Small House Big World


Work + Travel: Earning a Living on the Road

Anna Edgren • December 21, 2015

Deciding to live in an RV and travel full-time was not a quick or easy decision to make. One of the big issues I had early on in process was figuring out if I would be able to support myself and make money while traveling.  Because sure, traveling the country sounds like fun, but is it affordable? Is it practical? Is this a manageable lifestyle or have I lost my mind? 

At the time of this decision, I was 30 years old – certainly not ready to retire. I don’t have a crap-load of savings. I don’t have any passive income rolling in. My only means of income is a paycheck each month. And beyond the monetary reasons, I also wanted a job so that I could keep building up my skill set and learning and growing and all that fun stuff.  I knew I would have to find a way to work remotely. 

The option to work remotely has only been possible very recently, historically speaking. Technology born in the last 20 years has finally come together to make it not just an option but a GOOD option. Readily accessible wifi, small and easily portable laptop computers, mobile internet in the form of 3G and 4G, and of course mobile phones themselves.  Although putting together this arsenal of tools is a substantial investment, it is one that can open a lot of doors. 

You don't need quite this many.

You probably don’t need quite this many gadgets.

Kelly had figured out the secret of working remotely (and working for himself, which is a whole other beautiful dream) a while ago. He was also interested in the idea of travelling while working, and I knew that if we could both figure out a way to make money remotely, we could go exploring and support ourselves at the same time. The freedom that comes with location independence was extremely appealing to me, and Kelly was my shining example of success. And frankly, I was tired of getting out of bed at 6:30 in the morning to go trudging through the snow while Kelly curled up in my warm blankets. 

To be clear, I didn’t hate my normal work routine. I didn’t mind riding the train to work, I would usually read or listen to music and entertain myself. The problem wasn’t so much the commute itself, it was the fact that I was REQUIRED to make the commute, day after day after day. Rain or shine (or snow). Tired or energetic. Happy or sad. 

daily work routine comic

And of course, I was REQUIRED to be in Chicago. I like Chicago fine, but what about, you know, everywhere else I hadn’t seen yet? 

So I asked the company I had been working for if I could work remotely, and they said no.  

There is often an unspoken assumption about working remotely –  that perhaps it is not as legitimate as working from an office. That you can’t accomplish the same things or put in the same amount of effort. Lazy people want to work from home – people who can’t hack it in the “real world.” There are also a whole host of spammy “WORK FROM HOME” ads on the internet promising you $10,000 a month “EASY MONEY” for selling such-and-such. These do not lend any credibility to the concept.


But working remotely doesn’t mean putzing around in your PJs all day. It means location independence. You don’t have to work from home, you can work from anywhere. Now there’s an idea with some appeal. For many people, the only thing holding them back from a life with more freedom to explore and travel is a stationary job. If you can somehow find a way to replace that stationary job with a job providing location independence, then you open up a whole new wonderland of life-possibilities.  

I was discouraged that the company I worked for didn’t see it my way, but I was determined to find a way to make it work. At that point, Kelly and I had already fully committed to the idea of living in an RV and travelling the country.  I frantically started job hunting. I had a twofold approach to doing this.

First, I looked for jobs in my field through traditional methods. I updated my resume on Monster, Career Builder, and LinkedIn. I tried to reach out to people I knew who may know of job opportunities as well. I got a substantial number of messages on LinkedIn, but they were all for positions IN Chicago. I had a stock response I would send out to these inquiries that basically said: I am DEFINITELY interested in this position, but only if I can do it remotely, is that an option? (It was rarely an option). 

I also looked at more self-employed type jobs that I could be good at: Freelance writing, selling things on Etsy or Ebay, editing, and transcription typing services, to name a few. (More on my whole thought process around finding a job can be found here)

Ultimately, I found my job through I have no affiliation with them, I just enjoyed using their service. The downside is that you pay a monthly fee to subscribe to the site. The upside is that they have a great database of flexible jobs of all kinds, including 100% telecommuting, which is what I was looking for. And unlike a lot of free job sites I encountered, the jobs are legitimate. It is unfortunate that you have to pay to use a service to find legitimate online jobs, but I know it helped me sort through the nonsense out there. (There very well may be a legitimate free service out there that I am unaware of – if you know any, feel free to comment below.)

So how has it been? Let me throw some adjectives at you: Wonderful. Fascinating. Challenging. A Game Changer.

The position I found is in Operations Management and Supply Chain with a small company that sells health and beauty products online. The entire company is remote, so they have a whole suite of tools they use to stay connected: Skype, Trello, Dropbox, Google Docs, Jostle, and GoToMeeting, for example. 

What was most surprising was realizing that with a typical 9-5 office job, it is often enough to just show up. Your butt is in the seat, your face illuminated by your computer, and people just sort of assume you are getting things done. 


But with working remotely, there is no assumption that you have done your work. You have to prove what you’ve done and show your work, day after day.  With my remote colleagues, we have clearly defined achievable goals that we continue to reach and hold each other accountable for. We communicate more, we have more productive meetings, and I have been blown away by how effectively our system works and how easily we are able to work together.  Working from home means some flexibility with your time, which is huge and important and wonderful. But it also means sticking to your commitments and making sure you are productive, organized, and have set aside enough time to accomplish your goals.

Some days I want to be home. I don’t feel like getting dressed and I don’t feel like seeing anyone. I need peaceful silence and concentration. Other days, I want to get out of the house. I want to go to a coffee shop, have a conversation with a stranger, and take a walk somewhere I’ve never been before. The flexibility to be able to shift your environment whenever you care to is a beautiful thing. 

Not to mention I also used to be so PAINED by having to stay an extra half hour at work. Working remotely I know that if I am in the zone, I can stay in the zone. I can work an extra hour here, and take an extra hour off over there. I have the flexibility to prioritize my life in the ways it needs to be prioritized. 


Working remotely means the chains are thrown off: You can decide where you want to be, and how you want to work. For some people, that means a nice home office, set up just the way they like it, with zero commute time and the ability to be home with their families immediately. For others, like Kelly and me, it means that it is entirely possible to become what is essentially a modern-day nomad. As travel becomes cheaper and the tools to support high-speed internet connections in remote areas of the country and world continue to improve, it is possible to find a rewarding job, make money, and travel at the same time. A balancing act for sure, but what an exciting idea. 

It’s not for everyone, of course. Many people enjoy having an office and enjoy the stability of a home base. And of course there are benefits to having frequent face-time with coworkers and developing in-person relationships. Many people thrive in that type of environment. The exciting part about increasingly available remote-work opportunities isn’t that “EVERYONE SHOULD WORK REMOTELY.” The exciting part is that it is a legitimate option for people who would have the desire to approach work in a different way.   

The freedom that is created by utilizing digital tools is something to be embraced, and I firmly believe that as technology continues to improve and mindsets begin to shift, the number of people happily working remotely will continue to tick upwards, towards the betterment of the entire workforce. I for one am happy to be a part of it!

rv and worktravel and workwork from homeworking remotelyyoung full time rvers

Anna Edgren • December 21, 2015

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  1. allison December 21, 2015 - 10:49 am Reply

    Anna! I am so happy I found you guys. My love and I are launching our Operation Airstream in 1.5 years (not that I’m counting the days or anything), and getting all of the stuff in place to head out on the open roads. I have learned so much from you! Thanks for all of your insight. I’ve been working remotely for 10+ years now, so that’s figured out, but my guy needs to figure out his remote/passive income streams. Super good info here!!

    • Anna Edgren December 21, 2015 - 10:59 am Reply

      Hi Allison – Awesome that you guys are planning to make the leap! We are SO SO happy we did. 🙂 I am glad to hear you are finding the blog helpful, that makes my day!

  2. Pookie December 21, 2015 - 3:38 pm Reply

    Fantastic read! We are in the process of getting ready to live full-time on the road and it’s so great reading about remote workers. I currently work from home 3 days and 2 days in the office. Some people can do it and other people need the structure of an office. I find I am SO much less productive when I’m stuck behind a desk at the office.

    • Anna Edgren December 21, 2015 - 4:58 pm Reply

      That’s good to hear! Remote work has its challenges, but overall I have found it to be SO much better.

  3. Scout December 23, 2015 - 4:24 pm Reply

    So encouraging! Thanks for all the info & kudos to you! We are in the process of planning to travel fulltime…but our biggest hangups are making money on the road & medical insurance. I’m not as worried about making money (could always work odd jobs), as I am about having health insurance. Any tips about finding affordable health care for fulltime travelers?

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