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How to talk end-of-life planning over the holidays

Family time is great for family talks. Here’s how the experts recommend approaching this delicate (but important) conversation

Family Christmas Lunch At Home.

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If your parents are still around, they are undoubtedly getting older (as we all are). That means you should discuss what happens when they stop getting older — i.e., when they die. Because there needs to be a plan, and it needs to be made before you and yours are dealing with grief and logistics. And it turns out, the holidays are the perfect time to do it.

Now, it might seem odd to discuss death at a family celebration, but hear us out. For one thing, the holidays may be the only time when you see your family over several days without anything in particular to do. This is fertile ground for conversations.

The other reason is that the holidays are inevitably a time for reflection, a marker of time passing. People get thoughtful, contemplative. So yes — a good moment to discuss weighty matters.

As for how to do it, we asked a couple of experts. First is Elizabeth Eddy, co-founder of Lantern, an end-of-life planning service available at no cost to eligible Haven Term policyholders through the Haven Life Plus rider.

And then there’s Mitch Mitchell, Associate Counsel, Estate Planning at Trust & Will, a service which, as the name suggests, allows you to make either of those crucial documents. (Eligible Haven Term policyholders also enjoy no cost services from Trust & Will, also through Haven Life Plus.)

Both these services are online, easy to use, and well worth suggesting to your family during an end-of-life planning chat. And here are some tips for having that conversation:

In this article:

What to talk about

So now that you know the when and why, let’s talk about the what. What exactly do we mean by end-of-life planning? Start by asking about a trust or a will, though there’s more to it than that.

“Many folks assume two things about end-of-life planning,” says Eddy. “One, you only need to do it if you’re rich, whereas in fact there are many other reasons to plan such as dependents, your healthcare wishes, and reducing logistical complexity for people you love.” Having a plan, written down, will help prevent a lot of headaches, and potentially intrafamily squabbling, down the road.

The other assumption, she says, is that “if you have a will, you have an end-of-life plan.” To be clear, a will (or trust) is absolutely an important part of end-of-life planning, but it isn’t the only thing.

On the contrary, she says, “if you think of end-of-life planning like a pizza, a will is one slice. A complete plan includes things like organizing all your accounts and passwords” (banking, prescriptions, social media).

There’s also other legal paperwork. Eddy mentions healthcare directives, guardianship, and trusts. There’s also financial planning, including funeral expenses and life insurance. (We can help with that.)

Eddy also mentions “legacy planning — dealing with your stories and memories — and so much more.” Lantern offers planning guidance to help you or your family members navigate these difficult questions.

How to talk about it

Clearly that’s a lot to talk about. So how should you go about it?

“Advice for conversations like this is highly dependent on the personalities of your parents and you, your relationship dynamic and your experiences with loss,” says Eddy. If yours is the kind of family that talks easily about death, the conversation might be easier than it would be if such topics are taboo.

Mitchell says it’s important to remember that, although you may be ready to have this conversation, “most people do not want to talk about these things.” Also, “your parents may have negative experiences around death, and this conversation may make them think about the death of their own parents.”

However, that can provide an opportunity. “In my mom’s case, she might be thinking about her dad’s death and the probate experience and how that was not great,” says Mitchell. Although such memories aren’t enjoyable, if that kind of thing is on your parents’ mind, they might be more inclined to make plans now to save you from going through the pain and difficulties that they experienced.

As for what not to say, “assuming it’s true, make it really clear upfront that nothing is wrong,” says Eddy. This might seem unnecessary — as far as you’re concerned, you’re just being practical — but some people will assume you’re only discussing end-of-life because you’ve realized it’s imminent. Proceeding with sensitivity is always a good idea, but especially with a subject matter as weighty as this one.

A conversation starter

“Everybody else is doing it…” How many times did you use that phrase with your parents when you were a kid, seeking permission for something? Well, now’s the time when that approach is really useful.

“Introduce the topic with a story that normalizes the conversation, such as ‘Cousin Jeff just did this for his partner and kids and said it made him feel so much better knowing things were taken care of,’” says Eddy. Not only does this make the idea of the conversation seem normal, you also have a concrete example of why it’s useful.

If there is no “Cousin Jeff,” start the conversation “by talking first about what you have done,” says Mitchell. “It may come across as intrusive if you start by just asking questions about your parents’ plans, whereas if you couch it more as ‘So we finally put together our plan — it was easy, I’m glad I have the peace of mind…’ that may open a door to a more direct conversation.”

Plus, seeing that their own child has their affairs in order might just inspire them to make sure theirs are, too.

Don’t sweat the details

Be aware that, however well the conversation goes, it will be the first of several such discussions. If your parents have no plan, they’re unlikely to complete one while they wait for the turkey to finish cooking. (With Trust & Will you can, in fact, make a will in much less time than you need to make dinner, but if a person has never considered end-of-life planning before, they’re unlikely to be fully prepared to make decisions on the spot.)

For the first conversation, “you don’t have to go into details of the plan, just make sure they know how to find and access the relevant services should they need them,” says Eddy. You should also make an agreement for a follow-up talk. What you’re trying to accomplish with your first conversation is for your parents to agree to make or update a plan, not complete and sign it right now.

Actually, sweat the details a little

If your parents say they already have a plan, be aware that it may still need to be looked at. “If they have a written plan of some kind — a will, trust, power of attorney documents — they’re most of the way there,” says Mitchell. “But there may be some idiosyncrasies.”

Maybe their plan doesn’t cover things which didn’t exist when it was written (such as the entire digital world), “or perhaps it’s done on a typewriter with a lawyer who’s no longer practicing, and if we wanted to ask someone about it we’d have to start afresh.” If a plan exists, Mitchell suggests asking “‘When is the last time anyone looked at it to see what it said?’” If it’s been awhile, it’s best to ask them to take another look.

And as for you…

It turns out, your parents (or other loved ones) aren’t the only ones who are mortal. We hate to break it to you, but so are you.

So if you do discuss end-of-life with your family over the holidays, be aware that they will probably ask you — quite reasonably — about your own plans. Your folks aren’t the only people in your family who are getting older, so if you don’t have your own plan in place, it might be time to fix that. Haven Life can help.

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About Michael Davis

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Haven Life is a customer-centric life insurance agency that’s backed and wholly owned by Massachusetts Mutual Life Insurance Company (MassMutual). We believe navigating decisions about life insurance, your personal finances and overall wellness can be refreshingly simple.

Our editorial policy

Haven Life is a customer centric life insurance agency that’s backed and wholly owned by Massachusetts Mutual Life Insurance Company (MassMutual). We believe navigating decisions about life insurance, your personal finances and overall wellness can be refreshingly simple.

Our content is created for educational purposes only. Haven Life does not endorse the companies, products, services or strategies discussed here, but we hope they can make your life a little less hard if they are a fit for your situation.

Haven Life is not authorized to give tax, legal or investment advice. This material is not intended to provide, and should not be relied on for tax, legal, or investment advice. Individuals are encouraged to seed advice from their own tax or legal counsel.

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Haven Term is a Term Life Insurance Policy (DTC and ICC17DTC in certain states, including NC) issued by Massachusetts Mutual Life Insurance Company (MassMutual), Springfield, MA 01111-0001 and offered exclusively through Haven Life Insurance Agency, LLC. In NY, Haven Term is DTC-NY 1017. In CA, Haven Term is DTC-CA 042017. Haven Term Simplified is a Simplified Issue Term Life Insurance Policy (ICC19PCM-SI 0819 in certain states, including NC) issued by the C.M. Life Insurance Company, Enfield, CT 06082. Policy and rider form numbers and features may vary by state and may not be available in all states. Our Agency license number in California is OK71922 and in Arkansas 100139527.

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