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4 dating lessons to apply to your job search

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How to make your career slightly less painful than your last breakup

Whether you’re fresh out of school or thinking about a career change, finding your calling in life is a lot like stepping onto the dating scene for the first time in a while — or ever. (Photo by DocuSign on Unsplash)

Dating in today’s world can be remarkably tough.

Between finding the courage to go see if that girl looks as good from the front as she does from behind… and thinking of something witty to put in your Tinder profile without sounding like, well, a Giant Nerd…

Let’s just say finding a romantic partner that fits the bill to a T is a full-time job on its own.

And speaking of jobs… figuring out what to do about your career can be just as challenging. Particularly if you have no idea where to go from here.

So in an experimental double-whammy fashion, I’ve put together some lessons I’ve had the unfortunate pleasure of learning in both my dating and work lives, with the hope that you can have a minimally rocky journey toward self-discovery.

Cue the theme music.

  1. Money can’t buy love.

In case you missed the memo, true love cannot be bought. Or, as Woody Allen once put it:

“The most expensive sex is free sex.”

Now, I’m sure some people are able to quantify the value of their presence and fake affection in monetary terms (see: “escorts near me”).

But there are just as many guys who seem to think that expensive gifts and monthly rent payments are enough to send a girl’s love hormone production into hyperdrive.

As if tickets to see the Weeknd and trips to South America are proven cures for “she’s-just-not-into-you” syndrome.

And yet so many people seem to think that getting paid “enough” is the solution to getting workers to give two turds about their job.

That beer fridges and webinars on inclusivity in the workplace are what makes the modern employee tick.

That tickets to see the Weeknd and trips to South America — do I sound like a broken record yet?

Now, on the one hand, I don’t think there’s anything sacrilegious about trading hard work for good pay and decent perqs. Everyone’s gotta make a living somehow.

But sometimes, you can end up with a job that slowly eats away at your soul, even though you’re making decent money.

The kind of job that comes with supersized servings of the Sunday blues.

And has you counting down to 5pm well before you’ve logged in for your 9am daily scrum.

The kind of job that throws you into an existential crisis the moment your weekday alarm goes off.

I once had a job like that while working at a marketing agency.

And while I wasn’t making six-figures or getting any special fringe benefits… on paper, it was a much better deal than any job I’d had before.

It also turned out to be the most number of times I have ever contemplated quitting.

Could I have been paid better? Sure.

But in the end, I realized I didn’t really care about what I was doing.

Everyday, I’d wake up with the horrible realization that I was truly wasting my life away.

And coming from a career working in kitchens where I’d voluntarily worked for free because I actually loved cooking… I felt like no amount of money could fool me into loving this job.

That’s not to say that the job itself was objectively shitty. It just wasn’t a good fit.

And for someone who has a really hard time pretending to like something he doesn’t, I’ve learned that I’d rather scrape by doing things I enjoy instead of suffering through what most people refer to as “work.” 

Because the privilege of pursuing your passion has no price tag. Not a permanent one, at least.

  1. Exploring your options helps you get clear on what you actually want.

Whether you’re fresh out of school or thinking about a career change, finding your calling in life is a lot like stepping onto the dating scene for the first time in a while — or ever.

You’re nervous, and possibly a virgin. Any girl who’s more than a 5 is automatically upgraded to an 11. And despite what you said about dirty blondes and older women six years ago, you’re kinda digging J.Lo’s new look ngl.

You’re like a fat kid in an ice cream shop. Except this shop only offers single scoops. 

Case in point: what you think you want may be a poor reflection of what you actually want.

The same goes for when you’re trying to figure out what kind of job you want to have long-term. 

Because even though you may have heard about all the popular professions that “successful” people enter into, like doctors and lawyers and engineers… log onto Indeed.com and you’ll find all sorts of well-paying jobs that you never knew existed, posted by companies you’ve never heard of (or you probably did but their boobs weren’t as big back in high school).

In a world where teenagers can pay off their parents’ mortgages by selling pictures of bored apes, there really is no shortage to the number of ways you can make a career for yourself.

Which means the only way you’ll be able to develop even the faintest idea of what kind of work you want to do for the next chapter of your life is to go out and try shit.

Because how do you really know if a job is the right fit for you until you’ve gone and done it?

Back when I was in high school applying to universities, I remember writing in my application that I wanted to be a “product brand manager.” Like I had any clue what that meant.

The truth was I really didn’t know what I wanted to become. Not because I was indecisive. But because I didn’t know what I could become. 

Up to that point, I’d never had a real job. I’d never tried different lines of work to see what I liked and what I didn’t like. So what the hell was I supposed to know about picking a career when I wasn’t even old enough to drink?

Even now, after having been a warehouse order picker, dishwasher, sous chef, knife sharpener, UberEats bike courier, project manager, and personal trainer, I’m still not really sure as to what I’m going to do for the rest of my life.

But spending time in each of these roles has given me a better sense of what’s important to me when it comes to building a career and choosing the kinds of projects I want to work on.

Cooking has shown me that you can in fact love your job.

My time at the marketing agency showed me how much I hate working jobs I don’t love.

Being a personal trainer made me realize how much I value doing my own thing.

As much as “players” (does anyone even say that anymore??) and “fuckboys” get shit on, there’s some logic to their promiscuous ways.

Because no matter how exciting forensic accounting or investment banking may sound — and no matter how fit Ashley looks in her Tinder pics — you’ll never really know if it’s a good match until you’ve given it a shot.

  1. Compromise does more harm than good.

Compromise is the birthplace of resentment.

People who like to compromise think they’re coming up with win-win scenarios. But really, it’s more like a half-assed win-win. And having half an ass is just as bad as having no ass. Which means nobody wins, because wtf are you supposed to do with half an ass?

Look, I’m tired, so I’ll get right to the point:

Compromising is pretty much what happens when you give up on going after what you want because you think getting something now is better than the possibility of getting nothing for the rest of your life.

It’s basically like saying you’ve lost all hope in your ability to achieve your goals and turn your dreams into a reality. So you settle for whatever life throws your way.

Which is why you see so many unhappy couples sulking around. Couples who haven’t had sex in centuries. And sleep in different beds. 

Couples who are too afraid to part ways because they’re afraid they won’t find anything better.

As if you couldn’t possibly find a better romantic partner in a world with almost 8 billion people.

But what do these couples do?

They stay together. They try to “make things work.”

They pretend to be people they aren’t, and get really good at smiling on command.

They agree to do things they don’t really give two fucks about in the name of “love.”

Next thing you know, you feel super guilty and betrayed about the fact that your partner has admitted to faking 47% of her orgasms. Not including anal.

And for me, that pretty much sums up what it felt like working a job where I had to compromise who I was to try to fit in with the culture.

Where I agreed to do things that not only bored the shit out of me but also went against my values.

Where I pretended to be someone I knew I wasn’t. Where I became exceptionally skilled at being a “yes-man.” And faked professional orgasms well over 47% of the time. Especially while getting fucked in the ass.

All this to say that while settling for low-hanging fruit may seem like a harmless move, it can cause a lot more undue suffering, stress, and rectal damage than you think, depending on your temperament. 

Sure — you might not snag your dream job tomorrow. I’ve come to terms with the fact that I’ll probably be pinching pennies for the next decade before I figure out how to make whatever the hell it is I’m doing work.

But I’d rather fail at chasing my dreams than pretend to want someone else’s.

Because having half the ass you want is just as disappointing as having no ass at all. 

  1. “There are no beautiful surfaces without a terrible depth.” – Friedrich Nietzsche

Ok — holy fuck. This turned out to be waaaaayyyy longer than I expected.

Which is sort of the same level of surprise that hits you when you realize that the amazing person you thought you fell in love with is borderline psychotic.

(Admittedly, this can also make for some pretty wild adventures in the bedroom)

That’s not to say that I myself am free of any weird and possibly disturbing idiosyncrasies.

But what I’m really getting at is the other side of the truism about judging books by their covers. That sometimes what’s written in the pages might not exactly be what you signed up for. 

Because a lot of the time, how someone looks on paper — or in their well-angled selfies — can be awkwardly different from who they are in living, breathing colour.

I’m not just talking about catfishing. I’m talking about how there’s often a lot more going on behind a pretty face than meets the eye. 

Unresolved daddy issues… reality-skewing insecurities… a peculiar obsession with numbers that end in -wenty-three.

People are complex creatures. And it takes a bit more than just a couple dates to really get a sense of who someone is when they’re *not* trying to impress you.

The same goes for whichever company or boss you end up working for.

Because no matter what they tell you during the interview about how great it is to work there… no matter how many times they plaster the word “inclusive” on their website… or all the times they’ve been voted “best employer” by some organization you’ve never heard of…

The truth is every company has its share of ugly features and assholes.

And depending on the kind of person you are, those features may be enough to make you run the other way. 

But you’ll never really know until you’ve done your own research.

Back when I was cooking, I was given opportunities by two different restaurants to essentially try out for a spot in their kitchens. At the time, both of these restaurants were easily among the top 5 hoity-toity eateries in the city. So for anyone eating at either of these places, the experience was more or less the same (at least in terms of the cheque size). 

But behind all the fancy plates and pebble-sized portions, the kitchen cultures at each restaurant sat on opposite ends of the how-much-should-we-shit-on-our-staff spectrum. At the first place, they actually fed me a full dish of pan-seared goose liver while I was working. At the other place, it was like the sous chef got off on cussing out all the cooks. 

Which goes to show that 1) it’s probably good for your mental health to get laid every once and a while, and 2) how a company presents itself on the outside to its customers sometimes has nothing to do with what it’s like to interact with the company on the inside.

Now, you may not get the opportunity to conduct a full-fledged ethnographic study of an organization’s workplace culture. But a healthy touch of cynicism can go a long way to helping you see a company for what it’s truly like to work there rather than being blinded by what you hope to experience on the job. 


At the end of the day, there’s only so much you can do to sidestep getting your heart broken, whether it’s with a romantic partner… or a career that seemed like a good match… or a company that looked like they were winking at you.

So if there’s one piece of advice I hope you take away from all this, it’s this: never put someone else’s dreams ahead of your own.

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