Today, I start my 26th job in my career. It’s been a long, interesting road, and I’m sure I have some fun discoveries yet to come … plus a hope or two (but we’ll leave those as surprises).
I’m only counting paid positions, here. I’ve got a lot of volunteer things over the years amongst my day-to-day jobs. But that’s probably another post…
Strawberry picker (Herridge’s)
Herridge’s was a market on Southdown Road in Mississauga, next to the Petro-Canada refinery (yeah, I know, strange place for a market), owned and operated by the Herridge family for years. Somehow, and I think my mom was the one who arranged it, my friend Neil and I were hired to pick strawberries in a field Herridge’s ran at the corner of Winston Churchill Drive and Lakeshore Road.
We barely lasted a day.
I look back on that experience and realize just how privileged I was growing up. It’s literally back-breaking work – strawberries grow on the ground, not vines, and the fruits are too soft to use machines. We left because it was boring and hard. I think I was 12. But I’ve never forgotten that one day.
General Labourer (T&T Diesel)
My dad took me to work. At the time, he was a General Manager at Truck & Tractor Diesel (T&T Diesel), a subsidiary of Truck & Tractor, an equipment reseller where my dad had been working for years selling John Deere machines. The T&T Diesel division built generator sets from large diesel engines married to alternators atop custom steel frames.
I swept floors. Moved things around with the forklift. Sorted nuts and bolts. Built my boss (Richard) an office (with help, obviously – I was not a skilled carpenter then, nor am I now). I got dirty a lot.
But I earned enough for my first stereo, which I used for years.
Salesperson (Black’s Camera)
My mom announced that Black’s at Trafalgar Village was hiring and that I should apply. I think I got the job only because I knew that ISO and ASA were the same thing, and how to use specific speeds for certain lighting conditions.
Anne was my manager, a lovely woman from Hamilton who was happy to bend the (rather thick) official rule book to keep the store running well. I was the youngest amongst the eight(?) of us, the rest were either at Sheridan College or otherwise working full-time.
This is where I learned Monty Python.
Trafalgar Village was a “death mall”. It’s only claim to success was being across from the GO Train station. Otherwise, it was painfully quiet. We would fill Fujifilm canisters (not Kodak, the lids didn’t click in place) with lens cleaner (which was liquid when held upside down), close the lids, and chuck the canister down the otherwise empty hallway and wait for the BOOM.
When Anne went to the Black’s in Jackson Square in Hamilton, the Assistant Manager from the Hopedale Mall location got promoted. He used the rule book as a bible. I think half the staff quit in the first month.
Computer Technician (Ark Technologies)
I took Co-op education in high school. My placement was at a computer store in town that I’d been going to, in hopes of getting actual colour on the computer we had at home. (Spoiler alert: you can’t get colour on an IBM 5150.) I’d been there so many times that I barely got an interview – they just hired me.
Co-op allowed for 140 hours. After that, they had to pay me. (Yes, co-op was free labour. It was all about the experience.) And they happily hired me, and I phoned in my resignation to the asshole running the Black’s at Trafalgar Village.
Rob and his father-in-law were the ones I saw most days. I learned about IRQs, how to format RLL and MFM hard drives, and accidentally wrecked the first IDE drive because I didn’t know it didn’t need formatting. But I was good at what I did. It hurt to quit when I went to university.
End User Services Support (Digital Equipment of Canada)
I continued Co-op in university. Four of my six terms were with Digital Equipment of Canada, working in their Kanata office, west of Ottawa. It was the first time I lived somewhere on my own, renting a room I had to find, food I had to buy.
I was the co-op student running the End User Services support queue. I was part technician, phone support, programmer. And I accidentally crashed the company mail servers when I was trying to pester my co-worker about stealing my monitor. My boss, conveniently also named Geoff, actually had to hide his laughter when he gave me hell for it.
This is where I cut my teeth on support: how it should be done, how to cut corners effectively, and get people back to happy again. And I learned that ethernet loops have a maximum length before the signal drops out.
Computer Technician (PC Factory)
Although Digital paid me well, I decided to do a full year at school to catch up on my marks, after switching from Math (Computer Science) to Arts (English Rhetoric and Professional Writing). And money got a bit tight.
One other lesson I learned in co-op: budgeting. But budgeting only got you so far when you weren’t swapping every four months to more income.
I got the job because apparently I was the only one the manager interviewed who knew how to deal with IRQ interrupt conflicts. And that got me in the back of the shop dealing with all the weird shit that people had to deal with (a fair few of them, students).
Richard and Rob were the two guys I worked with the most. Richard was the manager, a hardened geek who was easy to get along with. Rob was a sales guy.
Technical Writer (Oasis Technology)
My fifth co-op term was writing user manuals for a company that wrote financial transaction software. It was my first exposure to high-performance, high-availability software.
My manager, whose name I can’t recall, was a little Asian woman who edited with a thick red marker. I earned my ability to take criticism from her – none of it was personal, it was just business.
(I also worked with a sales guy named Storm Morgan, swear to the gods.)
Web Consultant (1996 - present)
About the time I was working at Oasis, the world wide web was becoming prominent. I’d already done several assignments and personal websites in HTML, and I sold myself into building a website for a nearby company called the Movie Poster Warehouse.
And that became a pattern: I would pick up companies here and there, doing their websites. Other companies included McKinley Masters and organizations like the Westgate Spanish Parents Association.
I still do this work, when needed, though I admit I don’t have the same passion for it now as when I was younger.
Technical Writer (Xerox Canada)
My last co-op term was a dud. I was going to be an internet instructor, but we got conned into working at a coffee shop. The university terminated the deal and I found myself looking for work. Somehow, and I literally cannot remember how, I ended up working with Xerox doing RFPs and other documentation. It was short term, only a couple of months, but it was higher pay that I’d received for other jobs.
And then I was out of work, again…
Technical Writer / Web Developer (Arkipelago)
My buddy Gerry had taken a job at a small company in downtown Toronto, originally for architecture, though the company started making software. They needed someone two write the manual.
The boss there was an asshole. One moment, he was your friend; the next, he was screaming at how bad an employee you were.
I met Brenda and Marek there, and I still count them as friends to this day. Brenda, in particular, would later give me the single greatest experience of my life.
Technical Writer (Prologic Corp)
I left Ontario at the beginning of 1998, moving to Vancouver. I had no apartment, no job. But my significant other at the time arranged for me to help at her company, Prologic. They wrote financial software, though I can’t quite recall exactly what it did. I was only there a couple of months.
But it let me get settled, prepared for the job that I still hold dear in my heart…
Technical Writer / Vendor Relations Manager (Radical Entertainment)
I worked for a video game company. I got paid to play.
Okay, it wasn’t all sunshine and lollipops. It was were I faced my first layoff. It scared the hell out of me. I survived it, though one on our team was let go, something that to this day, I still don’t believe. All I did was write the manuals – these guys wrote the libraries that made the games three-dimensional.
To this day, they are the most brilliant and talented programmers I have ever worked with. Even with all the things I’ve seen since, I still stand in awe.
Several of those people are still friends, and I’m very thankful for knowing them.
Web Developer / Sr. Web Developer / Development Manager / Technical Director (Critical Mass)
I had to leave Vancouver. I had to leave a job I loved. I ended up in Calgary mostly as I’d run out of country to the west, and I had family and friends in Alberta’s largest city.
I landed an entry-level job with a very hungry little agency that was doing work for Proctor & Gamble, Smirnoff, Denny’s, Nike, and Mercedes-Benz USA, the latter of which I would work on for almost five years.
It was a sweat shop. We worked hard, long hours. But I was recognized for my work and abilities, and promoted. And when I was stupid enough to speak my mind about how they should be hiring leadership in our department, they told me to put up or shut up, and I became a manager.
This is where I started to learn how to be a manager. Emphasis on start. I had no idea how deep that pool was going to go, nor was I prepared in any way to shoulder the burden of running a large team who all looked to me for direction. I learned very quickly that honesty (learning to say “I don’t know”) and confidence (following up with “but we will figure it out”) was going to be critical. I was with Critical Mass for a decade, and it was easily the most education I ever received in business.
Digital Specialist (Canadian Broadcasting Corporation)
But before I slipped into management, I got a strange email from my friend Brenda (remember her?). She was saddled with figuring out how her group was going to support CBC Television’s 50th anniversary. And the CBC had decided to put their museum on a VIA Rail train and run it coast-to-coast for 3 months. She needed someone who could do technical support, run the computers, deal with blog posts and photography (and originally video, too), and who the hell could she find who want would to do all of that, living on a train?!
Gee, I wonder.
Yes, I got married since, I had kids. I moved to another country. This? Still the best experience of my life. Although it ended up being a little over a month and a half, the sheer insanity and rush and intimately close camaraderie amongst the group was something I’ve never experienced since. I still look very fondly back on the two months (late August to mid-October of 2002).
Returning to Critical Mass after that was interesting…
Technical Director (Critical Mass, Costa Rica)
Critical Mass’s advantage over other companies was that we were Canadian, based in Calgary. And in the early 2000’s, that was a huge advantage. Then Calgary started to get expensive and at the same time, the digital marketing industry was pinching pennies from all angles. The best option? Go offshore.
In mid-2008, three of us went to Costa Rica. Day 1 was in a borrowed space, a former post office, with stolen wifi, one cell phone to make calls, and an air conditioner that created a small lake in the middle of the bare concrete floor by mid-afternoon. We had to hire everyone, find a permanent location (which itself needed construction), buy all the software and hardware, get the networking set up, and we had to deal with things like ongoing brownouts from the wonky electrical grid and earthquakes (a 6.4 that nearly shattered our front windows).
People said I would be on the beach every day. We were three hours away by car (which we also had to buy). It was an experience I greatly appreciate having, and I never felt better than when I returned to Canada.
I was fired three days after landing.
Solutions Architect (Evans Hunt, contract)
Barely 20 seconds after being fired, I was set up to hang out with Evans Hunt, mostly Critical Mass ex-pats. My project was to help them set up a new website for Tourism Calgary. After a couple of years of doing almost pure management, diving back into programming was a bit of a slog.
It was like stepping back into family. These are people I knew, trusted. There was no onboarding, it was “get going”.
But it was only a contract, and most contracts end.
Web Developer (Pitch Digital, contract)
A small two-person company that did small work. Which was fine. It wasn’t really what I wanted to do, but bills have to be paid. You do what you have to do.
Solutions Lead (Evans Hunt)
I got a call from Bill: full-time, leading work, get training, etc. I was happy to have the benefits, the stability.
One catch with running a company of mostly senior people, though: Career growth? Nearly none. This was almost coasting: continual, understandable work. The challenges were in the quirks of the individual projects. Met a few new people, brought in a few of the old gang.
At this point in my life, I was unable to balance work and home. Alex was working evenings, I had to manage the kids in the morning and in the evenings. And I was working 12-16 hour days.
I burned out. Exploded, really. I learned that my support network wasn’t remotely as present as I’d hoped.
Web Developer (University of Calgary, contract)
Bill arranged a meeting with the University of Calgary, who was looking to rebuild their ancient web platform. My interview was a room with eight people. I was shitting my pants: I felt zero confidence from burning out, I was on heavy anti-depressants, and I knew no-one.
But, somehow, I got the job. I found confidence.
Manager, Web Services (University of Calgary)
And then I got hired full-time to run the Web Services team, which I was already working with as a result of the contract. And for the first time in years, I grew … and fast.
ITIL, union management, security and CVE triage, higher education, CI/CD, Docker/Kubernetes, automated testing, and politics. Holy cow, the politics. It was the politics in the end that drove me out. There were things I felt needed doing a certain way to benefit the long-term operations, but my many years of experience were poo-poo’d in favour of kissing up to a group of back-stabbing executives.
I know it sounds dramatic, but I had never run into that level of politics before. And I discovered I didn’t like it.
My way of managing it was through Duane. He was the Project Manager for the project, I was the Technology Manager. You’d think we would be at odds with each other … and we were. But we found in each other significant trust. It was the start of a beautiful friendship.
Manager, Information Systems (Travel Alberta)
Duane recruited me for the role. It was 60 people in total. I ran IT with a contracted services company for general support. And we quickly dug a hole when I started auditing all the services, because I had to pay for a lot of them, and I wanted to know what it was all being used for.
We turned over too many rocks and very quickly gained a bad name, because we dared make things clear and auditable. And that was because at the University, I knew that the annual Office of the Auditor General audit was often dreaded. And this time, I was the OAG’s target.
And lucky me, they targeted us as the first ever cloud service audit. Everything I tried to address came to fruition. I didn’t have to say “I told you so”, everyone knew I had predicted it.
The politics, again, ended up doing me in. How a group of only 60 people can be that toxic amazes (depresses) me. They laid Duane off (and then my manager, who helped make that decision, yelled at me, bizarrely). In the midst of COVID, I pulled the plug.
Manager, Service and Support Platforms (Shaw Communications)
Duane’s sister set me up for this position. The manager, Navid, originally looked at me for a different role, but felt this was a better alignment, given what I’d done. To a point, I didn’t care, because I was rather desperate to get out of a hole.
I learned more about legacy in the span of 13 months than I could have gleaned from any course. Telecommunications companies have massive limitations about what they can do – they’re regulated, and making one bad change can knock out thousands of their customers.
Thankfully, I was arms-length from the critical stuff, dealing mostly with the self-service portals and knowledgebases. It wasn’t riveting. In fact, it was easily the most boring job I’d had to that point: everything was planned far in advance, and I wasn’t involved in any of it. I … managed.
So when I got a call from Adam, an old colleague from my early days with Critical Mass, I listened.
Head of Technology (Venture Communications)
Rebuild the digital team. That was a challenge I liked. Reestablish the service, build up the practice, sell to clients. Stuff I knew, and knew well.
It was a challenge complicated with the fact that I wasn’t really able to move the levers I wanted. Sales was handled outside of my space, I couldn’t easily insert myself into practices, and not having client contact made upselling a lot more difficult.
A few months in, though, I got a call that only made those early days seem like a walk in the park.
Vice President, Technology (Believeco/ChangeMakers)
Venture merged with five other companies. Not acquired, merged.
The company went from ~50 to 350 overnight. We had tentative leaders, and massive in-fighting on the board. (There still a lawsuit outstanding amongst the various founders/shareholders.) I was tapped along with another to lead the Digital team. We decided how things needed to be done, set up the team, and got to work.
I still think the team was well-run. And I say that having taken a step back from the leadership, allowing my now-manager to deal with the business whilst I dealt with the technology.
But we couldn’t control the business, which was poorly led from the very beginning. I need an entire blog post to describe how all of this ended up going south.
Suffice to say, it didn’t end well for me. Twenty-eight years after the fear of being laid off for the first time, and numerous layoffs since, I finally succumbed.
Sr. Technical Consultant (MNP, contract)
Duane came to my rescue. He needed someone technical to help out with a project. It was that simple. I was thankful to have something to supplement our financial situation, which had suddenly imploded.
Although I was a contractor, I did some technical leadership, some mentorship, and helped with a few ideas with Duane’s manager.
All the while, I had to keep looking for a new job. And that was proving a lot harder than I’d feared. The market is flooded with people who are a lot younger than me. I had two interviews, only one in-person. Neither went anywhere. Of all the applications I put in, most went unanswered.
One advantage of being regularly present, though: visibility. And that led to a moment that I am highly thankful for: an offer.
Sr. Manager, Rapid Innovation & Development (MNP)
Welcome to job #26. I don’t have much to say about it, obviously, since it’s Day 1 (and I’m still helping Duane on his team for the short-term). But based on all the conversations I’ve had, this should be a fun challenge.