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You Will Fail (And That's Okay)


I get knocked down, but I get up again, you're never going to keep me down - Ancient Proverb

It was December 2018, the end of what many may have considered a tumultuous year had 2020 and 2021 not thrown a pandemic-sized curveball into our collective faces. Donald Trump would be the first US president to meet a North Korean leader (which was not the flex he thought it was), the Golden State Killer was finally apprehended after 32 years through an ingenious—yet morally and ethically questionable —betrayal of our genetic privacy, and Meghan Markle joined the British Royal Family in what would turn out to be the second-largest conflict in British/American history.

The war of 1812

Honestly, it's fairly comparable.

I had been on the hunt for a new job opportunity, and I managed to arrange an interview with a market research company based out of Toronto, Canada, which was about an hour south of where I lived. Toronto, for those unfamiliar with Canadian Geography (and how dare you), is kind of like Canadian New York. Vancouver is Canadian L.A., Ottawa is Canadian Washington, and the province of Saskatchewan is Canadian... well, basically everything in the middle.

By the title of this article, you can probably infer that this interview could have gone better. I bombed harder than a mime at open mic night. As I walked out of their office into the cold, Canadian winter, I felt an overwhelming sense of defeat (and not just the regular sense of defeat most Canadians feel when winter starts). I was overcome with a myriad of different emotions: anger, disappointment, confusion, indigestion—I had eaten an entire Margherita pizza before the interview—but mostly it was just disappointment. Also, I don't want to deflect accountability but eating that entire pizza definitely did not help my performance.

The position seemed like a perfect fit. I had been working professionally with the company's technology stack for close to four years. I have a post-grad certificate in Big Data Analytics which was a huge bonus as I'd be working as part of their market research app. A friend of mine was a highly-respected developer at the company and had personally recommended me for the position—things really couldn't have been much more in my favour. I was critical darling "The Shawshank Redemption", and the Oscar for Best Picture was mine to lose.

A scene from the Shawshank Redemption

Basically how I felt going into the interview.

Except Shawshank Redemption didn't win Best Picture. And I wouldn't, either (in case you're curious, Forrest Gump beat both Shawshank AND Pulp Fiction that year. Also, am I nailing this analogy?) Here's the thing: even though I had every advantage going in, the simple fact is I just had a bad interview. It's not that I wasn't prepared, or that it was anything outside of my capabilities. I just ran into a snag mid-interview, I panicked—cooler heads did not prevail—and by the time I figured out what the issue was, it was too late. I swallowed my pride and walked my interviewer through what I would have done to finish the challenge.

I didn't get a call back; as depressing as rejection letters can be, they at least provide a sense of closure. I was devastated but not entirely surprised. The old feelings of inadequacy began to flood back in (thanks for that, first year of college), and I honestly began to question if I even wanted to be a software developer anymore. It was like getting last place in the Olympics—sure, it's exciting just to be invited, but chances are that you'll never backstroke with the best of them. Even worse, you might end up on an Olympics Fail Compilation video on YouTube. I stopped applying to jobs and taking calls with recruiters.

A skiier taking a tumble at the Olypmics

Great, this is definitely going to end up on the internet.

We've all been through the process: the endless resumes shipped, the billions of cover letters you write (because somehow we haven't collectively agreed to cast cover letters straight into the depths of hell where they belong). Months without hearing back on any prospects. The technical recruiters who claim they're excited to work with you, only to ghost you like a bad Tinder date. The feeling that maybe you're just not cut out for this. It can be difficult to stay motivated through it all. I faced it when I was starting out in my career, and it's something I still deal with today.

Here's the thing about failure—it's so much easier to get hung up on the things that went wrong instead of celebrating the things that went right. Negativity will drag you down like an anchor. One of my best friends called me ugly in 2007 and honestly, I still think about it; that kind of stuff sneaks up on you years later like an acid flashback. Getting caught up in the minutiae of a bad experience can easily avalanche into something much bigger, especially when you're stuck in your own negative echo chamber. It can be exacerbated even further when working in a hyper-competitive field full of toxic egos and gatekeeping.

A scene from Star Wars with Obi-Wan and Luke outside of Mos Eisely

'You'll never find a more wretched hive of scum and villainy.' 'Mos Eisely?' 'No, the StackOverflow comment section.'

And that could have been the end of the story, but...

About three weeks after that interview I heard back from a company I had met with a couple of months prior. Things hadn't worked out at the time—the position I applied to ended up closing since the project had fallen through. However, an opportunity had come up, and I was the first person they reached out to. That opportunity ended up becoming one of the single most defining points of my career, paving the way for basically the entire trajectory of everything I've accomplished since. I've led teams and projects, helping to scale applications used by millions of users. I've been a Bootcamp instructor, a mentor, and a conference speaker. I even built an app for the Royal Canadian Navy, making me responsible for at least some infinitesimally small percentage of the Military–Industrial Complex.

Here's the thing: you will fail, and that's okay. They say opportunity seldom knocks twice, but sometimes it does rings the doorbell. Sure, maybe this time it was someone subpoenaing you to appear as a witness in court, but who knows—next time it could be a package that got lost in the mail that's finally arrived to change your life. There are already far too many failure-related proverbs so I'll spare you the yearbook quotes, but take it from me: don't give up, and definitely don't slam back an entire Margherita pizza before an interview.

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