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Getting ahead of holiday spending before it starts
“Are we doing the gift exchange again this year?” my sister Becca texted me last weekend. It was the first of October. There were still pumpkins on my porch that hadn’t even started to rot yet.
My first reaction was mild horror. It’s October! Let me have my sweaters and my apple cider in peace. But then I remembered last December, and the sort of low-grade money chaos that hit our family around the twentieth, and I wrote back, “Yes. And let’s figure out the rules now.”
I’ve come around to the idea that the holidays are a lot less stressful, money-wise, if you have the awkward conversations before anyone’s tired and overcommitted. Early October is perfect for this. Nobody’s panic-shopping yet, and nobody’s flight is booked. You can still talk about it like a reasonable adult instead of someone who just saw their credit card statement.
The stuff that sneaks up on you
Holiday spending, at least in my experience, isn’t really one big expense. It’s a hundred small shared ones that pile up. Somebody buys the turkey. Someone else picks up a bottle of wine for the host on behalf of the whole group. Each one feels too small to talk about in the moment. Then January comes and you realize you fronted about $300 worth of “I’ll get you back” and you’re not totally sure from whom.
Last year, for instance, my brother-in-law Greg booked an Airbnb near my parents’ place for all of us siblings, because the house couldn’t fit everyone. Super generous of him to handle it. But nobody talked about splitting it ahead of time, and when he finally brought it up in mid-January, it felt like a surprise bill. A couple of people got a little prickly. Nobody was wrong, exactly. The timing was just terrible.
If we’d had that conversation in October, it would’ve been a two-minute exchange in the family group chat. “Hey, I’m looking at a place for the four of us, it’s about $600 total, so $150 each. Everyone cool with that?” Done. Instead it became a whole thing.
Saying the numbers out loud
I think the main reason people avoid these talks is that saying money numbers to family feels a bit crass. Like you’re turning the holidays into a business transaction. I get that. I really do. But in my experience, the vagueness causes way more hurt feelings than the numbers ever do.
So this year, I’m trying to put real figures on things early. For the gift exchange, we agreed on a $40 limit per person, which felt doable for everyone, including my younger cousin who’s still in school. Picking a number that works for the person with the tightest budget seems like the kind thing to do, even if a few of us could go higher. Nobody wants to be the one who shows up with a scented candle while someone else brought an air fryer.
For travel, the plan is that whoever books something shared posts the total in the group chat right when they book it, not weeks later. It’s a small habit. But it means nobody gets blindsided, and nobody has to play detective with their bank app in January.
My parents usually host, and this year we talked about everyone bringing a dish or chipping in for groceries instead of letting Mom quietly absorb the whole cost the way she always tries to. She protested, naturally. Moms do. But I think she was secretly relieved.
Why this feels motivating to me
There’s something oddly freeing about getting this sorted early. It’s like doing your packing the night before a trip instead of the morning of. Same amount of work, totally different stress level.
Once the shared stuff is figured out, I can actually look forward to the holidays instead of dreading the money part. I know roughly what I’ll spend and who’s covering what, so I can set a little aside each paycheck between now and December, nothing dramatic, just enough so that the shared costs don’t land all at once.
I also think it makes the actual holidays nicer. When you’re not doing silent math at the dinner table, wondering whether Greg’s going to bring up the Airbnb again, you can just enjoy the mashed potatoes. That’s worth a slightly awkward group text in October.
Becca, for the record, has already drawn names for the gift exchange. She did it with an app on her phone and sent everyone a private message. I got Greg. I’m thinking I’ll get him a nice notebook for keeping track of who owes him what.
The OweMate blog is written by the people who make OweMate, a simple way to keep track of money between friends and family.