The holidays are a time to gather, reflect, and connect with loved ones. They’re also a unique opportunity to have important conversations—like how your family wants to plan for the future. Whether it’s talking about inheritance, taxes, estate planning, health care, or long-term financial goals, getting everyone in the same room is a practical way to ensure everyone is on the same page.
That said, with the state of the world today, everyone’s a little bit on edge. I’m sure most of us are curious what interesting debates will ensue around the dinner table this holiday season and may be a bit nervous how things may play out. That’s why it’s so important to focus on what is truly important and meaningful to our family, rather than all of the things that are outside of our control. Yet, it’s also extremely important to navigate these important, but sensitive subjects with our loved ones effectively and with grace. Diving into money and the state of your parent’s long-term planning while opening gifts or enjoying a family meal might not land very well. To help you approach these conversations thoughtfully and effectively, here are three strategies that we have found might help you navigate these touchy subjects.
01 | Give People a Heads-Up
Let’s be honest, nobody likes to be blindsided or caught off-guard. Finances, health care and estate planning can be a sensitive subject for many families, and springing it on them out of the blue mid-holiday festivities could backfire. Instead, you should try set the stage and provide some context ahead of having these all-too-important conversations.
Also, whether we’d like to admit it or not, we’re all self-interested. We see the world through our own lens and can get suspicious of people’s intentions when it comes to sensitive subjects like finances. So, when setting context make it about them and not yourself. Make sure to highlight why you are bringing up this all-too-important topic and focus on the benefits to them personally and your family as a whole, rather than focusing on yourself.
Start by planting the seed in casual conversations before the holidays. For instance, you might say, “I read this really interesting article where I learned some interesting facts about estate planning and the law in [Illinois] that I wasn’t aware of. It really got me thinking about the importance of making sure our family is financially prepared for the future. I’d love to talk about it when we’re all together, would you be open to that?”
This approach gives your family time to process the idea. When the gathering gets closer, follow up with more intention, or forward them an article that you read, so they can read it in advance. Ask the host—whether it’s a sibling, parent, or adult child—if you could carve out time for an important conversation. If there’s hesitation, listen to their concerns and work together to find a solution that makes everyone comfortable.
Remember, this isn’t about forcing anyone into a conversation they’re not ready for. It’s about creating space for dialogue and collaboration with your loved ones.
02 | Create the Right Environment
Timing and setting can make or break a productive discussion. Talking about estate planning and what may happen after the death of a family member while unwrapping presents or watching football just isn’t the right moment. Instead, schedule a dedicated time and choose a calm, private space.
Be upfront with your family about why you want to have this discussion. You might say, “This isn’t easy for me to bring up and may seem odd, but I think it’s important for all of us to be prepared for the future. Can we have an important conversation to make sure we’re all on the same page about what we want and what matters most to each of us.”
Encourage everyone to come with questions or concerns. Make sure to approach the conversation as a collaboration, where your goal is to learn about them, their goals, and wishes. When people feel included and you can approach these conversations from a place of love, while focusing on them and your families’ best interest, they’ll be more likely to open up and engage in a constructive dialogue. My advice is to always lead with questions and curiosity, not to preach or tell them what they “need” to be doing. People want to be heard and understood, if you can spark an interesting conversation about your loved ones’ wishes when it comes to their healthcare, finances, and the importance of protecting your family for generations to come, it can spark a meanful conversation and lead to a bonding experience for your family. Not to mention, you might learn something really interesting about your loved ones, their wishes, plans for the future, and views on life that you never knew before.
03 | Focus on the Big Picture
For decades, the subject of finances amongst family members has been a bit taboo and something our grandparents (and maybe even our parents) generations were taught shouldn’t be discussed openly and honestly. These private and sensitive conversations about finances and what would happen after someone is incpacitated or passes can also naturally be very emotional. That’s why it’s crucial to emphasize that this isn’t just about finances—it’s about creating a shared vision for the family’s future and why waiting to have these important conversations could cost your family dearly.
Frame the discussion around your family’s values. For instance, you could say, “This is about making sure our family is taken care of and that we avoid unnecessary stress later. Planning now can keep us connected and reduce confusion when life throws us challenges.”
If things get tense, remind everyone of the shared goal: ensuring the family’s well-being. Keep the focus on legacy, not just logistics. You don’t have to solve everything in one conversation, but laying the groundwork can make it easier to revisit the topic later.
Final Thoughts
The holidays are about more than just celebration—they’re about connection and an opportunity to build a stronger foundation for your family’s future. Starting a conversation about estate planning, finances or long-term care planning might feel awkward, but it’s one of the most meaningful ways to show your family you care and address these important subjects before it’s too late.
By taking a practical, inclusive approach, you’re not just talking about money—you’re fostering a legacy of trust, security, and togetherness. And that’s a gift worth giving.
Earlier this week, someone very close to me said something that really struck a nerve and resonated with me. My family doesn’t live nearby and I have to travel to see them, so my friend asked me how many times I see my family per year and asked me to do the math on how many more opportunities I may have to see them. It was eye-opening and really put things in perspective on how I should use my time with family this holiday season. So, instead of debating politics and the state of our world today, I’m going to do my best to try to focus on what’s important for our family. If there’s anything you take away from this article, I truly hope this helps you focus on what is truly important and reframe what you choose to discuss with your family at the dinner table during the holiday season.
For additional practical advice to navigate the holidays stress-free, check out this article on maintaining family harmony during the holidays.