I realized, pretty immediately, that I wouldn’t be good at leading a double life.

I don’t get as much time as I would like to spend around my friends. I would say significantly less than your average 25-year-old. I work at night, I have to be up early and all of my energy is spent convincing obese men that I like them. My impressions of other 25-year-olds is that they have a social life, they go to clubs more than the library, they are happy with living with roommates and making slave wages. They seem a lot happier starting at the bottom.

To be clear, though, I do not think 90% of the “entitlement” reputation foisted upon my generation is appropriate or even true. I don’t want to be childish and point the finger back at the Boomers but I think if my generation is entitled, it’s a legacy that’s been inherited and I’ll leave it at that. And honestly, some of us are entitled. However, when you view this through the lens of our culture, where every input from every direction promised us that things would be better than they are, while our elders behind the scene were fucking up a lot of things.

Basically, for a 25-year-old who works in a job where office time involves a significant amount of cunnilingus, I thought I’d be having a lot more fun than I am.

My day job is disgraceful. I’m a technical writer for a software company that is only now establishing an online presence. The software is Windows-only. My audience is people whose children buy them computers for Christmas. When I studied literature I felt like I was reaching for something, I don’t know, more. Maybe I wanted to be an actual, honest-to-God writer? Or a critic? Or maybe I just wanted to have a job where the challenges of communication didn’t rival those that faced Annie Sullivan?

My boss, Angela, has no writing experience. English isn’t even her first language. To be clear, my other boss, Adele, at least worked as an escort for several years before moving into administration. Angela has less credibility than an ex-hooker Madame.

She seems to have graduated from the “fail upwards” school of management, whereby individuals sheepishly stay with one company, since their skills would not be useful anywhere else, and after enough time are promoted to a level where they can be carefully mollified since they have no real responsibility and very little accountability.

Like any good jackass, Angela is quick to blame everyone else for her shortcomings. She still stumbles on the concept that one must express desires, typically aloud in a work environment, in order to have them filled. While it can be frustrating employing individuals who do not have any measure of extra sensory perception, I’m sure she would be shocked to discover how common this phenomenon is. You probably work for an Angela too.

She has though, in her resourcefulness, attempted a remedy for her many, many problems. “Meeting-ize the problem away” is what I imagine this method is called. Whenever she wants to talk about something with me, she asks me to set the agenda and choose the time. Thanks.

She pulled me into one of these meetings recently and we began our little chat.

“I’m concerned,” she started. Ugh.


“I’m worried you might not be a good fit here.”

“Why is that?”

“Well, I feel like I’m editing a lot of your work.” She’s the head of a writing department?

“Well, I will definitely try to do better.”

“You’re not a very good writer. If you don’t get better, we’ll have to let you go.”


“Great. Well, back to work then.”

Angela has displayed her evil genius. She’s suckered me into caring about losing a job I hate. A job where I literally fall asleep and dream about quitting. Now I have to try harder to get paid $15 an hour for the most boring job ever conceived.

Angela doesn’t like me. She says she picks up on hostility from me, which of course is nothing short of baffling. Whenever Conor is home, talking about his boss, who seems to be completely sane and reasonable, I reflexively mock and insult him out of sheer jealousy. Sometimes I fantasize about what it might be like to work for someone competent. Or sane. Or who wears shoes at all times in the office. Dare to dream.

The irony, of course, is that I would actually be a better escort if my annoying day job didn’t get in the way. If I could stay out late I’d make much more money. It is truly a shame when your responsibility of being a barely competent technical writer gets in the way of your dream of being a prostitute.

The weekend after my meeting with Angela, one of my friends asked me if I wanted to grab a movie at Yonge and Dundas. Lisa is a genuine honest-to-God writer. She’s one of the funniest entertainment journalists in Toronto. She loves kooky movies. We were roommates in college. She now has a job that she loves. I have a job that I hate and another that I tolerate. It’s one of those situations where feeling good for someone else makes you feel shitty for yourself.

One benefit of being overscheduled is that you have to go see matinees, which is a real personal finance success tip. We met outside the AMC and subway station and went in together. I asked her how her job was going and complained loudly about mine. AMC tried to sell us some Toyotas and Coke. It was the most relaxing afternoon I’d had in a while.

“Hey, dude, you’re a writer, right?”

“Um, yes.”

“And do you have, like, a real editor?”

“Of course. Writers need editors. Literally every writer in the world has one.”

“Right, so does your editor review your work and let you know what’s wrong and what to fix, or do they just tell you need to do better?”

Lisa gave me a strange look, “She tells me what to change and I change it. Obviously.”

“Oh, that’s cool.”

Sometimes I feel like I’m going crazy with these two jobs.

After the film, we decided to go out for drink. Since it was a Saturday, I had to work that night, so I knew I couldn’t stay out late and I was pretty exhausted from the week. I couldn’t keep this pace up for much longer. I was doing my regular 9-to-5. When you figured in all of the time it takes to get to and from calls, waiting for other girls who might have the same driver and the calls themselves, I was up to at least five hours per night, four nights a week. Even though it’s exactly what they’re paid to do, the drivers rarely dropped us off after calls and would make us sit in the car with them, even if we lived ten minutes away. No one had the balls to talk to anyone in the administration about it since complaining in this industry just gets you fired. If you aren’t willing to put up with a certain amount of shit, there’ll be another girl right behind you who will. Everyone is testing your limits around here.

We chose something quaint on Yonge and I ordered a Jameson and Diet Coke. The Atkins diet, I’m convinced, is some sort of medieval torture. The most frustrating part of it is that I lost a lot of weight sticking to it. The most annoying diet in the world actually worked for me. It meant that beer, which Lisa was having, was out.

“I’d love to go out tonight,” I said, explaining for what seemed like no reason, “but I have to work. I have a data job now that I do on weekend nights.”

Conor had thought up telling people I worked in data entry, because it’s often done after offices close and, unlike saying that you’re a bartender, no one can ever come “visit” you at work.

“That’s cool. How did you get into that?”

Oh shit, a follow up question. Why didn’t I anticipate that?

Then it occurred to me. Lisa was my friend. I didn’t want to lie to her. I lied to everyone all day almost every day. I didn’t use my real name or my real history with hardly anyone. Nothing about my personality was real. I was okay with that for someone else, someone I didn’t care about or genuinely disliked. That didn’t bother me. But the people I loved had a right to know.

“Actually, I just lied to you,” I said, "I’m doing something else.

“Okay. Are you a stripper? I’ll come see you and cheer you on!”

“Close. I’m actually a hooker. I kind of… went full-tilt on that one.”

“Hey, it’s cool. If it’s okay with you, then I support you.”

“I need to. I need to get out of debt. "

“How much do you make?”

I told her.

“Wow. Just… wow.” She said, “I’ll think about getting into it. My boyfriend might not like it. What does Conor think anyway?”

“Well,” I started, “I was more miserable being in debt and he figured that he could get behind whatever makes me, you know, not miserable.”

“Good Luck, babe.”

“And I lied because I was worried you would judge me. And I also think it’s something I’m supposed to lie about, but I don’t want to.”

That got right to the crux of the issue, I thought. I should be ashamed of this. My fake name, the fact that the website doesn’t show my face; it’s all to protect my safety and anonymity, but it also smacked of shame. This was something I was never to tell anyone I cared about. And these people, they were supposed to judge me and cut me out of their lives. That’s the narrative, isn’t it? That being a prostitute would isolate me from love. That I didn’t deserve it.

I didn’t lie, I told the truth and the sky didn’t crash down. We were still friends. I still had my life. I came out as an escort and nobody ran away.

“This afternoon will cost you nine hundred dollars by the way.” I told Lisa

“Awwww, I should have asked for something naughtier!”