First, you might ask: What is a side quest?
A side quest is anything you choose because it feels like a fun experience. In video games, side quests don’t advance the main storyline. They give context, color, skills, allies, and unexpected rewards.
Life works the same way. Your “main quest” might be career, stability, healing, love, or purpose. While a side quest is the optional adventure. The detour. The experience. The thing that isn’t necessary for survival, success, or status… yet somehow fuels you more than the “important” stuff. The secret might even be that it’s where life begins. It’s where you get to truly taste life because you’re no longer living on autopilot.
A side quest can be:
- learning something with no plan to master it
- going somewhere just because you’re curious
- saying yes to a moment instead of a metric
- following a feeling instead of a formula
Side quests are the experiences that make those things feel like something.
They’re where you:
- remember who you are
- stumble into joy
- collect stories instead of credentials
- become interesting to yourself
A side quest is intentionally choosing experience over optimization.
How to Live a Fulfilling Life Filled With Side Quests
Somewhere along the way, life started convincing us that it was meant to be lived in a straight line. Life would throw its own detours at us anyway. But we’re supposed to live life in a linear fashion: School to job to promotion to house to retirement.
To live life by a checklist. A timeline. To follow the path you thought you wanted at 18 or your early 20s, when you still know little about life, and then stick to it for the rest of your life.
But the best lives don’t play like that. They sprawl. They wander. They explore. They’re built out of side quests, the moments where you truly let yourself live for no other reason than to experience.
Side quests are the moments you didn’t optimize. The things you did because something tugged at you, not because they advanced the plot.
I think about the best moments in my life, and they’re all of the in-between moments that are the most memorable. The times I gave into joy.
Some of my favorite side quests include:
- getting my yoga teacher certification, with no intention of ever teaching yoga.
- I had just turned 27 and was in my publishing career at Disney. I made the best friends, learned a lot, became more spiritual, flexible, calm. It became one of the best, most fun times in my life.
- My Substack Publication has been my side quest since May 2025, and I love it!
A fulfilling life isn’t about winning the game. It’s about playing it for the sake of enjoyment.
Okay, onto the How-To’s
First: Stop Asking If Something Is “Worth It”
Side quests don’t justify themselves. They don’t come with ROI spreadsheets or five-year plans. You take the pottery class because you feel like creating. You say yes to an experience you usually wouldn’t because you have nothing to lose. You wander around and let yourself lose track of time. You say yes to the invite even though it scares you a little.
If you only do what makes sense, your life will be very efficient and maybe not as fun! Fulfillment lives in the unnecessary.
Second: Treat Curiosity Like a Compass
Curiosity is the most underused navigation system we have. It whispers instead of shouts. It doesn’t care if the destination makes sense.
You feel curious about:
- a neighborhood you’ve never explored
- a topic you know nothing about
- a person who doesn’t fit your usual type
- a version of yourself you haven’t tried on yet
That’s a side quest calling. Could you answer it before your brain talks you out of it?
Third: Romanticize the In-Between
Side quests thrive in the margins. My favorite parts about traveling are that in between all the main places I want to visit, I always enjoy the getting to the areas most. For instance, in Paris walking from the Arc de Triomphe to the Eiffel Tower on a freezing December night was my favorite part of the trip. We were going from one destination to another, saw all the beautiful Christmas lights. Took wrong turns, and saw the prettiest streets, the most incredible views. It was fun, freeing, and just so enjoyable. The air was so frigid that night that my gloveless hand turned purple, while we looked for a place to go into to warm up, we found the most beautiful hotel with Christmas trees, and the iconic Parisian Ferris wheel.
Similarly in Sintra, Portugal, we were stuck on a bus at the top of a hill for an hour. “Should we get off and walk?” I said. And we did, and wandered into the cutest little quaint town, met interesting townspeople. The cop who had been directing traffic decided to show us their favorite restaurant, and invited us to their community events. Explaining that though he was the Chief police officer, he was also the community commissioner. It was quirky, and unbelievable that a place like this existed. I felt straight out of a movie.
A fulfilling life isn’t built only on milestones, and side quests don’t always look cinematic.
They look like:
- a Tuesday afternoon at a coffee shop
- a notebook you keep just for nonsense
- walking a different street
- trying something new
- stopping to take pictures with your disposable camera
I like to think the best parts of life happen when you stop rushing toward the big, iconic moments.
Fourth: Collect Stories, Not Proof
No one asks for evidence at the end of a well-lived life. They ask for stories.
Tell me about the thing you did just because it made you feel like yourself again. Tell me about the stranger who changed you for a season. Tell me about the phase where you said yes to everything. Side quests give you narrative depth. They turn you from a checklist into the main character of your own life.
Fifth: Let Your Life Be a Little Unhinged
A side-quest-filled life looks odd from the outside.
It includes:
- detours that don’t “add up”
- interests that rotate like seasons
- phases that don’t become permanent
Good. You are not a corporate strategy. You’re exploring, experiencing, embracing! A side-quest-filled life won’t look linear. It won’t always look explainable. It might look like starting over more than once, or changing directions just because. You are not doing it wrong, you’re just letting yourself have a human experience.
Finally: Remember, This Is Not a Speed run in some video game
This, as much as it is a reminder to you, is basically something I constantly need to remind myself. You don’t need to complete everything. You don’t need to unlock all the achievements. You don’t need to know where it’s going. A fulfilling life is one where you keep choosing living over arrival. Where you follow what lights you up, even for just a moment, allow joy to be small, silly, and frequent.
Maybe that’s the secret to life:
“This might be a side quest, but it feels like the point.”
The main quest was never the destination. It was learning how to wander well. Where you trust that detours aren’t distractions, they’re where you find a life worth living.
