side quests by design

Subscribe
Archives
October 10, 2025

🛡️ In defense of the side quest

I included this Tumblr post in my introductory email you got when you signed up, but it bears repeating. (Especially since it’s been a little while since most of you received that email.)

Text: I feel like I'm at a point in my life where I know I need to advance the main quest, but instead I faff about doing side quests because the main quest is intimidating and I don't feel like I've leveled up enough to be able to handle it.
Source: mauve-alert on tumblr

In a roleplaying game, the main quest is the primary storyline. You must complete tasks related to the main quest in order to complete the game. Along the way, you unlock abilities, build upon skills, and rack up experience points. Side quests are optional and don’t directly advance the main quest, although I don’t know anyone who skips them, at least on the first playthrough. You gain experience that will assist you in the main quest, for one thing. And also, they can be fun. (Sometimes.)

You’d think I would have learned some life lessons from early experience playing video games, but no. Instead, I ended up taking the 10,000 hour rule to heart. Before I understood that the pop culture interpretation of this recipe for expertise is an oversimplification (and possibly misinterpretation) of a study, I took this to mean that you had to have a single-minded dedication to your craft if you wanted to be any good at it. This was your main quest, and you had to spend all your time working on that thing until you were an expert.

I didn’t question it initially because it totally aligned with messages I heard from the adults in my life. A common refrain on my childhood report cards: has potential. If only I paid attention in class, if only I turned in my homework, if only I followed through. My grades ran the entire gamut, so by my parents’ logic, my ability to get those A pluses in some subjects meant I wasn’t stupid, just lazy. And the only cure for that was to ground me from activities that distracted me from studying. Grades still subpar? That just meant I still had too many interests outside of studying.

Much later, in grad school, I conducted an experiment that went something like “drop all your hobbies and see what that does to your mental health” and still: one professor pondered my work halfway through the semester and sighed, “I wish you’d pick one of these concepts and stick with it for a few weeks.”

So. It turns out narrowing your focus that much isn’t good for your mental health or your creative output. And I wasn’t even capable of it when I tried to force it.

Screenshot from The Simpsons. Caption: No TV and no beer make Homer something something.
“Go crazy?” “Don’t mind if I do!”

None of this is news to anyone who’s had a creative practice for any length of time, of course. It turns out exploration and play have an important role to, well, play in the creative process. But, speaking for myself, the guilt starts creeping in way too often and I need to remind myself that it’s okay and even necessary to switch gears.

So what is this newsletter about? I’m not totally sure yet, to be honest. I’ll be sharing some of my own side quests, looking for common themes between them. I would love this to be a conversation between us so I hope you’ll share some of yours too.

Thanks for embarking on this adventure with me, and I hope you have some excellent side quests of your own this weekend.


Shoutouts to Amy, who prompted me to finish up this draft as we ran together across San Francisco, and Oscar, who gave me the final push to edit and hit publish. :)

Don't miss what's next. Subscribe to side quests by design:
Start the conversation:
Powered by Buttondown, the easiest way to start and grow your newsletter.