Moving to Japan from Singapore, what are our best options?

Just want to say that I love this sub, I’ve read many posts and you wonderful people have been very helpful; I’ve learnt a great deal just from lurking around here!

So last month wifey (F31) and me (M40) made a trip to Japan, stayed in the countryside with a couple of friends and love the country so much that we are now considering moving there, at least for a year to fully experience it. I know, we are so unique! /s

We are Asians, degree holders, currently in Singapore, quite a decent place itself.

This is not my first time to Japan, and I’ve always loved the culture. While I don’t know Japanese, I know Chinese and I’m a language lover so I think taking up Japanese will be a nice challenge.

I’ve read all the information in the Wiki of this sub (shout out to the amazing Mods for the diligent job compiling it, it has helped me a great deal!!!).

I’m self-employed, earning a decent tech salary (quite comfortable for Singapore). Wife is at the beginning of her career in Singapore and struggled a bit too adapt to Singapore but she’s getting on well.

We are exploring a few options:

1. Wife gets a visa to study something in Japan for a year (she loves craft and Japanese culture). I tag along and work remotely. Pros: we may get to experience the countryside. Cons: wife’s career disruption. She’s having two minds because while she loves to study craft, she also loves her current job which didn’t come easy for her.

2. Wife gets into a company that allows internal transfer to Japan. Pros: less career disruption, easier time adapting. Cons: It takes more time to plan this move, and we’ll likely end up staying in Tokyo, not the country side as we are hoping for.

3. I arrange for a GEO to hire me in Japan and get paid by my own Singapore company. I need to research more on the legality of doing this. Wife then can work remotely for her current company. Pros: we can live in the countryside. No disruption to both our careers. May be fast to arrange. I may be able to even get a skilled visa which will fast track me to Japan PR in 3 years (it’s not the primary concern, but seems great nevertheless). Cons: costly (GEO cost, paying Japan tax, may affect my Singapore residency if I stop paying tax).

4. Wife or myself go for a master’s degree in Japan. The other tag along and work part-time. Pros: upskill ourselves. Cons: costly. Most likely we will also have to stay in the bigger cities.

We’re still doing priliminary research and are considering those options for now.

I would love to find an option that allows us to live in the countryside without disruptions to either of our job. Option 3 seems great and we will probably research further into this.

Do you think my priliminary assessment looks correct? Did I make any wrong assumptions, or missed out on any important points? Is there any good paths that I missed out?

Thank you so much wonderful people!

by Acceptable-Trainer15

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