The trials and tribulations of driving around strangers – specifically a corporate, privileged, middle-aged woman.

When people find out I’m an Uber driver, they cannot hide their surprise, nor do they try to. Which I find odd, because you don’t find out someone is a garbage man, and then stare at them like:

Because that would be rude or classist, or something. But when a perfectly capable, educated, young white Canadian woman decides to be a taxi driver, people have a hard time accepting it. I think it might have something to do with me embodying their worst nightmare…but I’ll get to that! Whenever it is brought up that I drive Uber, people ask me if I’m serious, and then when I tell them I am quite serious, they think it’s hilarious. And when riders get into my Uber they CANNOT HELP but ask my back story. It happens almost every ride (unless someone my age gets in, in which case we sit in the car in silent acknowledgment that the Baby Boomers fucked us, and we’re all just trying to get through the effing day in whatever way possible) — but otherwise; it is an ABSOLUTE GUARANTEE that I will hear one (or all) of the below:

“So how long have you been doing this?

“Did you go to school?

“Is this your full time gig?

“What do you want to do long term?”

Which is also interesting, because why don’t you ask someone my age who works at Foot Locker that? Why don’t you ask every person in the service industry that? Did you go to school? Why do you work at Loblaws? Is this your full time plan? How did you get into this? What went so wrong in your life, that you’re a servant to the people???

So, usually this is all stuff I tolerate because honestly, whatever. I’m not about to explain to every 40+ person that gets into my car the state of affairs for us educated youths. However, the other day I get this corporate lady in my cab, and she was BESIDE HERSELF with me. She has daughters (they go to private school uptown!), and I could tell she was gravely concerned about my situation. I was driving her downtown, and she started with the usual:

“So is this your full time gig?”

“No, I have like 3 jobs actually.”

“Oh wow, what are your jobs?”

“I’m a bartender, an Uber driver, and a freelance writer.”

“Oh wow! Writing! Did you go to school?”


“For what?”

“Writing actually.”


“I went to University of Toronto and then Ryerson.”

“Oh wow, and you didn’t get any connections through school?”

“I did, I’m working on it.”

At this point, she thinks I’m lazy, because in her middle-aged mind, there is no way I could have two degrees from great schools, and be in the position I’m in. I obviously didn’t utilize my connections enough. This won’t happen to her daughters!

“What kind of writer would you be if you were successful?”

“Any kind, as long is it were creative writing.”

“Well, that’s a very hard job to get.”


“Why don’t you be a writing correspondent for news, like CBC or something? I know some people in television.”

“That’s not creative writing, and I feel like they would hire someone with a Broadcast Journalism degree over someone with a Writing & Rhetoric and Film degree.”

“I just think that it’s hard to get creative writing jobs.”

“Yeah, I know.”

“So do you mind having several jobs?”

“I mean, I don’t want to live like this forever, but I don’t mind it.”

“With creative writing, you might want to consider going back to school.”

I didn’t respond to that, and then;

“Do you have a boyfriend?”


“Oh. Why not?”

This lady was disappointed in me. She wanted some part of my life to be working, and I know why: It’s because I was her nightmare. A mid-twenties woman, with two degrees, aspiring to be an artist, refusing to partake in higher education. In her mind, I wasn’t driven. I was just like, allowing my life to happen to me. At one point she said “It’s all about networking” as if I’ve never tried networking before.

“Why don’t you try one of those dating apps?”

This chick was also apparently really into giving me advice that I had never thought of before, NOT. (See previous rant on Bumble Bios).

“Not really my thing. I think it’s weird meeting people online.”

“Well, writing isn’t really a social job, so unless you go back to school or get another job I don’t know how you’re going to meet someone.”

“Well, I met you today.”

“I guess that’s true.”

There was a moment of silence, and then I SHIT YOU NOT, SHE SAID:

“How do you afford this car?”

For a second, I considered lighting my pipe, twirling my moustache and saying, “I forgot to tell you about my fourth job, wherein I actually blow 70 year old billionaire men for money — ODDLY ENOUGH, it only covers the car — which poses the question, why not drive a cheaper car? Class, baby! I’m all about class. I know what you’re thinking — why not blow MORE men? It’s kind of dumb that I don’t blow QUITE enough old men for me to retire from being an Uber driver, it’s kind of like, once you’ve blown a few, what’s a few more? Honest answer? I like to make up the difference with my three other jobs. Working is fun! A sense of purpose you know?” Exhale from my pipe and tip my hat.

But instead, I just pulled over and told her I would cancel the trip, free of charge, but I wouldn’t be driving her the rest of the way, and she would have to call another Uber.

She was OUTRAGED, she was like “You can’t kick me out in the middle of a ride.”

Actually, GET THIS… yeah I can! THAT’S THE BEST PART OF BEING AN UBER DRIVER! MY CAR, MY RULES! Go try and pull that shit at CBC!

Categories: CULTURE