Getting Started with Desk to Dirtbag

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Getting Started with Desk to Dirtbag

I’m Ryan, creator of Desk to Dirtbag. If you’re new to the world of vagabonding, perpetual travel, and location independence, this page is for you! It contains all the information you need to get up to speed and be able to start your own journey!

What Desk to Dirtbag is About

Desk to Dirtbag, simply put, is about trading the drudgery of a conventional life for a choose your own adventure story.

At the end of 2012 I said goodbye to the traditional 9-5. I sold or got rid of most of my belongings, converted my pickup truck into my home on wheels, and set out exploring the western-half of the United States in pursuit of adventure in the great outdoors.

What was to be a year-long break turned into a never ending trip… Backpacking across Colombia, then settling down in Medellin, and most recently driving from Seattle through Central America and then on through the length of South America.

Desk to Dirtbag is an adventure travel blog dedicated to inspiring armchair adventurers and weekend warriors to get outside, break away from the 9-5, and pursue life on their own terms.

Don’t look back on your life and say “I wish I would have…” or “If only I…”

We all have the ability to LIVE a better story.

This blog is dedicated to inspiring you, my readers, to make a drastic change in your life and pursue what it is you truly want to do. To live a life that is rich in time and experiences as well as being financially sustainable in the long-term.

Fire your boss and map out your own adventure.

We are conditioned over the course of our entire lives on what we “should be doing” with our lives. Go to school get good grades, go to college, get a good job, buy a house with a big, fat mortgage, have children, and then spend 40 years in the rat race keeping up with the Joneses.

After that you can retire, travel the world, and finally really enjoy your time.

Let’s flip that story upside down.

P.S. For those of you not familiar with climber vernacular, a dirtbag is someone who takes things to the extreme and forgoes the traditional comforts of life (a home, family, job, etc) to pursue their passions (climbing, travel, and the great outdoors) and desired way of life 100%.

Getting Started with Desk to Dirtbag
  • Start taking action
  • Live a better story
  • Don’t wait for “someday”

“Life is too short to watch it pass by from a desk… Break away from the 9-5.”

Words of Warning

1. Choosing this path will not be easy.

Choosing the unconventional route in life will never be easy. You will be met with looks and words of concern from friends and family. It will be tough to embrace a life of risk and uncertainty.

There will be days you will question whether you made the right decision or not. It will not be always be easy. But like any great adventure, it wouldn’t be worth pursuing if it was easy. Doing hard things really does matter in life.

2. It will not happen over night.

It is very difficult to uncondition yourself to the story of the conventional life. Someone needs to plant the seed in your brain initially–that you can quit your job, travel, work for yourself and makes ends meet.

But that seed needs to grow and root itself in your head–sometimes for years–before you are willing to set out down this path.

You realize this is what you want. Then you still need to figure out how to pursue it, how to make it happen successfully and in a sustainable manner.

And even then the process doesn’t end. It is an ongoing adventure that will keep you learning, evolving, growing, and challenging you.

3. It *is* possible.

I read similar stories of people who quit their jobs and were traveling the world, living life on their own terms, and I’d say to myself “Man, I wish I could do something like that…”

But always thinking in the back of my head that I don’t have what it takes to do it and be successful.

Now, a few years later *I* am actually doing it… I am making money online through my website, through freelancing, and other endeavors, and I am living life on my terms, where and how I want.

I haven’t totally “made it” yet, but I am heading in the right direction, and I know that with focused effort and forward progress that I will get there sooner rather than later.

Take the First Step Right Now

When I look back on where I am, and what I have done that has brought me to this point, there is only ONE reason I can think of

You might laugh, but seriously, I think it was starting this blog.

I started this website to hold me publicly accountable to friends and strangers alike. To say, yes, I am going to embark on this adventure and nothing is going to stop me.

It was only meant to be a year-long adventure, but the adventure continues in new and amazing ways.

I could have never predicted that I’d be living down in Medellin, Colombia when I set out in my truck in January of 2013. This blog and this journey continues to take me in new and unexpected directions.

If you are looking to change any aspect of your life or you want to accomplish something specific, I strongly, strongly recommend that you start a blog.

Starting a blog will prompt you to think about what you want in life, to put words down on digital paper and clarify your thoughts.

So many people just blindly go through life without even knowing what it is they truly want. Don’t be one of them.

A blog can hold you accountable, a blog can be a virtual resume, and blog can connect with a community of people that you would probably never otherwise connect with.

The impetus for the change you seek in your life could really be something that simple.

Pick a domain name and buy it (it’s only $10year), I use, as well as a hosting service with a 1-click installation of WordPress, I use SiteGround, and there you have it: your own personal vehicle for pursuing what you want out of life.

If you are looking for more info about the resources I use and love, check out the tools I use every day.

Imperfect action taken TODAY is far better than the perfect plan “some day”.

Interested in starting a blog or big life-changing adventure? I’d love to hear from you directly. Shoot me an email at and tell me more about yourself and what you are looking to achieve. I read every email, but it sometimes takes me awhile to respond.

Join the Adventure

I’d love to have you follow along on the adventures, and I hope to inspire you to blaze your own path. I’ll even send you a few awesome resources as a thank you…

Thank You So Much!

The Internet is an amazing place and I feel fortunate to have staked out my little online home here at Desk to Dirtbag, and that YOU are taking the time to read what I have wrote.

It is always so awesome to hear from my readers, especially those who I have been fortunate enough to inspire, inform, or otherwise influence.

I just wanted to say that I really appreciate you stumbling across my website and I really would like to hear from you directly about how you stumbled across my page and what adventures you are pursuing. Email me at

Thanks so much for your support! And if you’ve made it this far, I’d love for you to come say hi to me on my Instagram account, my preferred social network, or on my Facebook Page. I look forward to getting to know you!


P.S. If you have found this page helpful, please click the ‘SHARE’ buttons on the side. Thanks!

Comments 22

  1. Came across your US National Parks article on Pinterst. I have been researching long road trips forever and recently took up hiking! My husband and I will be retiring to travel the world and this seems like the perfect place to start. The dream is a pick-up truck with a camper in the bed of the truck. Thank you for the inspiration and I can definitly use your article as the starting point to insert all my wants along the way that I have already looked into and gathered.

  2. Ok, so today, I put a retainer on my topper.
    It is a Leer 122 and it will be sitting on a long bed 1997 F150

    Today, I have decided at 55 years old, it is time to live.

    Goal is 2 yrs from now or sooner.
    Time is dependent on building rig, test camping on weekend, to urban camp for a week, to giving up apartment to …… POOF

  3. What do you pay for health insurance? Do you have a retirement account? Are you earnings subject to USA tax only or also the country were you are at the time?

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      At the moment of writing I don’t have comprehensive health insurance, just travel insurance. Thankfully medical care outside of the U.S. is very affordable. I do have a retirement account. Earnings are certainly subject to U.S. taxes, no matter where you earn your money (although some can be exempt with the 330 day rule), and you aren’t normally subject to taxes in the country where you are traveling.

  4. I am going to start traveling next year. I am going to put a shell on my pickup truck and take baby steps first

  5. Hello I’ve been toying with the idea of car living I enjoy camping I know this is different just not sure how I wanna start or where any ideas greatly appreciated

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  6. Hola Ryan,

    So glad to have found your blog!
    I am leaving for Medellin tomorrow night. I am looking forward to the adventure I will find in Colombia and find myself back again!

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  7. Hi Ryan!
    Amazing stuff! I admire your courage and determination. My husband, Neil and I are planning to drive from southern Oregon to Guatemala and back, leaving in December this year. I’m curious to know if you traveled/drove through Mexico this year, 2017. I guess my concern is anti-Trump sentiment (we encountered some last year, 2016, in Guatemala, right after the elections), and any hassles you encountered just because of being a gringo and being perceived as a Trump sympathizer.
    Reading through your blog, I couldn’t quite figure out the dates of your Mexico road trip.
    Thank you for your blog.

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      Hey Aura, it was 2015 when we were driving through Mexico, as the primaries were taking place. I remember one time where a local mistook my “Washington” license with D.C. and said “so you hate Mexicans there?” You might want to ask around in the PanAmerican Travelers Group, but I haven’t seen anyone who has had any hostilities or problems due to Trump. Fortunately most people distinguish between the individuals and their elected leaders. I remember being in Yemen during the height of the Iraq War when EVERYBODY there hated Bush, I didn’t have any issues there either.

      1. Ryan,
        Thank you so much for your response!! I might come up with a few more questions in the next few months, as we get ready for our trip. Thanks again for your blog. Take care and safe travels.

  8. Hi Ryan,

    I’m starting out on a new adventure in my life… I finally bought the truck I’ve been wanting for years and want to convert it into a liveable unit for myself and my dog. I’m not new to living out of my vehicle, however with this new truck I’m wanting to “up my game” if you will. I would like some help- or am willing to hire someone- to build and install a bedframe and storage system in the back of my truck. I would do it myself but I don’t have the tools and probably skill level to pull this off by myself. Do you know of any companies or individuals that do this? I’m in the Washington/Idaho/Oregon area. Thanks so much for your blog and all the info!! Look forward to hearing from you 🙂

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      Hey Audrey Jo! That’s awesome to hear, I’m not aware of any companies that specialize in small scale projects like building out the back of a pickup truck, but if you’re in the NW, I could connect you with my buddy in Seattle who built out the back of my truck to see if something might work. He did mine in a long afternoon, he works construction professionally as well. Shoot me an email or let me know if you’re interested.

  9. I’m planning to drive from the US to Panama and back over a 6 month period. I intend to visit every country in Central America. I have a new vehicle and would like to have full coverage on it for the duration of my trip. I have a couple of questions about getting auto insurance. First, is there a company that I can purchase full coverage through that will cover me in case of theft or accident throughout all of Central America? Second, I know some countries require you to purchase liability insurance at the border. Do these companies also offer full coverage? Thanks for your help!

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      Hey Kevin, I believe there are companies that might offer coverage throughout the trip, but I’m unaware of which ones specifically. I would join the PanAmerican Travelers group on Facebook and ask there for specifics. In regards to full coverage at the border, I think the answer would be no. Mexican coverage had options for full coverage but it depends on the age of your vehicle. My old truck wasn’t eligible for instance.

      1. Clements Insurance is a great one. They are responsive and comprehensive. Had a buddy in Zimbabwe who had a Land Cruiser that needed a transfer case oil top off. The dealer left the drain plug out and toasted the tranny and transfer case. They sent him a check.

        Another good one if you can get access through a family member is USAA. They are one of the best.

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