Need advice: US tech worker (40y/o) moving to Japan to join Japanese spouse – finance/career tips?

I'm a US citizen in tech (user experience designer at a regular corporate job, not FAANG/big tech) who recently married my Japanese spouse (in Japan). We've decided I should move to Japan first, with plans to eventually return to the US in 1-5 years. Spouse visa process is underway and expected to take 2-3 months. I'll need to leave my current US-based job when I move, as they can't support remote work from Japan.

Key Context:
– I'll be living in Tokyo
– Almost no Japanese language skills currently
– Have ~1 year of modest savings to live on
– Spouse works full-time in Tokyo (moderate income, nothing fancy)
– We're planning to start a family soon
– Will likely move back to US in 1-5 years to be near aging parents
– Looking for stable income; bonus: if it allows freedom to do side gigs
– Prefer simple tax/paperwork situations due to (actual) OCD that makes complex administrative tasks especially stressful

I'm considering these options and would deeply appreciate advice/insights from others who've been in similar situations:

  1. Start freelancing/contracting
    Pros: Flexibility, potential for higher income
    Concerns: Never freelanced before, dislike networking/sales, weak portfolio, unsure whether to structure as US LLC vs Japanese business entity (godo kaisha), uncertain about targeting US vs Asian vs Japanese clients

  2. Find role at multinational US company
    Pros: Familiar work environment, easier taxes, likely better pay and stability
    Concerns: Few openings in my field, highly competitive, previous experience at big corps wasn't great

  3. Work for Japanese company
    Pros: Local presence, less complex tax situation(?)
    Concerns: All recruiters say to wait until I'm in Japan before giving interviews, language barrier, lower typical compensation

Looking for:
– Experience from others who've made similar moves
– Suggestions for options I haven't considered
– Specific advice about business structure if going independent
– Recommendations for finding English-speaking work in Japan
– Tips for managing international finances/taxes
– Ways to make this transition smoother

I know this is a lot to ask, and I'm grateful for any insights or advice you can share. I'm not looking for an easy path – just trying to make informed decisions. Thanks in advance.

by breaksofast

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