This month, I took my first vacation in a while, and visited Japan for the first time. It was an amazing trip—I'm definitely going to be one of those annoying people who can't stop saying "Well, Japan does it this way, which is way better than how it's done here" about literally everything. I used to travel a lot (college debate), but since starting a company I've been a bit busy, and I haven't travelled internationally since November 2022, around when ChatGPT first launched.
A lot has changed and improved about AI assistants in the interim, and I noticed the difference it made on this trip. In the future, this will all be normal and unremarkable, but it's interesting to be living through the change as it's happening. That's what this post is about. (I might blog about how great Japan is another time, but I feel like that's been covered pretty exhaustively by every tech bro who's visited Japan.)
The Pre-ChatGPT Era
My last two international trips were to Australia and Korea. Australia happened before ChatGPT came out, and Korea was before it could do anything useful. I remember finding my solo travelling experience in Australia underwhelming, other than the Sydney Opera House, which was beautiful. Sydney might just be overrated (I think it is; Melbourne is way better in my opinion). But also, solo travelling creates an overwhelming and stressful planning experience for someone with my disposition (doesn't like committing to anything way in advance, wants to keep options open, overanalyzes the opportunity costs of doing X instead of Y, and so on).
Korea was better because I was hosted and shepherded around by a friend who grew up there, but it was easy for me to imagine how lost and confused I'd have been if I didn't have that support. In contrast to these trips, I found Japan to be straightforward to get around, not too stressful to plan last-minute, and easy to leave room for spontaneity without missing out. A big reason why was Claude.
Always-On, Contextual Translation
It's so obvious it doesn't need to be said, but having a little dude in your pocket that can speak somewhere between 50 and 100 languages fluently is pretty neat. The little dude also has a bunch of background knowledge, so unlike Google Translate, where you type in words and hope that it gets the right formality and context, Claude and ChatGPT gave me the perfect things to say for my situation: "I'm done eating," "Sorry for bumping into you," "No, no, please go ahead of me to use the udon ticket machine because I'm going to take 2 hours to pick out the one I want," and so on.
Also, menus. In the Olden Times, translation meant either typing (I can't type in Japanese) or speaking (can't really do that either). Now, you can just take a picture of the menu, or the udon ticket machine, and be like "what's this," and usually get a pretty good answer. Lots of the travel advice I got was "You'll have better/more affordable food if you go to a place with less English," which is all well and good, but before Claude I probably would have had a meltdown trying to order in a place like that. This new superpower meant I didn't really have to stress about where to eat—I could walk in wherever, plop down at the counter, and the little dude in my phone would help me figure it out.
Curiosity Black Hole
Solo travelling is lonely. One of the fun things about being in a new place is observing things and talking about them with your friends.
Why are these guys dressed up so nice on the bus at 11am? Shouldn't they be like at work or school or something? Why are these older ladies all getting off at this stop? Where are they going? Everyone in SF seems to think Buddhism is about meditating really hard and experiencing bliss. What's going on with all these deities? Is this a rice field or a tea field I'm seeing out the shinkansen window? And where's Mount Fuji??
When you're alone, you have no one to ask questions, share your intrusive thoughts, or unpack whatever just happened. Maybe some solitude is a good thing—there's something to be said for being a lonesome man brooding in the streets of Tokyo on a cloudy day. But I enjoyed having a "companion" to bounce all my thoughts off of.
This was especially nice in museums, where the posted information doesn't always give you enough context to really understand what's going on. (And it's been a while since I studied world history.) "OK, so they were making sculptures of horses in the Kofun period. How did horses get there. Who brought them over? Wasn't that expensive? Why did they bring over horses?" Basically, thanks to AI it's ok to be a kid again and ask a bunch of silly questions, and no one gets annoyed at you, except maybe the person behind you trying to also see the horse sculpture while you're asking questions about it on your phone.
Anxiety Balm, Planning Lubricant, Sponteneity Slot Machine
AI labs love to use trip planning as an example of how their models can be useful (it's bland and doesn't scream "we are going to take your jobs," and it's simple enough that it won't fail on-screen). But these have never been super compelling to me. If you go to Claude or ChatGPT and say "Plan my trip to Tokyo," it will come up with the median Reddit opinion of what you should do in Tokyo, which is fine I guess, but not particularly special. You might get a bit further by providing extra information about yourself and your interests, but even then, you'll get like the 3 most generic popular things with a high semantic similarity to that interest.
However, I did find the models useful for planning—not just in the way it was shown in the demos. I started planning my trip by asking trusted friends for recommendations (thanks, Thomas!). This is a much better starting point than random Redditors. Then with a universe of known good ideas, the AIs became useful for actually executing on the plan. It's a bit like coding—you have to know what you're doing to know what to ask for, but once you do, you can get good stuff out. I could never do all the things on my list, but I was able to triage, figure out which things made sense together, set reasonable numbers of things to do each day, and so on.
More importantly, though, as I alluded to earlier, having a "safety net" of sorts made it easier to take it easy and be spontaneous between the bigger, planned items. People with anxious tendencies like me often worry about ending up in a situation where they over-plan, leaving no time for serendipity, or under-plan and end up bored in a hotel alone. This would have been a huge problem for me, but it wasn't, because relying on Claude/ChatGPT meant I didn't have to fear the second situation as much. I knew as soon as I settled wherever I was staying that night, I had a planning buddy that could suggest things to do at time T near place P based on my interests, and probably, it would be fine. It was also helpful for navigating specific situations while I was in them, like buying a shinkansen ticket, boarding the train, using coin lockers, all that stuff. It's sort of like having a concierge who can talk you down from the cliff when you're freaking out about messing your trip up.
Allowing the trip to be more spontaneous made it better in many ways. I was able to make a game-time decision about whether to throw in Kyoto and Nara (which I did, and I was really glad I did). The old me would have given up on this, because handling all the logistics at the last minute (shinkansen tickets, hotels, how late can you stay without getting stranded in Nara) would have overwhelmed me, and I'd have probably chosen to play it safe. Things that would have taken multiple Google searches, hours of poring over Reddit comments, and so on are now a couple keystrokes away.
Conclusion
Travelling now is different than the Before Times. There was something charming and analog about the old way that future generations will probably never understand. (Although, c'mon, it was over once we invented smartphones.) But what surprised me the most was that relying on new technology allowed me to, in many ways, have a more analog trip, spending less time panicking, Googling, and planning, and more time living in the moment, knowing it would all work out.