How to Talk to Your Loved Ones About Estate Planning During the Holidays
As the holidays fill our homes with twinkling lights, warmth, and family traditions, they also give us a rare gift: time together. And with that time comes an opportunity to talk about the things that matter most.
While most families celebrate the season surrounded by love, many also avoid the conversations that protect the people they love most. The truth is that discussing what happens when you're gone isn’t about fear—it’s about love, clarity, and legacy.
This season, you can use these moments of connection to open heartfelt conversations that lead to meaningful action and a plan your family can rely on.
Shifting the Conversation About Death and Money
Most people avoid estate planning for two simple reasons:
1. Talking about mortality feels uncomfortable.
2. Discussing money often feels taboo.
That’s why a majority of Americans still don’t have an estate plan, or have one that stopped working years ago, and they don’t know.
But what if we changed the way we think about these topics?
What if planning for the future wasn’t about preparing for an ending, but about protecting the people you love at the beginning of their next chapter? Estate planning is an act of love. It gives your family clarity and direction at a time when they’ll need it most.
When you view planning this way, choosing a guardian, selecting beneficiaries, or making end-of-life decisions becomes less about control and more about compassion.
● What values or stories do I want my family to carry forward?
● How can I make things easier for them when I’m no longer here?
● How can I protect their financial security?
● What message of love do I want them to remember?
When your planning is rooted in love, the conversation becomes a gift, not a burden.
How to Bring These Conversations Into Your Holiday Gatherings
Once you shift your mindset, the next step is gently inviting your loved ones into the conversation. Holidays naturally bring out gratitude and togetherness, making it an ideal time.
A warm and simple way to begin is:
“You mean so much to me, and I want to make sure you’re always taken care of, no matter what happens.”
From there, you can ease into practical topics.
Tips for a Meaningful, Comfortable Holiday Conversation
Choose the right moment.
After dinner, during a quiet walk, or while sitting by the tree or fireplace are ideal moments.
Invite their thoughts.
Ask questions like, “What would make things feel easier for you if something ever happened to me?” It turns the moment into a dialogue, not a lecture.
Acknowledge the emotions.
“It’s not an easy topic, but I feel peaceful knowing we can talk about it together.” Naming the discomfort removes tension.
Focus on your values.
Share what matters most to you, your hopes, your beliefs, your dreams for your loved ones.
Once the emotional foundation is set, gently transition to the practical items that bring clarity.
The Practical Pieces Your Loved Ones Deserve to Understand
Explain your why.
If you’ve chosen someone as executor, guardian, or decision-maker, share your reasoning. Transparency prevents hurt feelings and future conflict.
Discuss your wishes for care.
Explain whom you’d want making medical or financial decisions if you are ever unable to do so.
Share where things are.
Your family doesn’t need account balances, but they do need to know what exists and how to access it. (In my WELL Planning process, we create a complete asset inventory so nothing is ever lost.)
Share your legacy beyond finances.
Stories, values, letters, or videos often matter more than money. As part of my WELL Planning process, you can record a WELL Interview to ensure your voice and wisdom are preserved.
With intention and empathy, this becomes one of the most meaningful conversations you’ll ever have—not grim, but grounding, loving, and connective.
Turning the Conversation Into Meaningful Action
Talking is powerful—but the real protection comes from a legally sound plan. That’s why I created the WELL Planning Process (Wealth, Estate, Life & Legacy). It goes beyond documents and focuses on creating real results for your loved ones.
When you create a WELL Plan with me, you will:
● Build a complete asset inventory
● Receive ongoing guidance so your plan stays current as your life changes and as the law changes.
● Capture your stories, voice, and values
● Ensure your loved ones know exactly what to do and whom to call
WELL Planning turns estate planning into a lifelong relationship, not a one-time transaction.
Imagine the peace your loved ones will feel knowing exactly where everything is, more so if you have digital assets, what to do, and how to honor your wishes. That peace is the greatest gift you can give them.
The Greatest Gift of All
Talking about death and money may not feel festive, but protecting your loved ones, easing their future burdens, and giving them clarity is one of the most loving gestures you can make.
Holiday conversations about your wishes can bring your family closer, reduce future conflict, and preserve your legacy in the most heartfelt way.
Your Next Step
This holiday season, take the opportunity to talk about what truly matters—your love, your values, and your vision for your family’s future. Then let me help you turn that conversation into a plan that protects your family for generations.
📞 Schedule your complimentary 15-minute Discovery Call: https://calendar.app.google/LsWdX5dizipbLh2YA
This article is a service of Oluwaseun Adeware. My WELL Planning Session ensures you make empowered decisions, get financially organized, and create a plan that works when your loved ones need it most.
Office Address: 61-43 186th St, Fresh Meadows, NY 11365