life is not an optimization problem

lessons from chasing the perfect path

Introduction: The Pattern

I have spent years trying to optimize for the best outcome possible. In high school, I aimed for the highest grades possible, so I could get into competitive university programs. Each test meant I needed to score perfectly, and the closer to 100% I was, the better. So I did: near perfect grades, the right clubs, the polished application. I originally wanted to go to Waterloo’s Systems Design Engineering program. When I got in early, I was relieved. Finally, I got what I was working for.

Then in May, I also got accepted into Waterloo CS — a program I never thought I’d get into. Suddenly, I was stuck. SYDE or CS? I made pros/cons lists. I asked current students. I researched online for hours. The question haunted me: what if I made the wrong choice? What if I mess up my university experience, or my career?

I chose CS. To this day, I still don’t know if it was the “right” choice. I’ll never know. But that decision—and the anxiety surrounding it—set the pattern for the next five years.

The Co-op Optimization Cycle

The Implicit Rules

At Waterloo, there’s an unspoken hierarchy to co-ops. First term, any job is fine, you just need experience. Second term, aim higher. By third term, you need a US company. Fourth, fifth, sixth: you need to aim higher and higher. Each co-op should be “better” than the last, a clear upward trajectory building toward the ultimate goal: a return offer from a top tech company. This was a common mindset that I fell into, and it was very draining.

Waterloo even gamified this with the ranking system during job search. You could rank employers from 1-10, they could rank you, and an algorithm matched you. Should you rank your dream company #1, or play it safe? The entire system trained us to think this way.

My Start

In the beginning, I was very grateful with just getting any job and getting experience. My first co-op search was a bit rocky (first offer got rescinded, second offer I got laid off — that’s a story for another day). I ended up doing a shorter co-op term as a contractor, working in small team. I loved it and learned so much.

But then I managed to land an internship at Amazon (with a lot of luck) for my second co-op, and it gave me a lot of drive to continue the momentum. I remember thinking back then that I had “made it.” I never would have thought I could get the offer. My parents were proud and all my friends congratulated me.

The Reality

But I quickly realized it was not at all what I thought it would be. Sure, a well known name on my resume opened a lot of doors later, but that summer was full of stress. I felt intense imposter syndrome during the internship. Everyone around me seemed smarter, more prepared, more naturally talented. I felt like I wasn’t qualified to be there, like the interviewer had made a mistake and any day now someone would figure it out. I was also living in Vancouver, a new city where I didn’t know anyone, on the other coast of all my friends and family. It was a tough and lonely first few weeks.

But I ended up meeting so many people, and some of them I still talk to today. My most cherished memories were not of all the work itself, but the friendships I built with other interns when staying late at the office, complaining about work, exploring the beautiful hikes in Vancouver, and learning to sit in the discomfort of not knowing anyone and building a life in a different city.

The Treadmill

I knew I wanted to try different companies and cities for my co-ops. After Amazon, I kept going. Microsoft in Seattle, Datadog in New York City, Amplitude in San Francisco. Each time, I thought: this is it. This is the one that will make me feel like I’ve done enough.

But it felt like every four months, there was a “better” option to chase. Every time I got a new job, I would feel happy—for a little while. But this constant cycle made me feel like I was never satisfied. I would compare myself with others and feel behind. The goalpost kept moving.

Breaking Point

Finally, it was time to optimize my new grad offer. This was supposed to be the culmination of everything. Six internships building to this moment: choosing where to start my career. This time, it felt much more real. Internships were temporary, but this felt like the official start of “the real world.” There were so many things to consider: compensation, location, career growth, and whether my friends and family would be close by.

I was 95% sure I knew what to choose. But that 5% haunted me. What if I was making the wrong choice? What if I could do better? I kept thinking and comparing different options.

And I still didn’t know. The promise of optimization is intoxicating: if you just work hard enough, research thoroughly enough, plan carefully enough, you’ll find the right answer. The optimal path. The choice that maximizes your outcome.

It worked for high school → university.

It worked for co-ops → better co-ops.

Surely it works for everything?

Why Life Isn’t an Optimization Problem

The problem is, you’ll never know. If I choose Company A, I’ll never know what would have happened at Company B. Maybe that team would have been amazing. Maybe I would have learned more. Maybe the connections I made there would have led to opportunities I can’t even imagine. Or maybe I would have been miserable, burned out, or laid off six months in.

There’s no A/B test for your life. You can’t run the experiment twice with different variables and compare the results. You just have to live one version, and let the other one go.

What Is Your Path?

I never stopped to think about why I’m doing all of this in the first place. I worked hard in high school so I could get into a good university. I worked hard in university to get good internships. I worked hard during my internships so I could get a return offer. And then what?

I wanted to do all of this so I could be financially stable and happy. Every hour I spent worrying was an hour I didn’t spend hanging out with friends, or enjoying my hobbies, or just existing without anxiety.

I have friends who chose startups over big tech. Friends who went into finance, or healthcare, or grad school. They’re all learning and growing in different ways. There are many different paths that lead to fulfilling lives and careers. There isn’t one “best” job, one “best” city, one “best” decision.

What I Know Now

I think back to 19-year-old me, agonizing over SYDE versus CS. I wish I could tell her: it doesn’t matter as much as you think. Both paths would have been fine. You would have learned different things, met different people, ended up in a different place: but you would have been okay.

The optimal choice isn’t to find the optimal path. The optimal choice is to pick a good path and commit to making it great.

I’m learning that past a certain point, what matters more to me is:

• Spending quality time with people I care about

• Doing good work wherever I am

• Being kind to myself and others

• Pursuing things that give me joy, simply because I want to

• Actually living, not just planning to live once I’ve achieved the next thing

Life is not an optimization problem. It’s a series of good enough choices, made with incomplete information, by a person who keeps changing.