The Best Decision I Ever Made Was Barely My Own

And why I’d strive for that magic again.

In 2012 I took a working holiday on the underside of the world that changed the course of my life. I met a girl, got focused, and learned to balance who I was with what I wanted to be.

I got this shot because a stranger told me I’d figure out my life in Australia.

“Never, never shall I forget those days of travelling before we reached the posada. Unforgettable days and nights when it was our hearts that sang after we were too tired to speak our happiness.” —Banco, Henri Charrière

In the fall of 2011 I moved back home after yet another summer of painting, a diploma in business administration to my name. Much to the dismay of every parent of a wheel-spinner, I’d opted to finish my stint at business school with the amicable (albeit less concrete) diploma in General Business Management. This decision was not made in haste, I’d done just fine in those 2 years working in teams, grazing across the topics and jargon of the business world, and had only to choose my area of specialization to complete the BBA. Choose now; Accounting, HR Management and Leadership, or Marketing. I’d taken 200 level courses in these disciplines, and it dawned on me that making this choice would lead me into the business of business. But what of my dreams?

Before moving to Vancouver Island (when I started spinning my wheels) I’d taken up painting as College Pro Painter. An acquaintance (now friend, I MC’d his wedding) was a fresh-faced franchisee of the amateur painting outfit that gives real entrepreneurship experience to university students, and he staffed up with myself and a couple other students who had never painted. Over the course of two summers I’d seen his excitement turn to disappointment and stress, a hard earned lesson that ended in bankruptcy and an early end to the summers painting. I took a few things from this;

A lesson — Be a friend and be the boss, but do both distinctly.

A trade — Painting was a blast and gave me the confidence to blast holes in apartment walls without fear of repercussion. It kept my summers full and my skills had clear value. Better skills, more valuable.

A mantra — Do something that you actually care about. That opportunity that seemed okay gets nasty quick when it keeps you from great stuff happening all around you. The ladder of priorities in this finite lifetime is greasy for inconsequential work.

Even though it had been many happy seasons painting, time and time again picking up the brush and cutting through the West Coast summers, I felt like I was on someone else’s path.

I had found that first summer job in Victoria on my own, and was buying whites shortly after the interview. The next summer my foreman called me up and told me our manager was putting together a crew at a new company. She was a blast to work with and we got on well, so I switched on autopilot and we had many good times and sunny days. The following summer that manager decided to start his own outfit and I was honored to be a part of that first crew. I realized then that I was on his path, taking the opportunities handed to me and letting the time burn away.

The relationship I had when I’d moved out that way was a few months behind me, my older brother had moved to the coast, and I was having an Eat Pray Love moment. I was riding my BMX more and spent my days like any dirtbag should hope, but with winter around the corner and money in short supply, I liquidated and moved back to my ancestral home, a city surrounded by the country, Calgary, AB.

My dad worked in the resources sector. He grew up in Fort Williams (now Thunder Bay) Ontario, in a small house, one of the few that has since been torn down. Growing up we never wanted for much; I was lucky to attend a private school with small class sizes that became a community, I had my own computer with a beastly CRT monitor (R.I.P. Compaq) and 256k internet to download pirated software to make unlicensed stickers and ski graphics with. Even though it meant waking up before the sun and early evenings, it served the humbling vision that his children were able to do what we set ourselves to.

What of the youngest though? The boy who years prior had uncorked some anticipation by embarking West to Business School, a departure from the other children and their Arts in the East? His last horse, planless mustang, painting away a college diploma while his friends sons took jobs in offices downtown, attending functions to fundraise, downpayences upon houses etc.. I’d talk about going back to school, this time to study Industrial Design! My mother was an interior designer by trade and an artist, and my dad was always a gear-guy, an affliction that I inherited. Designing products sounded fun. I was aware of the portfolio requirements for these universities but doing literally nothing about it as the deadline loomed.

One day in the same room I slept as a child my dad came to me and told me about a career councillor who had proven messiahic in shaping the play-dough life of his friends son, who, he reminded me, had attended the same school as I. As a resident freeloading under his roof I was more than happy to indulge, and that meeting put me in a position of entitlement such that is I feel it’s worth writing about it on Medium.

I’d driven myself to this home based business within the geopolitical bounds of my first College Pro Painting territory, where it all began. Blocks from my ex-girlfriends highschool and the Pita Stop we ate at and later painted, where I first discovered Halifax style sweet sauce (probably not the only reason I moved there this year). In this familiar neighbourhood I took on the familiar role of the guided. Some of the tests were similar to those my high-school Career and Life Management teacher had given us, but the all day affair dug deep. I was happy to learn of some redeeming entrepreneurial qualities, and while I can’t recall exactly what else I learned about myself that day I remember being struck by the hilarity of how excited this silvery expat seemed by the prospect of me. We had concluded that if I had REALLY wanted to go to design school, I would have been working on my portfolio pieces and not getting jazzed up and partying with my buds. The two were mutually exclusive in his opinion.

It was weird as heck, but both my parents drove down at the end of that meeting and we all sat down together. I was struck by how they had dressed. Those familiar with the matter might call it a modern interpretation of the outfits they wore to my first interview for a private school, letting their hopes hang in the choice of color and materials, wearing their expectations as accessories. He sat them down and told them the good news, that I was great and he was excited and that he didn’t think I needed to go to school but we had come up with a better plan — to go to Australia!

Being as it was, I had no other plans whatsoever, the idea of a gap year had never been raised before but now that it had it seemed like a pretty exciting prospect. The premise was that I’d go down there and get just any job and eventually I’d start hustling popsicles on Bondi Beach and work my way into the success you’d hope to see today. From what I understood, the uber-entrepreneur instincts at my core should take over and I’d just make it, from whence things shan’t be the same again. This plan was made for me, and I set about creating the ultimate packing list for my journey.

It was pretty well researched and I’d made some smart, safe bets like the Osprey Waypoint 65 travel pack, Ex Officio boxers, Tilley socks with a warranty, and a fresh pair of Clarks chukkas which I already owned one pair of. There were a few intentional lifestyle choices too — I bought a corkboard, which is a zip-zinger style cruiser cut skateboard with cork instead of griptape for sans shoe, and a full on woven hemp getup of cargo pants and a long sleeve shirt, convertible pants. I packed into cubes and filled miniscule Nalgene bottles with essentials (one small vial of Old Spice cologne I have kept to this day, frequently not finding any use for it)

Spec’ing things online has always been one of my favourite pass-times. I started with car configurators as a sort of gateway, then when I was getting way too serious about Paintball I would spec and photoshop custom ‘markers’. Some of my early design sketches are interpretations of custom milled and anodized blocks. Building dream bike build kits was constant, and when it came time to upgrade my brother and I’s PC, I reached right past the Dell and spec’d a custom build. It should go without saying that I found purpose in this packing list and I was excited by the possibilities my Amazon shopping cart suggested to me. But it all came crashing down a few weeks before my trip when I realized I was on Amazon.com and not Amazon.ca, and this was before they were even remotely on par. All of those sweet, significant tools to enable my adventure were now out of reach, and I decided to leave my Hennessey Hammock in Canada, for there was no adventure to be had without a CRKT multitool/spork keychain. I was forced to step out into the wilderness with next to nothing (spoiler: I overpacked)

I’ll spare you the minutia of the experience that I had in those 9 months on the bottom of the planet, but point out 3 significant outcomes.

1. I met my partner, a caring and hilaaaaarious woman that’s the only light I will need to pack with me when we move to the East Coast. With her, I’ve seen and done more than I had or would ever have imagined. To be closer to her I pursued an exchange semester in Basel and had the groundwork in German, enough to actually succeed and get something out of the opportunity while ordering exactly what I want in a bakery, usually. Six years later she has held up better than any other gear I got in Australia.
2. I decided against all premonition that I was serious about design school and found time to produce a foundation of sketchbook work that I brought home and digitized. These over-thought projects and concepts combined into a design portfolio that got me into a couple schools. Here something I created gave me the privilege of being able to CHOOSE the school I wanted to attend.
3. I learned what meaningful work meant. Ah, the callcenter in Brisbane, still among my favourite jobs. It was a privilege to speak to supporters of some of Australias most impactful charities, many remarking on my accent, updating them with the latest news and asking for their help once again. Left to envy was the company culture, late starts, freedom to sketch all day, take in literature’s greats and British tabloids worst. I loved every day of that job. The intrinsic reward and measurable impact on others lives was too hot to handle, and set a high bar.

So please believe, I’m glad the single most impactful choice in my life was made based on a suggestion from a stranger profiling me. I celebrate this decision fraught with uncertainty, how it led me onto a path full of what if’s and could be’s. Today I’m working in a field I find fascinating among really talented people. I’ve made a life with a partner I met by chance on a trip I never intended to take. The experiences that random choice led to have given me an unquenchable thirst for more. More than I can even imagine by myself.

Now, I seek out these opportunities to switch it up and check assumptions about where my life should be going. A few months ago, shortly after graduating from design school and starting work in a research lab, an instructor sent out a blast to the recent grads. Upon it I *click click clicked*. What might be if I applied for the fellowship this stranger wished more designers would go the route of? Who could know? When I got an invitation to take part in that fellowship I had two days to commit to moving my life across the expanse of Canada from coast to coast. Gone away from the mountains I love and the gear-centric industry I’ve been trying to break into. Away from the network I’ve worked to network with, wasted name tags. Two days to forsake all that had become comfortable.

So obviously, with my partners blessing, I decided to take that chance. I like to think the decision was made for me.

And what of the lost souls I’ve encountered since that trip, or the ones who have their lives all planned out? What do I tell them?

“You should go to Australia on a working holiday!”

Thanks for reading! If you’ve ever just let good things happen, let me know on Twitter. Follow me to hear more about my next ‘go-with-the-flow’ leap — moving across Canada to try something new.