• Tim Mathis

How do you pay for travel and adventure? A dirtbag's 3 financial fundamentals


A few years ago my wife Angel and I were in Lake Tahoe, having just hiked 120 miles on the Tahoe Rim Trail, and were preparing for a road trip to Seattle, Portland, Bend, and Moab, before flying to New Zealand for a few months of hiking and travel. We hadn't worked a normal 9-5 in years, and we were building a small business alongside organizing our lives around travel and adventure.


While we were catching up with a friend after the hike in Tahoe, they asked us how we pay for our lifestyle - a generally free existence full of entrepreneurial projects, travel and adventure. After that conversation I started compiling some of our experience, and at this stage I've thought a lot about how normal people manage to finance their dreams.


I've written on this much more extensively in The Dirtbag's Guide to Life, (and to be honest Angel is the real expert who keeps our accounts in order), but I wanted to share my favorite fundamentals here. If you're staring down a daunting dream, it's helpful to know a few essential principles for leaving a traditional full time work path in order to travel, play outside, and start creating your own thing from the ground up without venture capital, a trust fund, or a wealthy benefactor.


After years in the game, these are three non-negotiable principles that I've come to see as essential to building a life where you're free to wander. Bonus points because they aren't the rules I would've guessed a decade ago, and they might not be what you expect.


1) No debt plus marketable skills equal freedom, even if your income and savings aren't huge.


Having a ton of money and a high income are great, but they aren't actually the key to freedom. The key to freedom, in my opinion, is eliminating debt and developing skills that you can always fall back on if you need to.


For a bit of personal background, the life situation that Angel and I created for ourselves just a few years before that conversation in Lake Tahoe in our mid-30s was a pretty darn good one, from the perspective of people looking to live an independent life.


We've never been independently wealthy, and we still can't afford not to make enough income to meet our expenses for more than a couple of months. However, after more than 15 years of working and saving diligently in our careers, since our mid-30s we haven't had any significant debt, and we have a fantastic safety net because we have highly marketable skills. I'm a psych nurse, and Angel is a nurse practitioner. If we run out of money or our given hustle isn't working, it's really easy to pick up work in order to quickly make enough money to survive.


Even if working a traditional job isn't either of our first choices of how we want to spend our time, that combination of low debt and an easily marketable skill makes it feel like that life options are endless, and we aren't locked in by any specific job or financial obligation.


It might seem counterintuitive, but if you want to have genuine freedom, it's really helpful if you can figure out how to make yourself valuable and easily marketable. Put another way, it's easiest to live without a job if you know you're going to be able to get one if you need to. And if you're aiming to put together a flexible life in the long term, especially if you're young, and especially if you aren't financially independent already, reliable first steps are to train to a skill where you can be sure you'll get work, and pour your energy into paying down debt.


Unfortunately this isn't a quick solution. Angel and I spent more than a decade on this aspect of our own little freedom project, training to careers in nursing, shopping in thrift stores and cutting expenses to pay off all of our significant debts. But it is a gold-standard effective one. If you want to and you are strategic about it, I believe that most people can get to this point by their 30s like we did.


2) Even if you're financially flexible, there are a couple of difficult psychological steps: a) believe you can figure it out, and b) commit to hustle until you do.


Even after you have financial and career flexibility, there are difficult psychological steps in making a transition from a stable, long-term career path into a life that's creative, entrepreneurial, and travel/adventure-based.


I'm personally a creature of routine who likes stability, and giving up a traditional contracted job in order to drift around and figure out how to survive doesn't come naturally. The first difficult step, for me, has been to accept that I can figure it out. That somehow or another, I'll figure out how to make enough money to survive. This belief comes more easily to some than others, and I almost think it's a psychological advantage if you've grown up without much money, because you understand exactly what is necessary and what isn't. In any case though, it's a pretty natural thing to cling to stability, but stability is often 1) an illusion and 2) the enemy of pursuing the things you dream about in life.


Even after you take the plunge, and leave your steady job or take that extended leave of absence, there's a psychological pull to retreat back to the stability of the known. If you do that though, you'll never fully learn what you're capable of.


I'm a nurse, I can work whenever and wherever I want. There's a bit of hyperbole there, but not much. But in order to do what we've done since 2015 - travel, work on creative business projects, and maximize our flexibility - we have had to commit to the hustle of making it work across the long haul, even at times when it would've been easier to just take a normal full time job.


The longer you keep your commitment to figuring out how to make it work outside of a steady job, the easier it gets. You'll build skills, you'll figure out how to cut costs, you'll figure out how to make money on the side, and you'll figure out exactly how and where you want to spend the money that you do have. The confidence required to live free doesn't necessarily come naturally, but it builds over time the longer you do it.


For us, there have been times when it's made sense to primarily focus on work in our trained careers as nurses, and those skills will always have their place in our financial strategy, but for anyone building an adventurous or entrepreneurial life, it's important to keep a significant amount of energy and focus dedicated to the bigger picture goals that are core to your identity.


3) How do you pay for travel and adventure? Diversify the ways that you make money and cut costs.


The basic financial equation required to do your own thing across the long term is simple, at least in principle: you have to figure out how to keep your expenses lower than your income. In order to do that, there are really only two things you can do: increase your revenue and decrease your expenses. This is where the rubber hits the road: the practical answer to the question of "how do you pay for travel and adventure." How do you make more than you spend while also traveling the world, starting your own business, hiking a bunch, or doing what you want?


There are different ways that you can achieve this goal, but in my experience most people who commit to travel, adventure and personal freedom across the long term diversify. That is, they figure out a bunch of different ways to cut costs, and a variety of ways to make money.


Since we committed to this sort of lifestyle Angel and I have figured out a lot of strategies that work for us, and it's worth listing examples from our experience to help you think about what this can look like.


a) Maximizing revenue streams.

I mentioned above that Angel and I have spent years of our life avoiding traditional contract-based work. But that doesn't mean that we don't work. In fact, we probably work more when we travel than when have normal jobs. I'm almost sure of it. It's just that the jobs take the form of a series of side-hustles. And they're organized so that we can do them in a way that's compatible with a peripatetic lifestyle.


Since 2015, I can count at least a dozen ways that Angel and I have earned a non-negligible amount of money. In descending order, from most to least lucrative, roughly, here is the list:

  • Nursing - a per diem job where I can pick up shifts as needed/possible, several short term contracts (including a few in Las Vegas and one in New Zealand that enabled us to travel), and Angel's part time position online where she makes her own schedule.

  • Organizing adventure storytelling events through our business Boldly Went.

  • Writing books and selling them.

  • Medical direction at outdoor events: Angel contracted with Destination Trail's series of 200 mile races this late summer/early Fall in 2018.

  • Working a contract job to make podcasts for The Race to Alaska

  • Renting out our house

  • Recruiting Patreon donors for our old Boldly Went podcast.

  • Leading adventure tours through a hostel in the Seattle area.

  • Renting out our Oru Kayaks

  • Podcast/event sponsorships from businesses

  • Selling merchandise from Boldly Went.

  • Selling our personal stuff

All of these have involved thinking about the things we own, and the existing skills we have, and figuring out how to make ourselves valuable to other people in a way that we feel good about charging for. A lot has involved using our nursing skills, but a lot of it has also been about using our creativity, or recognizing that the things we own are potential resources to sell or rent.


b) Dropping expenses

During the same period since 2015, we've spent a significant amount of time figuring out how to minimize our expenses. The effort we put in here ebbs and flows depending on how much income we have, but I believe it's been just as important to keeping our lifestyle sustainable. Some of the major decisions we've made have included:

  • We sold our condo in Seattle because we couldn't rent it out in the long term, and a large percentage of our income was going towards our mortgage.

  • We bought a house in Tacoma that we can rent out for a decent profit above cost.

  • Since 2015 we've spent at least 18 months without a proper 'home' because we were renting ours out and traveling, thru-hiking, or otherwise figuring out cheap places to crash.

  • Angel spent time learning to manage our own investments and dropped our financial advisor (I include this in the 'dropping expenses' section vs. income because this has been about managing the money we have vs 'earning' - even if investment has become an increasingly important part of our income as we've gotten older.)

  • We dropped to owning one car vs. two.

  • We switched insurance carriers to lower our monthly bills.

  • We free camp, hike, and sleep outside most nights when we're traveling and the weather tolerates.

  • We couch surf with friends when we can't do that.

  • We use travel points on our credit cards whenever we can to pay for expenses.

  • Everything is used or from a thrift store.

  • We've dabbled in 'geo-arbitrage' - when we wanted to spend a chunk of time focusing on developing our business Boldly Went, we went to Mexico to do it, because it costs less to take a month off to work on a project in Veracruz than it does in Seattle.

  • We've never really changed our spending habits from the time we were poor kids just out of college until now, when we theoretically could spend much more money safely.

The world continues to evolve, and we continue to figure out new ways to make and save money. And, the more financially stable we become, the more we're able to focus on the financial strategies that we enjoy the most. Personally, nowadays I'm investing time and energy in writing more and getting better at selling it, because it's fun and that's a dream I've always had. Angel is working on another business project focused on teaching other people the things she's learned about financial management and investing. We will both still work as nurses for the foreseeable future in some way or another, but we'll likely never be fully defined or locked in by our careers again. (I hope I haven't just jinxed myself.)


The takeaway lesson in all of this is that managing a life outside of a full-time job requires flexibility and creativity - which is great, because those are likely skills you'll have already if you're someone who wants a life outside of a full-time job. There are endless ways to figure out how to make and save money, depending on your skillset and background, and if you want to have a high degree of freedom, it's helpful to identify multiple strategies you can use.


Conclusion: Freedom comes from seeing money and work for what they are: a means to an end.


In the end, all of these principles are about the same thing - which is, using your job and your money to live the type of life you want. If what you want from life is travel, adventure, and creativity, then avoiding debt and developing skills that will allow you to raise funds whenever you feel like it will give you freedom to do so. If you dream about big adventures that require a lot of time and flexibility, then developing the psychological resilience to deal with the risk involved (and leave money on the table) will help you make it through the anxiety of existence without a stable income. And if you want to build a life focused on outdoor adventures or creative projects that don't pay, it'll help you if you can figure out a variety of other ways to make and save money.


I can attest that this kind of life feels pretty damn flexible. It's great to feel like there's no one job obligation that feels like it truly owns you. You'll always have to figure out how to make money to keep doing what you want - but the goal is to make the 'keep doing what you want' part the focal point of your life, rather than the 'making money'. This sort of life feels creative, and a bit unstable, but instability doesn't have to be threatening if you have marketable skills as a fallback. Your taxable income at the end of some years may be low, but you definitely won't feel poor if you have figured out options. A variety of options in life is the definition of freedom and the true opposite of poverty.


These fundamentals clearly aren't a comprehensive financial strategy. For a lot more I hope you'll support one of my own financial strategies and pick up a copy of The Dirtbag's Guide to Life. It has a lot more to say about money and the logistics of building a life centered on the things that you love and genuinely matter.

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