TheWhat's Next Playbook

The Insurance Conversation You Need to Have This Year

Healthcare costs keep climbing and policy rules keep changing. Here's what to review now — before you actually need the coverage.


Healthcare costs are doing what they always do: going up. But right now we're in a weird moment where the rules themselves keep shifting — Medicare Advantage changes, Medicaid eligibility tightening in some states, long-term care insurance companies quietly hiking premiums or stopping new policies altogether.

Which means if you haven't looked at insurance coverage lately — yours or your parents' — this is the year to do it.

Not when there's a crisis. Not when someone falls or gets a diagnosis. Now, when you can still think clearly and actually have options.

What "reviewing insurance" actually means

I don't mean reading every page of every policy, though God bless you if you have that kind of patience. I mean answering these four questions:

1. What does current health insurance actually cover for long-term care?

Most people think Medicare covers nursing homes or in-home care. It doesn't — or barely does. Medicare will pay for rehab after a hospital stay, but only for a limited time and only if you're actively improving. Once you need ongoing help because of dementia or chronic conditions, you're mostly on your own.

If your parents have a Medicare Advantage plan, the coverage might be slightly better — or significantly more restrictive depending on the provider network. You need to know which.

2. Is there long-term care insurance, and is it actually any good?

Some policies are solid. Others are full of holes you won't discover until you try to use them. If a policy exists, dig it out and read the elimination period (how long before benefits start), the daily benefit amount, and what it actually covers. Some policies won't pay for care at home. Some cap benefits so low they'll cover maybe a year in a facility that costs $8,000 a month.

If the premiums have gone up a lot, that's not unusual — but it might be time to decide whether to keep it or let it go.

3. What happens when the money runs out?

For most families, the answer is Medicaid. But Medicaid has asset limits and look-back periods, and the rules vary by state. If someone might need Medicaid in the next few years, you need to know what those rules are now — because financial moves made today can disqualify someone three or five years from now.

This is where a lot of families accidentally screw themselves. They help a parent buy a car or give money to grandkids, not realizing it starts a penalty clock.

4. Are there any gaps we can still close?

Maybe it's too late for long-term care insurance — most companies won't issue new policies after age 75 or if there are already health issues. But there might be other options: hybrid life insurance policies with long-term care riders, annuities that include care benefits, or even just moving assets in a way that protects them.

The point is to know what's possible before the options narrow further.

The actual conversation

If you're doing this with parents, don't lead with fear. Nobody wants to hear "we need to talk about what happens when you can't take care of yourself."

Try this instead: "I've been reading about how much healthcare rules have changed lately, and I realized I don't actually know what your insurance covers. Can we go through it together so I understand what's in place?"

You're gathering information. You're trying to understand the plan. That's less threatening than implying there isn't one.

If you're doing this for yourself, the same principle applies. This isn't about imagining worst-case scenarios until you spiral. It's about reading the documents you already have, checking whether the coverage still makes sense, and deciding if there are moves worth making while you can still make them.

The one thing to do this month

Pull out the insurance documents — all of them. Health insurance, long-term care policies, life insurance, anything that might matter if someone gets sick or needs care.

Read them. Or at least skim them with a purpose. If you don't understand what you're reading, that's not a personal failing — insurance documents are designed by people who get paid to make them confusing. But you need to know what's there.

Then decide: is this enough, or do we need to talk to someone who can explain what the gaps are?

Because the truth is, you can't plan for every possibility. But you can know what you're working with. And right now, while things are still stable, that knowledge is worth a lot.


Get the weekly playbook.

Practical elder care planning, every week. Written for adult children who want to get ahead of this before a crisis forces their hand.

Subscribe — it's free →
← All articles