How I Became a Professional Vagabond

In 2014, my life became a near-constant barrage of questions. From the perspective of our friends and family, the sudden transformation that my wife and I experienced made little sense. One moment I was an overworked business owner with failing health, the next we were bouncing around the globe on a permanent vacation. Everyone wants to know how I did it, so here it is; this is the story of how I went from hospital bed to hammock in eight weeks.

The adventure begins…

I sit, in a daze, listening to the monotone voice of a man who has repeated himself one too many times. “In the unlikely event of a loss of cabin pressure, oxygen masks will drop from the panel above you.” I peer at the overhead panel, wondering if any other emergency might warrant the use of oxygen masks.

We’ve sold almost all of our possessions, said good-bye to our friends and family, and bought a one-way ticket to Bali. My wife grips my hand nervously as the enormous aircraft meanders its way towards the runway. We are both wondering the same thing: “What the hell are we thinking?” The next couple of years will be far from ordinary: Indonesia, India, Vietnam, Thailand, Cambodia, Malaysia, the Philippines, the UK, and then, who knows?

This new way of life will be quite an adjustment. It has, after all, been just a few months since I spent the bulk of my time working like a crazy person and looking forward to my weekly panic attack. From my seat on Flight SA316, this 10-year period feels like little more than a bad dream. Who would have thought that I, of all people, could achieve such a dramatic change so quickly?

The hospital bed…

I don’t believe people are looking for the meaning of life as much as they are looking for the experience of being alive.
Joseph Campbell, The Hero’s Journey

I grew up in an entrepreneurial family and started my first business at the age of 13. By the time I was 25, my companies were serving major corporations around the world. If you’ve ever worked with a listed corporate, you’ll know that it’s about as fun as getting a colonoscopy. Around this time, a particularly unpleasant “panic attack” put me in the hospital, and the ominous warnings from my doctor forced me to have my mid-life crisis a little earlier than most.

The world is overflowing with beauty, wonder, and adventure. There is more to experience than anyone could hope to fit into a single lifetime. Yet there I was, trading the best years of my life for a paycheck. As I considered my predicament with my new perspective, everything came into sharp focus. Something needed to change.

The first step was obvious. We needed a clear picture of the life that we wanted to live. So, my wife and I sat down and started to list everything that we wanted to do, see, learn, and give. Several weeks later, we completed the first draft of our bucket list, which has since become the central theme of this blog. List in hand, we lacked just one thing: a vehicle that would finance it.

The eight weeks…

The path to success is to take massive, determined action.
Tony Robbins, Awaken the Giant Within

In short, we wanted to become full-time global adventurers. To the man on the street, this is an outrageously unrealistic goal and, at the time, I didn’t even know if it was possible. So, I decided to look for someone who had already achieved what I dubbed the “professional vagabond” lifestyle.

Suffice it to say, I was shocked to find not just one or two individuals, but an entire professional vagabond sub-culture; a group that Tim Ferriss calls the “New Rich.” Within a week, I had identified almost 100 perpetual travelers and, as I continued to dig, found that the vast majority of them had achieved income automation through ecommerce.

Online business, I decided, would be my vehicle.

At the time, I didn’t have a fortune to invest. So, together with a partner, we went to the drawing board. We wanted to find an easy way to start an online business without risking much time or money. We studied various strategies and deconstructed existing online businesses. Slowly but surely, we put together a simple action plan.

Our plan had two primary components:

1. The traditional approach is to buy low and sell high. We were going to flip this on its head by selling high and then, using the income from the sale, buying low.

2. Rather than creating a traditional online store, we were going to create a string of offers that would appeal to customers at different points in their journey with us.

It took less than a week to set up our proof-of-concept business: a website that sold cycling safety products. When we were satisfied with the site, we posted a couple of ads on Facebook and paid for them to appear in front of potential customers.

The hammock…

Money isn’t the goal; money has no value. The value comes from the dreams money helps achieve.
Robert Kiyosaki, Rich Dad, Poor Dad

While there was a bit of additional cleverness to our marketing, product selection, supplier relationship, etc. the process itself was really quite straightforward:

1. We organised our products into a sequence based on their selling price.

2. We presented the offers to cyclists, in sequence, using social media ads.

3. When cyclists clicked on the ad, they were redirected to our website.

4. On average, 8 percent of these people made a purchase.

5. When the order was placed, our supplier was automatically notified and the product was shipped directly to the customer.

The magic was in the type of the offers that we selected, the order in which they were presented, and our approach to fulfilment. We had no staff, no warehouse, no stock, and almost no overheads. The results were modest but, at the time, hard to believe. Within six weeks, our new business went from a cold start to $1 000 per day!

I was utterly gobsmacked. During this period, I nearly developed carpal tunnel syndrome by repeatedly clicking the refresh button on my PayPal account. In the years since, I have learned a thing or two about marketing and managed to achieve far greater results, but I will never forget the excitement of those first few weeks.

Just do it!

Conditions are never perfect. “Someday” is a disease that will take your dreams to the grave with you. If it’s important to you and you want to do it “eventually,” just do it…
Tim Ferriss, The 4-Hour Workweek

The world is changing. So often, we cling to the safety and familiarity of the 9 – 5 and end up trading the best years of our lives for a paycheck. These days, a day job is optional, and it takes little more than a firm decision and a bit of insight to leave it behind.

I am convinced that anyone can achieve my results if they copy the steps that I took to reach them. That’s why, after years of full-time adventure, I have finally produced a step-by-step “Vagabond Business Case Study” to show others how to replicate my success.

If you’d like to take action and set up an automated online business of your own, click here to download the case study.