I am late-30s, American digital designer planning to marry my Japanese fiancée in November in Tokyo. I don't live there yet but will travel there for marriage. Immediately after, I will get a spouse visa (which seems very permissive for work/starting businesses) and move to Japan a few months later.
I've never done freelancing before and would like to use this as an opportunity to start. I'm wondering if anyone has advice: Would it be better/easier to:
- base the business in the U.S., and then operate it while in Japan, OR
- base the business in Japan once I'm there?
Key details/concerns:
- I'd likely be solo, not take on employees. Assuming I'd do sole proprietorship or LLC (or the Japan equivalent of an LLC)
- I have low literacy with taxes and business stuff in general, so I'd likely rely on outside help for tax prep/business setup. Would favor whatever option is least complex from a tax/legal perspective probably, even if I sacrifice a little money to do so.
- In addition to freelancing for others, I'd like to be able to launch little side projects I can potentially monetize. Eg. Make a paid web app, launch a small paid iOS app.
- I'm mildly worried about legal liability if something blows up, so anything to reduce personal liability seems good. – I unfortunately know VERY little Japanese, so I'll work entirely with English-speaking clients (likely in U.S. but Japanese or APAC clients who speak English would also be great if it's an option).
- We would stay in Japan for at least a year but may move back to the U.S. depending on other factors. Could be 1 year, 5 years, or maybe never.
What I'm seeking:
I'm overwhelmed at this point. I've done a lot of research online but I still don't have a strong sense of which option is better. If anyone could share their experience or advice (esp. if you've got through it yourself) I'd be incredibly grateful. 🙏
by breaksofast