Three Tips for Having Hard Conversations Before It’s Too Late

My father was an only child, and growing up, we always made the drive from my native Colorado to the Ozarks of Missouri, where my mom’s family lived. My childhood Christmases were spent in my grandparents’ house in the woods, and I have many fond memories of our time there. These days, Christmases look a lot different. We’ve added spouses and another generation, and for our nuclear family, our holidays are now spent driving the ten-minute drive to my parents’ house.

As a child, there was a consistency to holidays – the tradition, the time with cousins, and the magic of waiting for Santa. As an adult, the holidays have become a much more nuanced time. There are gifts to be wrapped, events to be planned, and attended. There are year-end tasks that need to be completed. But there’s also a reckoning that I think comes with the closing out of each year – a recognition that time has passed.

This can feel especially poignant when we don’t see our parents or grandparents on a regular basis. The holidays can be a time that brings into focus their current life stage, which can often lead to questions about longevity, quality of life, and how prepared we are for future transitions. I’m very fortunate that my mother’s parents are still with us. I don’t see them as often as I used to, and nowadays, when I do, our visits, while still fun, also carry an underlying tone of worry – are they still ok? Who’s keeping an eye on them? What’s the plan if something happens?

Why Proactive Conversations Matter

A few weeks ago, I came across an opinion piece in the New York Times where the author shared her own journey with aging parents. She discussed the challenges of navigating a season of uncertainty and the many hard conversations with her dad that followed. My own dad is currently having the experience of a lifetime – a cruise to Antarctica – something I’m so thrilled he’s able to do. Nevertheless, the article did remind me that there will come a day when I will need to have some of these conversations with my own parents, begging the question – what’s the best way to do that and when?

When I consider that question in the context of my professional experience, the answer is quite obvious: don’t wait. It is a natural human tendency to put off unpleasant things. It’s the basis of procrastination, and as anyone who’s had to write a lengthy English paper can attest, it’s really easy to put something off that you don’t want to do. However, that same group of people can also probably attest to how much harder it is to write an English paper at midnight when you could have been writing it in chunks at 7 pm over the course of the two weeks you were given to complete the assignment.

Or how about saving for retirement? We all know that it’s better to start saving early. You reap the rewards of compounded returns when you begin investing for the future at an early age. And on the other hand, catching up for your financial goals can be incredibly difficult once you’ve become accustomed to a certain lifestyle.

When it comes to hard family conversations, the general wisdom here holds true as well – it’s much easier to have them earlier, particularly when they’re helpful but not yet critical. I’d much rather have an important conversation without the pressure of an imminent decision. From a legacy planning perspective, these conversations are more effective and less stressful when they happen before a crisis forces them.

As we prepare for the holidays and spend time with our loved ones, many of us will have the opportunity to engage in some of these conversations. Others will discover they have to have these conversations. With that in mind, here are a few suggestions for navigating hard conversations with aging parents thoughtfully and well:

1. Let Them Know That, Ultimately, You Want What’s Best for Them

Start with love. I hope that is the place you’re coming from, and if it’s not, maybe take some time to think through how you can reframe your own mindset. These conversations are hard because they feel unloving. Telling someone they shouldn’t be driving anymore or that it’s time to change their living situation doesn’t feel loving, and that’s why these conversations are difficult. However, it helps if, from the outset, you let your family member know that your ultimate goal is to care for them.

In our line of work, we’ve walked with many clients as they navigate some truly challenging situations with aging parents. Often, children want what’s best for their parents, but because they’re already involved and didn’t get to have the conversation before it was too late, it has become contentious. The parents feel like they’re being forced into something they don’t want. The child feels like they have no good options. And everybody is upset.

But, as is true in so many complicated things, anger and frustration are just a cover for fear – they’re signs that what’s at stake is something that really matters. There are moments in life when we have to lean into difficult things, and there’s no way around them. However, I believe that when we start that conversation from a place of love and care, it changes the tone. Telling someone that you love them and you want to do what’s best for them reminds them that you’re not at odds with them and, at the very least, sets a kinder tone for the conversation.

2. Frame the Conversations as a Hypothetical (Because If You Have It Early, It Still Is)

Ask questions like “if something were to happen tomorrow that left you with diminished capacity, what would you want us to do?” or “at what point do you think it would be no longer safe for you to drive/live alone/manage your own finances?”

My parents are still healthy and active. They just sent me a picture of them smiling from a sea kayak next to an iceberg. I’m not too worried about their quality of life or their autonomy right now, and I’m very fortunate that we have a good relationship, which is why I want to start asking them these questions now, while there’s still time for us to have a lower-stakes conversation. 

What’s nice about the hypothetical framing is that it also encourages them to think about what they want, and it gives them permission to change their minds. But that also means this is an ongoing conversation. I want to periodically check in with them and ask questions, such as, “Hey, just wanting to make sure you’d still prefer in-home care if something happened?” Keeping the conversation light but also consistent helps normalize topics like longevity planning and autonomy, hopefully making them easier to discuss down the road.

3. Ask If There Is a Plan: If Not, Make One

We regularly talk with clients about estate planning, and we’re always delighted when they finally put one into place. Still, very few people want to talk about the plan once they’ve built it, and that’s understandable. It’s uncomfortable to sit down with your loved ones and talk through how your stuff is going to be divvied up or what kind of medical decisions you want made in the event you can’t make them yourself.

The problem is, if you don’t have the conversation, then they don’t get the opportunity to ask questions and fully understand your intentions. The result is that when they get to that point, they feel the guilt of trying to make decisions without knowing what it is you really wanted – what your intentions were surrounding the legal language of your estate documents.

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We know that the holidays can be a complicated, yet hopefully joyful, time for many. This season, and always, we hope you find the time to be present where you are, and that being present creates space for you to have meaningful financial conversations with your loved ones about the things that matter. 

As always, if you find yourself with questions, such as what to do if your estate documents are outdated or nonexistent, we’d love to set up a time to discuss your concerns as well as your wishes.

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