Bruce Helmer and Peg Webb
For many families, the holidays are the one moment of the year when everyone comes together without the usual rush of deadlines, school schedules, or conflicting calendars.
And while nobody wants to turn a festive gathering into a financial seminar, these warm, unhurried moments can open the door to something surprisingly valuable: meaningful conversations about money, intentions, and the kind of legacy you want to leave.
These discussions don’t have to be heavy. In fact, when handled with a gentle touch, they can be among the most positive, affirming conversations you have with your family all year.
Start with values, not numbers
The biggest mistake people make when talking about money is assuming that it has to start with dollars and account balances. It doesn’t. A far more natural way to open up is to talk about your personal values.
• What traditions matter most to you?
• What do you hope your wealth accomplishes for your family or your community?
• What stories do you want the next generation to remember?
Framing things around values allows families to connect emotionally before pivoting to the more practical, and sometimes more difficult, details later.
Use the “all-in-one-room” moment
The holidays create the kind of environment that financial advisers often wish families could recreate year-round: relaxed, comfortable, low-pressure and conducive to honest dialogue. Instead of trying to schedule a formal meeting in the new year, casual conversation over dessert often feels more genuine.
It might be as simple as saying, “There’s something on my mind that I’d love your thoughts on,” or, “We’ve been thinking about our long-term plans, and we want to share what matters most to us.”
Clarity is a gift, not a burden
Meaningful conversations aren’t about reviewing documents or assigning responsibilities. They’re about preventing surprises and giving loved ones confidence that they understand your wishes.
Your children or heirs don’t need to know every financial detail. They only need to know how to support you and honor your wishes. Transparency now relieves them of confusion later, especially in times of stress or grief when they may need to locate documents, understand your intentions, or make decisions quickly.
Share the “why,” not just the “what”
If you’ve made decisions about how assets are divided, what causes matter to you, or what end-of-life preferences you hold, sharing the reasoning behind them now can help avoid misunderstandings later.
This isn’t a legal conversation; it’s a relational one.
Invite dialogue and curiosity
We often find that parents are surprised by how much their adult children want to know, and how relieved they feel once the topics are on the table. Encouraging questions makes the conversation two-sided, not a lecture.
A small next step keeps the momentum going
To ensure the conversation leads to progress, commit to taking a small, manageable next step: reviewing beneficiaries in January, meeting with an adviser, organizing documents, or simply agreeing to talk again next year.
The holidays offer the perfect backdrop for these conversations. They don’t need to be characterized as “serious.” Instead, when you shift the topic from “difficult financial talk” to “preserving what matters most,” you may find that these moments deepen your connections rather than disrupt them.
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The opinions voiced in this material are for general information only and are not intended to provide specific advice or recommendations for any individual.
Bruce Helmer and Peg Webb are financial advisers at Wealth Enhancement Group and co-hosts of “Your Money” on WCCO 830 AM on Sunday mornings. Email Bruce and Peg at yourmoney@wealthenhancement.com. Advisory services offered through Wealth Enhancement Advisory Services LLC, a registered investment adviser and affiliate of Wealth Enhancement Group.
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