My Dad Is Retiring Soon – How Can I Get Health Insurance Before I Miss Important Appointments?

Running out of money in the middle of a retirement is a top fear for many retirees, even those who have a comfortable nest egg that’s above and beyond what one would need for their lifestyle. Indeed, healthcare costs tend to be the major wild card that upends retirement plans that lack enough additional padding […] The post My Dad Is Retiring Soon – How Can I Get Health Insurance Before I Miss Important Appointments? appeared first on 24/7 Wall St..

May 17, 2025 - 12:04
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My Dad Is Retiring Soon – How Can I Get Health Insurance Before I Miss Important Appointments?

Running out of money in the middle of a retirement is a top fear for many retirees, even those who have a comfortable nest egg that’s above and beyond what one would need for their lifestyle. Indeed, healthcare costs tend to be the major wild card that upends retirement plans that lack enough additional padding to cushion from those hefty, unpleasant financial surprises.

While fear shouldn’t be the main emotion that dictates one’s moves in retirement, I’d argue that it never hurts to be prepared for a worst-case scenario of sorts. A backup plan can never hurt, especially if there’s room to pull levers on the financial plan to reduce spending and bolster a portfolio’s longer-term growth.

In this piece, we’ll check in with a Reddit user who’s worried about their dad’s lack of health insurance coverage once they retire.

Undoubtedly, once one leaves the workforce, their benefits tend to go away. While there is a wide range of health insurance options to choose from, it can be difficult to know the precise one to go for without a bit of help from a financial advisor who’s well-versed in insurance policies. Let’s look in at a few moves our Reddit user should consider as their dad begins to wind down for retirement.

Key Points

  • This Reddit user’s father is retiring soon, but health insurance coverage remains a giant question mark.

  • ACA, Medicaid, and COBRA are all options to look into. Bringing on a financial advisor also can’t hurt!

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ACA, Medicaid, and COBRA are popular options among retirees

Coverage under the Affordable Care Act (ACA), perhaps best known as Obamacare, could be looked into, especially if the soon-to-be retired dad will have a limited amount of passive income coming in. The dad, who’s in his 60s, may or may not be eligible based on passive income that’ll be coming in and other factors that a financial advisor can clear the air on.

Additionally, Medicaid, which allows low-cost coverage for pre-existing conditions, should be explored in addition to COBRA, which allows the recently retired to keep their employer plan. Of course, the latter would be the pricier of the two options. Though, depending on the circumstances, it could be a better way to go for those who want to keep things the same. As always, check in with a financial advisor so that they can determine eligibility and unique needs that our Reddit user’s father seeks to have in retirement.

The dad could keep a part-time or full-time job for the work benefits.

Undoubtedly, health insurance premiums can get rather pricey, especially if one finds they’ll need more coverage and care as they age. And while ACA, Medicaid, and COBRA may make sense for the Reddit user’s father, I’d argue that the best way to go is to get a part-time job with health insurance benefits. Undoubtedly, going part-time can be a fantastic way to transition into a full retirement while being able to retain benefits and a “nice-to-have” income boost.

Of course, many employees only offer such generous benefits to full-time (or semi-full-time) staff. In such a scenario, a low-stress job that entails at least 30 hours a week could make a lot of sense if the Reddit user’s dad is willing. Indeed, “barista FIRE,” as it’s called, entails low-stress work as one looks to explore new jobs one would have never thought they’d have the opportunity to try out.

The bottom line

Of course, many employees only offer such generous benefits to full-time (or semi-full-time) staff. Either way, if affordability is an issue, I’d argue that the Reddit user shouldn’t cancel coming appointments but rather meet up with an advisor so that they can begin the application (either COBRA or Medicaid) sooner rather than later.

Even if time is of the essence, finances come second to health, especially if the father has a medical condition that needs to be urgently addressed. Sure, it can be a stressful scramble to deal with the sudden and unexpected retirement of a loved one, but having a financial advisor in one’s corner can really help reduce the sense of great overwhelm.

The post My Dad Is Retiring Soon – How Can I Get Health Insurance Before I Miss Important Appointments? appeared first on 24/7 Wall St..