How to Stay in Japan?

I'm in a bit of a unique situation. I am US military stationed in Tokyo. I have lived here since 2022 and my assignment here is until 2025. My problem is that I love Japan and I do not want to go back to the US. I feel like three years in Japan is not enough for me and I want to stay here longer (although I don't know for how long). Thus, I am trying to figure out the best way for me to stay in Japan. The current setup I have is perfect: I work as a US pharmacist and make a US pharmacist salary, I live in a standalone house in Tokyo (huge by Japan standards) near the Chuo and Ome Line which makes it easy to travel anywhere, I get 30 days of leave/PTO per year plus all Federal holidays off plus extra days off as rewards for various things, I get to practice pharmacy while also doing fun/cool/adventurous military things, and to top it all off I get to do all that while serving a purpose greater than myself that I believe in (mostly). Unfortunately, with the way the military works it cannot last forever. So the main hurdle I need to figure out is what kind of job I should get, how to get it, and how to best steer my career. Since I am a pharmacist by trade, a job in which I can use that skillset so it doesn't deteriorate while maintaining a high-ish salary would be ideal (>$60-80k annually, which is even low for a pharmacist but that's enough for me to care about earning). I am not totally committed to the pharmacy career field (while I am grateful to have such a lucrative and secure job I find it boring and unfulfilling), but it might be the only way for me to maintain my current salary, and if I get a non-pharmacy related job it might be difficult for me to go back later. Some options I've thought of so far:

1) Find a US-based remote job that will let me work from Japan. I feel like this would be the most ideal option, but I don't know if I will be able to find a US employer that would be willing to let me work internationally, especially as a pharmacist. Maybe I could find another medical-related, non-pharmacist remote job, but the salary would likely be significantly less. I also don't know if this is something I could permanently do for the rest of my working life. As for visa/immigration, I have a Japanese girlfriend that I might be marrying in the future so that's not an issue I'm concerned about right now.

2) Try to get assigned to another military base in Japan after this assignment is up. The problem with this is while it buys me a few more years in Japan, I will be in the same situation I am now in another few years. However, this would allow me to take more advantage of some benefits the military offers, one of which is a Masters Degree program in International Relations that the military pays for. I could then use this Masters Degree to help me find another job that might help me stay in Japan. In addition, if I get another assignment I will be likely be placed in a higher level of command, which would help me in terms of overall career progression and probably job competitiveness as well.

3) Try to find a regular civilian job in Japan. I am really trying to avoid this option for the reasons we all know (poor work culture, long hours, poor treatment of foreigners, and low salary and high taxes to top it all off, etc). Compared to a remote or military position, this would likely make it a lot harder for me to travel as well, which is something I'd like to do if possible. It'd also be nice to be able to visit my family in the US on occasion, which would likely be difficult with a regular Japanese job.

These three are the only paths I can think of so far; if you can think of any others please educate me. I have some big life choices to make soon so I would be very grateful to hear any input or ideas!

I'm not sure how the agreement works with being in the military to stay in Japan vs. working and living in Japan through the means of a work, student or spouse visa. Do you have some kind of special visa that is from the military that allows you to stay in Japan? There are many questions to ask and it's honestly not just a straight-forward answer.

How long have you been in Japan now?

You said you want to work in a pharmacy, do you mean within the scope of the military with English-speaking clientele? Do you speak Japanese?

Have you ever tried working in Japan before? (Work life is absolutely draining and terrible in Japan.)

What's your actual goal in Japan? If you were to change your visa, the only ways to really be able to stay and work would be either a student visa, work visa to work in an actual Japanese company or a spouse visa.

Do keep in mind, there are always caveats to any of these options as Japan makes things quite difficult for foreigners to work and live in Japan and always needing to update their visa each year, unless you're lucky to get 3 years to update it.

As mentioned, there are still way more questions involved and it's not just so simple to answer. I'm still confused on the pharmacy idea you have in mind. Why do you want to work in that field specifically and I'm curious how you'd be able to do that in Japan unless you're absolutely fluent in Japanese and medicine.

There don't appear to be nationality requirements to work as a pharmacist in Japan. Instead, you must have already cleared certain difficult conditions, including obtaining N1 level of JLPT, completing a 6-year program at a pharmacy school, and fulfilling other requirements. In addition, passing a national exam is mandatory, and in this exam all subjects are conducted in Japanese.

I don't know your language proficiency, and while I'm glad to hear about your love for Japan, but here I must mention that this dream is likely to be very long and tough one to achieve.

Easy one first, option #1 does not work. Employed by a foreign company but being physically in Japan is not "working in Japan" and you would not have a status or residence.
Second point, your salary paid by the military is quite high by Japanese standards. If you were working locally as a pharmacist (fully fluent and with the requisite qualifications) you might start around 8M ($50k), but going outside of that what would you do that would or could half of that?
There is someone on the forum that works in the pharmaceutical industry that might chip in. I have a friend that recently started a job in the medical field - they're earning around 3M/year - not much.

Would like to add option #4
Work for a global company in Japan. I myself work in an Irish global large CRO (Clinical Research Organization) in Japan and I am surrounded by pharmacists. Alternatively there are global and local Pharma companies.

US based Pharma companies or CROs may also have a program to hire ex military. I know that my company (ICON) has such a program. Itfs obviously geared towards people in the US, but if you get in your application at a more global level (eg for a position as a Project Manager) you might appeal to these companies as being a veteran.
https://careers.iconplc.com/veteran-leadership-training-program

If you have Japanese skills (at least N2) that would be preferable. In my experience most jobs in this field in Japan are mostly focusing on Japan rather than the wider APAC field and even in global companies internal communication in Japan tends to be in Japanese. But (me included) I have colleagues who are not perfect at Japanese. But I think in my company everyone is at least at N2.
You might land a more regional / global role where that isnft important. Eg I know someone at Novartis marketing in Japan and she speaks virtually no Japanese at all.

The salary in this area is good compared to Japanese standard. Not as good as maybe in Europe (I donft know about US) but you can easily live with it.

I would suggest you reach out to some recruiters such as Michael Page (but there are many others out there) to test with them the attractiveness of your profile to these companies. Recruitment in this area is continuously ongoing and there is high demand.

BTW, this work culture thing I think is a myth to a large extend.
I worked at a US global CRO in Spain for 8 years then moved to Japan and worked for a Japanese domestic CRO for 5 years and now work at an Irish global CRO in Japan. Yes, I work more than 37,5h per week. But I am not working more now than I was working in Spain. Even in the Japanese CRO I was working normal hours.
And if I look at my US colleagues and the hours of the day they are sending emails I definitely think they are working more and at worse hours than I do. Plus in the US you also only get a low number of PTO days, are supposed to take PTO when you are sick etc. If you want a lot of PTO then neither the US nor Japan is made for you. Then you need to move to France. But PTO in Japan isnft that bad. There are I think about 17 public holidays per year (which is a lot) plus many companies close for a few days around New Year , Obon or GW. And your PTO allotment increases year over year. I am now in my 4th year and have 22 days of PTO. (Plus the days the company closes and the public holidays)
Yes, many Japanese donft take all their PTO, but there is a law now that you must take 5 days. And there is no reason for you to follow that culture of not taking PTO. I always took all my holidays. Yes, maybe may I get away with it easier because I am not Japanese and simply donft feel guilty about taking PTO. But so you are.

And the drinking culture also has reduced a lot compared to a few years ago with Covid.

So for me working in Japan or Spain doesnft really make a difference in my work life.
Working in Germany is a bit different where people are kind of supersentitive to overtime, PTO and work life balance to a degree that seems a bit overly protectionist to me (I am German but only worked for about 3 years in Germany).