Searls of Wisdom for February 2024

As I teased and subsequently recounted on my podcast (Breaking Change, available where all fine podcasts are sold), I decided to be that piece of shit flying cross-country with Apple Vision Pro strapped to my face three days after it launched:

Of course, here I am a month later typing this with the same computer strapped to my face, but from the much more socially-acceptable confines of my home office.

Overall, I'm prepared to call February a success, if for no other reason than it was sunny and 83ºF yesterday, which allowed me to spend a few hours lounging at the pool. Probably not great news for the planet, but absolutely clutch for my 2024 base tan.

Speaking of planes and sunny destinations, this month I want to write a little bit about how and why my perspective on travel has changed over the years.

Reason being, the experience of travel seems to be constantly getting worse along two parallel tracks:

• Individually: as people gain experience traveling over the course of their lives, they gradually reach a point of diminishing returns of dopamine as the act of travel goes from being breathtakingly novel to predictably mundane
• Universally: as airlines optimize, hotel chains consolidate, global cities homogenize, and social media drives overcrowding, we all have more cortisol coursing through our veins thanks to an objective increase in travel's unpleasant drudgeries

[Disclaimer: everything I'm about to say here is dripping with the tremendous privilege of having the time and means to travel so much of the planet that one could even imagine becoming bored by it. If you haven't had the opportunity to travel or are otherwise not as jaded as I am, I wholeheartedly encourage you to take the opportunity to see as much of the world as you can.]

I've talked to a bunch of people recently who feel they've reached some kind of tipping point, where the pleasure they reap from travel is now so much less than the stress they experience that it's no longer worth it. Why spend all that money for the privilege of squeezing yourself into a dirty tin can full of unruly passengers only to arrive in a city that looks just like every other city, stay at an under-staffed "luxury" hotel that charges half your mortgage payment each night, all to visit a world famous tourist destination overrun with people elbowing one another to take the best selfie?

Last summer, we visited Greece for the first time. We had an extra day to kill in Athens, so we figured if we were going to do anything we may as well see the Parthenon. Athens has a lot of remarkable qualities, but it's so impossibly congested that the combination of wildfire smoke and car exhaust made it difficult to walk for more than an hour before getting winded. Nevertheless, we braved the crowds and this is what we found:

If you think that's bad, here's a behind-the-scenes look at what takes place all day, every day a mere 100 feet away as people wait in line to climb the steps:

Sheer madness. What's there to do after reaching a site like this but take a picture, gesture an arm in the shape of a checkmark to your companions as you make a mock "swoosh" sound, and then suggest leaving as soon as humanly possible?

There was a time when the traditional approach to planning an itinerary—you know, picking a major destination, hiring a travel agent, and booking all of one's flights, hotels, and reservations months in advance—made logistical sense and resulted in enjoyable-enough outcomes. But in the winner-take-all attention economy, in which the same 50 global destinations attract billions of eyeballs glued to Instagram and TikTok (and which are attached to fingers that can book a trip in a few extra taps), it's increasingly unlikely that choosing a trending travel destination will lead to the majestic experiences portrayed in viral posts and reels.

You know it's bad when the influx of so many new millionaires (News+ link) has resulted in the ultra-wealthy retreating to the ends of the earth and to increasingly far-flung, seemingly undesirable destinations. Hell, I know two families who took cruises to Antarctica last year. (Both reported it was less fun than they imagined and that David Attenborough never tells you about how bad penguin shit smells.)

I, for one, want off this ride. I've seen plenty of the world. I've eaten the same disgusting KFC meal on four different continents, only to try (and fail) to wash away my shame sitting under the same Kohler showerhead before drying myself off with the same scratchy Hilton bath towel.

Surely, there must be a better way.

The better way

So, if out-of-control baggage fees have got you down, but you're still intent on leaving your house at some point: what does it look like for someone to travel well?

One of my best friends Jeff dropped a veritable truth bomb on me about his outlook on travel over a decade ago, and it's taken a long time for the wisdom of what he told me to sink in. He traveled the world long before I did, for far less money, and much more happily. The secrets to his travel success?

It was all about prioritizing four things:

• Depth of experience over breadth of geography
• Boring neighborhoods over luxury hotels
• Cultural engagement over sight-seeing
• Earnest improvisation over thorough planning

Do less. Stay rural. Skip landmarks. Decide as you go.

I'll share one quick story on each.

(Yes, I realize my travel stories are almost always about Japan. It happens to be the place on earth I've invested the most time in exploring, but all of these points apply just as well elsewhere!)

Depth of experience over breadth of geography

As a Type-A completionist, I have a bad habit of confusing whatever I can do with what I should do, and one way that manifests when traveling is to design whirlwind trips where I'm spending one or two nights in every locale, only staying long enough to see the most popular thing and eat at the highest-rated restaurant before it's time to move on.

But breaking that habit can pay off. Christmas before last, we rented an apartment in Osaka for eight or nine nights. We had a lot of friends to see in the region, but we made a conscious decision to stay in one place and travel each day to meet people as opposed to darting around between different hotels. In the end, I'd have stayed longer if I could, even though the apartment was on the top floor of a four-story walkup, not particularly well-maintained, and situated in a mildly-dilapidated neighborhood known for its (relatively) high crime.

The logistical benefits to emphasizing depth over breadth are obvious: fewer stays means less time wasted packing and unpacking, getting situated, and so forth.

Less obvious are the serendipitous joys of observing a place's subtle details over time. How things smell. The way the light moves throughout the day. Traffic patterns and people's schedules. It's surprising how quickly the brain flips from feeling as though one has merely stayed some place to having lived there.

And then there are the anecdotes that are only made possible if you plant ass in a single place for more than a few days:

• The apartment building turned out to be surrounded on all sides by love hotels, which made people watching a 24-hour source of free entertainment. I found myself frequently crossing paths with people whose day was just starting as mine was ending, only to run into them again at the same convenience store 9 hours later as I got my morning coffee
• I found a run-down coin laundry just a block from the apartment that wasn't listed on any maps and had (despite freezing temperatures) no doors. It didn't even have a change machine. As I got in the habit of washing my clothes there every other day, an older woman recognized me, struck up conversation, and—as thanks for breaking change for her, perhaps—even offered to wash and fold my laundry so I wouldn't have to wait on it
• I mistook a coffee roaster in the neighborhood for a cafe, and as the owner politely shooed me away, a customer of his overheard the conversation and took the time to point out his local restaurant where he brewed the man's beans. When I visited him the next day, we had a great chat about how the neighborhood had changed over the years. He didn't even charge me for the coffee
• I visited a nearby yakitori place and the bar was full of ruffians who were really pretty rude to me, with one mocking my mediocre Japanese (which only gets worse when I'm anxious). Rather than give up, I came back a few nights later and the staff not only recalled the exchange, they proceeded to teach me some new slang to aid in my task of clapping back at assholes

It can be really hard to force myself to slow down. I want to see everything, everywhere, as quickly as possible. But I can't think of a single instance where I ended up regretting taking my time, enabling all five of my senses, and mindfully engaging in an experience.

Boring neighborhoods over luxury hotels

The neon lights and skyscrapers of Tokyo's most famous wards are alluring to travelers, but—like most downtown cityscapes—they weren't designed to entertain tourists. I've tried, really tried, to figure out how to stay in a major city center and have a consistently good time. Alas, it always seems like everything is crowded when I need solitude, loud when I want quiet, and deserted when I'm feeling bored.

After finally internalizing that slower, more deliberate travel experiences are more rewarding than manic cross-country tours, I stumbled on a corollary: that I was better off staying in places designed to be lived in rather than commuted to.

In mid-2017, I had a few days to kill so I booked a stay in Shimokitazawa, an ascendent and hip neighborhood just west of Shibuya. (It's unfortunately taken off in popularity with travelers since then, so I don't know if I could recommend it in 2024.)

I chose it, in part, because other people seemed to love living there despite the fact its defining characteristics were decidedly not my jam. Shimo is often described as "bohemian", with vinyl record shops on every corner. Fashionistas swear by its selection of vintage clothing stores. For the intersection of antiquers and art snobs, it's a veritable paradise. I couldn't be less interested in any of those things!

But hell, it was only a few days—why not try on a different vibe to see what it feels like?

I dove in headfirst: browsed Japanese releases of my favorite LPs, saw a live performer playing at a small jazz venue, and ensconced myself in several bathroom-sized wine bars. I had too much dignity to walk into a fashionable boutique on my own, though, so I met up with a young woman we'd met at Tokyo DisneySea a couple years prior, and she kindly led me on a brief shopping tour through that side of town.

I met a lot of cool people during my stay, even though I confirmed that their scene is not my scene. That said, I just so happened to be there during the town's annual curry festival which was very much my scene. So I ate well, at least.

In the end, the fact I took this opportunity to immerse myself in a different subculture is something I'm grateful for. Glancing through a porthole into someone else's way of life is something you can't do if you're isolated in a business loop of skyscrapers and staying at a Park Hyatt or a Conrad or a Ritz Carlton.

If anything, one of my biggest travel regrets is that I chose to foist whatever hotel chain status I earned through business travel onto our vacations: instead of staying someplace we'd enjoy, I always prioritized efficiently cashing in tens of thousands of expiring hotel points. This incentive always screwed with my expectations. Worst case, I'd be disappointed by the level of service of each chain's top-tier brands. Best case, the hotel would be so amazing I never wanted to leave it (in which case, what's the point of being so far from home?).

The proof is in the pudding, I guess. Once I'd stayed in a few luxury hotels in urban city centers, I had trouble keeping major cities across Europe straight. Meanwhile, I find myself reminded of a detail from my long weekend in Shimokitazawa every month or two, at least.

Cultural engagement over sight-seeing

I have had a meaningful emotional reaction in response to witnessing a famous landmark a grand total of zero times.

(Actually, that's a lie. Getting into a nothing fight with one's spouse at the end of an exhausting day schlepping back and forth in record heat between Barcelona's various cathedrals and basilicas could be fairly described as "meaningfully emotional.")

I'd say I don't know why tourists visit famous landmarks, except that I do know. We all know. So we can say we were there. It's a way to stave off any sense of our lives' meaninglessness as if one could attain significance by association.

Fuck that noise. Buy a cameo from your favorite B-list character actor instead, it'll last longer.

Japan's perennial embrace of short-lived food trends taught me how futile it is to try to keep up with whatever's popular. Waiting two hours in line for a massive bowl of shaved ice that turned out to pretty much just taste like ice is probably the moment I snapped out of the fascination over what other people think is the "best" of any given thing when traveling.

When you're just one in a horde of humans swarming an intensely popular location or venue, nobody's going to learn your name. No waiter or waitress is going to take the time to engage in conversation. No one will remember you when you're gone.

While I'm still overly discerning in where I choose to dine, I've calibrated my search over the years to find hidden gems that aren't well known. And instead of forgetting each restaurant as soon as I check it off my to-do list, I try to make repeat visits to the places I like, even years apart. There's a noodle place outside my favorite temple in Kyoto that I've probably eaten at half a dozen times and which—while they serve excellent food—has cemented itself in my memory primarily due to its proximity to one of my favorite places.

Tokyo is a city of tens of thousands of bars, but rather than try to drink my way through all of them, there's this one bar in particular I've chosen as my "home base". It's in the middle of a wild nightlife district surrounded by inarguably nicer bars. It only has six seats. It has a limited bottle selection. I hope I never need to use its minuscule bathroom. But it's got an owner with great taste in music, and he's got a subversive sidekick who covers every third day, and they share a collection of clever and hilarious regular customers. No visit to Tokyo is complete until I make a pilgrimage.

Since I first found this bar, I've gotten to experience Tokyo longitudinally in a way I wouldn't have been able to otherwise. I've seen the cast of characters evolve and age over time. I've tapped into their perspectives like a focus group interpreting the news of the day. I met Hiro back when his beloved Hiroshima Carp were on top of the world, saw him again after they slid into mediocrity, and was there to congratulate him when they pulled themselves back to within spitting distance of the league championship. Visiting this bar is like starring in my own personal Cheers spinoff but all in Japanese and with less sexual tension but with somehow even more smoking.

Last year, shortly after the owner declared me a 大常連 (extremely regular customer) he realized I was headed to his hometown of Matsumoto for RubyKaigi and he insisted on setting Aaron and I up with his father for a private tour of Matsumoto Castle. It was over the top and amazing.

You can't understand a culture without forming relationships with locals and you can't form those relationships by following crowds of tourists. Simple as that.

Earnest improvisation over thorough planning

As a certifiable control freak, I can deeply understand the impulse to lock down every variable in the run-up to a trip. Know what cities you'll be in on what days. Make sure you've got a place to sleep every night. Book advance tickets that might sell out otherwise. Reserve the restaurants you really can't miss.

This is all well and good and there is nothing wrong with making detailed plans, except for the fact that not doing any of that is even better.

In all my travels, I've rarely been as bummed out as when I'm having an awesome experience someplace and suddenly realize I have to leave prematurely because I've already made plans to be someplace else instead.

Of course, some minimal amount of planning is absolutely necessary. Airlines typically won't let you board an international flight without a return flight booked. Immigration control may not let you in if you don't know where you plan to stay. Plenty of things worth doing require advance arrangements. I'm going to a conference in a couple months (and you should too!), and it only made sense that I'd buy my ticket and book a hotel room nearby as soon as I knew I'd be there.

But what I'm not doing is booking any transportation or lodging before or after that conference. I don't need to. The thing about planning is that for all possible values of today, Today Justin knows what Tomorrow Justin will want to do better than Yesterday Justin did (and much better than 3-Months-Ago Justin did). It's the principle of the Last Repsonsible Moment, just applied to travel.

Last year, I spent three hours at RubyKaigi's after-party in Matsumoto circling among different groups and asking them for advice on where I should travel next. A few suggested Hokkaido. A surprisingly large group was from Matz's hometown in rural Shimane and lobbied for me to follow them back there. Maybe because the spring weather was warming up, a surprising number of people pointed me to the southern island Kyushu and specifically its remote volcano-adjacent city of Kagoshima.

So I woke up the morning after the conference, decided the Kagoshima idea sounded like the most fun, and bought a train ticket while I walked toward the station. Booked my hotel en route. Eight hours later, I was enjoying the sudden climate transition (firmly T-shirt weather) as I slurped my first bowl of the local signature ramen. I must have been in an adventurous mood, because within a few hours of checking into my hotel, I proceeded to pour myself a stiff drink and only stayed conscious long enough to book the last available room on the remote island of Yakushima for the next night.

What followed was one of the most memorable excursions of my life. Simply amazing. I'm nervous I won't be able to top that experience. (Come to think of it, that's something I've never said about an activity I planned months in advance.)

Anyway, travel sucks but it doesn't have to

Thanks for giving me a chance to share my outlook on travel. I wish I'd been ready to listen to the same advice sooner in life, but I'm glad I finally did.

Okay, see you next month. Hopefully I'll be able to talk about how successful and trouble-free my first major bathroom remodel went.

Now, go away. I have to go book a few hotel stays for a trip that's two months out and here I wrote this big long thing making me feel bad about that. (But I'm going to book them anyway. Our better angels can't win them all.)