Diana Proemm is a 54-year-old ski bum, adaptive sports professional, dual US-German citizen, and lifelong wanderer who has spent three decades saying yes to unlikely opportunities. (dianaproemm.com)
Diana describes leaving Ohio in the mid-1990s, bouncing between ski towns, remote lodges, and outdoor jobs, and building a life through curiosity, persistence, and conversations with strangers. From working in Alaska’s grizzly bear country to hitchhiking through Chile, volunteering on organic farms in New Zealand, and repeatedly selling nearly everything she owns, Diana’s story never really settles down.
Along the way, she became a certified recreation therapist and adaptive sports director, helping people with disabilities access the outdoors while slowly piecing together enough financial stability to keep chasing freedom. We discuss seasonal work, Workaway gigs, online income, living cheaply abroad, why she believes many women underestimate what they’re capable of, and the social dynamics of working with wealthy clients at the Yellowstone Club.
Now living in the Austrian Alps, Diana reflects on getting laid off, starting over in a new country, and maintaining faith that the next opportunity will appear when she needs it. At an age when many people are planning retirement, Diana doesn’t know where she’ll be next year—but that’s never stopped her before.
Full transcript: dirtbagrich.com/dianap
Recorded in June 2026.
Transcript
This is an AI-generated transcript. Typos and mistakes exist!
Blake Boles (00:00)
Diana Proemm, welcome to Dirtbag Rich.
Diana Proemm (00:04)
Thank you, Blake. It’s nice to meet you.
Blake Boles (00:08)
How many times have you sold all of your possessions, liquidated your life to go travel world?
Diana Proemm (00:17)
effectively twice. once with my ex partner in two thousand fifteen before we went on world travels and then again, which I, you know, thankfully didn’t collect as much this time, but in two thousand four I sold everything that didn’t fit in my car. So yeah, sorry, two thousand twenty four, yeah.
Blake Boles (00:38)
Two thousand twenty four. Okay, you’ve done it twice now. And and have they both led to total revelations and you know, your life becoming so much simpler. Everything you dreamed might happen if you took this path happened.
Diana Proemm (00:58)
Well, in 2015, I had this wild hair up my butt. I’d wanted to go travel again with a backpack like I had done in my 20s. And thought it would be cool to do that again. And I was kind of in a weird place in my life, and so I was like with my partner, I was like, I’m going with or without you. And then he decided to jump on board.
And we went into Central and South America and we were gone for six months, but and ultimately ended up leading to the demise of our relationship. But I mean what I learned was I was pretty happy on my own, because he had left for part of that journey, and I actually had a really great time when he wasn’t there.
Not to say that there was anything bad about that, but I think I realized at that point that it was time for us to separate. We had been together for twelve years and and it wasn’t getting any better throughout the trip. If anything, it just kind of, you know, brought up things that weren’t being addressed and needed to move on. And so when I came back to the US, we ended up separating and he ended up doing his own thing, but
And then the second time, I got my German passport. So I have a dual passport now. And I’d always wanted to live and work in Europe. And with my partner at the time, we were supposed to, after our travels, he was supposed to build a zipline in the Bahamas. We were gonna go there, do that, make some money, and then go to Europe and try and make it work there. But then of course we
and ended our relationship, so that didn’t work out and then I was kinda stuck not stuck, but back in the USA and that kind of fell through and it always was in the back of my mind that I wanted to come to Europe. And then when I finally sat down and figured out how to get my passport because my parents, Hans and Heidi, are from Germany. And they helped me get the passport and then once I had that I had online work
And I talked to my boss about living and working in Europe if he cared. And he said no. And so I was like, okay, this is my ticket. And then I decided to, in the fall of 23, after I had gotten that all settled, I sold all my stuff again, except for what could fit in my car. I left my bike and stuff. I kind of had this plan. I left my bike at a friend’s mountain bike with my mountain biking gear so that when I
got to Europe he could ship it and then I took all my ski gear knowing that after my world tour I would end up in Europe hopefully and then I would could go home and bring my ski gear back and so I’d have my ski gear for the winter which was the plan and I ended up getting I mean as far as what I learned I learned that I could still travel fairly cheaply and I hooked up a
with a friend from high school who lives in Abu Dhabi and then we went to Sri Lanka together. She was there with me for a week and then I stayed there for three months as a sub guide doing a work stay for these people and then from there I ended up back in Abu Dhabi and then traveled through Europe, visited some family in in Germany.
And then I had a gig working at a mountain bike park in surf out in f a little tiny little town of Fist. There’s a bike park there. And then that unfortunately didn’t work out because it was too many hours for my job that I was doing online and the amount of money I was making online versus at the bike park was not compatible. And so I had to forego that. And then by proxy ended up a different place at a hotel in a place called Badgestein. And now I’m here expatting quote unquote living the dream that I had foresaw when I was eighteen.
Blake Boles (05:20)
what pops into my head is that that narrative you just described, I think really fits a lot of world travelers in their twenties. Of I was gonna travel with my partner, we start we broke up and then I I met up with my friend in this other part of the world, and then this opportunity dropped into my lap, and then I took this job over here, didn’t quite work out, and now I’m over here.
But Diana, you’re in your fifties. And it sounds to me like you’re still traveling as if you’re in your twenties. And and this is why I wanted to have you on on the podcast, because it sounds like you’ve been living this way more or less ever since you were eighteen or or in your twenties. Is that accurate?
Diana Proemm (05:53)
Yeah. yes and no. I mean, in my twenties I ended up bouncing around quite a bit. it’s when I did I I mean, I left home in nineteen ninety-five and then I moved to Big Sky to be a ski bum for a year, and then I fell in love with a not so nice man and followed him to Alaska and ended up breaking up with him that fall and then in that winter I roomed with a gal who Got me this gig working out in the Alaska bush. And then
Blake Boles (06:40)
What what kind of work was that? I have to know.
Diana Proemm (06:43)
it was for a place called Katmai Land Incorporated. It was Brooks Lodge. It’s it’s a fairly it’s a little bit larger compound than most remote fishing lodges in Alaska because there’s park service there. It’s in Katmai National Park. There’s if you it’s like one of the largest populations of grizzly bears in the world, it’s where if you see the salmon on the f the the falls and the salmon are jumping into their mouth, that’s right on the Brooks River where we were.
Blake Boles (07:11)
that’s where those photos are taken. Okay. Good to know.
Diana Proemm (07:13)
Yes. Yes.
Yeah. And so my roommate thought it would be a great thing for me. So of course I was like, yes, absolutely. And the amount of times I almost died on that summer was pretty astounding. And then I ended up leaving there and I I I don’t know why this happened because I left Big Sky early with this guy, because of course he said that he wasn’t
We would have to break up if I didn’t follow him in January. He was part of he was one of the builders of the original tram that they built to the top of the mountain. And then he was done in like January. And so I was, you know, didn’t want to lose him at the time. so I followed him. But then after I left the bush, I went to Crested Butte and met up with a friend that I had met out living out in the bush. And then I couldn’t find a job and I was broke. And so I I went home with my tail.
Between my legs and but I ended up getting a a like a volunteer position with the National Park Service in Ohio. So I didn’t have to live at home because I was already twenty four, twenty f no, I was twenty five at the time. Yeah. Yeah, I was twenty five. And then from I mean, it’s such a random like these random things that I did. And then I from there I worked that winter at this like renting snowshoes at I can’t remember, Virginia Kendall or
Blake Boles (08:21)
Mm. How
You just answered my question. I was curious. yeah.
Diana Proemm (08:40)
I think state or national park the park there in the Cuyoga Valley. And and then I I was back at the little ski area where I learned to ski working and help, you know, working there. And I was talking to one of the guys and I was like, you know, I really want to get back out west. I’m not sure how to do it. And
I talked to his son and his son lived in Park City, Utah, and he the the words I distinctly remember to this day and what keep what’s like the driving force of my life is he’s like, Well, you you were in Crested Butte, right? And I was like, Yeah, he’s like, You couldn’t find work and I was and at the time I I tried a little bit, I probably didn’t try hard enough. And he was like, Well, I guess you didn’t want it bad enough. And that was like, Whoa, okay. And so I ended up calling my boss from the bush.
Blake Boles (09:31)
Mm.
Diana Proemm (09:34)
And I was like, I’m going back. And I sold I had at that time like a old 1990 Ford Mustang. And I sold that and and moved and moved back to the bush. And then that summer I met some people and I ended up traveling to Nepal, Thailand, and New Zealand. And when I was in New Zealand, I stayed there for three months doing the work, like the woofing, the willing workers for organic farms. I’m not sure if you’ve heard of that, but that was also works day stuff.
Blake Boles (10:03)
Mm-hmm.
Diana Proemm (10:03)
And then
I ended up working at a beautiful little like I guess what they would consider a boutique hotel or place, helping out there. And then I ended up getting some work searching for skinks and up in the high alpine terrain. And then I worked with a bunch of dudes on trail crew and they basically flew me up on a helicopter. All the boys had to hike in, but they flew me up in a helicopter.
Well it’s just like these random things that I got myself into. I don’t know how I did it, but it was just like, this sounds great. And I would just do it and I would say yes to all these opportunities and and then, you know, I went back into the bush because I came home broke, of course, after six months, and then went back into the bush and then I met some people it was a random storm one night and there were we had a big party at the lodge, people got stuck and I met a guy from a another lodge.
Blake Boles (10:38)
Huh.
Diana Proemm (10:58)
I was a guide and we randomly got in this conversation and he’s like, Yeah, I’m looking for a guide. not a guide, somebody to do shuttles and lunches for me down in Chile. And I was like, Yeah, sign me up. And again, you know, like random. And he’s like, took my number this on a tiny little piece of paper. And I I’m I I have no idea how he kept this, but
Blake Boles (11:12)
Yeah.
Diana Proemm (11:26)
I never heard from him. And then in November I was home visiting my folks and I get this call from him and he’s like, Hey, do you want to go to Chile? And I was like, Are you kidding me right now? Yes. Yes. So I ended up going to Chile for the winter, working for him and traveling while they were, you know, not working. And I did a hitchhiking trip with his girlfriend up the Carataro Stral. And we I mean, I was hitchhiking to do the shuttles and stuff because that’s what he said. And as a female
At that time in my late twenties, you know, I I looked at the sky David and I was like, Are you kidding me right now? I have to what? To hitchhike? After, you know, my my mother, I can hear her in her head like, You can’t hitchhike ever, don’t ever get the car and then the first guy that picked me up was in this garbage truck. It was like the it was hysterical. He was so happy to have the screen gun his car and my god. I mean, it was just it was so random. I and then
Blake Boles (12:18)
Ha ha ha.
Diana Proemm (12:24)
Yeah, I came back from that trip. Okay.
Blake Boles (12:25)
I I I want to pause you right here, Diana,
because th this is this is good stuff. And I also want to like zoom out and maybe like classify what it seems like you’re you’re doing here. And because I feel like this applies to a lot of people who want to like work in the outdoors or be close to nature, not have an office job. I I imagine you were motivated by by all of this. And it sounds to me like what you were doing was you go to some
Cool outdoorsy spot. You’re in Alaska, you’re in Crested Butte, Colorado. you try to find work there, or somebody had told you about an opportunity there. And then it seems like you’re meeting people and they are directing you towards the next opportunity. And it’s just this long succession of meet interesting people who live in interesting places and they will connect you to whatever your next cool opportunity is. That doesn’t mean they always work out, but that sounds like more or less how you led.
your life. It doesn’t sound like you were you were sending in job applications from far away. And and of course, you know, at this moment I assume we’re still a a bit in the early internet days. And and so you were just going out there and you were you were doing it. Like you said, you were you stopped waiting for permission. You you stopped half asking it. You you just went for it and you said yes to all these opportunities. Is that right?
Diana Proemm (13:48)
Yes. And yes, you are correct. When I was living in the bush I got my first hotmail account. And that’s I mean, we we didn’t communicate. When I lived in the bush, we we o the only communication we had was a two way radio phone.
And the guys in King Salmon at the the air taxi could hear our conversations that we’d have with our families. Which which was I I mean, yeah, we didn’t have we talked to people, like we talked to each other because we didn’t have any other ways to communicate. We didn’t have any phones, we didn’t have any of that stuff. And I think about that all the time, and I wish that
We could go back to that because I think we’ve lost a lot of I think there’s a lot of things lost in translation because we’re so stuck on our phones these days. So
Blake Boles (14:37)
Do you think it’s still possible
to just move to someplace cool, try to find employment there, and meet people al along the way and let those people guide you towards whatever comes next in your life? And is that impossible?
Diana Proemm (14:52)
No, I think it’s possible. I I do. But what I’ve noticed is is my latter, you know, in the last few years, and maybe it’s because I’m older, I don’t really you know, I stay at nicer places and I don’t stay at the hostels. Where I met the majority of people, besides like working in the bush because we were together twenty four seven every day, you know, I d I don’t meet the people as much. And
So I think if you’re younger, like if you’re in your twenties and you’re staying at hostels, then yes, there’s I think a myriad of opportunities and a wealth of opportunities that you could have. And to be honest, when I was traveling in New Zealand, like all those places, the I found my way to these cool places by talking to other people in the hostels. And, you know, it’s a it’s definitely a different vibe as as you get older.
to find that those unique connections to different opportunities. I find that a little harder.
Blake Boles (15:58)
Let’s continue analyzing from this age twenty-nine moment. I’m curious, what what did you study? Like what did you think you were preparing yourself for when you were younger? And then did you get off of that track or did you always want to be like a migratory outdoor bum?
Diana Proemm (16:21)
I had no idea what I wanted when I was eighteen. I went to school. I started in criminal justice because I wanted to be a cop like a undercover cop. And then I went to Germany with my family after I graduated. And then I was like, I wanna be a stewardess or in travel. And then I got into that field and that was more of like in the transportation realm versus travel realm.
And so I I busted out of that and went into physical therapy. And then I had to cheat to pass like my, I don’t know, microchondria or whatever whatever that was, science classes. And so I decided to get out of that. And I ended up in photography, commercial photography, and
I really, really love that. I always wanted to be a national geophotographer, but I just didn’t know how to do it because A, we didn’t have internet. I didn’t know how to bang on the doors back then. I didn’t know how to find the right people. I wish I had, I wish I could tell my younger self to just go beat downdoors or, you know, at this day and age, like beat down editors or whatever. But yeah, at the time that’s what I wanted to be. And so I think that it was just my way of finding my way.
Through the world and getting to these cool places because that’s what a nat geo photographer would have done, right? I just never knew how to sell any of my photographs at the time. So I carried that camera around all over though, my old Canon AE1 and you know, film camera, film canisters. Carried it all around, but never really sold anything.
Blake Boles (17:42)
Mm, mm.
Hm. Hm. Yeah, I
I appreciate
the the honesty. also at this age twenty-nine moment, were you tired at all of moving around, of these seasonal opportunities, of not having a a single home base, or did you still feel invigorated by that?
Diana Proemm (18:18)
Mm, it it never bothered me. I was always bouncing around. I I I don’t think I had a steady place until my ex and I bought our condo in Bozeman in 2007, right before the downturn of the economy. I was bouncing around from place to place, ski ski area to ski area, whatever. Yeah. I was a lot I loved it. I loved being transient.
Blake Boles (18:42)
Yeah.
Yeah. And what about the work itself? Like what kind of purpose did you find in the work and maybe talk a little bit about e exactly what you were doing in these ski areas.
Diana Proemm (18:58)
well when I was in Alaska, before I had left Alaska, I I had met some people and one of my really good friends was doing Challenge Alaska, which is working with people with disabilities, teaching them how to ski, adaptive skiing. And I fell in love with it. And I had been doing some soul churching soul soul searching around the age of 30, of like, I’m tired of making, you know, working at REI for $10 an hour. I really want to make some money. And
So I was doing some soul searching and found that I wanted to be in the outdoors, but I also wanted to have some medical stuff there as well. And how could I blend it? And then I I came upon adaptive sports. And then I ended up in Idaho to go back to school for recreation therapy and became a nationally certified recreation therapist. And then by proxy, I I started bouncing around. I moved to Telluride after school.
And then that’s where I met my ex. And he was also a big, big advocate for adaptive sports. And so that’s kind of how we met. And then I ended up getting to go to Mammoth Lakes, California, and work there for about a year and a half doing that. And then and then we had an opportunity to go work back in Bozeman, which I was really excited to be back in the Big Sky area.
But both of us had gotten hired on to work for ch the Marlborough Challenge, it was called at the time, working for Philip Morris on the Crazy Mountain Ranch. And so we did that for a couple years. And then after the downturn of the economy, they got rid of that program. We all got laid off. And I ended up getting back into adaptive sports and became the adaptive sports director for Eagle Mount.
which hosts people with disabilities. They do horseback ride, they do all the things. And I ran the Bridger Bowl ski program, like the Bridger Bowl program that ran for eight weeks and helped down in Big Sky and trained. I was part of the professional ski instructors ski instructors of America with the Northern Rocky Mountain region. I ended up really like growing that program and getting people certified and all that kind of stuff.
Blake Boles (20:48)
Mm-hmm.
Hmm.
Mm.
Diana Proemm (21:17)
So that was like a huge passion of mine at the time.
Blake Boles (21:20)
Sounds like you
really leveled up professionally. You got to keep doing something that felt really like meaningful to you. And how how did it go with your age thirty intention to make more money, to not be constantly scraping by?
Diana Proemm (21:36)
Well, it went okay. when I was working at Yelmot, I wasn’t making a a ton of money because it was a non profit, but I was super happy. I mean I the the compound we worked at, you know, the facility was kinda out on the south end of town, kinda outside of town. And then of course I got to go to the ski area every day to work. So it was it was a pretty sweet gig for me, you know. I got paid to ski and work with really cool people.
Blake Boles (22:07)
And were you able to eventually save money? I mean, you you told me you bought the the condo, maybe not at the right time in history, but h how were you able to escape the the classic like ski town or outdoor town trap of always grinding, doing service level labor that’s not very well paid while life around you gets more and more expensive?
Diana Proemm (22:34)
yeah. I don’t know. I ended up leaving Eagle Mount and then I worked for the Yellstone Club and I kind of got sucked into that through the winners, which was decent pay. And then that’s right around the time that I ended up wanting to go travel for the winter. And we then we sold our house. We had
I don’t even know, maybe five to ten thousand dollars. I I don’t even remember. It wasn’t that much. But I had some savings because I put money into retirement when I was working at Eagle Mound and you know, had my own little savings account. And so we ended up just spending the money that we made off the condo and traveling off of that. And then that was about six months, and so at that point I needed to find a job.
So I wasn’t finding anything online at the time. So I ended up moving to Texas to work one on one with people with disabilities through their program there through the state. So
Blake Boles (23:41)
You’ve told me before that you’ve used work away and other kind of work volunteering, get free housing, sometimes get free food, to be able to save money. That what does that look like for you?
Diana Proemm (23:58)
I d I mean I’ve done it all over. I think the cool thing about the workaway stuff is that you can I mean when I was in Sri Lanka, my food, my housing, everything was included. So all my online work was just getting banked into my savings account.
and so that worked out really well. And the same when I worked in FIS and then also in Badgestein at the hotel, I had housing and
I had some free meals, not all free meals, and then I got a stipend of I mean maybe a thousand, fifteen hundred Euros. I can’t even remember. It wasn’t even it’s not that much, but it was enough for me to buy myself food and do the little activities I wanted to do. And so again, else I did was bank money. In two thousand four, I pretty much just bankrolled, you know, all my all my money that I had made that year. And so that’s what I did.
Blake Boles (25:01)
And I I want to return to this theme that maybe some people might be asking themselves right now, which is like, how how have you managed to have this way of living feel ex more exciting and adventurous than like stressful and full of anxiety? moving from one opportunity to the next. I I’m imagining you’ve never had much of a a long run like
future plan. correct me if I’m wrong. Like and and and please tell me if there has been like significant periods of of stress or serious self doubt or yeah, thinking I need to stop doing this. I need to do something totally different.
Diana Proemm (25:34)
Huh.
well most recently, so in two thousand and four I did all this travel and then I decided that I wanted to have a big girl apartment. I was tired of living with other people and I wanted my own kitchen. I wanted an apartment and I ended up finding this super sweet place where I’m at right now in the mountains, in the Alps.
and decided to stay here. The landlord was super cool. I have a huge terrace, mountain views, all the stuff, reasonable rent. And I was so excited, but I was, you know, again, nervous because it I mean it wasn’t cheap, but it wasn’t I it was tolerable. Based upon what I was making at the time, I I was like, okay, I’ll I’ll do this until I can’t. And then I
You know, and I was depending on my online work and then I ended up getting laid off in May. So I got this place in November of twenty-four, and in May of twenty-five I I lost I lost part of my income. I have some other stuff that I do that brings in a little bit of money that was kind of my savior. And then I also had a local job that I had got in March that pays the rent in my car insurance. So the only thing I really had to pay for was my food.
And any extra, you know, whatever else I needed to buy. And so I but of course at the time I I that was a huge chunk of money that I lost. And I had just signed on to this place. I had signed on to being an expat and I was terribly scared. And but I decided that it was all gonna work out. I had to keep the faith. Like I I really have worked over the years, like I listened to the secret when I got laid off.
and we had just, you know, bought this condo. We lost our butts on it, and we had a huge mortgage payment, and I had lost my job back then, got laid off as well. And so I kind of I read the secret and I was like, I own my house, I own my life. And so, you know, worst case scenario, I would just have to give this place up and go wherever. But it ended up somehow just all working out, and then I ended up back in
you know, back in the industry with online work similar to what I was doing in the fall. And so it ended up working out. And I had a great summer, got to travel a little bit. used I don’t even know if I ended up having to use savings or not, but it it just all ended up working out. And I always try to believe that. And ’cause I think if you stress too much, then it makes it worse. Cause there’s nothing you can do. And if you just sit and think about stuff, then
Blake Boles (28:21)
Mm.
Diana Proemm (28:34)
You know, try to figure out how to make it work. That’s been my whole life is how do I make this work? How do I how do I become independent you know, independently located? That was my big goal for a long time. And then I got this online work and I was like, now I can work from anywhere. And then it was just step by step. And it’s like, but it you know, it didn’t happen overnight and it was just trying to figure out how to make these things work and putting the pieces of the puzzle together.
Blake Boles (28:56)
Mm.
And at that moment where you said it all just sort of magically worked out, j just to be clear, that doesn’t mean like someone bailed you out or you had money come in from family or or some other secret source like that, right?
Diana Proemm (29:12)
No, no. In Austria they actually, funny enough, in June I ended up getting a double paycheck and from my company locally. And what to come to f I came to find out that they pay they pay fourteen months versus twelve months. So in June you get a double paycheck and in November you get a double paycheck. So it’s a
your bonus or whatever. And so I ended up having that extra money and then the little bit of money that I came in from another source. And yeah. And so, but yeah, everything is self-funded. I don’t I don’t have a trust fund. My parents don’t have my family doesn’t have a trust fund. I mean, they’re probably I mean, they’re you know, they’re living off of a very meager pension right now, my parents. Like they can’t give me anything. I think my parents used to give me, I think they threw me like two
two hundred or six hundred bucks when I was overseas the first time around for my birthday and, you know, threw me a couple of hundred here or there, but otherwise it’s all been self funded.
Blake Boles (30:17)
You’ve written a number of blog posts and also a guidebook directed at solo female travel over the age of 50. At what point did you start thinking that you wanted to explain your your approach and your experiences to other people? And were people asking you for this information, or did you decide one day I’m gonna share my life?
Diana Proemm (30:28)
Mm-hmm.
well, the traveling solo for over fifty is mainly a guidebook. It doesn’t really have a lot of stories in it. It’s just a a guide for women who wanna travel and maybe have never traveled before or, you know, want some basic information. It has it’s just a a it’s just a resource. And it really came down to it was a completely random thing that I decided to do. And the gal that I was working with to help me write it and edit it,
She was like, Well, not there’s really no books out there like it. So she’s like, You’re on a good track and so therefore I ended up just putting it together. It was a really sweet little program that I used and they helped me, you know, edit
write, edit, and produce well basically the cover, the design, everything. They like they did everything for you. And it was like all one stop shop. It was great. And so I put it together just to try it out because I have another, you know, the the storybooks are coming out. And so it was a test for that.
Blake Boles (31:37)
Hmm. Hmm. And
Okay. And why did the world need a a guidebook for solo female travel over age fifty? W what is it that people in that demographic cannot find by just Googling, finding articles or reading other guidebooks or how to travel material that’s aimed at at all ages, for example?
Diana Proemm (32:09)
Well I’d love to say because it has some amazing secrets that I only know about. But I mean you can find the information everywhere. It’s just w mainly a one stop shop. to have everything there in a book. I mean I don’t yeah.
Blake Boles (32:25)
Okay. I I love the humility. That’s that’s great. But but I mean
I mean that’s that’s important to bring together disparate resources into a one-stop shop. That’s also valuable. what what is it about women over fifty who want to travel solo for the first time that that makes this like a a particularly interesting challenge to you and and what kind of like fears or anxieties have you noticed wrapped up in this?
Diana Proemm (32:36)
Mm-hmm.
Well, I think a lot of women get in their heads. They tell themselves they can’t do things. I’ve seen it over and over again, ’cause in my teachings with adults, mainly at the Yellstone Club, and I mean the Yellstone Club is a very wealthy population. It’s very high end, it’s very exclusive. And it would mind boggle me that the women that I got put with adult women a lot.
’cause they knew that I was good with with this with with these kind of women and it never ceases to fail me. They they would say, you know, I said, Well, why they they said, What, you know, I asked them what their goals were and their goals were like, I want to ski with my kids on the ridge or up on the higher terrain and I said, Well, why aren’t you? And they said, Well, I’m kind of scared. And I look at their skiing and I said, Okay, well let’s go skiing and I’d look at their skiing and
They were perfectly adequate skiers. They just needed maybe a little tweaking here and there, but it was the confidence that was keeping them back. And I and it was just always one of those things where I would try to encourage these women. I’m like, let’s go do this stuff. Like, you can do it. And and it I don’t know how many times I saw it over and over. Women talk themselves out of doing things. Men, they jump off cliffs, no problem. They don’t think about stuff. Women, they’re so tentative.
And I don’t know why. I mean, I guess over the years I’ve lost some of that tentativeness just because I’ve been kind of in the professional outdoor realm for a long time. And it was just I mean, that’s the the most common denominator that I saw was the confidence piece. And to tr to be able to travel solo teaches you how to be confident, how to
Be hypervigilant, how to look around, how to book things, how to do things on your own. And when you come back, you have this inherent confidence that you didn’t have before you started.
Blake Boles (34:54)
Where do you feel like that confidence emerged for you? What was it always there? Have you always been this way? Do to other women look at you and they’re like, You’re just some alien creature, you’ve never worried about this stuff, you can just travel anywhere in the world and be chill.
Diana Proemm (35:09)
Yeah, a lot of people do look at me and tell me that. And to this day, they’re they’re like, I could never do that, but I I admire what you’re doing. And there, you know, it’s not for everybody. This life is not for everybody. And I tell you that I will drive myself nuts sometimes as well, like being around myself because I don’t know how to sit still. And I’ve trying to to learn how to do that at the age of 54. I’m trying to learn how to just be still and be like
I should go climb up this mountain. I should go do this. And it never wins. Today I went and climbed one of the mountains and I look out my window every day because I couldn’t sit still. And that has been, you know, a big thing. But yes, my friends when I was younger, they’re like, You’re crazy, you know, and a lot of my friends are from Ohio. They’re you know, they’re they’re not they’re adventurous, but maybe not quite the adventurous of like, you know, like dropping down steep slopes or
you know, with a bike or skis and and you know, but when you’re in it as a professional working in the industry, you end up pushing yourself and you’re around these people who push themselves and that confidence builds. It doesn’t happen. Like you look at me today and I’m I can ride down a mountain really quickly, but it didn’t happen overnight. I I started skiing when I was 12 and then, you know, became a ski instructor in my twenties and you know built the confidence from there. And then
I’ve traveled so much that not really much bothers me anymore. I don’t get scared, except for the stupid cows, alpine cows up here. And I’ve alert. They yeah, those are crazy cows up here. Anyway, but no, not much scares me. So and it’s because of all the stuff I’ve done over the years.
Blake Boles (36:47)
They sneak up on you, those alpine cows.
Hm.
Yeah. And it sounds like a good amount was there in the beginning. This is your default personality. I’m curious, I I want to dwell on this can’t sit still aspect of your life. i in what other ways do you feel like you are just unsuited for conventional lifestyles, for traditional home, partnership or marriage, regular jobs, like
Diana Proemm (37:04)
Yes.
Blake Boles (37:27)
How how do you feel like you are just the the wrong person for any of that?
Diana Proemm (37:33)
Yeah, I you know, my ex was really good with me. He was very patient. Like I God love that man. He had so much patience with me. And i I d knew that when I was indoors too much, he would he would start acting like a chicken and he would start bouncing his head and at me. And I would just be like, okay, I’m gonna go for a hike.
Which always calmed me down. I I’m pretty sure, like now I look back, I’m I’m I pretty much had to have had ADHD. And I think the same thing happened with my mother when I was younger. Like she tried to ground me one time and I had to stay inside and I’m sure that lasted two hours ’cause the next thing I know I was back outside again and I bounce off the walls when I’m indoors. I mean it’s thank God gotten better over the years, but it
probably didn’t start getting better until my forties that I could actually sit down and not bounce off the walls. I have a hard time being in confined four wall spaces. That’s always been I don’t know why, but it’s always been that way for me.
Blake Boles (38:31)
Mm.
And when you get outside of those walls, once you escape the proverbial chicken coop and you’re you’re skiing or you’re helping someone else learn how to ski or you’re deep in the Alaskan bush, what does it feel like then? Like do you still experience stress? Is there a a calmness that comes over you? Do do you have a like a deep relationship with nature or are you sort of in a stalemate with it?
Diana Proemm (39:12)
No, I have a very deep relationship with it. I it it’s so healing for me. because I think it just helps center me, it helps calm me down. I’ve deferred to it for so many years, to keep as I called the crazies away. You know, I would always go for big hikes or, you know, no you’re not big hikes, but a couple hours go stomp up a mountain. And I learned that one actually when I was living out in the bush because
You know, you were working long hours with the same people every day and those people were like your family and drove you nuts and then you had the guests on top of that. And so there was a little mountain behind the lodge area. And I would go up there and go to the overlook and it would just help calm me, center me, and I could go back to work as a healthy, normal human being that didn’t get all aggro at people.
So that’s what I use it for.
Blake Boles (40:14)
What’s a moment in your adult life where you felt like you were betraying your your values or your core personality the most? And and maybe you thought like, what the hell am I doing?
Diana Proemm (40:27)
I don’t know if I honestly have anything like that because I’ve worked so hard to live the life that I’ve wanted to live. I can’t honestly think of anything that I’ve done that would
Blake Boles (40:44)
I I think that’s wonderful if that’s the case. Well well done. Yeah.
Diana Proemm (40:47)
Yeah.
I mean I I question my decisions nowadays of like what am I doing in the middle of the Alps? But it I don’t regret I don’t regret any of my decisions. I may wish that I have done things differently, but I don’t regret anything that I’ve done because it’s led me to where I am today, right?
Blake Boles (41:03)
Hm.
Which is my next question. where you are at this moment right now, d do you feel like there’s some aspect of how you’re going through life that feels unsustainable or or it’s not working for you? Are there any big parts of the puzzle that feel deeply unresolved and and troubling?
Diana Proemm (41:27)
no. I mean currently this is I I’m trying to use this year as my year of peace because last year I’ve had a lot of you know, I lost my job. I ended up losing my driving privileges for a little while because Austria and their bureaucracy. And so this year is kind of my year of peace. And I’m trying to I i where I’m at right now is not necessarily sustainable. Like
I don’t have I have yet to make any friends in this town besides the people in my house that, you know, are live in the other apartments or my landlords basically downstairs. And I’ve made friends outside of this area, but I think at some point I need to be closer to a little bigger town where there’s more happening, more ability to meet people. Cause I’m I’m a little too far. But sustainable as far as money-wise.
Blake Boles (42:18)
Mm-hmm.
Diana Proemm (42:24)
As long as everything keeps going the way it is, it’s good, but may or may not be sustainable. I don’t know. Because I got laid off last year. I started working for this company. You know, there was a gal that was pregnant and unfortunately she had a pre-me, so she’s dealing with that this year, the baby. And I don’t know if if she comes back, you know, at the beginning of the year in two thousand twenty-seven, I may have to find new work. And so that concerned me. And so
But I don’t know if I can you know, if I have to find another job or maybe I just go back on the road again for a little while and bounce around until I figure out the next move, you know. I don’t know.
Blake Boles (43:05)
I I imagine you’ve gotten asked about retirement or retirement plans or intentions before. I was asked this question at at a recent talk I gave about dirtbag rich. someone just said, What’s your plan for retirement? Just lay it out for me. And I I pushed back a little bit against the framing of of that question, but you know, he really wanted to know, you know, where are you gonna live? Who you’re gonna live with, how you’re gonna afford that.
Are you gonna stay in one place? Do you think you can afford to to stop working? do you think mentally, like mental health-wise, you can even stay put? these are difficult questions for me to answer. I’m curious how you tackle questions like this.
Diana Proemm (43:51)
that’s a very good question. That’s so long I mean, I don’t know. I guess it’s it’s kinda so long away, but not so long away. When I was with my ex, we had big dreams of going to Thailand and living there because it’s so cheap. I kind of still have that in the back of my head, but I honestly don’t know. I I have been, you know, saving on my own for a while, so I feel like
when that time comes I’ll hopefully be in an okay position to be able to retire with hopefully some, you know, social security and maybe even some money here from the government. but I don’t know. I I I think about it a lot ’cause obviously it you know, within the next ten years or more I might have to and what that looks like I I can’t say, to be honest. I can’t even figure out where I’m gonna be next year.
Blake Boles (44:45)
Again, Diana
living in her fifties sounds a lot like Diana living in her twenties and thirties and forties.
Diana Proemm (44:52)
It’s a horrible
It’s a horrible I c I yeah.
Blake Boles (44:55)
But you don’t you
you said you don’t have any regrets. It you’re not suffering you you outside of like periods of of stress or losing the job unexpectedly. You know, you still love this.
Diana Proemm (45:00)
No.
Yeah, I mean it’s funny ’cause I I have to laugh at myself ’cause I’m like, I could buy a van and I could travel to these countries that I you know, like Eastern Europe that I’ve been wanting to go see. I could I could do this, I could do that, and I’m just like, Stop it. My brain’s already going. So if I lose you know, if I lose this job I’ll be like, Okay, well, you know, on to the next, but yeah, we’ll see what happens.
Blake Boles (45:28)
On to the next adventure. Yeah.
let’s go back to the Yellowstone Club where you said you were working with like pretty wealthy families or or clients, and and for example, these women who were really great skiers but still felt this this fear, this resistance to to going on these bigger adventures. You know, they probably look at you. And I imagine if you’ve worked in skiing, this has been happened many times over.
which is like people from a much higher income bracket are looking at you and they’re asking you l questions about the life that you’re leading, and you’re telling them all these stories of ad adventure and travel and mishaps and nature. in those moments, do you feel what I what I wanna know is that this differential between
in incomes. Like you’re living on a on a much lower default income than these people who you’re working with. but you are in a bit of a position of of authority over them. They are coming there to learn something from you that they can’t figure out easily on their own. And and you’re having these moments of connection, of like real like human equal connection. even though when you go home at night you’re going to be inhabiting very different
world. So I wonder if you can just speak a little bit about your experiences, maybe yeah, serving people who are are rich, who are rich in this like traditional American sense of being financially wealthy.
Diana Proemm (47:06)
Yeah, I mean the Yellowstone Club is a very special special place. There’s, you know, there’s a lot of anonymo anonym how do you say it? Like people who want to be anonymous. So I have to be careful what I say. But there was a couple, elderly, you know, older couple and from the dot com place, a site, he was the CFO. And
his wife was on the chair with me and she’s like, give him, give him advice. He wants, you know, he needs to do, you know, and he’s got his earplugs in. He’s not listening to me. He’s not paying attention to me. And then his wife continues to go on about that she’s like, I just don’t want him to buy another house. We already have five or something. I don’t even remember how many they had. And I just sat there and I I stayed quiet. Just was like, okay.
I live in a, you know, one room apartment and you have are worried about having another house in your financial realm. I I mean, that was one of the ones that kinda stick out in with me. but it’s it’s a totally different world that they live in. I
it it’s hard for me to I just would always sit back and try and glean information from them. When I was on the hill, I was like, okay, let’s do this. Let’s go have some fun. But when we were having lunch or having conversations and like watching the other people, it was just a really interesting vibe. I I don’t even know how to explain it. ’cause these were some of the most wealthy people in the world that were there and you know, celebrities, that sort of stuff. And
It was just a surreal place and I always was just kind of felt like this little amoeba walking around, you know, being told that I need to go out and go ski with people, keep them safe or guide them around, you know. I don’t know. I don’t know how to
Blake Boles (48:59)
D do you feel like y you
you have managed to have these these genuine moments of connection with clients who are very wealthy?
Diana Proemm (49:07)
I feel that I did, yeah. I mean, I always tried to be inquisitive and a lot of times when people started asking me questions, it like I would they would they were so curious about my life and what I’ve done and how I’ve done it and and then you know, I hardly would ever get to learn about them, honestly. And it was one of those things where they were just always so inquisitive about my life, but I feel like
There was one f one family that I really connected with. They had some twins and I I kinda befriended them, but otherwise it was, you know, pretty professional and, you know, engaging as far as having a nice lunch with people that you don’t know.
Blake Boles (49:57)
That’s just one other facet of your life that I’m curious about, which is I I think ski instructors, for example, in their twenties are just very happy to be out there working with anyone, getting to be on the mountain. And and I’ve noticed among people who I know that yeah, as you get older, kind of working it doing service work for wealthy people becomes a bit less palatable, maybe a bit l more challenging. and and so I wonder if if your
relationship to this work has evolved over time or if you’ve developed coping mechanisms.
Diana Proemm (50:35)
For like working at the club or as a ski instructor, is that what you mean? Yeah, sure. I mean I honestly when I went to the club, because I had just come from working as a director, a lot of people relied on me, you know, depended on me and I was in charge and I was really happy to go there and have my bosses tell me where to go and who to ski with and I turned the blinders on when I went there and I because
Blake Boles (50:38)
Yeah, yeah.
Diana Proemm (51:05)
I couldn’t you weren’t allowed to take pictures, you weren’t allowed to do any of that kind of stuff. And so basically I went there to be a ski instructor, had fun with the kids, you know, we’d we’d go to lunch with the families and get to know each other and then and then I’d go home. And it just was always an interesting place like mentally to be. Wow, these people have so much money. How did these guys get so much money? And I always was just
kind of question. I’m not that I could ask them how they got all their money or whatever, but it you know, I’d ask them what they did for work or that sort of stuff. And it was just always very interesting to me. And one of my fellow ski instructors, like he made a picture that he was the artist. And I remember him drawing this cartoon and it had this basically probably sums up everything, but it was
Two people on a ski lift. One was a very clean cut, professional, you know, clean ski gear, brand new gear or whatever. And then the one the the other person was I would call him a dude, like a ski a s ski, you know, ski bum per se, a bro, you know, like hat, you know, disheveled stuff. Even though we were all ski instructors, we had to look good, but it was just like the
Blake Boles (52:21)
Bro.
Diana Proemm (52:31)
This thing, not necessarily for the club, but in general. But and it was it it said it had a little bubble, and it was the ski instructor saying, Can I give you some advice? And I always thought that was so ironic because you have this person who’s completely wealthy, you know, living the life of that he always wanted, or whatever, and then you have the ski instructor who’s like trying to give this person advice, which
I always thought was just I super ironic ’cause you know, we’re out there to keep people safe and we have our own special skills, but we’re teaching people with money. I don’t know.
Blake Boles (53:10)
Hmm. That
I think that’s why I find this so fascinating and why I’m dwelling on it so much, because there’s not many realms in which people from such different income strata get to interact and not just in this transactional, you know, here’s money, you provide service, we don’t have any conver you know, like a a restaurant waiter, for example. But when you’re a guide
And you’re out there for these long periods of time and you’re experiencing nature together and people are a bit more relaxed, you know, there’s downtime, then you have this opportunity to have these conversations. And I think it’s so telling that you didn’t get to learn very much from the people you were working with, because they were so busy asking you questions about your life and being a bit in awe of you.
And and thinking, and and I imagine there’s a lot of fantasizing, like how can I do what Diana does, or or something even vaguely similar to that. and so it’s it’s a different kind of version of the status game, for example. In one way, in one very conventional metric, you are lower status than they are. But in another way, in this much more holistic or almost like spiritual level way, I think a lot of people are looking up to you.
Am I romanticizing this too much?
Diana Proemm (54:36)
Probably.
Blake Boles (54:43)
I I’m definitely b blending other people’s experiences in with what I’m hearing from you.
Diana Proemm (54:39)
I d I d I don’t know if I’m seeing it the same way you are ’cause, you know I mean
Yeah. I mean, it was a it was a great experience and I’m super thankful to have had it. And when you are out there with people, you’re in the elements, it’s cold outside, the walls come down. You are just another person with them. You know, the y it doesn’t matter how much money you have, if you fall down this cliff face, you could die, right? So you have to have the right tools. And so they look up to you in that respect.
But you know, like we can look up to them to having all the money like all this money, but they have the same pro and they have problems that are different than ours. You know, mine’s maybe like paying the rent and this one has I, you know, don’t wanna have to deal with another house. I already have five or six or whatever it is, you know? And it it’s just different. But people are still hu underneath at all, it doesn’t matter. People are still human, they still
Blake Boles (55:36)
Sure. Yeah.
Diana Proemm (55:47)
They still have to have the Maslow’s hierarchy of needs. They need to feel safe. They need to feel loved. They need to feel, you know, like they have what their needs met. when you’re out there with them. So
Blake Boles (55:54)
Mm-hmm. Mm-hmm.
That’s a great lead into my last question for you, which is okay, so you’re here in Austria, you’re trapped in paradise in this small, beautiful town, mountains tantalizing you, looking out the window every day. And it it sounds like you already said it it’s not a very sustainable situation for you. You’re you’re gonna be fine, but what is a moment you’ve had in recent months where you’re like, this is why I’m here? Like one of those, this is incredible.
Or, you know, one of those moments of beauty or transcendence where where everything all the worries fall away and you’re like, This is how I ended up here, this is why.
Diana Proemm (56:31)
Mm.
Yeah, I would say this last weekend for solstice. So what they do here in the Alps, mainly to roll, so like we’re talking Kitzbuhl, kind of Central Austrian, I think Southern Germany, Alps, they do like they do these fires, tiny little fires on the peaks and
I joined there’s an app called FriendSeek and you can do you can sign up for these group, you know, these activities. And I signed up to do this two-day activity that we would e-bike from Kufstein into a tiny little town in the Kittsburg Alps, and then we would ride up to the top.
in the evening and watch the sunset along with all the fire and then they they have a big bonfire. And so what they do along all the mountains is they have all these bonfires. And it was truly like I mean it was hot, but just riding up and around these little villages and up of the mountains with the wildflowers are so pretty right now. And these are just experience that you would never get in America.
you know, they’re they’re just unique to this area, to the Alps, you know, maybe the Italian Alps and stuff, maybe France. But you get you you’re like riding through these cool little Austrian villages that have these beautiful flowers.
on their windowsills and, you know, gardens and you’re just riding through and you’re just enjoying life and then you get up and has a beautiful sunset. and then they the whole ridge lines were lit up with little fires and then the moon came out and and then the next day we did, you know, we rode back to Kufstein and it was, you know, more mountain you know, we got to jump in a a lake and a mountain lake and
Again, more wildflowers, more more lakes. It was just absolutely stunning. And I was like, okay, it’s all gonna be okay. You know, this is why I’m here. I just have to remember that I need to get out and do these things more, you know, and and it all it’s all gonna be fine. You know, it’s all gonna be fine.
Blake Boles (58:54)
Mm-hmm.
Mm.
Yeah, it’s beautiful. Diana, if people want to learn more about you online or read your guidebook, how do they do that?
Diana Proemm (59:20)
the guide book is currently on Amazon. looking at maybe putting it on my website at some point, but they can go to my website, all the links are there to find all the information. It yeah, Diana Prome dot com. Yeah. Yeah.
Blake Boles (59:34)
I’ll be sure to link to Diana Prome dot com. Yeah, great. Diana,
thanks so much for coming on the show.
Diana Proemm (59:42)
Yeah, thank you for having me.