There were many things I didn’t know at 23. In particular, that anytime you read the words “earn upwards of” in a job ad, you shouldn’t apply. Unless, of course, you’re poor. Which I was. And you’re a directionless university grad. Which I was. And you believe there’s a certain romance in the solitary life of a travelling salesman. Which, unfortunately, I did.
The job was selling advertising. I’d had experience selling things before. Mainly cheese in public school. So I applied and an interview was arranged. At a rest station. Off the highway. As if those red flags weren’t enough, the older gentleman interviewing me was sporting an ascot. Based on the way he spoke, I had the job before I’d even opened my mouth.
The premise was straightforward. The man ran a publishing company and would travel around to small towns throughout the province. Once there, he’d find a payphone (this was the ’90s), start calling the local charities and offer a deal they couldn’t refuse: a quantity of free day timers or cookbooks that the charity could then turn around and sell for 100% profit. In return, the charity would agree to have one of his sales representatives (that would be me) come into town and sell advertising in the day timer or cookbook to local businesses. This was where the profit came in. I’d receive a commission on the advertising I sold.
The earning potential, Ascot Man told me, was limitless.
He asked me how that sounded. Well, wonderful, naturally. It was a foray into the publishing business (I used that term loosely back then) and I’d certainly find good use for all the limitless money I’d be earning. I accepted on the spot.
The problem with his business model, I’d soon come to learn, was that, in a town of 1,200, there’s no need to advertise. Sure, if you’re one of two florist shops, you might consider gaining an edge on the competition. But if you’re the only florist shop?
Some tight-fisted business owner would inevitably bring this up as a reason for not buying an ad. Being an experienced salesman, I’d counter with a persuasive argument.
“But it’s to support [insert charity name],” I’d point out. “It’s for a good cause.”
If he wanted to support the charity, one grease-stained mechanic asked me, why wouldn’t he give the money directly to the charity? Why would he put it in my goddamned pocket?
I decided not to tell him about our in-house design services.
When it came to accommodations, Ascot Man had told me to offer the motel where I was staying a free, full-page ad in return for waiving the room fee.
“Naturally, they'll say yes” he assured me. “It’s too good a deal to refuse.”
Of course, if the town mechanic sees no reason to advertise, it makes even less sense for the local motel to advertise. Especially to people who already have bedrooms. In the end, no motel took me up. I’d have to pay for my room. Most times, I opted to make the long drive home which was the cheaper option.
And this was the worst of it: In order to make any money, I had to sell a certain amount of advertising. If I didn’t (and this happened more times than not), I made nothing. Once I factored in the gas, meals and motels, my job was actually costing me money.
A few months later, I threw in the towel. I wrote a letter to Ascot Man and faxed it off (this was the ’90s), citing all the injustices I’d suffered. I thought it would bring me some resolution. But it didn’t. I felt cheated. Swindled. I’d gone to university to make a better life for myself. I had a degree in English Literature, for fuck’s sake. And there I was, my cheap, brass-clasped briefcase knocking against my thigh, selling ads to hair salons. I deserved better. I’d sold myself short.
What I hadn’t known, as I sat across from Ascot Man at the rest station that day in my good pair of dress pants, was that one of us would be destined to fail time and time again in the years ahead.