How to Travel Full-Time in a Financially Sustainable Way, Part 4 – Working on the Road

How to Travel Full-Time in a Financially Sustainable Way, Part 4 – Working on the Road
The Professional Hobo

I subscribe to a blog called The Professional Hobo written by a Canadian full time international wanderer. She has all kinds of really useful tips for maximizing and stretching your travel dollar or peso as the case may be!

Now in my late 50s,, this particular option is not under serious consideration but I now realize that even after ‘settling down’ and being a homeowner for 17 years, at heart I am a gypsy who likes nothing better than a day without plans but full of promise! And San Miquel is just a wonderful city to wander around people watching and exploring the wildly electric assortment of shops, restaurants and galleries!

Hi, Joanne —

This is Part 4 of the series How to Travel Full-Time in a
Financially Sustainable Way. We’ve already explored ways to travel
inexpensively with Accommodation and Transportation tips. And we
considered the ins and outs of Selling Everything to free yourself
up for travel. Now let’s make some money!

As usual, get comfortable and please enjoy this wide collection of
resources to help get you on the road and making some money –
whether you’re a gap year student, career-breaker, successful
entrepreneur, or lost soul (or even all four).

No matter how you slice it, you need (at least some) money to
travel, and if you want to travel indefinitely, your savings alone
won’t cut it.

So it’s time to find a way to make some money on the road. Luckily,
there’s no shortage of options, especially if you’re creative, and
ideally passionate.

New Life, New Career

I am among the ranks who chose to throw in the towel and completely
redesign my life. I went from financial tycoon to aspiring
writer/volunteer goat milker in less than six months; quite a
dramatic transition.

The reasons people make dramatic transitions to a new life of
travel are as varied as the people themselves. But generally, we
fall into a few categories:

* We have a career burn-out, or other life event that forces us to
reevaluate everything
* Career changes are forced upon us, such as being laid off
we want to live and work abroad

Here are some ideas for how you can develop a business that allows
you to travel full-time:

Financial Travel Tip #43: Starting a Business You Can Travel With [

And if you have had change forced upon you, it’s not all bad. Here
is the silver lining:

Laid Off? How to Make the Transition Abroad From a Career Tragedy [

Location Independent Basics

Being location independent means you can work from anywhere in the
world, regardless of your actual location. You usually need a few
key ingredients, like a laptop and internet access for starters.
But you don’t have to be a blogger or web designer to have a
location independent career. In fact, you can travel full-time as a
telecommuting employee, a freelancer online, or you can flex your
entrepreneurial muscles with almost unlimited possibilities.

Here are the basics:

Financial Travel Tip #31: Location Independent Careers [

Living and working remotely requires a few tricks of the trade.
Here are some location-independent-traveler-tested tools to help
you manage your life and career:

Tools for Running Your Location Independent Business [

Converting your Business or Career into a Transportable One

You may want to take your existing expertise or business on the
road. This is good as you aren’t laden with the task of learning a
whole new set of career skills while getting your travel feet under
you. But rest assured – there’s still a learning curve!

Here are a few things to consider before uprooting your business,
from company structure to visas to taxes to management logistics.

Financial Travel Tip #30: Taking Your Business on the Road [

Teaching English Abroad

Teaching English abroad is both a viable and popular way to
financially sustain travels. Many gigs include accommodation, such
that if you are smart with your food and incidental expenses, you
can save money as you work, then use your savings to travel around
when your contract is up. I know of people who work for a year,
then travel for a year, then work in a new place for a year. It’s a
great way to immerse in your destination and develop relationships
with locals you wouldn’t otherwise meet.

Your students can range in age from pre-schoolers to senior
citizens, and schools can be private or public. Most schools
require a university degree (in any subject) as a minimal
requirement for the job, and some also require some form of
certificate for teaching English (such as TEFL). But, many
experienced English teachers abroad have also reported that once
your feet are on the ground at a destination, you’re more likely to
be hired, regardless of certifications.

I also hear that teaching English abroad can be very hard work, so
be prepared to earn your money. But it can be a rewarding way to
live overseas and to save money for future adventures.

I don’t have any experience teaching English abroad, but fellow
traveler and colleague Nomadic Matt has. He also wrote a
comprehensive guide to help you do it too:

How to Teach English Overseas [

Canadians: Here’s your guide
] to where and how to get working holiday visas.

Citizens of other countries, check your home country’s immigration
website (they usually have a section for citizens abroad), as well
as your desired destination country’s immigration website.

And if you need some ammunition to convince family and friends that
taking time off to live and work abroad is a good idea, here you go:

Kick-Start Your Resume by Working Abroad [

Career Breaks and Sabbaticals

If you’ve got a business that can’t move (and a butt that wants
to), or a career that’s largely enriching but from which you
occasionally need a break, you have options too.

I watched an incredible TED talk by Stefan Sagmeister about how he
closes the door to his business for one year out of every seven so
he can pursue personal interests and travel. And his business
thrives for it.

Check out his talk here:

The Power of Time Off [

And he’s not a freak of nature or an anomaly either. Sabbaticals
can be great for your business – and your personal life.

How Taking a Sabbatical Can Help Your Business [

Here’s an e-book/audiobook that gives you the dirt on taking a

Escape 101: The Four Secrets to Taking a Sabbatical or Career Break
Without Losing Your Money or Your Mind [

Career Ideas and Tips

Are you feeling clueless? Searching for inspirational ideas for how
to make money on the road? Here are a few resources to get your
creative juices flowing:

How to Get Free Accommodations (and Paid Jobs) on Boats [

Financial Travel Tip #42: Earning Income by Online Tutoring [

Still scratching your head? I’ll bet you have a personal interest
or passion that you could creatively translate into an income. And
you might even be able to do it for less than $100.

Make Your Dream Career a Reality for Less Than $100 [

I Practice What I Preach

My income comes from many different sources, from freelance writing
gigs to affiliate sales and sponsored trips. Here’s the scoop:

Financially Sustainable Travel Part 1: My 2011 Income [

Financially Sustainable Travel Part 2: Income and Expense Choices [

Financially Sustainable Travel: My 2012 Income [

Step by Step

When I started traveling full-time, I didn’t have a location
independent business up and going (or even an inkling of one), but
I did have a monthly income from the sale of my financial planning
practice to support me for the first two years.

Thus I quickly learned the first step to traveling in a financially
sustainable way: how to live and travel on a budget. (My income was
less than $2,000/month and I was traveling with a partner at the
time who didn’t have a reliable income).

The next step was to develop a location independent business that
would replace the income from my business when it ran out. In
researching travel options and starting my blog (which I initially
thought was no more than a glorified journal for family and
friends!), I quickly realized there was money to be made online
with freelance writing; a perfect fit with my lifelong penchant for
the written word.

But it took time. I worked almost full-time hours (often in
addition to up to 30 hours per week of volunteering) for the full
two years that I was “enjoying” my monthly stipend from the sale of
my business. When the two years was up, I had built a location
independent business to replace that income – barely.

I could have done it better. These days there are all kinds of
resources [
] to help you build a location independent business, restructure
your life, and travel. But at the time there wasn’t much out there.
Although I’m far from the first person to travel full-time with a
location independent business, I was certainly on the leading edge
of a growing movement. So I stumbled my way around learning to be a
good writer, develop a website, market online, pitch publications,
and monetize. My efforts were far from scientific!

If I Were Doing it Again Now

I wouldn’t try to reinvent the wheel. I’d tap into available
resources to get ideas and systems in place. Although most of what
you need to know can be found if you spend enough time online (I
know – that’s how I did it), I think it’s worth spending a little
money to reduce the learning curve and leverage your time with
somebody else’s knowledge and experience.

Here’s a starting point:

Three E-Books to Help You Make Money, Travel, and Change Your Life

Secondly, if I were doing it all over again now, I wouldn’t take
the leap into a life of full-time travel without having the
fundamentals of my new career in place first. Life on the road is
overwhelming enough; add in the pressure of building a business,
and full-time travels can quickly become overwhelming and

Take Your Time, Balance, Breathe…

Speaking of “overwhelming and unenjoyable”, when work-life balance
gets out of whack on the road, life can become pretty miserable.
Remember – you don’t want to trade one rat race for another!

Here are some sage lessons I learned a few years ago after an
episode of burnout on the road:

Travel, Work-Life Balance, Time Management, and the Paradoxes
Within [

If you’ve followed the advice in this series so far, you should now
be rolling in money and keeping your travel expenses low. Next,
let’s look at the numbers, with The Finance of Full-Time Travel.
See you soon!

Do you like what you see? Please tell a friend about this free
series, and give them this link [
] so they can sign up. I want to let as many people as possible
know that full-time travel is entirely achievable.
The Professional Hobo,

2 Romar Crescent, Toronto, Ontario M6B 1R8, CANADA

This is apparently her mailing address in Canad because as as far as I know the Professinal Hobo is currently traveling in Panama. You can follow her on both Facebook and Twitter! I do and also subscribe to her newslerter.


2 thoughts on “How to Travel Full-Time in a Financially Sustainable Way, Part 4 – Working on the Road

    1. Gracias, Jane. Si, this writing format comes sooo much easier for me than the 50,000 wprd novel that I cranked out and yes, that was the operative word last November. This type of conversational writing comes quite naturally to me and I remember that one of my grad school profs at the University of Calgary told me he or she enjoyed my style of writing that was entertaining yet informative and well researched. Naturally, this blog is a work in progress and I plan to add pictures, videos, links, quotations and everything I can thnk of to keep up and increase my readership which currently stands at about 25. I have yet to learn to put in tags and link it to other bloggers and expat/snowbird forums but i WILL as the winter unfolds. Sending you sunny and warm wishes from San Miquel de Allende!

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