Letter to My Younger Self

Dear 18 year old James,

Tomorrow’s the day you’ve been waiting for. You’re so excited you can barely go to sleep. When your parents help you move into Waterloo tomorrow, everything’s going to be new. New school, new faces, new beginning.

And let me tell you, university is going to be an incredible ride.

But freshman year will be tough.

You were one of the top students from your high school, and being smart was always part of your identity.

In the second week of class, you’ll have a chemistry tutorial. The TA says you can leave once you finish the problem set. You struggle on the first question, okay, I’ll try out the next one”, you’ll struggle on this question as well. Hmm, I’ll skip this one too.”

You’ll continue this process until you’ll realize you don’t know how to solve any of these problems. You look around the room and everyone else seems to be breezing through.

A classmate finishes and you haven’t solved a single problem. You asked for help, but you still couldn’t understand a thing.

Class ends and it’s just you and another friend in the room. Everyone else has already finished and left.

After 20 minutes, the TA in an irritated tone said, just hand it in.”

On the walk back home from that tutorial you felt insecure and incompetent. That’s when you realized that you are not the smart kid anymore. But don’t sweat it, later on you’ll understand that those around you are no smarter than you.

University will tear down your identity, but you’ll build it from the ground up. This will be your coming of age story. And dude, you’ve got so much to look forward to.

However things will change.

The people around you, your values, you’ll even transfer programs a few times. It’s all for the better though.

But there’s something that will stay constant. And if there’s anything you can call your greatest strength let it be this.

James, you’ve got a powerful mindset.

You came into university as a blank slate. You got accepted through the waitlist, you weren’t really involved in any extracurriculars, and your high school was decent—not amazing, but not terrible either.

But the thing about you is that you never put any limits on yourself. You never said, I can’t do it”, but always, I don’t know, but I can learn.” Early on you understood the importance of doing the thing you’re afraid to do”. This attitude will pay off big time.

For example, you’ll have tremendous difficulty finding your second internship. You’ll interview with over 20 companies and won’t get a single offer. It’s going to be a frustrating experience. You won’t know what you’re doing wrong.

Yet through all the rejection, you take it as a learning experience; as fuel to improve. You’ll work hard and you’ll make a pact with yourself to never let laziness be the reason for not achieving your goals. And irrespective of the outcome, you’ll be satisfied knowing that you gave it your best shot.

You’ll still be looking for your second internship a month after exams end, but you’ll find one. And you’re going to have an incredible time there.

Rest assured that from a career perspective you’ll be fine. You’ll surpass your own expectations and be in places you couldn’t imagine.

But before you start pumping your fist in celebration, you’ll understand that like grades, your career doesn’t define you.

You’ll have your own defining moment and this will come from a club you join.

In your second year, you decide to join the Canadian Undergrad Tech Conference (CUTC), the largest student run tech conference in Canada at the time.

The first year you join the team you’ll feel intimidated.

You’ll feel like you’re out of your league.

You’ll have a chip on your shoulder; something to prove. As a result, you’ll show up and put in work. You’ll surpass expectations and you’ll discover your strength as an individual: your optimism, execution, and resourcefulness.

You’ll be asked to lead the team the following year. But I’ve never led a team before. Who would want to work for me? I’m not ready.” Your internal dialogue will try and talk you out of it. But remember your greatest strength James? It’s that powerful mindset of yours. You never put limits on yourself. You may not know now, but you can learn. You must do what you are afraid to do.

And so you did.

This will be the toughest and best thing that will happen to you.

You’re going to work harder than you’ve ever worked in your life. During your winter internship, you’ll have a few nights where you stay at the office after hours to work on CUTC stuff until 3am in the pitch black cold winter night.

Your low point will come when you get a message from one of your advisers, a past leader of CUTC.

Hey, do you have time to talk tonight?”, she said.

Oh boy, what have I done?”, you’ll think to yourself.

You’ll meet with them later that night. You know this wasn’t going to be your run of the mill meeting. And it wasn’t. What have you been doing? This person says they don’t like working with you. We’ve been disappointed with you so far.”

They lit you on fire for a few hours. That meeting damn near broke you. You’ll look in the mirror that evening and ask yourself, What kind of leader am I?”

It’s going to hurt like hell at first, but you’ll only improve from that point on. Both as a leader and as a person. Eventually, the event will come into fruition and turn into something you’ll be proud of.

Some people may just look at it like it’s just some old event, but to you, it meant everything.You gave it your all. And it gave you so much in return. You’ll learn everything from building a culture, setting a vision, and what it takes to build something awesome.

Above all else, you’ll learn to believe in yourself. Most of your life you were timid, you lacked confidence, and you never thought of yourself as a leader. This time you did something you thought you couldn’t do. If you can do that, what can’t you do?

But all this success will inflate your ego.

You’ll think you know more. You’ll start to speak more than you’ll listen. You’ll start to close yourself off to other people.

Listen: No one gives a shit.

No one cares that you ran an event. Most people probably haven’t heard of it. This ego will become a bottleneck in your growth. Being curious and humble is what got you there in the first place.

Never lose that.

From where I sit now, viewing your journey, there are few regrets. But there is one that stands out.

You’re going to catch feelings for this one girl. You’re going to ask her out to dinner, with the intention of telling her how you feel. You guys are pretty much finished eating at this point and you ask for the bill. You still have not told her yet. I’ll tell her on the drive home”, you tell yourself. You’re driving her home now, and your heart is screaming at you to say something. But you arrive at her place, drop her off, and say your goodbyes.

That’s it. You didn’t tell her a thing.

You blew an open lay up.

This is going to be the story of your romantic life. It will cause you lots of pain and suffering. But it doesn’t have to be this way.

If you like someone, tell them how you feel. You’ve got nothing to lose. And if you don’t, trust me, you’ll regret it.

Rest assured James, you’re going to love university.

If you met me today I’m not sure you’ll recognize me. So much has changed. I mean physically I still look similar, but mentally I’ve grown so much. And this is the most important thing I want to share with you. If you take anything away from this letter let it be this.

What defines you, what will make you feel the most alive, is not what other people think about you, it’s not your transcript, it’s not the companies on your Linkedin. But it’s doing work that you care about, staying curious, and spending time with people you love.

It’s these moments that fill your heart, and make you feel whole.

Remember that, young fella.

Go and show the world who you are.

P.S. Take more pictures. I was trying to find some pictures to include in this letter but you have none. I know you were never a photogenic guy, but get over it.

Thanks to Ethan Benjamin, Rishi Dhanaraj, Jessime Kirk, Zarina Mamoukhova, Rahman Qureshi, Aditya Sharma, Sherry Wang, and Emily Yau for the feedback.

April 27, 2020

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