[NEED ADVICE] Planning to Transition from 正社員 to 契約社員 or Part-Time + Freelance

Hi everyone,

I’m currently in my third year as a 正社員 in Japan, holding a Specialist in Humanities visa valid until June 2027. I have a background in design and am looking to transition from full-time to a more flexible set-up.

I plan to approach my current employer to ask if I can transition to a part-time or contractual role to maintain my residence status. Simultaneously, I plan to register as a 個人事業 (sole proprietor) to take on a fully remote design role with a US-based company. I will be hiring an accountant to handle my taxes.

I have a few concerns re: the legality and logistics, I hope I can get some help here:

  1. Visa Renewal: My anticipated freelance income will likely exceed my part-time salary. Will having the majority of my income come from freelance work, rather than my "primary" sponsoring employer, cause issues during my next visa renewal?
    • Current 正社員 290k before taxes -> 契約社員 possibly 200k or less before taxes?
    • 個人事業 possibly 320k before taxes
  2. Hours & Compliance: How do immigration authorities typically view the split in working hours across two different roles? Are there any traps I should avoid to ensure I don't violate the terms of my "Specialist in Humanities" status?
  3. Social Insurance/Taxes: If I move to a part-time role, will my employer still handle my 年金, 健康保険, and 住民税? Or, once I become a 個人事業, do I become responsible for paying these independently for both roles?
  4. Immigration Precautions: Are there any steps I should take to ensure I am fully compliant?

Would love to hear about anyone with similar experiences to mine! Thanks so much

by EmuOdd7883