Emily Pennington is a 37-year-old freelance writer, former Hollywood assistant, and full-time outdoor nerd who once lived in a minivan for a year to visit every U.S. national park. (@brazenbackpacker)
In her 20s, Emily bounced between creative careers—first as an actress, then as a circus performer, then as a film producer’s assistant. The job paid okay, but the work felt meaningless, and after losing several friends to sudden deaths, she started questioning the whole plan. She cut her expenses, saved aggressively, and quit in 2020 to hit the road full-time.
That trip, which started as an attempt to reboot her life, turned into a book (Feral) and a new career as a freelance adventure writer. But the realities of making a living as a writer are far from glamorous. Emily breaks down exactly how much she made from her Outside Magazine column and book advance, how she cobbles together an income from travel writing and gear reviews, and why she still occasionally wonders if the whole industry will collapse. Emily also discussed the burnout of monetizing your passions, the constant anxiety of freelance work, and how she preserves time for hikes that aren’t “content.”
Now based in Boulder, Colorado, she’s finally settled into a routine that gives her the freedom she was looking for—working Monday to Thursday, keeping her weekends sacred, and skiing in the middle of the week whenever she wants. And because she can’t stop picking up new creative projects, she’s also fronting a folk-punk band called Trouble’s Braids.
Full transcript: dirtbagrich.com/emily
Recorded in November 2024.
AI Notes
This is an AI-generated summary and transcript. Typos and mistakes exist!
Summary
In this episode of Dirtbag Rich, host Blake interviews Emily Pennington about her transformative journey from a corporate career to becoming a freelance outdoor writer and musician. Emily discusses her experience living in a minivan for a year while visiting U.S. national parks during 2020. She shares her background growing up in suburban Houston with a Swedish mother, studying theater at USC, and working as an executive assistant in Hollywood. Emily details how personal tragedies and dissatisfaction with corporate life led her to pursue outdoor writing full-time. She describes her financial journey, including making $1,500/month from Outside Magazine and receiving a $50,000 book deal for her memoir ‘Feral’. Currently based in Boulder, Colorado, Emily balances freelance writing, gear reviews, and her new band ‘Troubles Braids’. She emphasizes the importance of maintaining authentic outdoor experiences separate from work and discusses the challenges and opportunities in the evolving landscape of freelance writing.
Chapters
00:00:13 Introduction to Minivan Life Experience
Emily Pennington describes minivan life as more rugged and less expensive than traditional van life, involving cooking outside and limited space. She shares a humorous anecdote about a raccoon entering her van.
00:01:39 Background and Early Career
Emily discusses her suburban upbringing in Houston, studying theater at USC, and early success in Hollywood acting before transitioning to circus performance and production assistant work.
00:09:36 Transition to Outdoor Writing
Emily explains how personal losses and dissatisfaction with corporate life led her to pursue outdoor writing, inspired by the Mr. Money Mustache blog and radical lifestyle changes.
00:14:58 National Parks Adventure
Emily details her year-long journey visiting national parks in 2020, including navigating COVID-19 restrictions and writing for Outside Magazine.
00:33:17 Current Life and Career
Emily discusses her current life in Boulder, balancing freelance writing, gear reviews, and her band ‘Troubles Braids’, while maintaining a flexible outdoor lifestyle.
Transcript
Blake Boles 00:01
Emily Pennington, welcome to Dirtbag Rich.
Emily Pennington 00:05
Thank you for having me, I’m stoked to be here.
Blake Boles 00:08
Tell me, what’s the difference between van life and minivan life?
Emily Pennington 00:13
Oh, man, minivan life, I feel like is even more rugged and dirt baggy, but also less expensive. It usually for me, definitely involved not having a fridge. So I had to get ice for my little cooler, like every three days. It meant a lot of cooking outside rather than inside because the inside was only a bed. And it also meant that my van was small enough for a raccoon to accidentally crawl inside once trying to like get to my cooler.
Blake Boles 00:57
But I bet in van life even larger animals can enter your
Emily Pennington 01:02
That is I mean that is true. That is true. This is yeah, the raccoon was a minor hiccup
Blake Boles 01:09
How long did you experience minivan life?
Emily Pennington 01:14
for a full year back in 2020 when I was visiting all of the U.S. national parks.
Blake Boles 01:22
And we’re going to get to that and we’re going to talk about your book that you got published telling the story of that adventure, but I want to start by finding out if earlier in your career, in your twenties, if you ever imagined that you would be living out of a minivan for a year.
Emily Pennington 01:39
Honestly, no, because I don’t think I was raised to believe that people who weren’t professional athletes could do huge adventures. I think that I was raised to believe that you had to work 40 hours a week and if you had weird hobbies, you had to figure out how to do them at night or on the weekends.
Or maybe at some point I would take one year sabbatical off work or something. But I don’t think I realized that it was possible to do it full time until I started dating someone in my late 20s who introduced me to backpacking and also he had previously spent six months biking from Los Angeles to Brazil with four of his friends. And I kind of flipped my world upside down that a regular person with a seemingly normal job in life could do that.
Blake Boles 02:43
Okay. And I know that this relationship figures pretty prominently into your story, but let’s dwell in the past here. Where were you raised and tell me about your young life and your education.
Emily Pennington 02:57
For sure, I was raised in a pretty normal-looking suburban Houston suburb in like a random house that wasn’t very expensive, but there was one caveat that made me kind of weird and different than everyone else who went to my school, which is that my mom is actually Swedish. She moved here when she was like 21 years old to be a nanny.
She is a big traveler. She put me on my first international flight when I was three weeks old. And I’m sure some part of that, I’m sure some part of that, even though I grew up with all of these people who felt really normal and very nine to five suburban, put this little seed of inspiration in my brain that it was theoretically possible on a shoestring budget to like get to Europe and go weird places because I got the privilege of going as a youngster.
Blake Boles 04:04
Okay, so normal suburban upbringing in Houston. And where did you go to college? What did you study?
Emily Pennington 04:12
I went to University of Southern California in LA. I skipped a grade, I skipped second grade, and then I was hell bit on getting out of Houston basically like the second I turned 17 and got accepted to USC, drove across the country in like this crappy Honda Civic and never looked back and studied theater.
I actually had to like threaten dropping out of school to my mom because she really wanted me to major in like marketing or something really sensible because I had really good grades. And I thought it was stupid. I thought it was really pointless to spend, you know, $30,000 or more a year to do something that you don’t care about and not just take a big swing at the thing you actually want to do and then figure it all out later.
Blake Boles 05:12
So theater was the thing you wanted to do.
Emily Pennington 05:15
Yeah, theater and film.
Blake Boles 05:18
And what happened? You were in LA, were you able to find a career in theater and film?
Emily Pennington 05:25
I think I was one of those people who had a few successes really young, because I looked really young and I joined SAG-AFTRA, the union for actors, really young, like when I was still in college. I booked a couple of movies, I booked a couple of big commercials, I got a big fancy agent.
And then I think just the grind of auditioning can read six times a week for a teenage daughter number two, I think it really takes its toll on you, especially as I got into my mid twenties. And I was like, how am I literally auditioning against 16 year olds who are here with their moms? Like, this is so wild, because I felt so much older than that. And so I, around the same time that I was quitting acting, I started taking lessons in a variety of aerial apparatuses, like circus dance performance, also in Los Angeles. And I got a job as a producer’s assistant, trying to figure out if I could work out a career on the backside, like on the behind the scenes of movie production. And so I basically moonlighted as a circus performer for the next five years, while also during the day having a full-time job as a producer’s assistant for a bunch of different people who are making big fancy movies.
Blake Boles 06:56
Okay, it sounds like you were working your butt off. Did you feel like you were moving up or moving towards something or just surviving?
Emily Pennington 07:05
Honestly, no, I feel like I got a crash course in how much of a boys’ club Hollywood is, and also just like the extreme nepotism in a lot of established industries like that. And then I also think I was simultaneously getting a crash course in a trend that, unfortunately, is still happening, which is just every creative field getting a bit squeezed by tech. So we were seeing the beginning of the streaming wars simultaneously, like circus was getting very trendy, which means that all of a sudden you have a lot of people who are at a beginner or intermediate or intermediate level who are trying to book the same gigs as you for less money. And I think we all know like that, you know, after the writer’s strike, there is now like a lot less, just in the last two years or three years, there’s been a lot less new content being purchased by Hollywood.
So I think it was a really interesting and challenging ultimately 10 years of being an assistant at an incredibly high level and realizing that I was like this little, I was like a little mouse on a treadmill, just like kind of moving up a little bit in the assistant world, but not figuring out how to like get out of the rat race, I guess like I felt like I was just like running in place. And that’s when I started kind of trying to break out and ideate on okay, what is something I could actually do like working for myself? How what skills do I have that I know I could hone again at night and on the weekends? And that’s when I started writing about all of the weird cool backpacking adventures that I was going on around the same time that I was dating the gentleman that I mentioned earlier in my late 20s. Sorry if that was a little tangential.
Blake Boles 09:09
Yeah, this is your life and you told me earlier that although you were performing at this very high level, you were essentially doing scheduling and travel booking and this didn’t feel like a very purposeful or like you’re really doing anything important for the world.
Did you feel like you were really searching for a deeper sense of meaning or contribution at this point and the outdoors started to represent that?
Emily Pennington 09:36
Yeah, absolutely. So I actually had like two, there were two really big years in my life where a couple of friends who were not very old passed away unexpectedly. So I had two friends die when I was 25 and just getting into the assistant game. I’d only been in it for two years. And then again, when I was 29, I had a mentor from college and then two of my younger friends also passed away very suddenly. And I think that that was what got my the wheels spinning in my head to figure out like, okay, the this weird experiment in like, bodily consciousness could be ripped away from us at any moment at any age.
I don’t know if I want to work in an office at all. I feel like it’s really pointless. I feel like the illusion of having, you know, having all these adventures when you’re in your 60s or 70s, and you’ve saved all this money for retirement feels leading and kind of like a, I don’t know, I guess like a just a big capitalistic ruse to try to, to try to get people to, you know, to work during their best years. And I really wanted to flip the script. And I really wanted to figure out how to start having some of those experiences or at least take, you know, a couple years off or make very little money for a couple of years and start to have some of those like more bucket list experiences that I think as a society, at least Americans often talk about having after age 60.
Blake Boles 11:20
I can see the roots of the minivan life starting to be here here and I feel like a lot of people end up in your situation especially if you’re in your early 30s and you’re feeling like you are excelling in your career but what does this career even mean it feels like it’s a bit of a sham but a lot of people have trouble extricating themselves from the situation if they have a lot of bills to pay if they have people they’re supporting if their partner is not on board with with crazy dreams and so what was it that started to allow you to actually form like this escape plan
Emily Pennington 11:59
I became pretty obsessed with this really popular personal finance blog called Mr. Money Mustache. Oh, yes. Yeah. He’s like kind of a master of like taking a very middle class income and going and doing a weird thing, which for him was retiring early at age like 31 or something insane. But for me, it more so meant really like getting very stoic about about expenses and realizing like, okay, I know I live in Los Angeles. It’s a really expensive city, but I also have a car payment on a Prius and I could totally sell it and get like a $5,000 beater and have no car payment. I could get roommates instead of having like a little studio apartment and just save money living with friends and I could, you know, go out to eat a quarter as often as I do now and I could, you know, really get strict about my grocery budget and things like that. And then on the weekends, I was still I was the one splurge I had, I think was probably like multiple tanks of gas to go backpacking and go on these adventures that were kind of fueling the beginnings of my writing career. So I upended my whole, I guess my whole personal life, even though I stayed in an assistant job and I was still in LA. But instead of spending, you know, instead of being relatively paycheck to paycheck making like, I don’t know, $65,000 a year, I was saving like $15,000 a year or something instead of almost nothing because I like axed so many expensive expenses.
I mean, and I did that for three straight years before actually hitting the road full time in my van, trying to see if I could like use my year of visiting the national parks to jumpstart a career as an adventure writer, hopefully publish a book. Also, I felt like worst case, like the only thing I had to lose was money, which I could just make back anyway, because I had just proven that to myself, you know. So it kind of felt like, okay, well, worst case, I just had a really awesome year for about $30,000. Like that seems like a pretty good worst case.
Blake Boles 14:40
Hmm. Where did this idea of visiting all the national parks come from?
It sounds like you started pretty small just writing about your, your backpacking, your outdoor adventures. How did you take this, this step change into this huge, ambitious goal?
Emily Pennington 14:58
Well, the national parks, first and foremost, were kind of the thing that rekindled my inner sense of wonder, but also like when the relationship with the guy who introduced me to backpacking and kind of introduced me to the notion that someone with a regular job who’s not a professional athlete could go on a grand adventure. When that relationship ultimately ended, it was going solo backpacking in California’s various national parks that brought me back to myself and instilled a sense of deep inner strength and helped me heal.
And so in addition to that, there’s a part of me that was being incredibly practical about the adventure because I knew I wanted to write a book. And there are already a lot of books about people hiking the PCT or the Appalachian Trail. And there were not a lot of books about people running around to the national parks. And it felt like the kind of adventure that would take a year, like a full year to complete. And it also just, there was something about like spanning the entire width of America multiple times that felt really captivating. Like I had never spent a lot of time on the East Coast. I had never been to, I don’t think I’d ever been to Washington State. I had never been to Alaska. So there were all of these corners of America that felt really foreign to me. And that was really compelling about it. And then the fact that I ended up undertaking the journey in 2020 was also really fascinating because it was a really divided year for the country politically and kind of socially as well.
Blake Boles 16:58
So you hatched this plan before the pandemic started and then you just had to like ride the wave of of weirdness and restrictions. Were you in the middle of this trip already when the pandemic really kicked into full gear?
Emily Pennington 17:13
Yeah, yes, I was. I was in Moab, Utah, when the decision came down to close Moab to all tourists. I drove to Zion the next day, watched in horror, like on my laptop in a crappy motel room that costs like $30. That Governor Gavin Newsom was going to shut down California’s borders in like a day.
So I had a day to like seize Zion and then drive through the night to get home. And yeah, I mean, I was very much on the road. I had already started my column for Outside Magazine, which was not part of the original plan, but definitely helped boost some of the funding for the trip itself. And yeah, I mean, just like everyone else, I had I had a full on two or two and a half month shutdown where I was just in my house, walking around the block.
Blake Boles 18:17
And were you still able to write about the outdoors during that period? I mean, for anyone who’s doing freelance work or anyone whose life depends upon them being able to travel, I’m in this category also.
It was just like the water spigot has turned off. And so were you able to, how were you able to continue your project? Because the weirdness continued through so much of 2020 and 2021.
Emily Pennington 18:49
Yeah, it ended up making it a lot more challenging. It ended up making the project a lot more about being OK with deep anxiety and solitude rather than camaraderie and visiting people in different states.
It made the logistics of the trip probably two or three times as difficult as they would have been otherwise, especially in places like Alaska where there were, you know, Bush plane and tour operators who just shut down for the entire year and just took a year off. Yeah, it’s during the actual two months shut down itself, I was lucky that I had a column at Outside magazine. And so I had just barely enough arcs with photos to edit where I could continue that for two months. And I had a satellite, like a smaller website called territory supply that was still making really good ad revenue because I think people were Googling hikes near where they lived. And so they sent a big blast to all their writers and they said, hey, we’re actually making a little bit of money. We’re going to help you guys out during this weird shut down. And you know, you guys can write one article a week and make a little extra money since you probably just lost all your clients. So I was really fortunate that I had a little bit to keep me busy during the two months shut down.
But then basically, as soon as the park started reopening, I was very much like refreshing those NPS, you know, National Park Service websites to be like, all right, like how do we fully draft a new plan as the parks like start kind of freckling across the country and reopening? So like Utah reopened really early, but I had already done those parks and then I kind of went to Colorado, hopped around as I was reopening and then kind of continued from there.
Blake Boles 20:49
And all of this is captured in your book, Feral, right?
Emily Pennington 20:54
Yeah, that’s right. Yeah, the book starts off like very freewheeling, very fun. I feel like the first half of the book is like a comedy.
It’s like a weird adventure story where like I said, there’s, you know, there’s literally a raccoon like in my van accidentally. My, my the guy I was dating for part of the book, he and I like backpacked down into the Grand Canyon and everything was very freewheeling. And then like as that relationship started to fall apart, and as the world became more and more chaotic, and you know, I think I had to grapple with a lot of my own inner deepens as well. It just became this weird adventure epic that was so much about surrender and so much about like, I guess kind of like the simultaneous strengths and limitations of the the human experience, even if you’re like a very willful person who wants to be on a big adventure.
Blake Boles 21:55
You’re an excellent writer and one of the paragraphs that I copied down from early in your book is, by the time I was 32 and had quit my job for good, my resume’s timeline was a Swiss cheese of inexplicable sabbaticals and wilderness wanderings. I always felt too big for my skin suit, bursting at the seams from all the wild animal energy swirling around in my veins. I was a maelstrom of unfulfilled desires, a dirtbag in a pantsuit, a cheetah tied to a stake. Ugh, I love that, especially a dirtbag in a pantsuit.
What, geez, what came of this book for you? Did you prove to yourself that you were like a capital W writer when you got this book deal? I know that you got money from it. That’s how you were able to relocate to Boulder, right?
Emily Pennington 22:44
Yeah, absolutely. It’s so funny because I think that like most people who work as creatives at a high level would probably say that they are never fully satisfied with their work because by the time something’s done, they’re on to the next thing that’s interesting them or challenging them.
But yeah, I mean, getting the book deal was huge. I was, I mean, I literally had a phone call with the woman who became my editor at my publishing house from the parking lot of a gas station in like West Texas where I had cell service. So like the entire thing, like pitching a book when you don’t have reliable wifi and like your life is falling apart and you’re living in a minivan is, I don’t know if I would like recommend that to anyone, but I think that like the experience of the year and all of the strangeness and all of the, like the planning and the replanning and the rebooking everything multiple times. I think it just like gave me a renewed sense of my own grit and my own ability to write out the waves that you need to write out to be a freelance creative, if that makes sense. And I think that I would say that like, first of all, selling the outside column, selling the column to outside magazine, because outside magazine had always been like this big, like, I don’t know, like magical monolithic empire to me. And so actually getting a retainer from them to be a columnist for a couple of years was incredible. And then parlaying that into my first published book made me feel like I had really arrived, I guess, as a creative, especially as someone who, you know, this was my third different professional creative pursuit, you know, like I had tried acting and kind of felt like I failed. I had done circus, didn’t quite so much feel like I had failed other than I realized that it was just not tenable as a full time job in today’s, like if you’re not in Cirque du Soleil, like you’re just not probably making a full time income. And so yeah, it was it was like a weird third times a charm. And writing is actually working out for me kind of moment.
Blake Boles 25:12
You mentioned earlier making something on the order of $60,000 a year as an executive assistant and still living hand to mouth for people who are really, you know, have no idea how much freelance writing pays or what kind of book deals, uh, you know, what the numbers are there. Can you talk in as much specificity as you’re willing to share about the numbers of your financial life at this moment, around 2020?
Emily Pennington 25:38
Um in 2020
Blake Boles 25:40
Yeah, when you were making the money from outside magazine, when you got the book deal. I mean, how much money were you living off of at that point?
Emily Pennington 25:48
Well, when I was in the van, um, my, because I had savings also from, from just totally, you know, flattening a lot of my expenses while I was an assistant, but, um, I was making $1,500 a month from the column itself, which was approximately what my budget was every month in the van minus, so I’m making all of the expensive parks, like airfare. Um, I had to, I rented a van in Alaska because I couldn’t drive through Canada because of COVID. Um, I, like, you know, flying to the U.S. Virgin islands and getting like the cheapest hostel I could find. Like I was doing everything as much on a shoestring as I could, except, um, you know, there just are some realities to visiting the national parks where you have to have an extra, like, I think in total, I had an extra, maybe $10,000 set aside because I knew Alaska was going to be expensive.
And I knew that Hawaii, um, the Virgin islands, American Samoa, which I ended up having to go to two years later, um, they all had their own, you know, associated costs in terms of, uh, lodging and flights. Um, but yeah, I mean, I, I think that it, I think it is sobering for people to realize that even someone at a major magazine who is on contract as a columnist writing, you know, three or four articles a month might only be making 15 or $1,600. Um, I’ve had friends who are shocked that I don’t make a thousand dollars in article. Um, I think a lot of writers right now, um, four years later are feeling yet another industry squeeze, um, where wages, I think have remained pretty stagnant or even gone down as rents have gone up.
And so yeah, it is like this ever moving target of trying to figure out how, um, yeah, I guess how to survive, um, how to survive and be your own boss, but also make sure you’re like taking time out for the things that you love. Um, and then to speak to your question in terms of like book deals. Um, I had a book deal that was considered a pretty good one for a first time writer with a decent social media following. Um, I got $50,000. Um, but to clarify again, you have to pay taxes on that. Um, 10 or 15% goes to your agent typically. Um, and you get that money in two installments. So you might get like $20,000 and then two years later or a year later when the book is done and turned in, then you might get another $20,000. So your full time job for six to 12 months is writing the book and you might only have like $20,000 in your bank account to do that. So it is really challenging. I mean, I definitely ended up freelancing for some publications while also full time writing the book.
Blake Boles 29:01
Yeah. Yeah. Thank you for laying all that out in the most realistic, unsexy terms possible.
Emily Pennington 29:07
Yeah, I feel like it’s important because people need to know the realities of the industry. It’s definitely not like a six-figure job for most people.
Blake Boles 29:17
Well, let’s keep talking about your existence as a freelance writer right now, because you have a very interesting backstory and, and since 2020, uh, what has been the arc, um, of your, of your income and your, your time, how much time do you spend working? Um, are you still, uh, living this kind of low income minivan life existence?
Uh, have you returned to something that, that looks a bit more, um, typical American? Uh, what’s your situation?
Emily Pennington 29:49
Yeah, that is a great question. I would say that I knew that the van life thing for me was always going to be an experiment. So I knew that I wanted to do it for a year and then come back to community, come back to, for a few years it was Los Angeles because that’s where all of my friends and my loved ones were at the time.
And then as it became more and more clear that writing was actually going to happen for me full time, I started picking up some gear review work for like CNN and for Conde Nast Traveler. And I think I got really lucky also because after COVID, the national parks and hiking and just Google searches, people buying outdoor gear, people going camping for the first time really exploded because after 2020, we still had to wait to get vaccines. There were still outbreaks in various places. People were still living very carefully, a lot of us. So I was really lucky that I was in the right place at the right time. I was like right at the epicenter of all of that as a writer with now a bit of a resume. So I saved my book advance because I was working so much on other content for different magazines and newspapers and decided that I was really fed up with Los Angeles. It was not good for my mental health and researched other smaller towns, but with some airport access and a lot of outdoor access, ended up moving to Boulder in May of 2023.
I spent my entire book advance on a partial tenuous, but probably from the outside, it looks like a very middle-class existence. I feel like the ways in which I’m dirtbag rich to quote your podcast are more in my flexibility, my access to the outdoors, my ability to travel for like, I don’t even know, probably two months out of the year. I’m lucky enough to get offered trips for work that I then write about and photograph and edit with a lot of frequency. So unlike at a nine to five, where maybe you get two to four weeks of paid time off, I get zero paid time off, but I might get sent to the Swiss Alps to go trekking and then go home and try to write about it. And I love that no one can tell me that I’m not allowed to do that as long as I get my work done on time. So yeah, I guess in a nutshell, I work Monday to Thursday and it does look a little bit like a full-time job. I’m definitely at a computer, but the best part is that I could randomly fuck off on like a Wednesday and go skiing if I felt like that.
Blake Boles 33:03
Yes, yes. That is a huge…
Emily Pennington 33:07
be doing this month, I think. Thanks. I feel like December’s always a little slow. So we’re just going to take advantage of the snow.
Blake Boles 33:17
I think that anyone, regardless of how much they work, if they are able to look outside and say, this looks like a great day to be outdoors, and I’m just going to defer everything that I think I need to be doing today till tomorrow or to next week, and I’m going to go enjoy the outdoors, that is an incalculable asset right there, to be able to act upon your whims to go enjoy nature. And so it sounds like you are rich very much in that way.
Emily Pennington 33:46
Yeah, absolutely. Like I said, I feel like that, and then also the incredible privilege of being able to go on some of these quote unquote bucket list level trips as someone who is now 37, when my body is still able to go on a big trekking adventure or raft down a river. It feels really amazing, even if I’m maybe not saving as much as someone who works in like tech or something.
I feel like a lot of the experiences that you would ultimately be saving to retire for, I’m kind of just doing them now and weaving them into my yearly existence, which feels like you said, incalculably valuable. Is that a phrase we can say?
Blake Boles 34:39
We are saying it now. We have anointing ourselves.
Emily Pennington 34:42
It’s like a tongue twister.
Blake Boles 34:44
And I feel like what a lot of people may rant and rave about like how good it is to work in Scandinavia, for example, the government guaranteed benefits. It sounds like you were actually doing a bit better than the average Scandinavian.
You have three day weekends, you’re off at 4pm, you have two to three months off a year. And tell me, how much do you think you’re working per week and try to include all the peripheral stuff, not just the actual writing, but the email stuff and pitching and the other stuff that goes into this kind of life?
Emily Pennington 35:16
Yeah, it, that is the tricky part. I mean, because, you know, if you look at my like, I don’t know, my quote unquote per hour rate, when I’m actually writing an article, it seems very high, but then the peripheral stuff has to factor in, right?
So it, it, there is a lot of like, even for something as simple as like, for example, I am supposed to review a bunch of ski pants for the next month. That’s a lot of coordination with, with different brands and different emails and different editors on what ski pants are going to do, and then ordering them and making sure nothing got lost in the mail. And so yeah, with all the boring logistics factored in, I probably were about six hours a day, Monday to Thursday, but with the occasional eight hour day. And then also the caveat that, you know, sometimes your free time is like sometimes I’m hiking in boots that I don’t love because I have to test them for work, but that doesn’t feel like work.
Blake Boles 36:19
I looked up some of the stuff you’ve been writing on a muck rack and I see a lot of gear reviews, some destination articles. And I’m curious, do you, how much of a sense of purpose do you feel doing this work, maybe compared to your executive assistant work that you were doing before?
Does this feel a bit more like you are doing something important for the world? Your writing is clearly high quality, but what’s your inner experience like with this freelancing that you’re doing?
Emily Pennington 36:53
I would say that this does feel a lot more fulfilling than, um, then when I was just like, you know, like getting coffee, booking people’s flights, making sure people’s schedules were, were organized nicely, um, as an executive assistant. Um, I would say some of the gear stuff can feel a little bit more like copywriting. It can feel a little bit more corporate, but I feel like I love that I have the freedom when things do feel more corporate to, um, highlight things that are important to me within a capitalist space, because we all have to, you know, I think we all have to make at least a little bit of money, especially if you live in America. So focusing on things like sustainability, um, focusing on why certain garments might cost more because of a sustainability aspect is really important to me when I am doing more quote unquote, like corporate gear work.
Um, and then when I do have the luxury of writing about like for outside magazine, I recently wrote about like the top hot Springs in the country. Um, I have another article coming up about like different Colorado mountain towns that are just as beautiful as the Swiss Alps. Um, I feel like when I, when I have the luxury of recommending from a firsthand experience, different, um, travel opportunities and why they’re worthwhile. Um, that feels incredibly fulfilling to me because, um, I, I feel like, I feel like having the ability to encourage people to go outside and to inspire awe is one of the greatest things that we can aspire to.
And so I feel incredibly privileged that even a portion of my career is now that
Blake Boles 38:42
So for anyone who feels inspired by your story and thinks I can just hop into a minivan and start taking some photos and writing some articles and get hired by Outdoor Magazine and then get a book deal, can you dive a little bit more into, how do you feel like you set yourself up for success in this field? Because I know it’s very competitive and it’s getting more and more crowded.
There’s lots of people who like you want to encourage others to get outdoors, but you have actually turned this into a sustainable career. So talk a bit more about how you think this has worked out for you.
Emily Pennington 39:22
Yeah. I think that one of the things that, um, that I perhaps did differently than people who just decide to randomly do van life because it looks a lot easier than working a nine to five is, um, I had those initial several years of doing the grind, like experiencing what it’s like to, you know, set up a tent at midnight on a Friday after work, because I had to drive five hours and then, you know, go backpacking the next day and then rush home Sunday night.
And I think that I, I, I took something that I already loved and I was going to do regardless of whether it paid me money and became an expert at it while I was still working a day job, even though it was a bit of a grind and there were a lot of sleepless nights. Um, and I think that having some of that initial experience, not only did it make me, I think more believable writing about it from a lifestyle, a lifestyle perspective, but also it lets me speak to beginners and people or newbies or people who do have a nine to five job, um, in a way that’s believable because I’ve, I’ve actually lived it and I’ve done it both ways. And so it’s not just like I have a partner with an anchor income and I can go hiking whenever I want. Um, I actually have like fully supported myself while doing both and now also fully supported myself while doing kind of travel writing and backpacking and outdoor stuff full time. Um, so yeah, I would say like find something you love and let it fundamentally change who you are before trying to monetize it.
Blake Boles 41:03
In a way, this ties back to your parents and there, was it your mom who said, you really shouldn’t try to do something like this. You should only do your passions like in the evenings and on the weekends and have a nice normal job.
Uh, cause that, that’s kind of what you just described, right? You had this experience of trying to have the normal hustle bustle grind in a big American city and then squeezing in time in the outdoors after that. Like you said, arriving at midnight and pitching a tent. Um, and that is, is where you came from. And that’s how people can relate to you. Am I getting this right?
Emily Pennington 41:41
Yeah, absolutely. I don’t know if my mom said that verbatim. I’m going to give her like a little bit of credit. But yeah, I think the implication of my entire upbringing was like, you’re going to get a four year degree. You’re going to go to a good college, like you should probably major in marketing or business. Yeah, there was very much an expectation that I was going to parlay being a straight A student into, you know, making six figures and having a normal life.
And there was something in my body that was just never able to do that. You know, I think from like moment number one, it was like, Oh, crap, acting isn’t working out. I’m going to get a day job, but I’m also going to be a circus performer. And then it was like, Okay, well, now I have this day job, but I’m also going to run away into the mountains every weekend. And then it was like, Oh, wait, maybe I can do that full time. And now it’s kind of funny, because I think I have one of those brains that can’t quit. So now that I now that like writing is a little bit more stable, and sometimes feels a little bit like a day job. Now, I’m like, in the last year, I’ve taught myself guitar. And I’m now like performing in like a folk punk duo called troubles braids around bolter. I think my brain I like I need to rebel against my own life so badly that I’m like, I’m going to learn guitar. Like, I’m just gonna fit pick the weirdest thing that no one’s making money doing and figure out how to do it.
Blake Boles 43:08
So this answers one of my favorite questions to ask, which is like, in which way are you deeply weird and don’t fit into society? And it sounds like you are not able to just do one career at a time.
You’re like always working on the next one. And as soon as there’s any sense of stability or like too much light at the end of the tunnel, then you’re like already plotting your escape to the next thing.
Emily Pennington 43:31
Yeah, exactly. I feel like, for better or worse, my brain just gets bored really easily. I think that I like figuring out how really difficult, subjective, creative fields work. I think I like seeing how people actually make a living doing things that are supposedly very subjective and then trying to figure out if it’s something that I want to get really good at.
For example, my band, it’s never going to pay my rent. I’m going to clarify that. But my band did just start booking. My band is now actually making some money. It is booking gigs that make dollars, which is bizarre. It’s so bizarre to be in your late 30s and be like, I don’t know. I guess I’ll just go be a rockstar now. I don’t know. I’m kind of bored. I guess I’ll just do this.
Blake Boles 44:30
It’s bizarre, it’s brazen. I mean, your online mental is brazen backpacker. And so it’s on point. How did you choose that name, by the way?
Emily Pennington 44:40
I chose it because I, well, I mean, I was backpacking a lot. Like I said, at the time there wasn’t. There were some solo female travel vloggers, but there weren’t, there were not a lot of solo female backpackers. So I think some of my early successes as a writer were writing about this thing that seemed big and scary, but also very evocative for a lot of people.
And so I was trying to do some gimmicky things with my Instagram, to be totally honest, at the beginning. So I was doing this thing that was like hashtag sexy summits. And it was like, like I would, I would like crock them. So they were so that I wouldn’t get flagged on Instagram, but I was doing like, I would have friends take like these like wild, like topless photos of me on top of mountains, even if it was snowing. And so I wanted to like kind of take this like almost like punk rock ethos into the influencer space rather than making it like me having my hair done and like wearing makeup on a hike and making it look very pristine. I want it to be a lot of, I think a lot of people, yeah, a lot of people do. And no shade. I mean, if that’s like how you feel confident experiencing the outdoors, um, then I feel like more power to you. But that’s not me. And I feel like I wanted, I felt like if I was going to do something that was like a big, weird side project, I wanted it to feel really big and weird. And me and not like I was trying to adhere to yet another box that society was like telling me that I needed to assume a role to be in. Does that make sense?
Blake Boles 46:27
Yeah. At this moment, so you have exciting things coming down the line.
Do you still have any like big lingering doubts about the sustainability of your self employed life? Do you worry that it might crumble? Are there any big unresolved questions or anxieties that you struggle with?
Emily Pennington 46:49
Yeah, and I think we talked about this very briefly before we hit record. But I think for anyone who works in a creative field, not just writers, I think they’re feeling like the weight of things like like Twitter getting bought or like Google constantly changing the algorithm. So it can often feel like you have a really good angle and you have connections and you have editors who like you. And then one little thing will change. And now everyone’s advertising revenue or affiliate link revenue switches or doesn’t exist anymore.
And so I would say. Personally, I’m going to keep chugging along and being strategic and trying to write amazing expert backed content from a first person point of view. But I think the the ways in which that is valuable in an increasingly digital world are constantly changing. And I think from a macro level, the every creative field has been incredibly upended by big tech companies. And so figuring out if those companies will ever get legislated against so that they have less of a monopoly is something that we’re going to see come to pass in the next couple of years. And I think staying nimble and trying to make sure that. Like trying to make sure that as a freelancer, you can kind of jump from from project to project as the industry itself changes, is going to be more important than ever, as you know, we’re now entering in the US, at least we’re entering like a big political shift. A new party is taking power. So, yeah, I think like living below your means and staying very light on your feet, so to speak, is going to be like more important than ever for the next few years as we sort sort through how the way we can send media is fundamentally changing.
Blake Boles 48:56
Amidst all this uncertainty, are you able to preserve your relationship to the outdoors? Are you still able to go out and enjoy a long hike or to really take advantage of those two or three months off that you have and not feel like you need to turn everything into an Instagram story, or into some form of monetizable content or future book pitch or something like that?
Emily Pennington 49:21
Yeah, absolutely. I feel like I most often do this closer to home, but I often like at least once a week, I would say I go on a hike where I don’t even bring my phone. I don’t take any photos and I don’t post anything about it because I think that the paradox of being a freelancer who’s monetizing your free time hobbies is that your brain is like not able to turn off when you’re doing those hobbies because maybe you’re taking photos or you’re reading every sign on a hike so you know the history so you can write about it for a blog or something. But yeah, I definitely have like turned off hikes.
I definitely have like, like I said, like, I mean, it’s funny that the band is making like a smidge of money, but like the band, it’s like this weird thing that doesn’t have to make money. It’s just a fun weird thing I do and it’s very it feels like a cool creative outlet that doesn’t have to pay my rent ever. And so I think making sure that I keep one foot in like side projects or side experiences I know I want to have that are worth nothing is really important.
Blake Boles 50:40
For those who want to find out more about your writing, your book, and especially your band online, point us in the right direction, please.
Emily Pennington 50:49
All right, so first of all, the band is called Trouble’s Braids. It’s taken after an old Tom Waits song. So you can find us at Trouble’s Braids Music. Instagram is probably where we’re most active because we can post like photos and videos and fun.
Little things, we’re working on, we’re working on recording a demo actually, now that it’s winter. So hopefully in a few months, we’ll have that on Spotify. And then for adventure stuff, for like hiking tips, for like weird photos of cool stuff in the Colorado Rockies, National Park Tips, you can find me at Brazen Backpacker and that’s on pretty much every social media.
Blake Boles 51:36
Fantastic. Emily, thank you so much for coming out to Dirtbag Rich.
Emily Pennington 51:41
Thank you, Blake. It’s been such a joy.