Turning Holiday Traditions Into Legacy Planning Opportunities

Many people hope their children and grandchildren will someday understand the meaning behind the wealth they’re building — not just receive it.

Most parents and grandparents want their heirs to know things like:

• Where this wealth came from
• What sacrifices were made to build it
• What values helped shape financial decisions
• Why the family business, ranch, career, or investments mattered
• What they hope the next generation will do with what they inherit

People want to explain those things — but conversations about money can feel uncomfortable, too serious, or like they’ll come across the wrong way.

That’s why I often encourage families to think about having a “legacy plan” — not a legal document, not a spreadsheet, but a simple plan for how you want to communicate:

• what you’ve built,
• why it matters to you, and
• what you hope it creates for your loved ones in the future.

A legacy plan can look like:

• sharing stories and family history,
• communicating your values and priorities,
• explaining the “why” behind your estate plan, or
• putting your hopes for your heirs in writing for them to read someday.

And here’s where the holidays come in:

You don’t have to schedule a serious meeting or sit everyone down on the couch.
You don’t need every detail sorted out, either.

The holidays naturally create a warm, relaxed environment where family is already gathered, and meaningful conversations can happen in small, simple moments — even if you’re just dipping a toe in.

Whether you already have a full legacy plan in place, or haven’t started yet, the holiday season can be a great time to begin sharing what matters most to you in simple, natural ways. Let me give you a few examples of what that could look like.

Holiday traditions create natural openings for talking about values

When you’re participating in some of your favorite holiday activities or traditions this year, you may get asked by a child or grandchild in your family:

• “Why do we always do it this way?”
• “Where did this recipe come from?”
• “Why is this holiday so important to you?”

These would be the perfect moments to connect your activities to a memory or a value. For example:

• “We volunteer every Christmas because generosity is a core part of our family.”
• “This dish came from your great-grandmother, who fed everyone even when she had very little — that resilience shaped our family.”
• “We exchange handwritten notes because gratitude has always mattered in our home.”

These are simple stories, but they can become the cultural foundation that helps future inheritances make sense.

Gifting can teach responsibility, not just generosity

If gifting is already part of your holiday routine, you can find a few simple ways make it more intentional and “legacy”-focused. For example:

• Contribute to a 529 or investment account and include a note explaining why you believe in the power of saving and compounding
• Let kids or grandkids choose a charity, and match their contribution dollar-for-dollar
• Give experience gifts that reflect a value: travel, learning, mentorship, service, creativity
• Share a short written message explaining what you admire about a child and what you hope they continue in life

Gifts don’t have to be big to be powerful. Typically it’s the message behind the gift that leaves the mark.

Storytelling gives inheritance meaning

Estate planning decides what goes to whom. Storytelling explains why it matters.

A will might say who gets the ranch, but the story explains:

• Why the ranch mattered,
• What it took to keep it,
• What you hope future generations experience there.

A trust might dictate how distributions will work, but a simple explanation like this changes everything:

“We structured it this way because we wanted to encourage education, independence, and generosity; not pressure anyone to follow a certain path.”

A family may not always remember the legal language, but they will certainly remember the intention. This is what helps bolster both the assets and the relationships behind them. And it is one of the many reasons we advocate for creating “legacy plans” like this.

Talking now prevents confusion later

Believe it or not, the main reason inherited wealth disappears within two generations isn’t taxes or markets… it’s lack of communication.

Heirs often aren’t prepared. Not because they’re incapable, but because no one ever talked with them about:

• What’s being built,
• Why it’s structured the way it is, or
• What the long-term purpose of the wealth really is.

That’s one of the biggest reasons I recommend having a legacy plan in place. Remember: a legacy plan is a written overview or guide that explains what you’ve built, why it matters to you, and what you hope it creates for your family in the future. It’s not meant to replace a will or trust (which address the legal and financial aspects). A legacy plan focuses on the human side of things, such as:

• What values shaped your financial decisions
• What you’re proud of building
• What sacrifices were made along the way
• Why you structured your estate the way you did
• What you hope your children or grandchildren will do with their inheritance
• What you don’t want wealth to create (pressure, entitlement, conflict, uncertainty)

Some families write their “legacy plan” as a letter. Some record it as a video. Some put it into bullet points or a short memo to their heirs.

It doesn’t have to be long — and it also doesn’t have to be perfect. It simply provides context and meaning that legal documents can’t.

We highly recommend you start these conversations sooner rather than later, even if you just start with something “light” or high-level, such as:

• “Here’s what we’re building.”
• “Here’s why it matters to us.”
• “Here’s what we hope this creates for you someday.”

Starting to provide this kind of clarity within your family and heirs can:

• Reduce confusion (“Why did they do it this way?”),
• Lower the chance of resentment or hurt feelings, and
• Help prevent family conflict later on.

Professionals can help turn values into plans

Your legacy will become most powerful when it’s reflected not only through conversations and traditions within your family, but also within:

• Your estate plan
• Your financial plan
• Your retirement income plan
• Trusts and beneficiary designations
• Charitable giving strategies

I would highly encourage to rely on financial advisors, estate attorneys, tax professionals, and insurance specialists to help ensure your structure supports your goals — not just legally, but on a more personal and meaningful level.

Final Thought

The holidays offer a natural opportunity to start sharing the meaning behind what you’ve built in your life, and to help your loved ones understand not just what they may inherit someday, but why it matters.

Whether you already have a full legacy plan in place or you’re just beginning to think about it, even one genuine conversation this season can make a lasting impact.

If you’d like help turning your values, memories, and wishes into a thoughtful legacy plan — one that protects your loved ones and aligns with your financial and estate structure — we’d be honored to guide you. Schedule a complimentary consultation with us to start the conversation.