Maui Didn't Hit

TL;DR: I came to a better understanding of my dislike for pure leisure after a disappointing trip to Hawaii, and course correcting for it since has improved my downtime.

I went to Maui for ten days last August, and I didn’t like it.

To be clear, this was a “It’s not you, it’s me” situation. Nothing against Maui itself—it just wasn’t a good fit for me.

Here are the reasons why I didn’t like it.

The ratio of travel time to familiarity was high. It’s a long flight from the Midwest to a place that, to me, felt less strange than parts of Florida.

There were a lot of tourists. Families with young kids, college students. No disrespect to them. But it all amounted to even the “hidden” beaches being packed, and I was surprised to not feel like I had space to explore.

I stayed in a resort hotel. It felt like a mall with bedrooms inside of it. I hope to not stay in a place like that again.

Maui was difficult and dangerous to navigate. You need a car. The roads are either treacherous highways with no center barrier or windy backroads with blind turns. Not helping this was that, on my first night there, I sat at a bar for dinner, and the guys next to me had several rounds of drinks before casually getting in their cars to drive home.

I didn’t know anyone there. Not even a friend of a friend. A friend of mine, who happens to have a large-ish Twitter following, tweeted to see if anyone in his network knew someone I could meet up with. Somehow no one took him up on it. Most people I talked to on the island were, see above, tourists who I seemed to lack compatibility with, and I ended up with too much time alone.

The main reason I think I didn’t like it, though—and I came to understand this after this trip—is that I’m bad at leisure.

I don’t find “chilling on the beach” or pure relaxation restorative. I prefer to be doing something—solving a problem, making something, putting effort toward something. When I go to the beach, I go to swim some distance. Not really big on splashing around. If this sounds like a flex, I’d actually prefer it the other way.

By the way, I literally don’t know how to write about what I’m thinking without saying something that could come across as a flex and so I’m starting to not care so much about it. Is that a flex?

Anyway, getting back to the point, I’d suspected I had this kind of disposition for a little while. I’ve gone to other places before and “hopped around town” for a few days, only to feel weird and anxious afterward.

Maui was disappointing, but it helped me confront an unconventional part of myself, and I’m already better off for having accepted it. Now, I plan my trips—and also weekends—accordingly. I preinstall things like work and projects to do, even mini ones, and I feel, like, five times better because of it?

I’m thinking that other activities that tend to default to leisure would also improve if I planned them otherwise. One that seems obvious as I’m thinking about it now is dating. I feel like date activities tend to center on keeping things casual and low-effort. “Just grab a drink.” “Feel the vibes out.” But I think I’d have more fun and probably be a better version of myself on dates that involve doing something.

Here are some ideas that sound better to me than meeting at a restaurant.

Maybe some of these are bad ideas. I’ll have to see. All to say, I suspect I’m more fun and a better version of myself when I’m engaged in something, rather than just chilling.

Anyway, here are some photos I took in Maui. The swimming was pretty good, actually. Now that I think about it.

I’m surprised to see this blog starting out as “strategies I’ve stumbled into for improving my life,” but it’s what I’m currently thinking about, so I’m going with it for now. I would probably give this blog post a C-, but I’m putting it up anyway. Hopefully the next one is less weird.

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