002. Entering the workforce

Jason Dorn
5 min readSep 7, 2021

My entry into the working world meant packing the contents of my bedroom into the back of my dad’s truck, and trekking 1,200km west to the bustling city of Calgary, Alberta.

Now school had giving me many of the technical skills I required, I could code basic HTML/CSS, I could mock up an UI in photoshop, I could edit photos and produce assorted fragments of design and graphics. But I was sorely lacking in what some may call the “soft skills” of design.

I couldn’t talk about design.

I lacked the vocabulary and knowledge to describe design.

I couldn’t even really defend my design decisions because the truth is… I didn’t understand them myself.

In short, I really had no clue what I was doing.

I was really good at turning blank sheets of paper into something else. But what I turned them into wasn’t always better than the blank slate had been previously.

This became readily apparent when my internship ended and I took my first paying job as a web designer with a small web studio, where I was paired up with another recent design school graduate named Mary.

The biggest difference between Mary and I was our educational background, where as I had taken a two year “tools”course she had taken a full blown 4 year art/design degree. While never condescending she could talk circles around me when it came to discussing our work.

She understood why you’d pick a certain typeface for a certain application.

She could explain how colour choices would affect the perception of the final piece.

She knew when to use photos over illullstrations.

She also knew when it was time to get out of a bad situation, something I had to go and learn the hard way.

I wish I could say my first gig in the real world was a resounding success, filled with cherished memories of high visibility projects, strong mentorship and the opportunity to build a strong foundation for my career.

The reality of it it was much more of a shit show.

The folks that had hired me were a married couple who’d had some success during the early web boom before the bubble burst on Web 1.0. Steve & Irene (Not their real names) had a docket of clients that included boutique student housing in college towns across the US, local home builders and whatever rag tag business walked in off the street.

I was immediately taken by how sophisticated and successful they seemed, the fancy cars, nice clothes and promises of the exciting team they were building. The fact that they seemed keen to let a pair of inexperienced 20-somethings have free range over the creative work didn’t raise any red flags for me… neither did the fact that a sheriff from the court offices came in one afternoon to document equipment/valuables in the office during my third week as the landlord was sending them to collections for unpaid rent…

Despite all the obvious red flags, I was still enthusiastic and excited to be applying my craft to real world client projects. Often we’d kick off a project with little more than a vague set of directions, and a exceptionally aggressive timeline to meet.

Given that this was still the early days of the web we were free to try any hairbrained ideas we wanted, mystery meat navigation, obnoxious auto play music, gratuities animations… we were free to do it all, as long as the deadlines were met.

Oddly enough we never really included the clients in many of these decisions, our approach was very much a black box, Steve and Irine would give us a burnt CD full of assets with a hard deadline, then we’d spin up whatever random concept suited our fancy, burn it to a another CD which they’d take to the client while we waited with baited breath to see if they “liked” our work.

Not surprisingly this approach didn’t yield great results, we’d often send 2–3 concepts for consideration to the client, with very little background rational, and the clients would use an equally arbitrary approach in approval/disapproval.

Steven and Irine would return from the client’s office and either say “It was great, get it finished!” or the more common response “They really weren’t sure about any of these, but they have this site from a competitor that they really like, let’s just do something like this. We’ve spent enough time on this already, just take the assets they provided and make it look like this.”

As crazy as it sounds those rejections actually motivated me even more, it didn’t occur to me that our approach was wrong, just that my skills needed to be sharpened. My animations need to be smoother, my typography needed to be edgier, and oh yes, more music.

Sadly this “I just need to make it even MORE STYLELISH was a trap I’d remain in for years to come.

Things at that studio started going south about 3 months into the job when paycheques started bouncing, we abandoned the office shortly after the sherif’s visit and we were told “just tough it out a few more weeks, a big cheque is on it’s way!”.

For some reason I allowed this to continue, sometimes we’d get paid, sometimes we wouldn’t. All and all I was owed about 6 weeks of back pay when I’d finally had enough. Another payday had rolled around and my supervisor (also not getting paid that day) said he’d talked to Steve and Irine and they really needed me to publish the changes to a client’s site immediately.

“Oh… and our paycheques?” I asked

“Not today I’m afraid” he said with a heavy sigh

“Yeah… I’m done. I’m going home.” as I put on my coat and walked out the door

Being the class acts that they are, Steve and Irine threatened to go through my company computer to find proof I’d been doing other paid work on “their” time (time they hadn’t paid me for as of yet…) and sue me to make things square… nothing ever came of that threat.

Eventually I did get all my back pay about 3 months later by going through our province’s labour board and filing a formal complaint a long with my other colleagues. With roughly a 1/2 dozen of us all claiming missed pay for the same period of time, it was a pretty open and shut case, but I was still somewhat shocked when the labour board called and said I could come pick up my cheque from the same office I’d been filling out paperwork in a few months earlier.

But the lesson was learned, when the paycheques stop clearing, it’s time to put down your tools.

Drawing boxes for money – In the early days of the COVID-19 pandemic I started to draft up a long form career retrospective on my 15+ years working in digital design. Looking back on how the world and industry have changed since the first line of HTML I wrote.

I wasn’t sure if anyone would ever read it, and there’s still a large chunk of the story yet to be written. But in the midst of the 4th wave of the pandemic, it could be a nice distraction from the doom scrolling. Stay tuned for future chapters.

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Jason Dorn

UX Research Lead, which my wife describes as a “user design specialist” (he/him)