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Everything I Know About Job-Hunting, I Learned From Dating

The last time I went job-hunting, it took me four years to get an offer that I was happy with.

During the latter half of that season, I also started dating. A lot. I spent every night scheduling meet-ups and swiping through my apps. I went for speed dating, consulted a matchmaker, attended a singles camp (twice), and even let my friends set me up on group dates.

At one point, I almost gave up on my love life and career, having sacrificed my Sunday night for yet another humdrum date, followed by receiving a tragic job evaluation just two days later.  

It felt like I living out two variations of the same experiences. 

Polishing up my CV? Not too different from revamping my online dating profile.

Getting rejected after making it to the final round of a job interview? Try getting ghosted after having the “what are we” talk.

As horrible and masochistic as it was to embark on those journeys simultaneously, I fully believe that the misery and monotony of dating helped me endure the tedium of job-hunting.

Likewise, attending interview after interview taught me to be confident and conversational, that it was okay to be choosy, and to not take it personally if things didn’t work out.

Trying hard is a good thing


I was almost thirty by the time I downloaded my first dating app. I wanted my partner and I to have an adorable meet-cute, like maybe we could be work-rivals-turned-lovers or he could rescue me after a, uh, paragliding accident in North Korea. I surrendered to fate, only to realise that almost five years had passed without me going on a single date.  

Likewise with work, I went about my tasks, confident that my hard work would be rewarded with either a promotion, or with a call from a recruiter. Surprise surprise, I stayed in the same job for almost a decade. Three out of four of my job-hunting years consisted of lamely sending resumes into the ether. Only during the last year did I turn that process into a discipline, which eventually led to interviews and offers.

Going after what you want isn’t desperate. It’s responsible. So why don’t we do it? Maybe, like me, you think that if you truly deserved good things in life, then destiny will reward you in good time. That sitting and waiting is better than taking the leap, only to fall flat on your face.

A bad interview isn't necessarily a failure


The first time I ever met someone from a dating app, I almost had a full-blown anxiety attack. What if I got ghosted? What if he liked me, but I didn’t like him, would it be weird? What if we ran out of things to talk about?

The date itself went fine – well, except for the part where he interrupted me halfway through my first bite of sushi to ask that we pray over the food – but when he asked if we could go for drinks afterward, I said no, and when he offered to walk me to the MRT, I said that I would call a Grab. Naturally, we never heard from each other again.

I was so intent on making the date successful, that once the conversation got a little awkward, I basically NOPED out of there before we even had time to warm up to each other.

The same thing happened with two subsequent dates. Halfway through, I’d find some small snag in our connection, and sabotage the whole thing before it had a chance to sabotage me. Every bad date left me so scarred that I could barely muster the energy to try again.

Until one day, I went on a date that had more of a friendship vibe. We parted ways nicely, and then it hit me: Nobody died. It was…fine? At the very least, I had fun meeting a new person.

Dates aren’t a failure just because they didn’t lead to a second date, let alone to a relationship. And the same goes with job interviews. Just because you don’t get a job, or just because the interview didn’t go well, doesn’t mean you wasted your time.

You got practice. You grew. You gained exposure. Now you have a better idea of what you want. And all of those things will give you the confidence to move on to the next opportunity.

Don't underestimate the power of chemistry


I once had a coworker who complained about how unfair our company was, because while she was certainly qualified for the job (even more qualified than some of our other colleagues), she wasn’t given the same opportunities as others because she wasn’t “likeable”. She felt that how she looked on paper mattered more than how she came across in person. 

I couldn’t help but think of the Nice Guys in my life who resented women for rejecting them even though they were “sooooo nice”.

I’ll admit that even as a woman, I was a little guilty of “Nice Guy” behavior – “I listened to all his problems, I was there for him, I did sweet things for him, but he still ended up choosing that other girl over me, UGHHH”.

But that’s just how life is. You can have all the accolades and qualifications, only to get passed over because the interviewer liked the other candidate more.

People choose partners and employees based on intangible, often emotional factors. You wouldn’t brag about your car and your salary on a first date, right? So in a job interview, you should talk about your qualifications, but if you want to stand out, make sure can share a human connection with your future employer – especially if that person will one day be your boss.

Act now, and inspiration will follow


Look, we all know that the early stages of dating are filled with highs. The mystery, the romance, the flowers and sweet gestures might start the engine, but they don’t keep the car running.

And the first few weeks of job-hunting might be exciting, but when those weeks stretch into months, and months into years, it gets tedious.

Fielding through messages on your dating apps is boring. Scrolling through lists of job requirements is a snooze. You won’t always feel inspired to look. I definitely wasn’t.

There came a point when I was so disillusioned in my job search (during one interview, my would-be boss straight up asked me why I even applied when I was so obviously unprepared), that when a friend told me about an opening in her company, I almost didn’t write in. And when I got the interview, I didn’t even prepare. I told myself that if things went down in flames again, at least I’d know it’s because I didn’t make an effort in the first place, which is better than trying hard and failing.

Weirdly enough, I got that job, because even though I didn’t chiong too hard for it, all of my previous interviews taught me what to say, what not to say, and how to say it.  

Everything worth having in life takes a leap of faith


As much as I’d like to think that everything just magically fell into place – since that job “randomly” came about through a friend’s referral – looking back, it took a whole lot of persistence, strategy, and discernment to wade through the false starts until I found The One.

And as much as I wanted to leave my previous job, it felt a little scary tendering my resignation and transitioning into a new place. Once again, I spiraled into what-ifs: What if I made the same mistakes in my new job as I did in my old one? What if after my new bosses get to know me, they realise they made a huge mistake in hiring me?

Would I get as sick of and jaded at this job as I did in my last one? Would I quit again? What if I got fired? What if I stopped trying? What if this is just who I am? 

These are the same questions I asked myself once I started to make real progress in dating. What if I opened up my heart, only to get hurt again? Or worse…what If I got into a relationship, only to find out that I am incapable of keeping one?

There are not guarantees in life. Fifty percent of marriages end in divorce. And almost no one who is millennial-aged or younger stays in the same job their entire life.

Whether you’re job-hunting, dating, or in a job and already attached, there will come a point where you’re just “not feeling it” anymore. There will come a point where you’re scared and you doubt yourself.

There’s this quote in Bojack Horseman that goes, “Time’s arrow neither stands still nor reverses. It merely marches forward.”

We can pause our processes or rage-quit altogether, but life goes on, whether or not we follow.

Time marches forward, but those moments of disillusionment will pass, if you let them.

And if all else fails, there’s still Coffee Meets Bagel and LinkedIn.

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