My Digital Nomad Origin Story

As I write to you now, it’s 2017. Back in 2012 I started a blog on Tumblr called “A Travlr, Darkly”.

I wrote two posts, and then lost my login information and I’ve never been able to log in again. Normally I’m pretty good with this sort of stuff, but now these two parts are drifting around on the web and I can’t touch them.

These are the first of any form of casual writing I’d done in years, and not to be done again until earlier this year when I started playing with words again. In other words, I was a little rusty.

Had I kept up “Travlr, Darkly” there’d be no Hobo with a Laptop. Which name do you think sounds better?

So here they are, a little over five or six years since they were originally written.

Before I became a digital nomad I worked for a leading web development firm in Toronto. This is the story of how that ended, and what was going through my mind when I made the decision to formally go nomad.

Part 1: Caught on Bliss

12 January 2012

365 days in a year, and I work all of them to some extent. In any given 365 days —I’m likely to push through $200k – $300k in website projects for one bespoke web development company; partake in 45 networking events; 2,000 clammy handshakes; 1,800 cups of coffee; date approximately 7 girls 2 of which become somewhat intense however in the end unfulfilling; relocate 3 times; hit my snooze button approximately 3,000 times and make just enough money to save exactly $0.

On this particular morning I woke up alone. I didn’t hit snooze once.

I woke up at 3AM and had been staring at the ceiling until 6am before I’d decided to go into work early. I didn’t think about much other than what I’d like to do if I finally had the nerve to quit my job, which I’d been fantasizing about since December.

The feeling lingering between me and the ceiling was hard to articulate, though you could cut it with a knife. It’s almost a non-feeling. Not a numbness, but an exclusion of bliss. Everything’s fine. Work is going well, my girlfriend keeps me hopeful, I’m working out again, and I’m on track. I’m doing a little more than getting by, and I lead a very social lifestyle. I think I’m happy and I always smile on cue without thinking.

I got out of bed and made my way into the kitchen, readied my Bodum and I put the kettle on. From there I had a shower, and then on to my closet to put on some clothes.

And then it came as suddenly as an aneurism, this lasting unanchored perspective had snapped into frame. I was finally able to grasp the significance of this chapter in my life as I stood before my lone, well-worn suit, hanging limp in the closet.

A suit I had wondered for one moment too long, whether it would be the very suit my parents would bury me in. I suppose it came from the feeling that I’d arrived at some plateau.

A boring monotonous one where nothing was too hard, too easy, and each day was another spin in the loop that life had become. I was interested in bigger things, but I was condemned to an occupation that Bill Hicks would take apart as passionately as he would a Marketing Executive; a Salesman.

Salesmen get treated like tax collectors no matter how nice everyone is, and it’s hard to tell an honest one from a shark because of the etiquette. I get treated like a shark. I could offer someone free cancer therapy and they’d be reluctant because my business card says “Business Development”. I hated that part of my job the most. Every chance encounter or pleasant discussion was perceived to be motivated by a sale or a referral once they got around to asking about what I do.

I got dressed and changed it up. I traded the suit for jeans and a button up shirt, chalking it up as a bad omen. I missed my bus, and later arrived at the work entrance the same time my boss did. Weird, because even when I’m late, I’m always early. We were the only two people in the entire office.

An awkward hello turned into him hunched grimly at an empty desk across from me, watching me prepare for my week. No conversation just half eye contact and deliberation. I backed up my contacts and closed my laptop. This is it.

I turned to face him. “Let’s talk, what’s on your mind?”.

My boss doesn’t know I’ve spent any available free time over the last 3 months dreaming up an escape plan.

He also doesn’t know I was waiting to find the right time to quit copacetically, as to not lose any banked commissions and have enough time to maneuver the hit to my income.

I didn’t realize how ill prepared I really am, and I certainly couldn’t spend the cycles thinking about it at the time.

I knew what came next, I’d already read the script on his eyes which were now fixed squarely on me.

He worked through his monologue nervously, which eventually resulted in my layoff. Brilliant. Spreadsheet says cuts need to be made. Call it a seniority argument, or pin it to the fact that he was being admirable as I was the only one without little mouths to feed. I’d feel better with the latter if I gave a fuck. He just laid off his newest rep with the highest yield the last fiscal year (other than management with fruitful relationships older than I am). I trump it up in my mind so it feels like it hurt him more than it hurt me.

I was outta’ there. No escort needed, and I practically laid myself off. I still casually had a coffee before clearing out my desk, said good morning to the usual lot, and was out before the guys on my floor got in.

That blissless feeling? Gone. Forced to reanimate, give my head a shake and make good on the promises I made myself. This new development meant freedom to set my own rules, and work how, where, and with whom I wanted to. I could feel it in my bones. This was not a mistake. This was a gut-confirmed fabrication of destiny —and she slapped me right in the face like any good lover would do when their sweetheart has become stagnant.

I felt that bliss I’d been missing for about an hour before I called my dealer and hit the liquor store. Where do I even begin to know where to take this?

Part 2: I’ll Be There.

2 Feb 2012

I planted the seed years ago. I once maintained a web log at age 18 around the time Google acquired Blogger. It was my first time living away from home, living on my own in Calgary, Alberta. I had obsessed over words and PSD files listening to early Sigur Ros until the early morning hours, sharing them online as a way to cope with being alone.

A feeling akin to one I’m burning tonight. In the early days of teaching myself how to use Photoshop, I remember one design experiment in the midst of long shifts and overtime, drenched in cut-out filters and typography containing the words “Sleep is for the homeless” and “You can never go home”.

Back then the cut-out filter was hot shit, and I was an innovator.

Ok, not really; it was the Instagram of yesteryear and I was a know-nothing —but it started my self-education in design and it was a thrilling period of self-exploration so I have no regrets.

The statements in that design were a teenage-angst-driven parody of consumer culture fueled by Postal Service and Boards of Canada. They were prophetic to me and reflected a lifestyle to which I’d become more familiar with in the years to follow.

Simply put; I figured the life that lay ahead was built on work for the sake of work, and I wanted none of it.

I thought that the only way to get any sense of inner peace was to be miserable by the very means to which it was acquired.

With only a small taste of independence at the age of 18, I knew two things for certain: Homelessness would suck, and don’t fall off the damned hamster wheel. It frustrated the hell out of me, and although I was creative about making ends meet, I had no idea what was truly possible with little effort.

Today, I view “homelessness” as a freedom and personal responsibility I think I can handle.

I know it now by other names such as “digital nomad” “homefulness” or “location independent”. Much less self-deprecating as it rolls off the tongue, however neither offer additional comfort to a worrisome mother.

Before I came to the occupation from which I was just relieved of, I took pride in making my numbers from verandas, cafes, parks, and locales out of town. I’d always felt a sense of privilege with this ability, as so many I’ve discussed my regime with have also had trouble adjusting to the concept, or saw a decline in productivity if they’d try to follow suit.

I found tools to make it easier to automate my presence and duties, to the point where people didn’t know when I’d fled town to make time for my personal relationships and taken a day off.

I’d been reading 4 Hour Work Week sporadically since before my layoff and I had just finished it. I’d say the most rewarding quality of this book is the absolute unwavering confirmation that my desires are not those of an insane person. I strongly suggest you pick it up if you are looking for the same flavor of vindication.

As much as it has renewed my sense of self and sanity in spite of what I now consider misunderstood choices, it has also illuminated where I’ve grown stagnant. After honest consideration of many factors that shape my life, I’ve begun cleaning house. It’s funny how right the poets are and how the things you enjoy about something initially become what breaks down later.

And so the purge began.

What started with losing my job evolved into giving my roommate notice, picking up my first passport, breaking up with my (gorgeous and inspiring) career focused girlfriend, selling everything I own, and creating a set of well-defined goals. In that order.

However, at this point, the only people drinking this location independent lifestyle Kool-Aid in my circles are the ones working every night with me to engineer our first attempt at creating a passive income.

This is probably the most volatile component of my now realized strategy, and I’m banking everything on it.

I feel like a kid again; an open book with everything to gain. On the other side of the coin I’ve developed a deeper respect for failure, and I’m crossing my fingers and toes this first shot at a passive income has legs.

The need for change was insatiable, I couldn’t bare it any longer.

This an excerpt from Digital Nomad Escape Plan: From Cubicle to Chiang Mai, Thailand. Download it today, and keep it for later.

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    1. It’s so true; at the end of the day, most of our stories all wind up being so similar. All part of a bigger shift!

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