How to Talk About Death, Money & Estate Planning Around the Holidays
The holidays have a way of bringing everyone back under one roof. There’s food, noise, stories you’ve all heard a hundred times… and usually at least a few conversations everyone avoids.
For many families here in Northern Kentucky and Cincinnati, the two topics that get dodged the fastest are death and money. They feel heavy. They feel awkward. And most people would rather keep things light—especially this time of year.
But here’s the truth:
Every family pays the price when these conversations never happen.
The good news? You can talk about these things in a way that feels grounded, loving, and practical—not grim.
Below is a simple way to think about these conversations, how to start them, and how to make sure they lead to actual protection for the people you care about.
A Better Way to Think About Death & Money
People don’t avoid estate planning because they don’t care. They avoid it because it touches two things most of us are raised not to talk about: mortality and finances.
But estate planning isn’t about “the end.”
It’s about making life easier for the people who love you.
When we help families in Boone County, Kenton County, and Hamilton County walk through this process, the biggest shift we see is this:
Estate planning isn’t a legal chore. It’s an act of care.
Instead of thinking about: “What happens when I’m gone?”
Think: “How do I set my family up so they aren’t scrambling in a crisis?”
Instead of: “I don’t want to talk about money.”
Think: “Here’s how I can give them clarity and keep them out of conflict.”
Once you reframe estate planning as a responsibility you take for your family—not to them—the whole conversation changes.
If you’re not sure where to start mentally, ask yourself:
What do I want my loved ones to know about my wishes?
What headaches can I save them from?
What would make their lives easier if something unexpected happened?
What values or stories do I want them to carry forward?
Those questions point you toward your legacy, not the loss.
How to Bring It Up Without Making It Weird
You don’t need a dramatic speech.
You don’t need to gather everyone in a circle.
You definitely don’t need to make it somber.
You can start with something as simple as:
“I’ve been thinking about how to make things easy for you if something ever happened to me.”
That single line does two things:
It tells them this conversation is coming from love.
It signals that you already have a plan—not a crisis.
Here are a few ways to make the conversation go smoothly:
Pick your moment wisely.
Not in the middle of cleanup.
Not when tensions are high.
A simple walk, drive, or quiet moment is usually enough.
Ask questions, don’t lecture.
Try:
“If something unexpected happened, what information would you want to have?”
“Would you know who to call?”
“Do you know where things are kept?”
People engage better when they feel included.
Call out the discomfort.
It drains the tension immediately. Something like:
“I know this isn’t fun to talk about, but it’ll bring me peace of mind to know we’re on the same page.”
Talk values first, logistics second.
People want to know why you’re making choices before you tell them what the choices are.
Once the door is open, then move into:
Who you’ve chosen to make medical or financial decisions
Why you selected certain people
How to access important documents
Where assets are located (you don’t need to share numbers—just directions)
When clients come through our Life & Legacy Planning™ process, we help them create:
An organized inventory of assets
Clear instructions for loved ones
Updated legal documents
A recorded “Legacy Interview” so their stories and values are never lost
Families consistently tell us that last part means more than anything else.
Turning a Conversation Into Actual Protection
Talking is a great start.
But talking without action still leaves your family vulnerable.
A solid plan should:
Keep them out of court
Keep them out of conflict
Keep assets out of limbo
Keep the kids protected
Keep the family from scrambling during a medical emergency
That’s why our Life & Legacy Planning process is built to do more than generate documents. It creates a long-term relationship so your plan actually works when your family needs it.
When you work with us, we:
Help you inventory everything you own
Make sure nothing is lost or “mystery money” your family never finds
Update your plan as laws and life change
Capture your stories, values, and wishes so your family always knows the “why” behind your decisions
The goal is simple:
Clarity instead of chaos. Relief instead of confusion. A roadmap instead of guesswork.
The Gift That Actually Lasts
Your family won’t remember whether the turkey was dry or who won the argument about politics.
They will remember whether they knew what to do when life turned upside down.
Talking about death and money doesn’t dampen the holidays—it protects the people who sit around your table.
If you’re ready to bring real peace of mind into the new year, we’re here to help you get started.
Take the Next Step
Book a free 15-minute Discovery Call with Freedom Law Services today in our Crestview Hills, KY office. Together, we’ll create a Life & Legacy Plan that protects your time, your money, and—most importantly—your family.
Call us at (859) 344-6742 or visit www.FreedomLawServices.com/call-today to book your discovery call.
This article is a service of Freedom Law Services. We don’t just draft documents; we ensure you make informed, empowered decisions about life and death for yourself and the people you love. That’s why we offer a Family Wealth Planning Session™. During the session, you will get more financially organized than ever before and make all the best choices for the people you love. You can begin by calling our office today to schedule a Family Wealth Planning Session and mention this article to find out how to get this valuable session at no charge.
This material was created for educational and informational purposes only and is not intended as ERISA, tax, legal, or investment advice. If you seek legal advice specific to your needs, such advice must be obtained independently, separate from this educational material.
