Working on the Road: The Unconventional Guide to Full-Time Freedom

Dr. Jessie Voigts's picture

I know that from speaking with thousands of our Wandering Educators, this group sure can dream of working on the road. Whether it is on sabbatical, becoming a digital nomad, realizing your writing goals, or focusing on international education abroad, there are many, MANY ways to work abroad. But it’s often very difficult to figure out HOW.

Enter an extraordinary new book by Nora Dunn, entitled Working on the Road: The Unconventional Guide to Full-Time Freedom. She’s the real deal – you can follow her on her site, The Professional Hobo, read her excellent articles on Transitions Abroad, or find her ALL over the internet, sharing honest information about money, working overseas, freelancing, long term travel, and living and working abroad. She’s a Canadian who sold everything (including a busy financial planning practice) in 2006 to embrace her dreams of long-term immersive travel. She has been on the road ever since, and is a writer on the topics of travel, personal finance, and lifestyle design. In addition to her monthly column (entitled “Dear Nora”) on CreditWalk, she teaches people on her own site how to travel full-time in a financially sustainable way. She has also penned the books How to Get Free Accommodation Around the World, and Tales of Trains: Where the Journey is the Destination.


 The Unconventional Guide to Full-Time Freedom


We were sent a review copy of her new book,Working on the Road: The Unconventional Guide to Full-Time Freedom, to review (thank you!). Let me state this clearly:

This is the BEST book I have ever read on the subject. 

If you are thinking of working overseas, this is the first thing you should delve into. 


 The Unconventional Guide to Full-Time Freedom - Working on the Road. A complete guide by Nora Dunn


Chapters include: 

  • Location Independent Way to Work on the Road
  • Non-Location Independent Way to Work on the Road
  • The Cost of Living on the Road
  • Challenges of Life (and work) on the Road
  • Embarking on the Travel Lifestyle
  • Before Getting Down to your Work on the Road
  • Tools for the Road (Regardless of How You Work)
  • Tools and Overhead Costs for Running a Business on the Road


The book also discusses includes taxes, visas, equipment, life balance, travel tips, professionalism, ways to get paid, and more. I especially love the stories she includes from real life people (and families) working on the road. There’s definitely a way to work on the road – and definitely plenty of mistakes to be made. Hopefully, with this guide, most of them will be avoided (the rest we’ll leave to fate!).


Here’s why I’m impressed:

  • Nora pays attention to Every Detail - no stone is left unturned
  • There are SO many different reasons AND ways to work on the road
  • The book is very clean and professional, and the design layout is enticing
  • The possibilities are endless
  • The knowledge contained here is incredible (thank you, Nora!)
  • This book provides a clearly lit path toward a pretty incredible dream 


This book? Pure inspiration, leavened with practical knowledge and useful tips


Note: depending on how into this you are at the moment, there are three content levels and price points for the guide (you can always upgrade once you’re in): 
•    Exit Ramp: 97-page Working on the Road Field Guide and its companion checklist. $49
•    Escape Plan: Working on the Road Field Guide and its companion checklist, as well as information on what to do with your stuff, how to manage and pay your bills, and the ups and downs of building a freelance business on the road. $79
•    Road Warrior: everything in the Escape Plan, plus an interview with founder Jim Wang on blogging as a business, working on the road with a family, special considerations for property owners, and The Big Bad Guide to Insurance Coverage Abroad. $147


Honestly? I read it all in one sitting, and then went back and read it again. It’s that inspiring.


We were lucky enough to catch up with Nora, and ask her about the book, inspiration, her years of knowledge, challenges and surprises, and more. Here’s what she had to say...


Please tell us about your book...

Working on the Road: The Unconventional Guide to Full-Time Freedom is a guide that shows people how to design their careers around the lifestyle of their dreams. As part of an extensive research process, I interviewed over a dozen people who all live and work on the road in a variety of different ways, from having telecommuting jobs, to location independent businesses, to various forms of work “on the ground” (or even “on the water”) as they go. They are singles, couples, and families of various backgrounds and nationalities – who all demonstrate that living and working on the road is possible no matter who you are. In addition to profiling different career options, I show readers how to arrange their affairs and lifestyle so they can travel long-term or full-time. 

I don't sugar-coat anything either; this is a lifestyle of dreams, but one that takes some work. I disclose pitfalls and factors to beware of, so that people don't have to repeat the mistakes I made in my own eight years of full-time travel and working on the road! 


What inspired you to write this book?

I was chatting with long-time colleague and friend Chris Guillebeau (a New York Times bestselling author and founder of The Art of Non-Conformity). He said “you know, Nora, you have all this experience living and working around the world. Why don't you write a guide and we'll publish it together?” That was over 1.5 years ago, and my guide holds the badge (of honour??) of having the longest publication process of his entire repertoire of Unconventional Guides

Part of the reason it took so long to write was because every time I thought I'd researched and exhausted all the ways you can work on the road, I met another traveler who was doing it in a fresh and different way. I wanted to paint as full a picture as possible to give readers a good cross-section of what's available to them if they want to seize this lifestyle for themselves. 


 The Unconventional Guide to Full-Time Freedom


What is the biggest surprise people find, in reading your book?

I've received three common themes of feedback that were of surprise to readers. 

One was the pleasant surprise that this is not yet another guide to show you how to make money online. Although I do profile various online and location independent careers, I'm also very clear about the fact that you don't have to be a web genius to make a living on the road. 

Secondly, readers are consistently surprised to discover that living on the road doesn't have to cost a fortune; in fact most full-time travel lifestyles cost less than you would ever pay to live in one place. (And no, we're not all backpacking hippies. When I want lobster, I eat lobster). To prove that point, I outline two years of actual expenses for a single, a couple, and a family on the road. 

The last surprise came from people who are already location independent professionals or full-time travelers, who didn't expect to learn anything, but ended up discovering lots of new tools and lifestyle and travel tips after reading the guide. 


What are the biggest challenges you've had, in adapting your work to be a digital nomad?

Probably the biggest lifestyle challenge I've had in working as a digital nomad has been one of work-life balance. Living on the road is not a vacation, and can't be treated as such. Travel activities and work obligations aside, even the daily tasks of life are more complicated on the road. It's a tricky concept to wrap your head around, and for me (as well as many other travelers I interviewed) it involves a learning curve. I discuss work-life balance in detail in the guide, and provide tips and solutions that I and other travelers have found to make it a little easier. 


 The Unconventional Guide to Full-Time Freedom


Can traveling families utilize this lifestyle?

Oh yes! I interviewed a variety of families who live and work all over the world, and they provide some sage advice for aspiring families. One of the families I interviewed is a husband and wife who travel full-time and earn a living on the road....with their six (six!) children. 


What's up next for you?

After eight years of being proverbially homeless, I've established a home base in the Sacred Valley of Peru: a beautiful spot that simultaneously feels like home and satisfies my urge for cultural exploration. But I've far from stopped traveling; I'm still on the road for months each year (in fact I just returned from two months in Colombia, Colorado, and Costa Rica). The difference is simply that I have somewhere to return to, and it's much easier to travel with carry-on luggage only

I'm also using my time in Peru to explore some offline ventures and personal pursuits that feed my soul in a different way. In the future, I expect to start developing and offering retreats to help people explore new lifestyles, expand their horizons, and learn a few things about themselves in the process. 


 The Unconventional Guide to Full-Time Freedom



Thanks so much, Nora! Click here to learn more about Working on the Road: The Unconventional Guide to Full-Time Freedom - and see how you can follow your dreams. 











All photos courtesy and copyright Nora Dunn