Follow-up: moving from full-time to contractor – finance questions about the transition

Hi everyone,

First of all, thank you to everyone who commented on my last post — the advice was super helpful and gave me a much clearer idea of what to confirm before moving forward. For reference, here’s the original thread: https://www.reddit.com/r/JapanFinance/comments/1n2obid/transitioning_from_fulltime_employee_to/?utm_source=share&utm_medium=mweb3x&utm_name=mweb3xcss&utm_term=1&utm_content=share_button

After thinking it through, I’ve decided to go ahead and take the contractor position. Now I’d love to get your advice on the transition phase, specifically from a finance perspective.

My current situation:

• Since it’s a contract position, the new company (via the recruiting agency) wants me to start relatively quickly.
• At my current company, I’ve already arranged for someone to take over my duties.
• Ideally, I’d give my company 1 month notice.
• I have quite a lot of paid leave days piled up.
• I’ll be joining the social insurance of the recruiting agency as soon as I start as a contractor.

Questions I’m struggling with:

1.  Is it allowed to remain “employed” by my current company using my paid leave while also being employed as a contractor enrolled in another company’s health insurance?
2.  If there’s an overlap (say, I’m officially employed by both in October), would that mean I’d be paying double health insurance/pension for that month? And if so, is that calculated and paid monthly, or adjusted later?
3.  In that case, would my current salary in that overlapping month realistically offset the extra costs?
4.  I also need to double-check, but if I’m still officially employed at my current company in October, I think I’d still be eligible for the performance bonus that’s paid out in December.

Would really appreciate any insights from people who’ve navigated this kind of handover or had overlapping employment in Japan.

Thanks again for all the advice last time!