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Leaving my job to go back to school. Want to keep insurance for as long as I can.

I got accepted to school that will lead to a career in medicine, so I need to quit my current job. I am a late career switcher and currently crunch numbers. School (full-time, in-person) starts in two weeks (5/29) and if I play by the rules and give a two-week notice, I need to tell my supervisor and HR that I am leaving this week. I know I don’t have to give a two-week notice, but it’s expected. However, I have a family (husband and kids) who depend on my insurance. My company pays 3/4 of the cost, so I pay $400-500 a month for the family. If I leave on 6/1, I get to keep the insurance for the whole month. If I give my notice this week, I doubt they will let me set my last day as 6/1 and will just tell me, 5/31. I have accumulated…


I got accepted to school that will lead to a career in medicine, so I need to quit my current job. I am a late career switcher and currently crunch numbers. School (full-time, in-person) starts in two weeks (5/29) and if I play by the rules and give a two-week notice, I need to tell my supervisor and HR that I am leaving this week. I know I don’t have to give a two-week notice, but it’s expected. However, I have a family (husband and kids) who depend on my insurance. My company pays 3/4 of the cost, so I pay $400-500 a month for the family. If I leave on 6/1, I get to keep the insurance for the whole month. If I give my notice this week, I doubt they will let me set my last day as 6/1 and will just tell me, 5/31.

I have accumulated over a month worth of vacation time. If I separate, they will pay me for this time. However, I will lose insurance.

COBRA will be expensive, and with one income it’s too expensive (since now we have to also pay for school). I know that I can use COBRA retroactively should I need it, but I do know I will need insurance because my child has a medical condition that needs to be treated. The plan is to eventually get a plan similar to the current plan I have (it’s roughly $1500). But! The rules in my state are that if I sign up for it from the 1st to the 15th, I will have insurance on the 1st of the next month, but if I sign up 16-31, then I will get it the following month and will have a gap in coverage.

So my plan is to not say anything about leaving this week. Tell them I will be taking vacation for the whole month of June. Then comes July 5 (I want to get paid for July 4th), I tell them I can’t come back because I just got accepted to school and school starts now, but that I would be willing to transition any remaining work in the evenings. I really don’t like this plan but I need to keep my insurance for as long as I can for my family, and I don’t see any other way to do it. I don’t want to burn bridges as my supervisor has been very nice and accommodating for the past several years.

Is there another way to accomplish what I need to accomplish and leave on a good note?

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