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Life on the Road: Taking the Leap

The idea to live on the road came to me in January of 2013. It was a romantic idea with a backbone of logic – for someone who wants to make a living with words and photographs, the road is an endless source of inspiration.

But like most of my best ideas, it was one that I shoved into the crazy box–the home of ideas that were too radical for this 30-year-old Midwestern boy with an expensive education and an office chair softening his ass.

A month later, during a boredom-driven Craigslist search, I got a glimpse of the future – the exact van I wanted was for sale 90 miles away. Even then, I dithered. But in ignoring the van… in not buying the van, I began to feel an immense amount of regret. Regret for an action that I hadn’t even made yet! If it felt this strongly then, imagine how it would feel when I was 67!

With road visions in front of me and regret behind, I pulled the trigger. I traded my reliable ’09 Subie for an unreliable ’86 VW Vanagon – my new home. It was February 1st, 2013. As I rolled creakily down the highway in a van nearly my age, I sat upright, flooded with doubts. What about relationships? What about money? What if this is a dumb idea? What if … ? The pedal was pushed to the floor, but I could only muster 63mph.

Just then, I broke into a really good laugh. 63mph was it – it was the name, it was the journey, it was everything. It was the beginning of an exploration of life that couldn’t be lived at the speed of society. My instincts were my new compass, and I would need them on the road.

There were many questions that nearly tripped up my leap to road life. After 14 months out here, I hope my experiences can help those contemplating extended travel.

Which vehicle should I call home?

It can be complicated, but simply: choose whichever vehicle you are in love with. It’s going to become your girlfriend, your boyfriend, your partner. You’re going to wish it good night and pet it in the morning (really, that’s just me?). If you don’t feel an emotional connection to it, don’t buy it.

Maybe you value precision and reliability and have a big savings account; the Sprinter could be your perfect rig. Maybe you value simplicity and ruggedness; the Tacoma could be the one. Maybe you’re living month-to-month and still dreaming of the road; your thumb and two feet will work great.


I chose the Vanagon because I had a feeling the pace of society was funneling me down an endless-burnout tube. I needed a vehicle that forced me to slow down, that gave me no choice in the matter.

I valued the quirky VW community and wanted to pick up some mechanical skills, so the Vanagon made perfect sense for me. The mechanic that helped me with my first breakdown said it right, “These old Volkswagen vans will make you a very patient man.”


OK … but what about money?

First, you’ll need to throw out the rules of make a lot consume a lot save a little repeat. Begin to love this trajectory: make some consume a little save a little repeat. You’ll still get to save a little, but you get to ditch the stress of making a lot to consume a lot. All of a sudden, you’ll have a lot more energy to live.

I saved up for my first year on the road because I wanted to freely roam, scouting out future projects and work. I spent about $18,000 the first 12 months, and I am now spending about $1,000 per month (on gas, food, insurance, beer, and whiskey). I learned about many ways to make money on the road, which I’ll get into in Part 2.

By accepting a life of less, you’ll be stepping off the treadmill of the American Dream, and this takes great confidence … and great faith.


Last August, on a hike in Alaska, I was talking with my buddy Kern about money. I asked him (another rambling man) if he ever worried about running out, and he blurted, “NO!”  before I finished the question. “I don’t know if it’s the combination of all my life experiences or my faith, but when I’ve really needed money, it’s always been there for me,” he said. “I can’t do budgets. If I did, I’d be running around pooping everywhere.”

In taking the leap, you must have Kern-like faith. Whether that’s faith in yourself, a greater being, or something you can’t explain, you’ll need a lot of it to follow your passion. The money (and the support) will not be there right away.

It must be nice.

Well, it is and it isn’t.

Living on the road is living with the extremes … living with extreme freedom and extreme sacrifice. I’ve traded the support of the system, companionship, and creature comforts for a life without rules.

Many romanticize a life on the road, but few actually do it because it’s uncomfortable. When you have no idea where you’re sleeping, or who your next friend will be, or when your next water source will come, or what lurks down highway 37, you can go nuts pretty quickly. The other (and only) option is to become comfortable being uncomfortable.


With the open road in front of me, I howl wolf cries of joy, and at the same time, I miss Sunday-morning bullshit sessions with my buddies. I reject the importance of money, but miss buying new skis on a whim. I’m proud that I’ve acclimated to sleep in -20F, but I miss warm showers.

I know people are jealous of my life, but I’m reluctant to think that what I’m doing is anything special. The minute it becomes something special to me is the same minute complacency hits, the minute ego takes over, and my blade goes dull.

Alright, where’s all your stuff?

All of my stuff, everything I own, is with me.

Moving into 75 square feet was an extreme exercise in necessity – 20 t-shirts to three, three pairs of skis to one, three bikes to one, a full bookcase of books to eight. Moving everything I had into my van helped me live a statement I already believed in… the more you know, the less you need.

I have one of everything, I’m a rolling General Store. I carry mountaineering gear, photography gear, ski gear, backpacking gear, mountain biking gear, climbing gear, hunting gear, fishing gear, spearfishing gear, cook gear, maps and reference books (one on every state and relevant outdoor subject). I carry a computer and a typewriter. Don’t try to rob me or I’ll bear spray you.


My gear is heavily used.

I once bought gear based on the brightest new orange dye or a brand’s marketing promise of waterproof breathability. I now buy for one thing — durability.

I have one pair of Carhartt shorts, one pair of Kühl cords, and one pair of Carhartt overalls. I’ve repaired my Kühl cords 11 times because I like how they fit. I carry one suit for weddings, and I spend two hours ironing it each time. Since I’m on the move, I have a secret that only I (and now you) know … I’ve worn the same pants 314 days this year.

Every time I take on something new (rarely), I get rid of at least two things. But not every crack of the van is crammed with stuff; having a free-space buffer gives my brain a little room.

Do you have a gun?

I was in a Montana pawn shop in July holding a $125 pump-action shotgun. I was trying to talk the gun-loving owner down to $100 when he said something I’ll never forget: “You know son, your best weapon is always between your ears.”

Your brain … your instincts … they are constantly sharpened on the road. Nearly every decision I make is done with limited information, so there’s always an emotional consideration. What does my gut say about that dirt road? What about that campsite? What’s that guy up to over there? I will bail real fast on a place, situation, campsite, or person if I get a bad feeling.

But I’ve felt incredibly safe living on the road. People have shared their couches, lives, steaks, time, advice, asparagus, and smiles with me. The media had done a good job of making us believe humanity is in trouble–but I’m now a believer in humanity again.

I did begin carrying a rifle for hunting two months ago, but I don’t keep it loaded and van-side each night. Not only is that a process, but it’s not designed for close-quarters combat. With guns, I think you should do whatever makes you feel safe, but as our pawn-shop friend implied, don’t assume that having a gun guarantees you are protected by it.

Don’t you get lonely?

Absolutely. Lonely is a word that has been demonized – if you ever feel lonely, something must be wrong. I don’t believe that. I think it’s natural for human beings to feel lonely sometimes; after all, we are pack animals, and we can’t always be with our pack.

When loneliness floods in, I try to turn the emotion around. I use it for action … action to explore a new relationship with the trees or wildlife or night sky … action to meet up with an old friend or go find a new one.

Loneliness can be an emotion that inspires great learning and exploration, but only if we accept that it’s happening and find a personal way forward.


How do you stay warm in the winter?

When it’s really cold, I make myself into a big burrito – a 20-degree bag inside a 10-degree bag inside a wool blanket inside a down blanket. When it gets dark at 4:30PM and it’s really cold, I find a bar and drink three beers as slowly as possible. Next winter, I will install a real heater in my van. 

Any big surprises?

From August to February, I didn’t experience a day above 50F. I had weighed 190 pounds my entire adult life, but during that seven-month period, I gained 20 pounds and held steady at 210. I was just as active (read: very active), but I packed away core body fat and calibrated to the sun-cycle, habitually sleeping 12-hour nights.

I would never have believed this type of body adaptation was possible until I made my home outdoors. 

Picked up any tricks along the way?

Many. Here’s one for when you’re camping alone and you’ve had enough silence for a bit: build a big fire, put your phone on your knee, press ‘play’ on a good audiobook, and stare back at the fire. It isn’t a friend plucking your favorite melody, but it’s damn good.


I’ll see you a little bit further down the road, friend.


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