So, a few years ago I wound up flying more than usual and wound up qualifying for United Airlines “Silver Premier” status.  Which is the bottom tier of their frequent flyer program, but which comes with some really handy benefits like extra checked bags and pretty frequent upgrades, at least when flying domestic.

It was handy enough that, after the first year of it, I haven’t wanted to let it lapse.  This has lead to the occasional very silly flight near the end of the year to make sure I’m meeting the requirements to keep it.  Usually I fly to Redding because it’s cheap but involves a lot of flight segments.

Anyway, I spent a lot of 2025 unemployed so I was not doing much flying.  As a result, keeping my silver status was looking really unlikely – it would have meant flying to Redding like 4 times!  I actually have a favorite coffee place there, but it’s not worth the flight by itself.

On the other hand, international flights give a lot more credit towards flyer status, and I do like going to Japan… but there was no way on earth that I was going to get time off at this time of year, especially with little notice.  I am very new to this job and I don’t have the seniority it would take to get a week off around the holidays.

On the (third?) hand… technically I was hired as a remote employee.  And while it’s not strictly speaking legal to work (even remotely) while you’re in Japan on a tourist visa it’s not like I was worried about the police breaking down my hotel room door to tell me to log off the VPN.  So technically I didn’t NEED to take time off as long as I just, you know, kept logging in and doing my job.

I mean, I wasn’t brave enough to get permission to do this.  I’m working on the principle that nobody told me I couldn’t.  Hopefully that will not come back to bite me.

The problem, naturally, being a 17 hour time difference between the place where my job expects me to be and the place where I wanted to be.  I worked the math out, and I would need to be online from 1 AM until 10 AM Tokyo time to keep up my normal shift in the US.

Could I do this?

It turns out… yes! At least for a week.  I’m not sure I would have wanted to try to keep it up any longer than that.  I especially would not have wanted to try to stay on this schedule through a weekend, for reasons that will probably be obvious.

The schedule I was keeping was very similar to when I worked the graveyard shift as a 20-something.  I’d wake up around 12:30 AM, log on to work, put in my shift and then get some living in between 10 AM and 5 PM, when I would crash again.

The reason this worked out for the five days I did it, but would have been a problem if I’d tried to keep it up was, well, there’s probably plenty to DO in Tokyo at 3 in the morning but probably very little of it is anything I would want to do.

Anyway, here were some of my takeaways from the experiment, starting with the things that didn’t go super well:

Firstly, I was expecting to be able to use the in-room TV as an external monitor.  My job is absolutely impossible to do with a single screen and I didn’t want to bring along a bulky-yet-fragile portable monitor.  Finding out that the hotel room I’d booked had a TV that was completely across the room from the only desk was, therefore, a bit of a setback.

Fortunately I had packed a HDMI-to-USB-C capture card, and there’s a free app for the iPad called Genki Studio that lets you use this to use the iPad as an external display.  I only have an 11″ iPad, so text was VERY small, but I made it work.

Secondly, the chair in the room was painfully low.  I wound up stacking every pillow I could find on it to get it up to a reasonable height.

Third, you would think that being in this sort of situation would make you really focus.  It didn’t.  I need distractions during my day and just didn’t have any really.  I wound up eating WAY too much, and a lot of it was junk food.  Towards the very end of the trip, I discovered that there was a supermarket next to the hotel so I was able to actually get some fresh fruit and yogurt instead of combini junk and felt much better about myself.

A side note: The hotel didn’t have in-room microwaves and there was no communal microwave.  Eating my “breakfast” and “lunch” cold was depressing.  Eventually I found that I could take my “lunch” at 5 AM and go and buy something from the nearby 7-11 which had microwaves.

Finally, I was happy to see that there was an ethernet jack under the mirror at the desk I was using to work from, and I’d even packed a USB-C ethernet dongle.  I was less happy to find that the jack was completely dead.  I poked around the room a bit and discovered that I could sort-of get to the infrastructure…

…but even plugging directly into the switch, I was only getting about 100mbps.  Which wasn’t any faster than the WiFi.  So I suspect that they only give each room 100mbps to work with, though admittedly that is PLENTY for Slack and email and the occasional Zoom meeting.

(Oh, on the topic of Slack?  It tried very hard to rat me out.  It was like “this person appears to be in Japan! let’s set their out of office statuses accordingly!” and I had to override it to tell it to pretend I was in California.)

OK, that’s the negatives.  There were some things that were awesome about working those hours, starting with the fact that I would get off work at 10 AM, just as things were opening but before any crowds could form.  That is my new pro tip for Tokyo travel – be at the place you want to be at before 10:30 AM.  Even places like Harajuku that are traditionally wall-to-wall tourists were very navigable at that time, though by noon the crowds had really kicked in.

Also, it’s Japan.  Even only getting a few hours a day was still a really good time.  I ate a lot of tasty food, I bought some cool stuff to bring home, I got to practice my language skills.  I’ve visited often enough that the novelty of places like Akihabara have really worn off, but I do love Tokyo.  Something about the way that 37 million people in one of the densest places on the planet can more-or-less get along without dissolving into chaos makes me feel comfortable.

Plus I saw possibly the coolest thing I have seen yet, and I regret that there was no feasible way to walk into the dealership and say “crate one of those up and ship it to this address in America”

Yes, it’s a goddamn Hello Kitty Super Cub.

And of course the big positive was that it got me the rest of the credits I needed to keep my mileage status.  Probably.  I’m waiting on the credit from the ANA flight from Narita to San Francisco to kick in, but that only takes a couple of days.