Confessions of an Ad Agency Dropout

Part 1: You Should Go Into Advertising

If someone ever tells you, “You should go into advertising,” I would ask you to think about why they’re telling you that.

When I was 20, I was a columnist for my university newspaper. This was in 2004-ish when VICE was still a relevant counter culture voice (at least to a privileged 20-something attending university) and I desperately wanted to be as cool and as funny as I thought their writers were. Needless to say, the columns I wrote were occasionally ignorant, often intentionally offensive (I would have said “provocative” back then), and somewhat funny (maybe). And I was too ignorant to think my ignorance mattered—I am very glad that none of this writing ever made it onto the internet.

During this time, our newspaper The Peak had its 50th anniversary. We had a big celebration at the campus pub two floors above our office and invited all of the alumni that had ever written for the paper. One of the guests was one of the “founders” of The Peak named Rick. A few hours before the party kicked off, Rick sat down in the Peak office and flipped through our most recent issue. He gleefully told us how bad everything was, how it lacked “edge” or “bite,” and—shockingly—that the paper was so much better in his day. There was one exception: my column at the back of the paper.

I don’t remember which one he read, but it was likely in questionable taste, written while I was drunk, or both. Regardless, a few hours later at the anniversary party, Rick sought me out. One of the very first things he said to me was, “You should go into advertising.”

Rick’s career in advertising left him grey, mine left me bald.

Over the course of the next 20-30 minutes, we had a detailed, slightly drunken conversation about why my writing showed the potential for success in advertising. My column had “edge” or “bite” or “attitude.” (I will talk about this more later, but it’s true that “attitude” can be found in all good advertising.) At the time, I thought Rick was cool as hell because he had long grey hair, was drinking a fair bit that night, and seemed to still have an edge that my 20-year-old self wanted to never lose. I was intrigued, but I ignored Rick’s advice for the next few years while trying to become a “real writer.”

I graduated university, moved to Montreal, and interviewed for a job at VICE. When I didn’t get that, I started a blog (don’t look on Google, I deleted it long ago) and began writing random things and pitching article ideas to various publications. Without any guidance as to how one goes about becoming a non-news writer or “humorist”, I didn’t have much success. Living in Montreal made me feel cool, but I wasn’t. I paid $300/month in rent and worked four days a week as a dishwasher/line cook at an Irish pub. I was probably depressed. So I moved to Edmonton.

A good friend of mine from the university newspaper was living there with his partner and their young daughter, and he told me I could get a job freelancing for the local weekly free arts newspaper (pretty sure every city had one of these in 2008). With his introduction of me to the Arts Editor, I quickly started writing movie, theatre, and music reviews and interviews for SEE Magazine (don’t look on Google, it shuttered long ago). But as any current or reformed journalist will tell you, it doesn’t pay great. I worked another kitchen job five days a week to subsidize my $50-per-piece writing gig throughout one Edmonton winter. I was definitely depressed. So I started thinking about Rick’s advice again, some four years later.

The moment I decided to give up trying to be a “real writer” is still very clear to me. I was sitting in my basement apartment, listening to a CD by Wavves that I didn’t like very much. As I wrote my snarky, holier-than-thou review, I said to myself, “At least this guy is making something. What am I doing?” As much as I didn’t like the music, I didn’t feel like my 250-word review was adding much to the world. This being the early days of Pitchfork, I didn’t want to be seen as just another guy trying to find a bigger audience for his pretentious music tastes. No, I wanted to write things people would read. I wanted to create stuff. And I wanted to make money. Writing advertising started to look pretty good.

Coincidentally, I had recently started watching Mad Men, so I started having romantic notions of being a modern day version of Don Draper. But I knew it was just a TV show, so I read Ogilvy On Advertising to get a better picture of what I thought the industry was really like. I was sold. A few weeks later, I moved back to Toronto and applied to the Advertising Copywriting program at Humber College with an awful spec ad. I got in.

Looking back on the advice Rick gave me nearly 20 years ago, I view that conversation very differently. Now I can see that the writing that spurred his advice had a lot of flaws, including some I’m embarrassed by. More than anything, it was cynical at its heart. And I think that underlying spirit was always in the back of my mind throughout my time working in advertising.

Our conversation did lead me to working nearly 10 years in ad agencies, including a lot of good memories, but it also made me bitter, burnt out, and jaded. We had very different experiences in the industry, as Rick retired from advertising and I walked away after a little under a decade. So my advice for a 20-something that fancies themself a writer would be quite different. And that’s essentially what this series is meant to be.

If you think advertising itself is bad, try making a career in advertising.