Nora Dunn – aka The Professional Hobo – packed up her life and sold everything she owned (including a busy financial planning practice) in 2006 to embrace her dreams of long-term immersive world travel. She’s as surprised as anybody that she really truly made a go of it and traveled full-time for 12 years! She now has a home base in her hometown of Toronto Canada, but continues to travel the world for about half the year.
Here’s an intimate (and inspiring) look at the ups and downs of her adventure. If you’re looking for insider advice on how to escape the rat race and build a location independent life, this is for you.
Table of Contents
- How long have you been traveling? Where have you traveled?
- What was your life like before you hit the road?
- What inspired you to start your life of travel?
- What struggles did you face when deciding to leave the security of your old life behind (emotionally, financially, relationally, etc)?
- How did you overcome those struggles?
- How have you supported yourself financially throughout your journey?
- How has your life improved since quitting your “normal” job?
- What are the biggest challenges you’ve faced?
- What’s one thing you know now that you wish you would’ve known first starting out on your adventure?
- Anything you would’ve done differently?
- What’s the biggest life lesson travel has taught you?
- What one piece of advice would you give readers thinking about leaving behind the 9-to-5 to build a location independent lifestyle?
How long have you been traveling? Where have you traveled?
In a sense, I’ve been traveling most of my life, but you probably don’t want to hear about my childhood 400-mile train rides across the border to visit my grandparents in the U.S. (something that instilled in me an evangelical love of train travel and eventually led to some book-worthy train adventures).
Okay, then. Maybe I should start with my experience of touring China with a ballet (I was in the orchestra) at the tender age of 16.
If my childhood train travel adventures didn’t plant the seed to explore the world, this trip certainly did.
Fast forward through another two dozen years of various vacations (most of which were of the all-inclusive ilk – a very Canadian style of pilgrimage to warm places during winter for a week of defrosting), and I hit the age of 30.
That’s when I sold everything to travel full-time.
Since then I’ve traveled through and/or lived in 55+ countries. (I’ll spare you the play-by-play; instead, here’s a map of the destinations I’ve covered).
What was your life like before you hit the road?
I was rich and famous…
Well, not quite.
But I had achieved a modicum of success through my financial planning practice. I made good money, and had all the accoutrements of a comfortable life.
I was also something of a medium-sized fish in the big pond of Canadian financial planning.
I had been recognized by the media for my holistic approach to financial planning and money management, which led to lots of newspaper interviews, tv appearances, and speaking gigs.
What I lacked, was time.
And time was what I needed to achieve my childhood dream of hacking my way into local cultures around the world. (Read on).
What inspired you to start your life of travel?
My childhood dream of hacking into local cultures was borne at an early age, when I watched a documentary about Europe. I didn’t recognize how people were dressed, the languages they spoke, the food they ate, nor the architecture.
What I really wanted to know at that age, though, was “how do the children play”?
That dream evolved over the years but the theme remained the same.
What do people eat? What do they talk about around the dinner table? What are the going concerns? How do people spend their free time? Where do they shop?
My last traditional vacation was a month-long trip to South Africa. I figured a month would be long enough to “crack the code” on the country and culture, but of course, it wasn’t. I returned home with more questions than answers!
But one answer that eventually became clear to me was that if I really wanted to pursue my dream of immersing into and understanding other cultures, I had to make travel a long-term adventure.
That realization was the catalyst for me to sell everything on an open-ended travel adventure that would last 12+ years.
What struggles did you face when deciding to leave the security of your old life behind (emotionally, financially, relationally, etc)?
The decision to travel full-time was surprisingly easy to make and follow through with once I hit “critical mass”.
By “critical mass”, I mean a severe case of burnout, peppered with depression, and topped off with two cases of bronchitis that devolved into walking pneumonia – which physically forced me to stop everything and really take stock of my life.
I realized in that moment that I couldn’t spend the next 30 years of my life “putting in time” in a life and lifestyle that didn’t bring me joy anymore, awaiting a conventional retirement age so I could start living my dream of immersive travel. I knew there would be a chance that in 30 years, I wouldn’t be willing (or possibly able) to do the things I wanted to do around the world.
Once the decision was made, everything else was small stuff. And as the saying goes: “don’t sweat the small stuff”.
How did you overcome those struggles?
Well, there was one thing that wasn’t so small, and ended up being a tricky situation….
When I decided to travel full-time, I’d been dating my boyfriend for six months. I felt that we were too far into our relationship for me to say “okay bye – I’m going traveling!”, but it was also too soon to say “wanna come?”
I opted for “wanna come”.
And while I’m grateful that he came along with me for the first few years on the road (it gave me confidence to have somebody alongside me), the truth is that he didn’t really share my dream of travel and it caused a lot of friction.
It got ugly when he ran out of money while we were in Australia – a situation that unto itself shouldn’t have happened (but that’s another story).
Our relationship was already rocky at best, but now I couldn’t just leave him on the other side of the world without any money. Instead, I supported him until he could find a way to support himself…
Let’s just say it made the last year of our relationship pretty ugly.
How have you supported yourself financially throughout your journey?
Which brings me to…money!
I didn’t know how I’d earn a living when I took off to travel full-time. What I did have, was a 2-year modest stream of income from the sale of my financial planning practice.
While it wasn’t a ton of money ($2,000/month CAD), and while I did have some savings to dip into if necessary, I learned to live on this income which in turn, inspired me to find creative ways to travel on a budget – like getting free or cheap accommodation around the world – in some pretty swanky places no less.
Shortly after I hit the road, I realized that my lifelong penchant for the written word, in combination with an ultraportable laptop and internet connection, could yield an income as a freelance writer.
I knew that developing a freelance writing career would take a lot of time, so I set myself the goal of replacing my income from the sale of my business by the time it ran out in two years.
It took a lot of work, but I succeeded!
How has your life improved since quitting your “normal” job?
The buzz word among just about every digital nomad or full-time traveler is so commonly used it’s almost cliche, but I’ll use it anyway (cuz it’s true)…
I choose when to clock in and clock out. I select where I work; “where” in every sense of the word.
And while it’s important to note that travel blogging and freelance writing is a full-time job, when that job is done for the day, I can close my laptop and explore whatever world exists on my front doorstep – a world that changes every time I change my location.
What are the biggest challenges you’ve faced?
Work-Life Balance has been a consistent thorn in my side from the beginning. This is largely because of the perception that travel = vacation.
While that was generally true in years gone by, with the advent of more and more digital nomads taking to the road, travel doesn’t necessarily mean vacation.
Travel can now be a lifestyle, and that’s a very different thing.
This perception that full-time travelers are on permanent vacation was the worst when I visited people and stayed with them, be they new friends I met on the road, or even my own family and friends on return visits home.
To everybody, my stay with them was a vacation. And while I am so grateful that people viewed time with me as a celebration, it consistently made carving out the time and space I needed to work incredibly difficult.
Not to mention, the sheer amount of energy required to simply exist abroad is massive.
Traveling full-time requires choosing a destination, deciding what city/area/neighbourhood to stay in, finding a place to stay, and figuring out how to get there and booking it. THEN the work begins on arrival, figuring out where everything is and how to live there…
This is practically a full-time job unto itself, and it doesn’t pay any of the bills either!
So, most if not all full-time travelers eventually learn that slow travel is the only way to survive.
It’s also why I ended up having a series of home bases along the way (in countries like Australia, New Zealand, Grenada, Peru, and Ecuador), in between spurts of travel that would exhaust me and require “settling down” for a bit.
I appreciated these home bases not only as being places to relax, unwind, and get some work done, but also as an opportunity to delve much deeper into cultural exploration, and to use my base to explore lesser-known areas that most travelers never get to.
What’s one thing you know now that you wish you would’ve known first starting out on your adventure?
The weight of your luggage is equally proportionate to your level of misery on the road! I started traveling with so much crap it was actually comical in retrospect.
Over the years, I pared down and down and down again, until eventually I managed to fit everything I owned into a carry-on bag and travel that way for two years.
Since then I reverted to checked-luggage for a variety of reasons. But if I am taking a short trip (as in, a month or less) to a warm climate, I still prefer to travel with carry-on luggage.
Here’s a crazy popular post I wrote about the various types of luggage I’ve had along the way (from backpacks to wheeled backpacks to rolling luggage and more), and the criteria travelers can use to choose the best type (and size) of luggage for them.
(Mitch’s Note: Nora is absolutely right – when it comes to luggage, there’s no one-size-fits-all recommendation. There are pros and cons to everything, and her post helps you decide what’s best for YOU. For more handy packing tips, read 19 Travel Packing Hacks Smart Travelers Do Differently.)
Anything you would’ve done differently?
I don’t spend a lot of time pondering questions such as these, because the ripple effect of changing one decision could have drastically altered the course of events that happened – and on the whole I’m pretty pleased with how my life has rolled, bumps and all.
However one thing I would highly recommend to anybody who is considering hitting the road themselves, is NOT to follow my example. Ha! If you have aspirations of becoming a digital nomad, do yourself a favour and establish the foundations of your new online career before you leave.
Otherwise, you’ll face the simultaneous challenges of both learning the ropes of a new digital nomad career, and also learning the ropes of lifestyle travel and trying to carve out your own personal style.
It’s a lot to handle all at once.
Want more practical travel advice? Check out this list of 25 top travel tips.
What’s the biggest life lesson travel has taught you?
While I could (and have, many times) pontificate how people around the world are all fundamentally good and blah blah blah, I’ve learned many more practical life lessons in my 12 years on the road. Here are the 12 Truths About Travel and Life that I learned – one for every year I traveled full-time.
What one piece of advice would you give readers thinking about leaving behind the 9-to-5 to build a location independent lifestyle?
While I think my best answer to this question has already been mentioned (establish your new online career before leaving), perhaps another piece of advice about the lifestyle in general would be to embrace what comes.
Travel is fluid. You’ll probably change your style of travel, and possibly your sources of income as well, a few times over. That’s okay!
Also, returning home is not failure.
I had to wrestle with the idea of setting up a base again in my home town – a place I thought I’d never live in again.
While I used to rail at the idea of “settling down”, the truth is after 12 years abroad, I’ve now come to value other things in my life, not the least of which are the close proximity of life-long family and friends, the chance to be a proper “Aunty Nora” to my best friends’ children (whose births I missed), and my ability to enjoy what remaining time I have with my aging parents.
And because I continue to travel for half the year, I have the best of both worlds. A few years ago, I was in a different place in my life and development, and constant travel worked for me.
Now, I appreciate my travels all the more knowing that I have a place to come home to, unwind, unpack, and focus on my business and other ventures.
Life – and travel – is an evolution, and there’s no right or wrong. Do what your heart calls you to do.
***Do you have a successful “escape the rat race” story? Wanna be featured in an upcoming case study? Shoot me an email for more information.***
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⚠️HOLD UP! Before you peace out to explore the world—have you thought about travel insurance? If not, let me tell you a little story…⚠️
Mitch is your typical nomadic backpacker. Or at least, he was. But after stopping in Colombia to take “one week” of salsa lessons, his life took a sharp left turn. He met a cute Colombian girl in dance class, fell in love, and got married. Over half a decade has passed since he left his career to travel the world as a digital nomad, and he’s never looked back.
Nowadays, he’s the blogger behind Project Untethered—where he runs an awesome email newsletter and Youtube channel teaching adventure-craved wanderlusters how to escape the rat race, earn money from anywhere, and build an “untethered life”.
Mitch's Travel Recommendations:
Travel Planning Resources - Everything you need to plan your trip on one convenient page.
Safetywing Insurance - This cheap travel insurance has saved me over $15,000 in medical bills.
Booking.com - Book accommodation without adding your credit card (in case you need to cancel).
Skyscanner - Find cheap flights.
Trusted House Sitters - Take care of pets in exchange for free (sometimes luxury) accommodation.
Flexjobs - Find remote jobs without having to sift through crappy ones.
Skillshare - Free trial to take unlimited classes that teach digital nomad skills.
Anytime Mailbox - Virtual mail service that can handle your mail while you’re away.
Wise - Send and receive money abroad cheaply (great for freelancers).