How I Became a Location Independent Entrepreneur

I’ve been asked a number of times recently to write up “my story”. Usually I try and write with you, the reader in mind, but it’s been made clear to me that sharing my personal experiences has a lot of value to those aspiring to become location independent (trust me, it’s not all travel and mountain biking as my Instagram might depict).

When so many “digital nomad coaches” post aspirational photos of themselves getting sand in their laptops or developing text neck at the beach, then claim the answers are all in their $49 ebook, it’s understandable many of you are skeptical.

My goal is to tell you one man’s story of how he came to be a location independent entrepreneur.

I am not a guru. I am not wildly successful. I have just carved out a humble existence while remaining independent of a single city or country.

I’ll run through how I found myself half way down this path before realising it was even a path, lessons along the way and my current situation.

Groomed to Work

My parents are humble people. Probably on the lower end of the middle-class back when I was born, they worked hard to pay for my sister and I to go to private schools (independent, non-state run).

When I was around 13, my parents divorced. That same income now needed to fund 2 houses, so money was always relatively tight.

It was clear I needed to make my own way if I wanted to buy things, so (no doubt with the encouragement of my parents) I got a job folding and delivering newspapers once a week which my dad helped me with. From there I worked at a McDonalds.

I remember my favourite shift at McDonalds – literally moving stock from a pallet to the freezer/fridge. Looking back, I enjoyed the mastery of these jobs – when I was learning something new I’d fast become an expert in the role. The problem was, the more efficient I became, the less I was paid as I worked less hours.

After giving plenty of notice and requesting to have the New Year’s Eve shift off, I found myself scheduled on that night. “It’s not that I don’t like the job, I just don’t want to work New Year’s.” They didn’t negotiate, I didn’t negotiate, so that was that.

Quitting my casual job at McDonalds seemed like a sensible decision as I’d planned to focus (read: I did not) on my Year 12 studies (the final year in school/college in Australia).

My parents didn’t see it this way. This was when I was taught “never leave a job without another job to go to” and “once you’re out of work, it’s very hard to find more work”.

Gotta Make Dat Money Tho

Later that year as cars became more important and it became clear I didn’t really care too much about school, I started stacking shelves at a supermarket for extra cash. I finished school with average grades – mostly B’s, and began the university course that my school’s “career councilor” encouraged me to take; Software Engineering.

At the time, there was no option of a Network Engineering (my deeper interest) course at university, though there was a Network Administration course at TAFE, a technical college.

Wrongly in Australia, a technical college certification doesn’t have the same sort of prestige that a university degree does, so many private schools and parents don’t want to see their kids go there.

Realising it was a waste of money and time, I quit my uni degree 6 months in and began managing the grocery department full time.

Dad wasn’t on board with this – he “wanted more” for me, but I knew it wasn’t forever. It was shift work, with a 4am Monday start. There was no chance I was getting up at 4am for the rest of my life.

The shift work however, allowed me to start working part-time with an internet service provider doing telephone support. Finally, work in IT!

Jobs Began to Look Like Stepping Stones

A willingness to learn quickly pushed me from customer support (“I’m sorry to inform you but you can’t access the internet without a modem”) to jack of all trades – helping with server cabling and rigging wireless antennas.

This is where I learned the benefit of small business – you get a lot of exposure to different tasks you wouldn’t otherwise have in a large company. But on the flip side, there’s a lot of disorganisation and flexibility required… A Sunday support shift also meant cleaning the office.

Over the coming years I hopped from job to job around every 18 months or so.

Corporate IT support to Government IT support. System administration to research and engineering.

My theory was, changing jobs every ~18 months was the fastest way to increase my pay and knowledge without looking bad on my resume.

Save Half of What You Earn

Neither of my parents have been particularly interested in finance or investing, but they both made it clear to me that saving was important.

When I began my first serious job, I was earning maybe $2000 per month after tax. Living with my father at the time, it was more money than I’d ever seen before. He told me “save half, spend the rest“. So I did. $1000 a month is still a huge amount of money when it’s more than you’ve had before, and you’re living at a parent’s place.

From then on, any time I got a raise, I continued to save half. Thanks to being a percentage, I still saw an increase in spending money, but unknowingly I was “paying myself first”, forming the foundation of what I now call a freedom fund. Something as simple as this has helped me to have a runway while travelling or starting businesses.

Absolutely Flogging the Game of Life

At  23, I was asked to join a team at a government organisation to begin what, at the time was my dream job. I thought for sure I’d have to wait until I was 40 before I got there – turns out things can happen faster than planned.

This certain organisation prided itself on employing those with university degrees. And yet there I was, earning “degree money” sans qualifications.

I bought a Mitsubishi Evo and somehow never got a speeding fine. My girlfriend and I bought a large parcel of land in the Adelaide Hills and at 24, we got engaged.

We’d planned to save our asses off for 2 years, get married, take a 3 month backpacking honeymoon, then a 9 month working holiday in Canada.

After, we’d return home, go back to our jobs (both of us had extended leave), build a house on our property and start a family. I had vague plans to “retire at 35”, but no real strategy for getting there.

What could possibly go wrong?

You Don’t Know What You Don’t Know

I married Jess 2 years later and after a painstaking wait, we flew out to Europe via a short stay in Singapore and Malaysia. We spent 3 months travelling around Europe seeing new cities, new cultures, old friends, new friends and relatives.

This trip alone challenged a lot of my preconceived notions.

I mean, Aussies are rich; overpaid and under worked. Even in Europe, so many people work 2 jobs for less than half of what your average Aussie earns each year.

Tough Australian males never show their emotions in comparison to the more “passionate” cultures. I remember getting off a bus in Italy to meet one of Jess’ relatives – a mid 40’s male crying, hugging and kissing us on the cheeks.

As it turns out, strangers are usually good people who don’t want to cause you any harm.

Oh, and it was even surprising to me that cars and bicycles can actually coexist on the roads. Who would have thought?

Change of Plans, Mate

3 months and an Icelandic volcano later, Jess and I arrived in Whistler, Canada to begin our 9 month working holiday.

I got a job – a mountain bike guide with the Whistler Bike Park. I might have hustled harder than I ever have to get that job. Here I enjoyed perks such as a generous $16/hr pay, that is if you get paid at all (hours would regularly go missing). Really, the goal was for the job to pay for my bike and to get a free lift pass.

During Winter I scored a more serious position in the IT department of Whistler Blackcomb where I was treated to a much more significant (read: more sarcasm) $18/hr – 4 days a week, 40 hours a week. I became pretty good at snowboarding on powder days while holding computer hardware under my arm.

Despite my frustrations with the lack of professionalism about, it was one of, if not the happiest time of my life. Ride bikes, hike, swim at the lake, hang out with friends, repeat. It was a dream come true.

During Winter I was treated to some incredible moments that no doubt changed my life in a major way, though it’s hard to pinpoint which ones contributed to what.

We were due to leave Whistler, but neither of us were ready to leave. I called up my boss and begged him for more unpaid leave – he gave me another 6 months. We saw out the winter. As summer rolled around, and we now we had a set leaving date I was determined to put my lifestyle first and ride out my time (pun not intended) as best I could.

The IT department let me do 20 hours a week (2 days), and I enjoyed a 5 days weekend full of riding bikes, BBQ’s with mates, swimming in lakes, even taking up yoga to try and fix some of the many injuries I acquired. Best. Life. Ever.

My wife Jess felt the pull back to family/friends. I felt obligated to leave. I mean, you can’t live that lifestyle forever, can you? We had great jobs, supportive families, awesome friends and a piece of land to return home to.

Sheeeeeit.

After 10 minutes on the bus out of Whistler to the airport, Jess was welling up. “Are we making the right decision?” Not what I wanted to hear.

I let her know we were making the right decision – blind confidence, don’t over think it. While over-analysing things is my default mode – I take pride in having optimism in the face of challenge.

We flew back into Adelaide and enjoyed our rockstar welcome home party.

Both of us went back to work on Monday. For a day or two, the familiarity was great.

On Friday morning after my first week back, I got the call. “Hi Jason, do you still want that position over in our department?”. Before I’d left, I planted a seed that I wasn’t sure would ever grow. 2 weeks after taking a year and a half off, I’d levelled up into a much more technical position. The pay rise followed.

6 months in, and on paper we were crushing it. Ticking off boxes in the game of life again. But neither of us were particularly happy with our situation. Reverse culture-shock is real.

I’d come home from work and tell Jess “I want to go back to Whistler.” She’d tell me she wanted to stay. We’d both go quiet and spend the next 24 hours of thinking about it. “I can make it work here,” I’d say. She’d follow with “I can’t do this, Whistler feels like home now”. Shit.

Accepting Life as It Is

Jess and I would go on like this for about 6 months. As we slowly lost our minds we decided to just “give Adelaide a good go for a while”. To some extent, it worked… At least short term, life was much less stressful.

We both sort of accepted life as it was, while a wiser me looks back and knew the cracks were clearly showing.

Ironically the time I recall as “getting on with it”, is when I really began to open my eyes to the options available in this world. I began to learn about investing, financial systems, perpetual travellers, freedom, flag theory and so on. Jess must have thought I was losing my frickin’ mind.

Anywhere but Here

We sold our land. We considered moving to Canberra where I’d have my pick of 6 figure government jobs. A week of mountain biking there was fun, but it wasn’t the right fit. Our bikes also followed us to Queenstown in New Zealand for 2 weeks to see if we could live there.

I’d learned about Malaysia as an option that is popular with a lot of Aussie expats. We visited Penang and also spent some time on the Perhentian Islands. Then we returned to New Zealand for 6 weeks of back country hiking.

None of this scratched the itch, so we figured visiting Whistler again couldn’t hurt. We went back for 3 months over Summer and while we were there applied for another Working Holiday Visa. Despite the same beautiful environment, loads went wrong and we ran back to Australia with our tails between our legs.

By the time our Canadian work visas were approved, we were back in Australia with “no intention of returning” to Whistler. We both knuckled down, I rode my bike a lot, and before long we were very unhappy again. WTF.

Close the Door Behind You

We had 12 months to enter Canada and start our visas. For 9 of these months, we were “certain” we were in Adelaide for life. But when it’s the last opportunity you have to give something a go and that door is closing, it’s hard not to take one shot.

We booked flights and both of us quit our jobs for good this time. Quitting my job was one of the hardest things I’ve ever done.

What I learned is, the door is best closed behind you. I’m not saying you should burn your bridges, but if there was an opportunity for me to take extended leave from work again, 12 months later I would have felt the pull back to Adelaide.

This time, our land was sold. So was almost everything we owned. We had no jobs to come back to. Outside of our family, friends and history, our lives were now in our backpack. We had very few ties to where we were from.

Opportunities Are Everywhere

I began to tell people what we were up to. No jobs, no set future plans. Knowing the employment situation in Whistler, I figured I’d need to be responsible for my income.

I started a hobby website on mountain biking when we first lived in Whistler. Turns out in that time I’d built a deep working knowledge of search engine optimization.

Two of my friends asked for feedback and advice on some new websites they’d been involved in. I offered feedback, free of charge to help them out, and I think the nature of this thorough feedback was enough to make them realise they could make use of my knowledge.

Thanks to a growing acceptance of remote workers, this sparked a career in technical SEO consulting. Messy beginnings, sure, but they forced me to learn a whole heap of new skills, such as:

• how, why, when, and where to incorporate companies,
• opening bank accounts abroad (becoming increasingly difficult for many!),
• services contracts,
• sales and negotiating,
• communication skills when doing work online,
• managing finances,
• time management when working from home,
• auditing, tax and other things to stay compliant,
• compensation methods (flat rate, time based, sales commissions, etc), and
• most importantly, deeply understanding other people’s needs.

In this time I’ve also played with selling a website business which was a past passion project, starting an Amazon FBA business and a joke Facebook page that really took off.

All of these things in themselves aren’t huge wins, but combined have helped me to build many new skill sets in short period time. This is one of the true benefits of a location independent entrepreneur lifestyle – you develop a skill set that, even if you fail today, can be applied time and time again in the future.

Change of Plans (Again)

The irony was, we settled in to our new lives and both had a fairly frank discussion not long afterwards. I recall both of us acknowledging “I don’t want to live here forever” in our own words during the same conversation.

Maybe we’d outgrown the lifestyle there. Maybe we’d had the place on a pedestal for so long, it no longer lived up to our expectations upon our return. Maybe it was the insane cost of living. Maybe we were so used to travel that staying in one place seemed like a compromise.

The idea of living Summers back to back seemed like a good one. We thought maybe we could live in Panama during Canada’s harsh winters and live the good life in Whistler’s Summers. We took a trip to Panama and had some good times but didn’t find it to be a place we’d like to spend a significant amount of time in.

Enter the 468 km² Micronation

We took a chance on visiting Andorra, a small state in the Pyrenees mountains between Spain and France. It’s a fascinating region that was put, at least on our map, by an iconic stage of the mountain bike world cup.

On paper, Andorra ticked a lot of boxes, but so did Panama. We were weary, but after visiting for 48 hours we had a pretty good feeling this could be home.

I won’t go on about the place as it’s all I usually do, but if you’re interested you can read my guide to living in Andorra.

Since arriving in Andorra here, I’ve continued building lifestyle businesses with my wife and our team. We still have so much to learn, but that’s part of the fun, right?

A Location Independent Lifestyle Doesn’t Mean You Have to Leave

Over this whole journey I’ve become highly independent of any one location. My income comes from location independent businesses that can be run anywhere with an internet connection. I bank in multiple countries and currencies. I’m a citizen of one nation and a resident of another.

There’s no need for us to live in Andorra if we don’t enjoy it, but the irony is, with all of this freedom we rarely leave. Visiting new country after new country isn’t as appealing to me anymore. But while we love it here, if we needed to, we can pick up our lives and move to another country fairly easily (logistically, anyway).

I feel this is the unseen, unsexy optionality of a location independent lifestyle. It can can mean a new country every week, just as it can mean the ability to choose the one place you want to call home. The choice is truly yours.

Just because kitesurfing in Lisbon is popular with a lot of the posse, doesn’t mean it has to be your choice.

Summary

If you’ve read this far you have my respect! I hope it’s clear that when you read anything from this site it’s the words of someone self-taught by experience (and plenty of mistakes).

You don’t need qualifications, you don’t need bags of money, you don’t need the support of your family. These things might help, but if you don’t have them and they are stopping you, they’ll become excuses.

What you need is a willingness to pursue something that may or may not work. And when it does or doesn’t work, pursue it harder, or pivot and do something else. Then repeat.

Let me know how it goes and leave me a comment below!