different. β And Grace was this totally different person from Jim, but she embodied this idea of human connection and community and the community that she created around her camp thrived outside of the camp in a way that deer crossing
Jenny Abegg (59:57)
Hmm.
Hmm.
Blake Boles (1:00:17)
didn’t deer deer crossing
Jenny Abegg (1:00:17)
Hmm. Hmm.
Blake Boles (1:00:18)
is a self-contained box. And, you know, if you’re going to be friends with people, you have to make that happen outside of, β outside of the camp and not back to school camp was this whole interconnected web of people and ex staff and campers who grew up to become staffers or just became these incredible people. And now we’re friends with everyone else. And, and I ended up working at that camp.
Jenny Abegg (1:00:37)
Hmm.
Blake Boles (1:00:46)
Gosh, 2006, I mean, the last time I worked there was 2023 with maybe a few years off for the pandemic and one year that I skipped. But like I had a really long tenure at that camp. so the community and the connections and the friendships that I’ve made there are extremely durable over time. And to be able to just show up and drop in to a two week long β camp experience, which is much more disrupt less disruptive.
Jenny Abegg (1:00:51)
Wow. Wow.
Blake Boles (1:01:15)
to your life than working a full summer of like nine or 10 weeks. You know, it really was something that I could continue to include in my life as, as I moved on and did other things. So hugely, hugely important. That’s how I ended up becoming the person who I am today. It’s, it’s the yin and yang of those two camps and the two camp directors.
Jenny Abegg (1:01:25)
Yeah, yeah.
The yin and yang sounds like a really good way to put it. Yeah, that’s very cool. And you’re still, you are still involved with unschooling. Is unschooling like β kind of a general term or is it, it, okay, it’s not, okay, okay. But you do run unschooling programs and that is that under a Blake Boles banner or under a different organization?
Blake Boles (1:01:46)
It’s a general term. It’s not like capitalized or trademarked or anything. Yeah.
No, Unschool Adventures is the company that I’ve had since 2008, in which I take teenagers who mostly use the term unschooler, but some of them might also be community college students or former homeschoolers, or they go to some like cool alternative school that’s super flexible. And it’s no problem if you go away for six weeks. I’ve even had a few public school students come. Lucky kids.
Jenny Abegg (1:02:00)
Okay.
Okay.
Yeah. lucky kids.
Lucky kids. β I wanna shift gears a little bit. everything, whenever I talk to you and in everything that I read from you, the word purpose comes up a lot. And you asked me about purpose when you interviewed me and I had a really hard time answering that question. It’s not something honestly that I think about very much. Maybe more subconsciously than anything. I’m curious.
how you would define your purpose and why is this idea of purpose so important to you?
Blake Boles (1:02:58)
I think we all need a sense of purpose, β and a sense of belonging. And so I don’t think it’s, it’s a weird thing to feel like this is important and necessary. just feel like I’ve ended up talking about it more publicly, β than most people do. And I think this connects back to my experience in school where I felt like no adults would give me a straight answer as to why we were doing what we were doing.
Jenny Abegg (1:03:11)
Hmm. Mm-hmm.
Blake Boles (1:03:28)
Why are we studying this? Why are we doing it this way? Why are you evaluating us? It’s like, it’s just because that’s the way it’s done. And you need to like just perform. And I was able to perform. was able to adapt and play their games, but, β that is not how I wanted to live my adult life. And so as soon as I had any say in the matter, you know, I found a way to, to take.
Jenny Abegg (1:03:34)
Mm-hmm. Mm-hmm.
Blake Boles (1:03:57)
my, you know, just to, to shape the way I spend most of my waking hours in a way that feels personally meaningful to me. And, and if you’re going to ask me like, what does that mean, Blake? What does it mean to be personally meaningful? It’s hard to say there there’s, there’s a visceral somatic feeling to it. I remember how it felt when I read that first book about alternative education by the author, John Taylor Gatto. The book was called A Different Kind of Teacher. And I was electrified.
In a way, like I had read books that interested me and maybe excited me before, but I was 19 and I read this book and I could not put it down. I was just like intellectually captive in such a good way. And I read it and then I was like, I need to read anything else that’s like this. And it went onto Amazon and found all the books. You know, if you read this, you should also read this, this and this. And, and so it was that, that feeling of.
Jenny Abegg (1:04:40)
Hmm. Hmm.
Hmm. Mm-hmm.
Blake Boles (1:04:58)
Of total focus and engagement and excitement. And I also felt this when I was at deer crossing and I went on the, the ascent backpacking trip where it’s not led by any, β camp counselors, but it’s designed and led by the campers in a small team. And you have to interview to get onto the ascent. β this sort of became a model for how I run my, international trips and, and we got to.
Jenny Abegg (1:05:18)
Hmm.
Blake Boles (1:05:27)
you know, bushwhack up to some local mountains. And then we went looking for some water slides. And when we couldn’t find the water slides, we just planted our asses down next to the river. And we told the staff who were trailing us sort of our insurance policies. we said, we’re going to stay here for the rest of the day. And they looked at each other and sort of rolled their eyes like, these lazy teenagers. And we were like, Nope, that’s what we’re doing. And that was a fantastic moment in my life.
Jenny Abegg (1:05:52)
Hmm.
Hmm.
Blake Boles (1:05:56)
And, β you know, could say, you know, living abroad in Chile for a month when I was 14 and getting to feel this sense of like autonomy, this, like this first sense that I was kind of popular. was only cause I had long blonde surfer hair and I was American and, very exotic in this, nondescript medium sized city in, Chile. β my first time traveling abroad with just me and my friends at age 19 in, in Europe.
And my first, totally like solo big trip to South America when I was 24, I could point to all these, these waypoints of, of experience where I just felt totally alive and engaged and not bored, not feel like I’m just punching some clock, β where I was curious, right? The people who I met were super interesting to me. And, and just, it’s this flywheel of
of enthusiasm and positivity and motivation. And I feel like my life just became like, keep the flywheel going. Like, don’t let it slow down. And like, it’s going to look like different things. But, but that is the purpose of my life is, is to keep feeling the spark, this joy, this motivation, this positivity, and to not let that die and just to turn into
Jenny Abegg (1:07:05)
Hmm.
Blake Boles (1:07:24)
to someone who’s just phoning it in in some big way. I think that represents failure to me.
Jenny Abegg (1:07:28)
Yep.
Yeah. Okay. I have two questions to follow up to that. The first is, does that ever feel tiring to keep the flywheel going?
Blake Boles (1:07:39)
No.
No, no, doesn’t. If the flywheel is going, then it’s not tiring. And even doing things that are physically exhausting, like traveling around all the time or staying up late dancing or going on an epic mountain mission with Hannah Hall, those are not things that I recover from them quickly. Yeah. Yeah.
Jenny Abegg (1:07:59)
you
Yeah, yeah.
As you’re talking, I’m thinking about the people in my life or just like people our age in general who perhaps never had upbringings like ours, never really got to see this way of life, never got to experience those camp highs that they’re in eternal search of for now and forever more, but they are feeling so stuck in middle age and…
they are realizing that they don’t want to live the rest of their life like this. Do you think that there’s potential? and I’ve read in some of your literature that like, the dirtbag rich concept is like, it’s very much geared towards like 20 and 30 somethings. I’m curious about like the 40, 50, 60 year olds who like, who feel stuck, who like,
maybe see you and see, or somebody like you and see the kind of like fervor that you live with and the feelings that you get to have and the experiences that you get to have and they want that for themselves. What about them? Like, do you ever think about them? Do you ever want, like I wonder, I guess like a personal wondering is as you get older, like will your message become more for them? Like.
Blake Boles (1:09:32)
I think we’re always writing for a slightly younger version of ourselves. And so is my message for people in their 50s and 60s? No, because I feel like I’m not qualified to write. I don’t know what that’s like. I do know what it’s like to be in my 30s and other people are settling down and I’m
Jenny Abegg (1:09:34)
Mmm. Mm-hmm.
Mm-hmm.
Blake Boles (1:09:50)
deeply questioning whether I have some sort of like Peter Pan syndrome as I continue to pursue adventure and novelty and travel and wanting to live different places rather than like settling down like most other people. So I feel qualified to write something for people in their 20s and 30s. And my other response, Jenny, is we all
Jenny Abegg (1:10:06)
Mm-hmm.
Hmm.
Blake Boles (1:10:18)
have like these impossible role models in our lives. for me, when I was early twenties and I was really obsessed with hiking the Pacific Crest Trail. And so this is right when I was finishing college. So 21, 22.
Jenny Abegg (1:10:31)
Mm-hmm.
Blake Boles (1:10:38)
And I was reading everything I could find about it. There was an article that was published about an athlete named Scott Williamson and the title of the article, it’s still available for free online. It’s called the unbearable lightness of being Scott Williamson. One of my all time favorite nonfiction articles about cool stuff in the outdoors. And this guy is from Northern California and he got into long distance.
hiking and then he had this incident where he was working at a convenience store and a guy came in with a gun and like shot him through the cheek or the jaw. You know, he survived it. But that was the moment where he said like, no, I need to like stop wasting my life away and just double down on this thing I love, which is the Pacific Crest Trail. And he set out to β
to yo-yo the Pacific Crest Trail to hike from south to north to south within one year. And he tried doing this over and over again. And this is what the article Chronicles are his attempts. And he leaves too early one year and gets stuck in snow in the Sierra. He leaves too late another year. And it’s just so hard to do this. It’s hard to hike the Pacific Crest Trail in one direction. This guy’s trying to be the first to yo-yo it. And that was one of these massively inspirational.
Jenny Abegg (1:11:32)
well.
Mm-hmm.
Blake Boles (1:11:58)
stories and role models who I never met. And then I went to go hike the Pacific Crest Trail. I had all the right ultralight gear. had Yogi’s Guide. So I knew where all the water sources were and the resupply. Thank God I didn’t, you know, package 52 resupply boxes and send them to PO boxes along the way. Yeah, because I quit after two weeks. And this is something that I, this is a story that I lead with in the
Jenny Abegg (1:12:04)
You
Mm-hmm.
Yeah, because I know where this ends.
Blake Boles (1:12:26)
introduction to the dirtbag rich manuscript in which I felt at that moment, like I was failing at both normal life in the sense of like get a normal job, have a normal career, and also my dream of being a dirtbag. Because if I can’t hack it with long-term hiking, because it wasn’t the physical part of the hiking that did me in, it was more of like the mental emotional game. And the best way I
Jenny Abegg (1:12:27)
Mm-hmm.
Blake Boles (1:12:53)
can explain it to this day is that I just felt like I was not of use to anyone. And I had already worked at β Deer Crossing Camp twice, β two full summers working there. And so I kind of knew what it felt like to be a part of this amazing camp community and be valued. And then all of sudden I’m just out there walking in the desert of Southern California by myself. And I’ve made some friends like fellow hikers, but they’re kind of like strangely similar to me.
Jenny Abegg (1:12:57)
Hmm.
Mm-hmm. Mm-hmm.
Blake Boles (1:13:23)
And I’m
just like, what am I doing here? What’s my purpose? And, know, I just felt kind of gross. I realized that I’m, it’s hard for me to just be like unshowered and like be coated with my own sweat and sunscreen day after day for, you know, I kind of imagined that I’d be more in the mountains and getting to jump into, to bodies of water, but no, in Southern California, that is no, that is not true. And so I quit and I felt.
Jenny Abegg (1:13:27)
Hmm.
Not in Southern California. Yeah.
Blake Boles (1:13:51)
quite bad about this. felt quite ashamed. told everyone that I’m going to hike the Pacific, the whole Pacific Crest Trail. really physically was capable of it. And yet all they wanted to do was go work at a summer camp. So I got off at interstate 10 in Southern California and hopped on an Amtrak train to, β to Pennsylvania, where my brother was working at a kind of a rich kids camp for kids from New York city. But he got me a job.
Jenny Abegg (1:14:05)
Hmm.
Mm-hmm.
Blake Boles (1:14:21)
just like that snapped his fingers and I ended up working at the camp that summer and I didn’t regret it.
Jenny Abegg (1:14:26)
Yeah, yeah. How interesting that for some people, like the idea of going south north or north to south or a yo-yo of the Pacific Crest Trail is enough, that is purpose for them. But for you, it seems like it’s a special cocktail of, there’s an intellectual element that I feel like maybe you need, but also the relational element seems very, very important. Yeah.
Blake Boles (1:14:38)
Yeah. Yeah.
Yeah. And just to close the loop on that, Jenny, so I
looked up to Scott Williamson and I still look up to Scott Williamson. And also I’m not capable of doing what Scott Williamson is doing, or maybe only at great sacrifice and by really bending who I know myself to be for a questionable reason. so I don’t know how
Jenny Abegg (1:14:59)
Mm. Mm-hmm.
Mm-hmm.
Blake Boles (1:15:14)
this book that I have to offer or the people I’m interviewing, how their life stories, you know, what they have to offer to, to other people out there who are in much different life situations, especially those with more β constraints with, you know, raising kids or they’re married and have a mortgage. And I don’t know, but I feel like there’s something important in here. There’s some spark that is shared among all these people.
Jenny Abegg (1:15:24)
Mm-hmm.
Yeah.
Blake Boles (1:15:43)
that I’m finding and that I find when I mind my own stories that I have not yet found in someone else’s book. And so that’s why I feel like I have to do this.
Jenny Abegg (1:15:54)
Hmm. And there seems to be sort of a level of responsibility of the reader to like you Blake Boles can do what you can to communicate what you believe in. And then you lay it out there and the reader gets to adapt it. Like you got to watch Scott Williamson do what he did on the PCT and then adapt β it. yeah, yeah. It’s important to know, to know oneself when you read something like that. Yeah. β
Blake Boles (1:16:08)
Yeah. Yeah.
Yeah, exactly.
Jenny Abegg (1:16:23)
Okay, when we chatted about my story, we chatted a lot about money. And I’m curious if we could get into this, just we have a little bit of time left. I’m kind of thinking it won’t take long because I imagine that your situation is rather simple, but you don’t own a home, you don’t own a lot of stuff, you don’t have a storage unit. What is your relationship with money? Do you think about retirement?
Yeah, tell me about your relationship with money. What does mean to you?
Blake Boles (1:16:56)
Sure.
I do have a small retirement fund, a Roth IRA and some other investments, which are at the mercy of the market. And I just have a lot of money that I’ve slowly saved up over the years that’s just sitting in a high yield savings account right now. And it really makes me, this is another form of security. β Just knowing that I have a lot of liquid assets, which are not exposed to the market that are
Jenny Abegg (1:17:17)
Mm-hmm.
Mm-hmm.
Blake Boles (1:17:26)
probably between five to 10 years of normal Blake living expenses. And that is like, whoa, that’s cool. That’s a lot. I am also aware that certain things can happen like medical emergencies or needing to support family members that could wipe this out pretty quickly. β But that is, it feels super important to me that I earned this without anyone β
directly helping me, not, you know, no, like direct contributions from family. I, from my granddad, granddad who died, I think I got $6,000. That was it. And, and the fact that I built it up slowly doing work that I really enjoy doing that feels like it’s a positive contribution to the world. And that didn’t stress me out or lead to burnout. that allowed me to work part time during all these years. That just feels like.
Jenny Abegg (1:18:00)
Mm-hmm. Mm-hmm.
Mm-hmm.
Blake Boles (1:18:25)
Like I’ve done something really, really right. β have I allowed my tastes and my expenditures to like gradually creep up a bit. So I spend a bit more when I go to stay in Munich this upcoming weekend to visit my sister and her husband. Am I going to stay in, in a room I got that it costs about $100 a night? Yes. Does this feel like a wild indulgence to me? It does.
Jenny Abegg (1:18:35)
Mm-hmm β
Mm-hmm. Yeah. Yes. Yes. Yeah.
Blake Boles (1:18:53)
It’s kind of like the day off after working at wilderness summer camp. Yeah. And
so I don’t feel like I’m trapped in this like forever super frugal, like I can’t imagine any life, but the life that I crystallized at age 21, β life that, that doesn’t feel like the kind of freedom I’m interested in, but I feel pretty proud about not letting my, β my spending habits.
increase very much over the years while I’ve been able to earn a bit more each year over the years or earn a bit more and then choose to work a bit less, which is really what I advocate for as part of this dirtbag rich time and money equation. Yeah, so I feel good about it. Jenny, things are going pretty well. Thank you for asking.
Jenny Abegg (1:19:35)
Mm-hmm. Mm-hmm.
Yeah,
yeah. Not many people can say that right now in May of 2025. So that’s awesome.
Blake Boles (1:19:50)
Also, no house, no kids, β no major medical β incidents. I don’t have to wear eyeglasses. I essentially never access the healthcare system. I do have health insurance. Yeah.
Jenny Abegg (1:19:53)
Zero stress. Yeah.
Yeah, yeah, it’s a lot, can be simpler than we make it out to be when you’re not tied to a lot of things and stuff. I’m gonna ask one final question that you asked me that I had an immediate answer to and I’m wondering if you do as well. The question is, how is your life currently not working? is there any way in which your lifestyle is currently not working for you?
Blake Boles (1:20:30)
My first thought is to provide the same answer that you provided when I asked you this question, which is to talk about β relationships and the possibility of like long-term romantic relationship. But
Jenny Abegg (1:20:34)
Mm-hmm.
Yeah.
Blake Boles (1:20:44)
Okay, I’m actually not going to go down that route because I actually feel like I’ve been learning a lot about myself in relationships and romantic relationships and what I need and what my values are. And I don’t feel that bad anymore for not being in a long-term relationship at this point in my life.
Jenny Abegg (1:20:59)
Hmm.
love
that. I love that for you. I… Fuck yeah. I’m glad that’s something that’s not not working. Yeah.
Blake Boles (1:21:06)
Thanks.
So my response to your question is, I want to continue being involved in the world of education and working with young people. And I’ve built this wonderful system for myself in which I get to design and organize and lead.
these international trips or these single place based retreats for groups of young people.
And I feel like this is a, part of life where I’ve actually gotten pretty comfortable in a way that that might be not to my long-term benefit. Yeah. And I’m yeah, I’m not concerned about making more money. I think if I like suddenly entered into a situation where I’m supporting a kid, then I would worry about making more money, but that’s not the main concern. It’s more like, do I really want to look back?
Jenny Abegg (1:21:59)
Tell me more about that.
Blake Boles (1:22:16)
and look at 40 years of running on school adventures trips. Cause right now I’m looking at about 17 years and maybe 20 would be a great place to, to just put a bow on it. β I’m a little bit concerned about my body and my back, not enjoying, β sleeping in random hostel beds and being on buses and planes for long periods of time. But I think that’s, that’s manageable. and so.
Jenny Abegg (1:22:32)
Hmm.
Mm-hmm.
Blake Boles (1:22:46)
What would come next? I feel like I’m supremely qualified to do just a few things in this world, which is to run a summer camp or to maybe run an alternative school. And summer camp would be, I think would fit with my sort of seasonal lifestyle habits. But a school is really appealing because you have these longer term relationships with young people. just spend more time with them and it happens year after year.
Jenny Abegg (1:22:53)
you
Hmm.
Mm.
Blake Boles (1:23:16)
And the question, Jenny, is, I capable of staying in one place? This is what people ask me. I, in a cavalier way, I say, sure, if I wanted to, I totally could. But could I? Would a school that I helped run be enough of an anchor point? Or would I somehow self-destruct? β
Jenny Abegg (1:23:32)
Hmm.
Blake Boles (1:23:45)
Would my notion of freedom and evasion of servitude, would that come back to bite me?
Jenny Abegg (1:23:53)
So
this is fascinating. I’m excited to know. I’m excited to watch you. My hunch is that there would be a hump that you would need to get over. That there would be a patch where you just wanted to quit the PCT and run to South America, metaphorically. I wonder what would happen if you stayed. Because to me, and when I hear your story, it sounds like one of the things that
Blake Boles (1:24:07)
Hmm.
Mm, mm, mm-hmm.
Hmm.
Jenny Abegg (1:24:22)
that drives you most right now is relationships. That is like one of the best parts of your life. And I can only imagine that that would be a highlight of staying in one place, in one community, and being the leader of it.
Blake Boles (1:24:37)
Hmm.
Jenny Abegg (1:24:39)
Wow. Well, that’s a fun note to end on, because I feel like we all get to stay tuned.
Blake Boles (1:24:40)
Yep. Yep.
Stay tuned. Stick around.
Jenny Abegg (1:24:51)
Wow, yeah, where will Blake Boles be in five years?
Blake Boles (1:24:57)
For only $15.99 you can buy the book and find out.
Jenny Abegg (1:25:01)
For $9.99 a month, can get email updates to your inbox. I would subscribe. It’s intriguing enough.
Blake Boles (1:25:04)
I mean, people do that with Substack really, so I’m not doing that. That’s staying free forever. β well, thank you. man,
like the deep updates and like, you know, midnight regrets, that kind of stuff for only $9.99 a month. Gosh, you just you just helped me figure out my next career step, Jenny. Thank you.
Jenny Abegg (1:25:18)
Yeah, totally. Oh, I-
I
would pay for that. That’s like an OnlyFans kind of thing. Like you should have an OnlyFans account in which you don’t share photos of your body. You just share dark nights of the soul of what it’s like to have Peter Pan syndrome in your forties.
Blake Boles (1:25:30)
Uhhh…
my God, Jesus. my existentialist
dirt bag OnlyFans. All right, I’m ready. I’m ready to co-found this startup. Let’s go.
Jenny Abegg (1:25:40)
You have an audience.
You have an audience. β Well, that feels like a good note to end on. Maybe. β Well, this was really fun. And I hope you know that I look up to you so much. And whenever I talk to you today, included, I just leave feeling like, like I want to live life more intentionally. And
Blake Boles (1:25:52)
Ridiculous note, I love it.
Jenny Abegg (1:26:10)
β yeah, that’s what you always leave me with. So thank you.
Blake Boles (1:26:15)
Thank you, Jenny. And this was a really delightful and meaningful conversation for me. So I appreciate you.
Jenny Abegg (1:26:21)
β thank you.