Part-time Job or Self-Employment? Planning for health insurance post-retirement/pre-Medicare
I am 56F/husband 58m, with 29 years in at a job with a pension and a low seven figure 401k and a low five-figure HSA. Debt free.
We are starting to think about what retirement would look like. If I leave my current position, we will be needing health insurance to bridge to Medicare.
I would like to find a resource to learn about different scenarios and tax ramifications, specifically about health insurance, which will be our biggest expense. We are planning based on the assumption that subsidies will not be there.
I may be able to work out some part time employment with different startup companies I’ve worked with in my current role. But I would like guidance on how to structure that.
Is it more advantageous to be an employee and have my comp in the form of a HRA? Or should I go 1099/self-employed so premiums are deductible? Any guidance or resources that would be recommended?