How I Quit my Job to Live on the Road

If you ride motorcycles and enjoy long distance travel, chances are you have dreamed of quitting your job to live on the road. 

In Spring 2016 I quit my job of 3 years to live on the road for 2 ½ months. I had no plan about what job I would have when I got back. I knew where I wanted to go, how much money I need to save to do the trip and pay my bills and that’s it. 

A little backstory, because the decision to live on a bike for more than a week or two isn’t something that just pops up out of the blue. There’s always something (or in my case many little things) that push you over the edge and makes you decide to make the jump. I moved to Portland from my home state of Montana in 2010 to go to Art School. To say the very least I was grateful to have the opportunity to go, but it wasn’t everything I dreamed it would be, and I spent a lot of time in my own head, beating myself up, and just feeling crappy all around. A combination of a new city, few friends I could relate to 100%, a heaping dose of homesickness, and big scoop of stress from school  led me to try and find a solution to “fix” how I was feeling. 


The “oppor-tunity”.

I “lucked” into meeting a woman who runs a Tattoo Shop in Vancouver, WA, who threw a once in a lifetime opportunity into my lap (or so I thought.)

She would let me be her apprentice, only charging me enough for her time and the use of her tools until I could buy my own, and best of all she’d knock off a year of the normal 4 year term (because I already knew how to draw.) Of course, I was naive and didn’t know it was abnormal to pay someone for the privilege of being their tattoo apprentice. I’d been doing research into the Tattoo Schools in Oregon and I just assumed cost was going to be apart of learning this new skill either way. To be brief, it was a very toxic relationship. I won’t go into too much detail, but the part that’s important to the story is that I was absolutely and truly miserable. I loved when I actually got to tattoo, but it was not worth the cost of being mentally manipulated and abused every day I stepped through the door of that shop. Yes, being an apprentice is hard work, it’s not easy, but after talking to the revolving door of artists who came and went at the shop, I learned that my situation was much worse than "normal." 

I think there’s really only three jobs in the world. 

  1. What I would call a “normal” job. You don’t want to be there everyday, there are bad, frustrating parts, but there are also “good parts”. Whether that’s a couple people you enjoy working with, benefits, the amount your paid. You know, things that keep you just on the edge of “I want a new job” and “I can’t leave this job.” 

  2. A job that you’re truly immersed in. What everyone else calls a “good” job. You’re tired all the time, and you work way too much, but you are truly invested in what you’re doing and how the business is doing . Most people assume I’m talking about people who work for themselves, which could definitely apply, but I’m also thinking of a few people I know who are die-hards for the companies they work for, who really believe in what they’re doing.

  3. Then there’s the jobs that make you utterly miserable. The environment is hostile, you never know where you stand with your boss. It is extremely unhealthy, you’re manipulated, and you feel like you wouldn’t be able to find a job anywhere else because you’re that shitty.  You have a lot of thoughts about self harm, because that seems like it would be better than the environment you’re currently in. There’s only one thing you like about it, which could be the money that barely lets you keep paying rent, or one other tiny aspect of your day.

 It became very clear to me that I was in #3. I think a lot more people are in #1, and just feel like their situation is worse than it actually is. It can be a lot harder to walk away from that kind of situation. You have a nice cozy safety net, ya, it isn’t always the greatest, but it’s there and pays you just enough to pay your bills, eat comfortably, and get a couple extra things every now and then. But believe me there’s nothing like a toxic environment to motivate you to make a change. 

I realized I no longer felt like myself. I graduated Art School in a blur, and it didn’t feel real. I had one year left of my apprenticeship and the end was in sight. I came to the decision to plan a back roads tour of Montana to try to reground myself, and I knew I needed to do it alone. I began planning immediately, it’s what kept me sane for the last year of working in that awful place. In the process of planning I started calling it my Pilgrimage. According to The Archetype of Pilgrimage: Outer Action with Inner Meaning;

a “Pilgrimage is a journey, a ritual, a commemoration, a search for something, perhaps something the pilgrim cannot express in words, perhaps even something the pilgrim does not fully perceive.” That felt exactly what I was trying to achieve, so it just fit. 

I had wracked up a lot of credit card debt between school and not making enough money to live, working at the tattoo shop. I was cleaning houses on my days off from the shop to try and bring money in. I wasn’t tattooing on a regular bases and half of my income from tattoos was going back to my “mentor” so, I couldn’t rely on it for income. I stopped doing anything “unnecessary,” and only ate canned soup for quite a while. I did the math about how much I had to put away every week to save enough for my leave date, and I stuck to it. It was a pretty bare bones budget, I saved for gas first, enough to pay all my credit card bills for 2 months, then my meager food budget of $10 a day, campsites, and the places I wanted to visit. I had a whole spreadsheet dedicated to it. What I didn’t budget for was emergencies, mechanical failures and the chance that I might have to break my “rules” and stay in a hotel. If you’ve watched the Pilgrimage, then you know I had more than a few emergencies. In the end I left Portland with just under $2,000. Total costs I wasn’t prepared for, including a tow truck, parts for the bike, and 5 unplanned hotel stays: Roughly $530. I was very lucky to have support from family, a little wiggle room in my budget thanks to detours caused by storms, and a little room on credit cards.

Once I got to my deadline, between planning and my toxic job I was more than ready to be on the road. It didn’t matter that I didn’t have everything I thought I needed, I was just thrilled to be on my way. In the middle of planning I lucked out and a gentleman who followed my blog bought me a ticket to Motos in Moab. The “little” detour was awesome and didn’t take too much out of my budget. I really enjoyed Utah much more than I thought I would, and it gave me a chance to get used to being on the road and shake out the kinks before I started my planned Pilgrimage.

I won’t talk too much about the actual trip here, if you don’t already know how it went you can watch the whole series on my YouTube Channel. What I will say is that it was 100% worth it. In the true nature of a Pilgrimage I got what I wanted out of it, and a bit more that I wasn’t aware that I needed. 

When I got back I did have a small period of time of feeling as though I was floundering a little bit. I went back to cleaning houses again, but it wasn’t quite enough to pay rent and stay afloat. Post-Trip Depression is definitely a real thing. However, once I got back in the groove of ‘daily life’, I focused on my goal and got a full time job about a month and a half after getting off the road. 

So what are my tips for you, to make the jump? 

First and foremost, you have to get over the mental hurdle of quitting your job or potentially asking for extended time off. I think it is very important to remember that if you’re determined, willing to learn, have a good attitude and work very hard, you can always get another job. It won’t always be the “dream job” or exactly what you want to do. However, realizing that if you quit your current job, you can always find another one if you really need it, is the first step to making the jump. 

If fear of quitting your job isn’t the thing that’s holding you back, take a good long look at the hurdles you're facing. Whether it’s fear of travelling alone, getting hurt, the bike breaking down, the financial hurdles, whatever it is there’s an answer and a way to jump those hurdles. Learn how to look at these obstacles from a different perspective. Think “how do I overcome this,” and not “no, I can’t because….”  To a certain extent it is a lot of planning and everything you can’t plan or be prepared for is believing everything will work out in the end. Long term travel is possible if you want it bad enough and are willing to learn, grow and be flexible. 

The next part is setting yourself a deadline. You need to make a plan to leave and stick to it whether you think you’re ready or not. Depending on what kind of person you are, how much money you have in savings, and how willing you are to go with the flow will affect how long you’re going to need to plan, save, and mentally prepare yourself. I personally gave myself just a little over a year to plan and save for the Pilgrimage. I already had my deadline, it was the official 3 year anniversary of when I started working at the tattoo shop. For you, it could be the beginning of the next season, your birthday, a milestone, or just whenever the hell you feel like it. It doesn’t have to be spiritual or have a meaning, just set the date and hold yourself accountable for leaving on that date. If telling a lot of other people about your plans will hold you more accountable, do it. 

Now comes the planning. Make sure you leave with some kind of plan. It doesn’t have to be a detailed plan like mine, you don’t need to know where you’ll be every night or when you’ll be back. But having a generic “I want to explore Nevada” or “I want to go from coast to coast”, some kind of goal is recommended. Even a direction will do. How long you plan is totally up to you and your deadline. If you want to do multiple years of travel, I recommend a couple months to even a couple years of saving and preparing for the  life change. If you want a break down of how I plan every single trip I take you can read that in detail over here.  Every plan and person is different, but there’s one thing that’s true about every long term trip. 

You will not come back the same person as you left. 

Last but not least, I think the thing I wish I would have remembered half way through my trip is this; Remember this is supposed to be fun, you have no responsibilities besides taking care of the bike and yourself. Enjoy the landscapes you’re riding through, take a moment to breath it in. Write as much down as you can and take more pictures, because you’ll want to remember every detail for the rest of your life.