These past two years I sang opera in a rustic barn two miles from campus, debated a real estate developer in a hostel in Austria and gave career advice to a thirty-year-old Israeli elementary school biology teacher who was thinking about transitioning to event planning. My externship somehow landed me at a PhD admitted students day for Africana Studies at the University of Pennsylvania, which was not where I expected to be on a Wednesday in March. Last summer I got broken up with at a Waffle House in Atlanta and the waitress asked if we were siblings — the most American thing that has happened to me since I moved here. Most recently, a Colombian man I met in D.C. tried to convince me, with great sincerity, to invest in DOGE coin. I also run an opera company in Bangkok.
My mom thinks I do too much of meandering. She says I take too many breaks, stop to look at flowers when I should be somewhere and that I always do things that are light in content but rich in meaning. She means this as a criticism. I am working on ways to properly disagree with her.
What I do, I think, is sidequest.
The term comes from video games, where side quests are the optional missions beside the main story. The game keeps moving without them. But they are where you find the weird NPCs, the secret lore, the landscapes that have no plot reason to be beautiful. They’re where the world gets texture.
I want to tell you about my visiting psychoanalyst professor who taught Swiss culture and politics. She studied under Slavoj Žižek. On a class day trip to the Art Institute of Chicago, she led us through yoga on the pebbles of a gas station parking lot during the bathroom break. Warrior pose, next to a pump advertising unleaded. I think about it all the time.
It lives in me now as proof that the world is stranger and more generous than it looks when you’re walking somewhere with intention.
The biggest part of sidequesting, I think, is asking the question you actually want to ask. Not the polite version of it. The real one. The one you’ve been sitting on for twenty minutes because you’re worried it’s too weird or too small or too honest. Ask it anyway.
I have learned more from questions like “wait, why does that actually work that way” and “can I ask you something kind of personal” and “okay, but what do you actually think” than from most things I have read. People will answer you if you ask them things directly and mean it. This is underused information.
The reason most people stop doing this, I think, is that free time has quietly become something to be embarrassed about. We have been so thoroughly trained to treat unstructured hours as a problem to solve that an afternoon with no particular output starts to feel less like rest and more like a character flaw, something to account for when someone asks how your week was. But busyness is not the same thing as a life, and a calendar full of commitments is not the same thing as a year you will actually remember.
There is a short-form Instagram based reality series called “Errands,” based in New York City, where people do small specific tasks and explain why it was an errand. For example, one man returned a Harvard ID he found because he googled the previous owner, discovered they had called Trump an orangutan in 2016 and decided that was a person worth meeting. The show treats all of this with complete seriousness, which is the point. The question “why is it an errand” is really asking — why does this small thing matter enough to follow through on? And the answer is always just because I had the impulse and decided to honor it.
That sincerity — of taking a whimsical thought seriously enough to actually do it — is what I’m talking about. The difference is that in “Errands,” the impulse arrives and people decide to follow it. What I’m saying is you can start there. You can make the whimsy the whole point from the beginning.
Say the thing you actually think. Ask the thing you actually want to know. You don’t have to perform disinterest or play it cool or pretend you weren’t curious. Curiosity is not embarrassing. It is how you end up with a life worth sharing.
Sidequesting is simple. Let a song you heard in someone else’s headphones stay with you. See a recipe on your phone and make it that night. Buy the strange fruit at the international grocery store. Walk somewhere you’ve always meant to walk.
None of this makes you more competitive or more lovable. What it does is make your life feel a little more like yours, which, when you think about it, is the whole point.
My roommate asks what I do to get into these situations. Honestly, nothing complicated. I say yes to things that seem interesting. I ask the embarrassing question. I let myself be moved by the oddly specific.
That’s all I’m recommending. Give yourself the permission to take the side quest. Look at the flowers. See what you find.
I dedicate this op-ed to my Grinnell friends, VO, CK, LNV, NN, ZYK, GB, BG, JK, RP, DG, JP, RS, BK and the quad.
Akira Keene Teotrakool `28 is a critical social sidequester and the Arts & Culture Editor for The Scarlet & Black.
