# Help me with this health insurance conundrum **URL:** \ **Category:** In My Humble Opinion\ **Created:** [June 4, 2026, 12:58pm UTC](https://boards.straightdope.com/t/help-me-with-this-health-insurance-conundrum/1030613 "2026-06-04T12:58:59Z")\ **Posts on this page:** 3\ **Page:** 1
**Author:** ![2\_More\_Bits](https://sea3.discourse-cdn.com/straightdope/user_avatar/boards.straightdope.com/2_more_bits/32/4148_2.png) [@2\_More\_Bits](https://boards.straightdope.com/u/2_More_Bits)\ **Post date:** [June 4, 2026, 12:58pm UTC](https://boards.straightdope.com/t/help-me-with-this-health-insurance-conundrum/1030613/1 "2026-06-04T12:58:59Z")
I own a small business but have some serious health problems and want to retire. (The business is good and I am confident it will sell, possibly quickly) Currently I get health insurance through a group plan the business buys (group= Me, spouse and one full-time employee). I won’t qualify for Medicare until July 2027. What do I do about health insurance if I sell the business before then? The group plan will cease to exist with the sale of the business so I don’t think Cobra is an option. I think an ACA plan would work but my understanding is that there is a rather small enrollment period window and so the timing of a business sale would have to be ideal. Anybody have any suggestions? ---
**Author:** ![MinkMan](https://sea3.discourse-cdn.com/straightdope/user_avatar/boards.straightdope.com/minkman/32/19170_2.png) [@MinkMan](https://boards.straightdope.com/u/MinkMan)\ **Post date:** [June 4, 2026, 1:13pm UTC](https://boards.straightdope.com/t/help-me-with-this-health-insurance-conundrum/1030613/2 "2026-06-04T13:13:37Z")
According to [healthcare.gov](https://www.healthcare.gov/coverage-outside-open-enrollment/special-enrollment-period/), a loss of existing health care coverage due to a change of employment counts as a qualifying live event that allows for you to enroll in a ACA marketplace plan outside of the normal enrollment periods, so it sounds like you should be ok with that route. YMMV and I’m just a schlub on the internet, so verify things yourself blah, blah blah… ---
**Author:** ![griffin1977](https://avatars.discourse-cdn.com/v4/letter/g/977dab/32.png) [@griffin1977](https://boards.straightdope.com/u/griffin1977)\ **Post date:** [June 4, 2026, 2:25pm UTC](https://boards.straightdope.com/t/help-me-with-this-health-insurance-conundrum/1030613/3 "2026-06-04T14:25:09Z")
> [@MinkMan](#): > > change of employment counts as a qualifying live event that allows for you to enroll in a ACA marketplace plan outside of the normal enrollment periods Yeah I had the reverse of the OPs situation (left my job to found a start up) and was able to enroll in ACA outside of open enrollment.