Holidays, Money, and the People We Love (and Sometimes Clash With)
We all know how hard it is to talk about money with family – and we also know why it’s important.
Not the abstract stuff – the real, personal conversations. Aging parents. Healthcare decisions. Who’s the keeper of important information? What happens if something happens?
I was reminded of this often when I co-hosted MoneyTrack, the nationally aired PBS series, where family and financial turmoil were recurring themes every season.
These are not conversations you want to have over text or in a rushed phone call. They’re emotional and nuanced, which is why – counterintuitive as it sounds – talking about them in person sometimes makes the most sense.
That’s what makes the holidays – imperfect as they are – a surprisingly good opportunity to fill in a few missing pieces about your family’s financial picture.
With one important caveat: not everything is your business. Knowing what is – and isn’t – in your lane matters just as much as the information itself.
When family is together, there’s usually more context and more opportunity to notice things you might miss otherwise. Maybe not at the dinner table– and not as an ‘announcement’. But quietly, when the moment feels right.
If you have aging parents, a few topics matter more than people realize, and they’re much easier to address before there’s a crisis.
Where important information lives:
Not every detail – just enough to avoid chaos if someone needs to step in.
Healthcare decision-making:
Who has medical power of attorney? Does everyone understand what that means?
How things are really going financially:
Are your parents comfortable, quietly stressed, or becoming more worried they could outlive their savings? Are there small things they’re no longer doing for themselves that might signal tighter budgets or shifting priorities?
Sometimes these family money conversations don’t start with a “money talk” at all.
I remember spending the holidays with my parents in Florida and noticing their dishwasher was clearly on its last legs. Instead of making a big deal about it, I quietly pulled my dad aside and said, “I just saw a quieter model on sale that would really make Mom happy. I have credit card points I need to use, and I’d love to do that.”
It wasn’t about the dishwasher. It was about noticing the small things they weren’t doing for themselves anymore – and what that might quietly signal. You don’t need to interrogate anyone. You just need to pay attention.
The Key: Read the Room
The obvious challenge is that the holidays already come with enough emotion. Money conversations can easily tip into tension or full-blown arguments if you’re not careful.
A few things help:
• Choose the moment carefully – one-on-one, during a walk or a quiet morning.
• Lead with concern, not control.
• Don’t try to solve everything at once – awareness is enough.
• Say the awkward part out loud.
• Know when to hit pause.
A conversation that ends respectfully (even unfinished) is still a success.
All of this is easier said than done.
For me, these conversations were productive based on choosing the exact right moment. Not when anyone is tired. Not when emotions are already running high. And definitely not after a second glass of wine.
I’ve learned they go best when the spirit is light – when no one feels cornered. Sometimes that means a walk. Sometimes a quiet morning. And sometimes it means deciding today isn’t the day – and that’s okay.
If the holidays give you even one small opportunity to start, that’s enough. A little clarity now can prevent a lot of stress later, when critical decisions may be much harder and time feels urgent.
At the end of the day, this is really about taking care of the people who once took care of us.
Happy Holidays Everyone!