A Winding Career Path

Like many people I meet professionally, I did not come to my career in a straight line. My path wound through the arts, bureaucracy, customer service and more before becoming the 2016 version of myself. I also meet people considering the jump to a new career, people who feel under-qualified and are more comfortable on the outside looking in, and I think it helps to remind them (and ourselves) that there’s not many of us that got where we are by following a straight and narrow path.

First Jobs

As my first job, I was handed my sibling’s long-running paper route, getting a dime or so for each paper I delivered to a neighbourhood not far from my own. I was maybe eight or so when it became my sole responsibility, and I’ve had employment of one form or another, more or less uninterrupted, for the rest of my life.

Jobs after the paper route included little league umpire, cashier, sandwich artist, coffee slinger, and an office job where I scanned product photos into a digital database distributed by CD. But the first job I considered career-adjacent came in high school when I operated a followspot for a local theatre.

I’d fallen in with the drama department at my high school, and they had a decent budget, somehow. We had lots of professional grade equipment (especially the lighting systems, tens of thousands of dollars of stuff). So I was learning a trade in school, and was happy to start getting paid for it. I helped a touring show, a few local theatre companies, and was sure I was on a straight path to my lifelong career. So I applied to university to get a theatre degree.


Well, I made a slight concession. I actually applied to become a drama teacher – that was safer. In case I couldn’t cut it as a lifelong member of the theatre scene, I’d settle on teaching high school students all about theatre – it felt like a safe way to hedge my bets at the time. As a side effect of paying to learn about theatre, I took more jobs in front of customers – food service, waiter, the hotel industry. I found that I wasn’t a natural at customer service, but I was good at it nonetheless, spillover confidence from drama classes.

After a few years, I wanted to put my career back on track, so I started a local theatre company. I worked the graveyard shift full-time at a hotel, slept until I missed half of my classes for the day, showed up for the rest, then spent the rest of the night researching, producing, directing, marketing, rehearsing or acting in whatever show was next on the slate. We put on some established Canadiana theatre, a handful of original scripts, registered as a non-profit, set up a board of directors, and started on the process of becoming a charity – the holy grail for arts organizations, giving you access to all sorts of funding options.

Then my father died.

So Now What

I had finished school, received my degree, and started working my way up the ladder in the hotel industry. But after my father died, I took a hard look at what I was doing with my life.

I decided that there was no money to be made as a starving artist, so I gave up the theatre company and let it dissolve. I knew I couldn’t get much further in the hotel industry without actually owning a hotel, so I left that behind. I gave my resume to a bunch of temp agencies, and resigned myself to join a boring office life.

I bounced around in a few companies, doing basic bookkeeping or database entires, before landing at a company called Newalta. I proved myself valuable enough to transition from temp to full time employee, and took advantage of their education stipends to take some accounting courses. Accounting would be how I could find a place in an office setting for the rest of my life… right? But my heart was never in it, and I procrastinated continually, only finishing because otherwise I’d have to pay Newalta back. I found myself with hours and hours of down time (accounting is very busy around the end of the month, and not so much otherwise), so I had time to pursue some hobbies during work hours.

Finding Coding

I made a choose-your-own-adventure game while at work, inside an Excel spreadsheet. I’d always liked the idea of making my own video games, but considered myself incapable of doing it. This was a nice compromise; I could write the script for a video game, do some basic logic in Excel, and in the end, have made a ‘game’.

That was enough success for me to believe in myself, and so when an idea for a video game came to me one day, I decided that I was competent enough to make it myself.

Coding over lunches and evenings, learning how to code during work hours, and partnering with a good friend, I released TumbleBall after a year of work. At some point in that year, I decided that accounting wasn’t for me – coding a game was way more fun.

I enrolled in a two year program that promised to teach a little code and a lot of design, absorbed everything that was taught, and found myself far more engaged and interested than I ever was learning about theatre or accounting. I picked up contract work making mp3 players for websites, digital maps, e-learning modules and other weird one-off projects, making actual money for creative work that I coded myself. It was hugely liberating.

To Digital Signage

My employer sought me out. My LinkedIn profile had enough of the qualities they were looking for to bring me in to meet. I learned about a new product, ‘Clickspace TV’, which promised a way to get digital posters onto the TVs in bars – but with the cool feature of editable text, so you could change the price or the special on the fly. I was skeptical, but appreciative of the opportunity, so I took the job as a Flash developer.

Four years later (and counting), I’m still learning more about code, digital signage and new technologies. I’m back to making a game, in addition to making or maintaining websites, servers, ads, social media feeds, or whatever is on the docket for the day. I go to conferences in tech, design, and digital signage, all of which speak to me and get me running in new directions with my job and my career.

The Result of the Winding Path

There are some straight-forward connections from my past to my current career; coders and accountants both work with databases, I’m comfortable with clients from years of customer service roles, that sort of thing. But the connections that actually propel me in my career are the ones that are harder to see.

Accounting taught me lessons that influence how I write software; I have a deep understanding of the importance of record keeping, legible code, version control, data gathering, and more. In those jobs I learned that creating a tool to make my job easier and faster was incredibly rewarding, helpful, and freed up my time to create more tools.

For a long time, I assumed that the various customer service industry jobs I’ve taken didn’t amount to much. But the hospitality industry makes up my current client base, and I understand their needs, their schedules, and their priorities naturally. I can deliver the solutions that they need, before they know they need it themselves.

Getting a theatre degree was the most useless thing I ever did – or at least that’s what I thought for the first two years after graduating. The benefits were harder to find, but over time I realized what power it had given me. Making theatre involves a collaborative effort with a hard deadline, so each show is like a tiny business, dissolving in a few months and onto the next. I was involved in some way in over a hundred productions, wearing dozens of hats, some creative, some bureaucratic, some a mixture of both. I proved time and time again that I can team up with a brand new mix of people and deliver on whatever was needed of me. That experience has opened so many doors to me, and faced with new projects now, I can always see a way through to get it done.

There’s more, of course – I use weird and random snippets of my past every day. But it’s not important, because it all adds up to the same thing.

If I would have come to my career in any other way, I wouldn’t be as good at it. I wouldn’t trade my winding path for anything.

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