The Money Conversations Families Avoid—But Shouldn’t
By Scott Van Den Berg, CFP®, ChFC®, CEPA®, AIF®, CRPS®, CMFC®, AWMA®
Most families spend the holidays talking about everything except money. We’ll talk about football, the weather, travel plans, old stories, and who’s in charge of carving the turkey. But the subjects that shape our futures—wills, healthcare wishes, legacy choices, financial responsibilities—often stay buried under the table.
I’ve spent more than three decades sitting with families at every stage of life. I’ve watched how silence creates confusion. And I’ve watched how clarity creates peace.
The holidays are one of the few times the people who matter most are gathered in one place. Done well, these conversations don’t have to be heavy or tense. They can actually remove pressure from everyone involved. The goal isn’t to debate every detail—it’s to make sure the people you love aren’t left guessing.
Here are the conversations most families avoid but shouldn’t—and how to approach them with grace.
1. “Here’s where things are.”
You don’t need to open your balance sheet. You don’t need to talk about every account. But your family should know:
- Who your primary financial professionals are
- Where to find key documents
- Who to call if something happens
- What accounts or policies exist
When this isn’t clear, even well-intentioned families end up stressed, confused, or in conflict. I’ve seen families with strong relationships fall into arguments simply because nobody knew where mom kept her will or what life insurance policy dad had purchased years ago.
A few minutes of clarity now saves your loved ones hours of worry later.
2. “Here’s what I want, and here’s why.”
This is where the emotional weight lives. Parents often fear hurting their children’s feelings, so they avoid talking about wishes or distributions. But when you don’t define your intentions, your children are left to interpret—not understand—your decisions.
The most common misunderstanding I see isn’t about money at all. It’s about meaning. When a parent gives more to one child than another, they often have a thoughtful reason:
- One child needs more support
- One took care of them during an illness
- One already received significant help during life
Without context, kids fill in the blanks with their own story.
A simple explanation—shared calmly and without numbers—can prevent decades of resentment.
3. “Who’s responsible for what?”
Most families never talk through the roles that come with aging:
- Who will help manage bills if needed?
- Who’s the executor?
- Who’s the medical power of attorney?
- Who knows the wishes around healthcare or long-term care?
Choosing these roles isn’t about who you love most. It’s about fit. The most organized child might be a better executor. The child who lives closest might be a better point person for medical decisions.
When everyone knows their role ahead of time, the family works as a team rather than falling into conflict during moments of stress.
4. “Here’s what we hope our money accomplishes.”
Money is not just dollars—it’s direction. Every family has unspoken values around money: generosity, frugality, privacy, responsibility, and opportunity. The holidays are a natural time to put words to those values.
Some examples:
- “We want our wealth to strengthen the next generation, not replace their sense of purpose.”
- “We want to support education, not lifestyles.”
- “We want the family to stay close and treat each other well. That matters more than the dollars.”
- “We believe in giving while living.”
When the family understands the values behind your decisions, the decisions themselves feel grounded, not arbitrary.
How to Start These Conversations Without Making Thanksgiving Awkward
This is the part most people worry about. You don’t need a formal meeting. You don’t need to bring out documents at the dinner table. You simply need an opening—something like:
“I want to make life easier for you all down the road. Nothing urgent. But I’d like you to know where things are and what I want if anything ever happens.”
That’s it. Calm, light, honest.
If the moment doesn’t feel right, wait for a quieter time—after dinner, on a walk, or over coffee the next morning.
The conversation doesn’t need to be long or perfect. It just needs to begin.
What Families Gain From These Conversations
Every time I help a family open these topics, something shifts. Anxiety goes down. Understanding goes up. Siblings who worried about disagreements begin to relax. Parents often walk away feeling lighter, knowing their kids are no longer in the dark.
By talking openly now, you protect your loved ones from the most common sources of family stress:
- Guessing
- Confusion
- Misinterpretation
- Conflict
- Delays
- Emotional burden
Clarity is not just a financial gift. It’s an emotional one.
A Simple Holiday Reminder
The holidays remind us what matters: family, connection, and legacy. Not legacy in the financial sense, but legacy in the human sense—who we are, what we stand for, and what we hope endures long after we’re gone.
Money conversations don’t have to steal joy from the season. They can add to it. They’re another way of saying: “I love you enough to make things clear.”
If you haven’t had these conversations yet, the holiday season may give you the perfect window—not for final decisions, but for beginning a thoughtful, steady dialogue that will serve your family for years to come.
And if you’d like support preparing for those conversations or want clarity around your own plan, we are always here to help. At Century Management Financial Advisors, we guide families through these decisions with purpose, calm, and care.