Optimizing Fun is The Opposite of Fun

Somewhere around early July, the messaging shifts. It's time to unplug. Set your out-of-office. Put the phone in a drawer. Every brand and wellness account and well-meaning coworker starts talking about summer like it's a system reset, a chance to finally rest.

I want to like this messaging, but I don’t.  And I have to tell you that I’m typing this newsletter while sitting at a beach boardwalk café because I told myself it would fun to have a “beach work day” and I have to be honest with you about that—I’m still working hard on permitting them to exist separately.

Look at how much fun I’m having! My devices said I had 4 hours of fun!

Here's the problem: "unplugging" has become something you perform, not something you do. You post the beach photo with the caption about being off the grid. You tell your team you're unreachable, then check Slack twice a day anyway, quietly, so no one thinks you've actually stopped being useful. The rest itself has become a deliverable.

That's not an accident, and it's not a personal failing either. If your job doesn't guarantee real time off, if your industry treats a two-week vacation as a red flag about your commitment, if taking a full break means coming back to triple the workload, then "unplugging" was never going to be a real option. A way to participate in the aesthetic of rest without the structural conditions that would make rest actually possible. You can't individually opt out of a system that was built to keep running through you.

And this is where it gets more interesting to me, because the same thing is happening to fun.

Watch how people talk about their leisure time now. Vacations get "maximized." Hikes get logged, mapped, tracked for elevation gain and calories burned. Hobbies get monetized almost as soon as they show promise or get abandoned because they're not "productive" enough to justify the time. There are apps for optimizing your bucket list. There is a whole genre of content about doing the "right" activities on your one trip to a place, as efficiently as possible, so nothing gets wasted.

I don't think this is really about vacations or hobbies. I think it's about what happens when there's no space left that capitalism hasn't already colonized. Even our resistance to work has started to get structured like work. We've internalized the metric so completely that we bring it with us into the one place it was never supposed to go.

And here's the thing about fun specifically: it cannot survive being measured. The second there's a metric attached to an experience, there's an evaluator watching for it, even if that evaluator is just you. Fun requires a kind of unselfconsciousness, a willingness to be absorbed in something without tracking your performance in it. It thrives on lightness and whimsy, not the urgency of task completion.  You cannot simultaneously lose yourself in something and audit how well you're losing yourself in it. Optimized fun isn't a more efficient version of fun. It's a replacement for it, wearing fun's clothes.

So, we end up with two versions of the same move. Rest gets marketed as an individual choice you make correctly or incorrectly, instead of something that depends on the conditions around you. And fun gets marketed as a project you execute well or poorly, instead of something that depends on you not executing anything at all.

I don't have a clean fix for either one. I'm suspicious of anyone who does, honestly, because a five-step plan for "authentic unstructured leisure" is just the same trap with better branding. What I can offer is smaller than a fix. A few ways to notice the pattern while it's happening, since noticing is most of the work.

One is to listen for the vocabulary. If you catch yourself narrating your own leisure in the language of output, maximizing, optimizing, making the most of, that's usually the tell. The words came from somewhere, and it wasn't from you actually enjoying something.

Another is to ask who the evaluator is. Before you log the hike or post the photo or check the box on the list, ask who that's for. If the honest answer is an audience, even an audience of one future version of you reviewing how the day went, that's the metric creeping back in.

A third is to let something be bad at being efficient on purpose. Take the long way. Do the hobby badly. Leave the trip half-planned. This isn't really about the wasted time. It's a way of practicing tolerance for the discomfort of not producing anything, which is exactly the muscle optimization culture has atrophied in most of us. This is what your journal prompt is about—make a plan around not making a plan.

Your Downshifting Journal Prompt Is:

What will you do inefficiently on purpose this week? Where can you go without GPS, figure out without help, or try without a plan?

And maybe the hardest one: stop treating the resistance to this as something you should get good at either. The moment "unlearning optimization" becomes its own project with its own metrics, you're back where you started, just with new vocabulary. The goal isn't a better system for resting or having fun. It's refusing the premise that either one needs a system at all.

That's harder to sell as a newsletter takeaway. It's also, I think, the only honest one.

I'm with you on this.  Let’s have fun.

xo,

S

Misc. Musings

-Fuck ICE.

-Maximum Pleasure Guaranteed on AppleTV is bringing me joy, because Tatiana Maslany of Orphan Black fame is an absolute joy to watch on screen, and we need more stories of dirtbag moms who always find a way.

-Reading: Nerve Damage by Annakeara Stinson. It’s weird and wonderful and edgy and cool.