F*CK I MADE A GOOD DECISION

How I became a finalist in a Microsoft AI challenge with 0 knowledge in AI

Warning: This is a cool success story, but that’s not the point.

Iris Deng
dengit
Published in
7 min readJun 24, 2020

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Hello Mediumverse,

WWELCOME to my series on “F*ck, I made a good decision”. Oh yes, I censor my swear words, deal with it. This series will unpack a collection of good decisions I’ve made, with each post covering the know-hows and whys of this very good decision.

*a very good decision is defined here as any type of decision making that led to some kind of success, in other words, a super subjective definition you should just roll with.

Zzzzzz, b-o-r-i-n-g.

Hey, stop it, tell your fleeting attention span to give me a chance. So the twist here is, all these good decisions I’ll be sharing were not known to me when I made them until they eventually proved to be good decisions. So instead of calling this “Hindsight is 20/20”, I’m calling it “F*ck, I made a good decision”, capisce? Beautiful.

Now full disclosure here: not all of my decisions are great, that’s why it’s special to write about the good ones. I’m stating this here now so you know this is a highly selective and filtered account of the best parts of my life and the good decisions that led to it. In fact, I’d argue most of my decisions have been terrible, some are so sh*t I think I need another series just for them, but more on that later.

Here, I share with you the best decisions I’ve ever made albeit unknowingly, in hopes that you can be inspired to make them but consciously and actively in your life so you can write your own success story. Alright, cut the cheesy crap, let’s get right into the first good decision of this series!

So if success is not the point of this story, what the heck is my point? The point is, I made a decision.

The TLDR: Embrace the unknown, it might surprise you.

Animated Illustration By Yours Truly.

Uhhhh…what cryptic piece of information was that? Well, I’m glad you want to read more.

EEarlier this year February (just before COVID-19 became a one-cough-wonder, too soon?), I embarked on a rewarding journey in the Microsoft x McGill University x Agorize Discover AI Challenge. What started as a simple curiosity led me to the semi-finals of this competition.

Without going too much into the details of the challenge, here are a few key things you should know:

  • This was a challenge open to all Canadian university students and recent grads to apply AI in solving a human problem in the world. There were four categories, you can read about them here.
  • I know as much about AI as the next person who has seen Ex Machina, so it’s safe to say, my knowledge in AI was (still is) very limited if not non-existent.
  • As a behavioural designer, the closest thing I had that would be relevant to this competition was some skills in UX/UI design, which is what I pitched about myself when I was trying to join existing teams on the challenge platform.
  • During this whole competition, I was finishing the last semester of my undergraduate degree, and juggling between studying for midterms and writing 25-page-single-spaced-papers. (I have taken my social life out of this equation for simplicity and maybe because I couldn’t afford one at this point..)

So you’re dying to know, how does an outsider of the AI space break into it?

Well, these are the steps I took:

I signed up on the platform, applied to get on N teams, got rejected by (N-1) teams, started to give up, almost did, until that 1 team responded. The night before the deadline to submit a pitch for the first round, I joined a team that I never in a million years thought would make it to the end. Why?

  • We weren’t like most other teams, we met strictly online through the platform, we came from different universities and we were all at different life stages. I was still an undergrad, while one of my teammates was finishing his masters and another was already a working professional. So it was a miracle we jibed together the way that made us a great team.
  • We were a small team, so we were disadvantaged in the “strength in numbers” department. This was later proved to not matter, as I experienced, it’s “strength in efforts” that mattered, above all else.
  • I was recruited last minute, ‘twas not a good sign…But quite immediately I realized many teams had their own UX/UI designer and that I could create value in the space of AI even as an AI-illiterate.
  • Being in the category with the largest amount of teams was extra challenging but that didn’t stop us.
  • Many things had to work, and luckily, they did.

I’m simplifying and skipping over a lot of the process here but fast forward 2 months. Here I am with my team at the semi-finals (we made it!) with over 100 participants and judges on a Microsoft Team Call.

Spoiler alert: we didn’t win our category.

Yes, very unfortunate, but then I was reminded of how:

  • The challenge started with 577 unique teams, and we were one of the 15 final teams to make it into the semi-finals. I’m amazed at how far we’ve come in such a short time and with the unexpected collaboration that we formed.
  • I came into this challenge merely with an exploration mindset, wanting to learn about how AI is being applied to change the world. I learnt much more than that.
  • I greatly underestimated the opportunities for people with vastly different skill sets but a common goal to compliment each other and make impactful things happen.
  • We should appreciate the power of technology more. To this day, I haven’t met my teammates in person because of COVID-19, but I feel just as close to them as any group project I’ve ever worked on. So leverage all the tools in your disposal to collaborate with anyone, anywhere, on anything!
My certificate of participation in the finals of the Discover AI challenge 2020.
A certificate of participation never looked so good to me. Thank you , , !!

As happy as I am to have been part of this surprisingly rewarding experience and getting that finalist high, I think the biggest gift this challenge has given me is the insight of: you can do literally whatever the heck you want if you really want to. Regardless of what you want to pursue, as long as you are curious, comfortable with uncertainty and is willing to work your-ass off for it, you can do it.

There are no new ideas here, just another good story to convince you that all the cliché sayings and adages are true. Now…

TTake this idea away: As often as you can, take a dive into the unknown, because when you least expect it, something f*cking amazing might just happen.

If you’re already following and clapping, that’s all I have for you, hope to see you on my next post!

Now, for those of you reading my posts for the first time and is contemplating whether you should stick around for more, here are some FAQs to help you decide:

Why this?

I am an idea philanthropist, I believe in making great ideas accessible and digestible so that more epic ideas can be born out of this open, inclusive and collaborative idea space. Additionally, you can expect every post of mine to feature my signature GIFs, exclusively illustrated for that post. Some people come for the GIF and stay for the story, you may do whatever you want, I’m not your mom. Although I’m sure she’s very nice. So why this? Why not.

Why now?

*insert convoluted, inspiring backstory, blah, blah, blah* Basically, I finally found some confidence under by bed, picked it up and headed straight to Medium without ever looking back. Like every self-centered person in the world (aka being human), I think my stories are worth telling. But I’ll leave you to be the ultimate judge of that. So why now? It’s now or never, and never say never*.

*You guessed it right, that was 100% Justin Bieber inspired. Sue me.

Why me?

Great question, simple answer. You just gotta take my word for it that I will produce content that you want to read that doesn’t exist elsewhere. To make this easier, if one day you stop loving what I post, go ahead and unfollow, no hard feelings, well, maybe just soft ones. And…if you’re a hopeless romantic like me, you may write me a “it’s you, not me” letter. I promise you I will be okay. So stick around if you have a good feeling about me. Afterall, only good vibes are welcome here :) So why me? You know why.

Iris is a Jamaica-born now Toronto-based graphic designer, illustrator, and self-proclaimed GIF connoisseur that goes by the pencil* name dengit.

*get it? pen name for writers, pencil name for….ah you get it.

CConnect with me through your choice of medium (pun very much intended).

LinkedIn, Website, Instagram, Email

Deng out.

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Iris Deng
dengit
Editor for

I tell stories using illustrations with a hint of wit and dark humor. If that inspires you, stick around :)