It was a bluebird day, and the sun was high in the sky. I drove fast with the windows down and the music loud. (Illustration: George Wylesol)

Young, Dumb, and Broke: Why Outdoorsy Types Suck at Money

It’s not just the gear purchases—it’s how we think about the future. Here’s the Outside guide to getting your financial $hit together, no selling out required.

Outside's long reads email newsletter features our strongest writing, most ambitious reporting, and award-winning storytelling about the outdoors. Sign up today.

When I was in my twenties, I did something very bad. I made about $290,000 disappear.

What that number represents is the majority of the six-figure salary and bonuses, after taxes, that I earned over the five years I worked in financial services. When I say that I made it disappear, I don’t mean that I lost it day-trading shares of I frittered it away, gradually, methodically, paycheck by paycheck. I was living in San Francisco, and the details are fuzzy (in no small part because I was often drunk during those years), but I can tell you that there were $60 rounds of drinks purchased without a second thought and $25 cab rides to the bars. There were $1,500 ski-season cabin shares in Lake Tahoe and a $150-a-month membership at Equinox. There were multiple Starbucks lattes per day and $18 organic steak salads eaten at my desk. But these are just the flashes through the fog, clues to an unpleasant memory I’ve blocked out. Because when I think too hard about the truth, it hurts my head: I have no idea where all my money went.

I did eventually learn to curtail the spending. When I was 27, I quit my job to travel and ski-bum, and by that point I had managed to save a small sum that could float me for a year. I called it my fuck-you money, because if I was ever in a situation I didn’t like—stuck in a job or with a boyfriend I wanted to leave—I could say fuck you and go. Living in ski towns is how I learned the dirtbag lifestyle, and to my surprise I took to it naturally and with enthusiasm. My savings sat untouched, and I survived off the wages I made operating chairlifts in Queenstown, New Zealand, and serving barbecue in Aspen, Colorado. I ate peanut butter and jelly sandwiches for breakfast and free staff meals for lunch. I stopped drinking for a while, snowboarded every day, and spent almost nothing. I was happy.

Embrace Your Inner Dirtbag

Personal-finance guru Mr. Money Mustache breaks down how Outside readers can stop wasting our hard-earned cash on expensive gear and trips and start putting it toward real freedom: the financial kind

Read More

When I went back to work, I chose outdoor journalism, placing myself at the intersection of two industries that would never make me rich. I lived frugally; my first job paid $42,000 a year. But as my salary grew, I ratcheted up my lifestyle to meet it. I never lived that extravagantly again, nor did I save much. My spending habits were an incongruent mishmash. I’d camp instead of pay for a hotel, and I wore the same puffy jacket forever, patching holes with duct tape. Yet I rarely thought twice about eating out or buying a new mountain bike every year.

My parents tried to talk to me about investing, but I’d roll my eyes and groan like a child. I didn’t want to be rich; I wanted to be happy. Talking about index funds felt beneath the enlightened alternative lifestyle I aspired to. I wasn’t interested in buying a house either, because a down payment would eat up all the fuck-you money, and then I wouldn’t be able to quit my job to travel or freelance or ski again. So the money sat in a savings account for years, losing roughly 3 percent of its purchasing power annually. By the time I was 34, the single most valuable asset I owned was my carbon mountain bike. Fuck me.

(George Wylesol)

I am bad with money. I’m also not abnormal. A 2017 survey by CareerBuilder found that 78 percent of Americans live paycheck to paycheck, while a 2019 survey by Bankrate found that 60 percent of us couldn’t cover a $1,000 emergency.

A lot of my friends are like me. True, most never had a finance salary to squander, but they’re also people who spent their youth playing in the mountains or traveling and now find themselves in their late thirties or early forties with not much more to their names than a garage full of gear and an all-wheel-drive beater parked on the street. Nothing wrong with that, except maybe the existential dread that comes with it: 77 percent of Americans say they worry about money, and 58 percent say that those worries control their lives, according to a study published by Capital One and the Decision Lab.

This was the stuff that haunted me at night, when there was no campfire ringed with pals to distract me. The older I got, the more it popped up: The fact that my little sister bought a house before I did. The realization that I was sitting on the same amount of savings I had when I was 26. The time a coworker told me she was “shook” to learn that I was 35—she could have sworn I was no older than 27—and I wondered how much of that was because I looked youthful and how much because my lifestyle had remained frozen in time.

My story doesn’t surprise Brad Klontz, a pioneer in the field of financial psychology. When I asked him why so many of us outdoorsy types are terrible with money, he confirmed my suspicions that at least part of it can be blamed on our YOLO spirit. That drive to chase bluebird days isn’t exactly compatible with sitting in front of a computer tabulating spreadsheets. “You’re not future oriented,” he says. “To be good with money, you have to be a little anxious about what comes next.”

In his research, Klontz has identified maladaptive habits that hurt our financial well-being. The one that applies to me and my friends? Money avoidance. People with this trait think money is “dirty, unenlightened, unspiritual,” according to a 2012 study by Klontz and other researchers at Kansas State University. Such people believe that there’s virtue in living without money, that the rich are greedy and wealth corrupts. Think about the outdoors community’s idealization of the dirtbag lifestyle. While most of us aren’t Alexander Supertramp from Into the Wild, burning our savings before heading for the Alaskan bush, we tend to choose experiences over things, enjoy the challenges of minimalism and being surrounded by nature, and reject the idea that money can buy happiness.

All this leads to a set of behaviors Klontz calls financial denial: simply avoiding thinking about money at all. You don’t look at your bank accounts. You don’t track what you spend or save. In his research, 36 percent of adults admit to being in some sort of denial about their financial difficulties.

The irony, of course, is that this attitude sabotages our ability to attain what most of us actually want: freedom. Not just the freedom to ski on a Wednesday if it snows ten inches, but freedom to make life choices like changing careers or moving across the country.

A lot of rich people understand this. Many have gotten to where they are by using simple concepts such as buy and hold investing. They’re quietly securing themselves long-term independence while the rest of us toil for the Man, funneling our ­savings into brief breaks from the grind, all the while telling ourselves that we don’t care to be wealthy.

What if there was a better way? What if we could normalize using rich-people tactics to continue living happily as if we were broke?

In 2014, I left Colorado and moved to Pennsylvania for my first job in journalism, as an editor at Bicycling. When I returned to Boulder four years later, I noticed something immediately.

The vans.

My God, they were everywhere. Parked all over town. Trundling down I-70 on the weekends. On a group camping trip to Fruita, I was the only one who slept in a tent.

Predictably, before long, I soured on tent life, weary of hearing nylon walls flap in the wind while my friends snoozed in blissful silence in their vehicles. I became convinced that I needed a van as well. Klontz has researched this phenomenon, called relative deprivation. “We feel deprived when we see that other people have stuff we don’t,” he says. It’s part of the reason Americans continue to report decreasing life ­satisfaction despite our relative wealth compared with other nations, and even through periods of economic growth.

Not even Klontz, who also lives in Boulder, has been able to inure himself against Sprinter mania. “One day I walked to work and counted ten of them,” he says. “No wonder I want one. But you don’t go, I want one because everyone has one. You have all these rationales. It’s about your status with the tribe.”

The desire to belong is a powerful motivator when it comes to how we treat money. While a $60,000 van is an extreme case, it’s the same rationale we use to buy a $7,000 bike or a $2,500 backcountry-skiing setup when we have credit card debt. Tropes like “spend money on experiences, not things” fly out the window when the experiences you love are enhanced by expensive things. (Try overnighting in the high country with a $50 department-store sleeping bag and tell me how it goes.)

This same desire to belong can also drive the opposite behavior—putting on the appearance of being broke even when you aren’t. We tend to surround ourselves with people who have the same money beliefs we do, says Klontz, and we get uncomfortable if we drift above or below them financially. This is why you see tech bros and dentists wearing patched-up puffies and eating instant oatmeal in trailhead parking lots (out of their tricked-out vans). “It’s the same exact human psychology as I need to drive a Mercedes,” says Klontz, “except it’s How poor can I live? It’s a competition for that.”

Ironically, you might reject money whether you grew up with it or never had it. “You see money-avoidant people at both ends of the spectrum,” says Klontz. “With poor people, it’s a cognitive-dissonance thing—I want to be wealthy and I’m not—so it helps to create a narrative around how rich people are bad. On the other side, if you grew up in a wealthy family and your parents cared about money, there’s a rebellious attitude or there’s guilt. You feel like you have to push this part of yourself away so you can belong.”

It can be a toxic combination. You believe that money and happiness are at odds, so you feel no incentive to save or invest. But you’re caught in the cycle of desiring the same nice gear and epic experiences as your friends. All the while, you don’t track what’s coming in or going out. The result, as a friend of mine put it: “In my mind I spend no money. And yet I have no money.”

This is the opposite of how wealthy people behave. The rich don’t hew to most of the stereotypes about them, says Klontz. In a 2014 study, he found that 58 percent of affluent people are first-generation wealth, not trust-fund babies. Most are frugal and highly focused on saving, and they delay gratification. “I always say it’s like a squirrel, saving nuts for the winter,” he says. “The squirrel that doesn’t worry about having enough for the winter dies.”

This is a recurring theme in financial psychology: how we think about the future, or whether we think about it at all, is at the core of how we treat money. I, for example, spent much of my teens and twenties believing that I would probably die young. No particular reason, just a morbid hunch. As I approached my late thirties, then, and assessed the new wrinkles and sunspots I saw in the mirror, I would often reflect grimly that I hadn’t really planned on making it this far.

Intellectually, had I truly believed I was going to die in some tragic accident in my youth? Probably not. But if you looked at how I conducted my life, you could only conclude that I expected to go out early in a blaze of glory. I never wore sunscreen. I didn’t put money in a 401(k). I had lived, for all intents and purposes, as if I’d never get old.

(George Wylesol)

Last summer I turned 37. Two weeks later, my fiancé and I broke up.

Andrew had always been the practical one. He made sure our bills were paid on time and researched realtors when we briefly looked into buying a home. In his absence, I became aware that this was yet another way I had never really grown up; I had outsourced all this stuff to him. Though I never wanted a conventional life, I thought with dismay that neither had I ever envisioned a life like this: single and close to middle age, with no evidence that I’d ever taken care of anyone but myself. I didn’t even have the cat anymore. (He kept it.)

This was also at the crux of my money worries. Those nights I lay in bed fretting that I wasn’t financially prepared for my future, what really sent my panic into overdrive was the thought that I couldn’t provide for anyone else’s, either. How was I ever going to afford a kid’s college fund? It wasn’t just that I’d only ever lived for my youth; maybe I’d only ever lived for myself. No wonder I was alone.

As I was moving out, a friend introduced me to a guy named Zach. Zach was 46 and a retired firefighter, but he did real estate now—­buying and fixing up properties, then renting or selling them. He owned a bungalow in downtown Boulder that he’d remodeled into a million-dollar home, where he generously allowed me to move in and pay below-market rent. He also owned properties in the mountains, where he spent most of his time. He never knew what day of the week it was.

Living in Zach’s house, enjoying his shiny appliances and eating grocery-store sushi on his million-dollar porch, I finally had my revelation: wealth was freedom. I’d had some inkling of this, of course. I had saved the fuck-you money, which enabled me to move through life without worrying about being fired from a job. When I decided to become a journalist, it allowed me to freelance. But I’d always kept it in a savings account, and now I saw my folly: it could have been compounding in value while I was skiing my 100-day season in Aspen or becoming a dive master that summer in Honduras. I suddenly felt a very strong desire to get my shit together.

I was fascinated by what Zach had achieved. He grew up without money, in a single-family household, but through aggressive saving and calculated risk-taking, had created a life in which he answered to no one. I learned that this approach to wealth building had a name: FIRE, short for financial independence, retire early. Popularized by bloggers like Mr. Money Mustache, FIRE proponents combine unorthodox frugality with smart investing to retire young and devote more time to their passions. Crucially, “retire” doesn’t mean you stop working. You retire from wage-paying work you don’t enjoy in order to start your own business, volunteer, or do whatever the hell you want.

It’s a deviation from the traditional model of wealth building, says Scott Trench, CEO of Bigger Pockets, an online platform that helps people achieve FIRE through real estate. Here’s what’s considered normal, responsible financial behavior, he explains: buy a home at the highest price you can afford, put 10 to 15 percent of your salary into a 401(k), and spend the rest. “But that’s fundamentally demotivating,” he says, “because I’m not going to access any of that for decades.” Start thinking of wealth as something that can give you freedom in the next five to seven years, he says. That’ll give you the motivation to execute FIRE: learn to live on the cheap, save your first chunk of cash to invest, and buy assets that not only appreciate but also generate passive income, like a house with a room you can rent out.

With our dirtbag ways, the outdoorsy set are especially well-suited to this lifestyle. We’re free-spirited, buck convention, and already find joy in creating our own experiences instead of having them served to us. (Most of us would rather cook a steak on a campfire than eat it in a five-star restaurant.) And Trench isn’t necessarily against spendy gear purchases. He points out that for most Americans, about 60 percent of our expenses are taken up by housing, transportation, and food—big changes will come from scaling back in any one of these categories. So buy those skis if you’re going to ski a lot. “The dollar-per-hour cost becomes very low,” he says. “But then do you really need to live in that hot apartment near all the bars? Or can you live somewhere more affordable?” To quote another FIRE blogger, Paula Pant: “You can afford anything, but you can’t ­afford everything.”

This is the part I’ve dreaded writing: A few years ago, my parents gave me some money. They’d offered in the past, when I was starting my journalism career, but I always shooed them off. I needed to know that my lifestyle was self-sustaining.

But around my 34th birthday I finally caved. My folks had bought a property years ago and put part of it in my name. Now they’d sold it, and I let them transfer to me my share of the proceeds. Because I saw the money as theirs—I was only the steward—I also finally let my dad tell me how to invest it in various index funds, then watched it grow at a steady, remarkable rate.

Still, I felt embarrassed about taking this money. I told no one. In a country where the gap between the richest and the poorest continues to widen, privilege—economic, social, racial—plays a major role in wealth building. I sometimes felt ashamed of the economic advantage I’d been given. My parents grew up poor in Taiwan, and through hard work had created a better life in the U.S. for my sister and me. We were able to pursue careers we were passionate about and spend our weekends playing in the mountains. This lifestyle in itself was a privilege too, the kind my parents had never known.

You believe that money and happiness are at odds, so you feel no incentive to save or invest. But you’re caught in the cycle of desiring the same nice gear and epic experiences as your friends.

Maybe because of their background, I had always admired people who came from tough circumstances—people like Zach, and like Brad Klontz, whose family was so poor, his dad used to take him to the local ski hill to watch people sliding down the slopes from the parking lot, because he had no other way to expose him to the sport. I respected them, but I also envied their stories, their ability to say they were self-made. Deep down I feared that this was something I could never claim. That’s a side effect of growing up comfortably, I tell Klontz. It undermines your confidence.

“Choose your low self-esteem,” he laughs. “You can feel bad because you grew up having more, or you can feel bad because you grew up not having anything.” Shame is closely linked to money, he tells me: shame we have too little, shame we have too much.

“Everyone is dealt a different hand in life,” says Trench. “It seems like people are afraid to be proud of their accomplishments if they start from a position of relative privilege. What I think people should be saying is, Here’s the hand I’ve been dealt. I’m playing that to the max of my ability. It’s just a much healthier dynamic with which to approach money.”

What happens if you don’t approach it that way?

“You play your hand suboptimally.”

At the beginning of this year, I took the money my parents gave me, plus the fuck-you money, and put it into a down payment on a house. I left Boulder and bought a place in a more affordable suburb, with a room I could rent out. In the months preceding this, I’d started reading personal-finance books, analyzing my spending, and making budgets. I also started wearing sunscreen.

During one particularly frustrating moment in the home-buying process, I told my mother about the complicated emotions I felt around accepting her gift. She reminded me that when she and my father bought their first home, my grandmother had helped them with the down payment. “Now we’re helping you,” she said.

The day I closed on my house was also the day Joe Biden was inaugurated. As I signed the papers in a glass-walled conference room, our new president was taking his oath of office. Maybe it was the momentousness of the occasion, or maybe I was thinking about my breakup, but as I drove back to Boulder, keys in my pocket, exhaustion washed over me, as if my body had been tensed up during a long ordeal and had finally realized that it was OK to relax. I didn’t know how long my muscles had been taut. During the hours leading up to the closing? For the months since my long-troubled relationship had ended? All those years I’d wondered if my life would ever move forward? Whatever the case, it felt like something important had finally been handled.

When I was young, I was afraid that buying a home would trap me, that it would anchor me to a place or a job or even a person. But today I felt more free, not less. In the past couple of years, I had seen enough to change my mind about getting older. I had watched loved ones experience illness, injury, loss. I was beginning to understand that getting old was not something to be so afraid of that I needed to act like it wasn’t happening. Getting old was something I might be lucky to do one day.

And if I was indeed so fortunate as to grow old, maybe I could also hope that I wouldn’t grow old alone. All the powder days and high-alpine adventures I still hoped to have, perhaps I’d have someone to share them with. And if I was really blessed, maybe one day I’d have young people of my own, young people to pass something on to. I had little control over either of these things, but at least after today I had something to pass on. This knowledge didn’t feel flimsy and romantic, like the idea of dying young. It felt like maybe in some small way I could live forever.

It was a bluebird day, and the sun was high in the sky. I drove fast with the windows down and the music loud. I sang along.

From Summer 2021 Lead Illustration: George Wylesol