Decide the Holidays in October

Let me guess how last December went.

Around the second week of November, somebody asked where you were doing Thanksgiving. Nobody had an answer, so it got decided by whoever called first, which was your mother in law. Then Christmas got decided by guilt. The gifts got bought in a panic on the 19th. The kids’ school concert landed on the same night as your client dinner, and you found out about the concert at 4pm that day. You spent the week between Christmas and New Year’s half on your laptop, half on the couch, fully on neither.

And at some point, probably in a car, probably on the way home from somebody’s house, there was a fight. Not about anything big. About who said what to whose sister, or why we always go there, or why you were on your phone during dinner.

The fight was never really about the holidays. Nobody made any decisions, so the season made them for you, and you both resented how they turned out.

Monday we talked about getting your work into next year’s budget before somebody else writes it. Same principle applies at home, and the stakes are higher. You run a business. You’d never let your Q4 calendar get built by whoever happened to email first. You do it to your family every single year.

Because by November the decisions are getting made anyway, by everybody except you.

Your parents are already assuming. Her parents are already assuming. Flights are already climbing, and the good rental by the lake is already booked by somebody who planned in September. Your kids’ schools have already published the concert and recital schedule, and some of it is already on a calendar that isn’t yours.

And the season is getting heavier, not lighter. Deloitte is forecasting holiday retail sales of $1.70 to $1.71 trillion this year, up four to almost five percent. Everybody’s going to spend more, travel more, and show up more tired. Last year’s APA poll found 41 percent of adults expected the holidays to be more stressful than the year before, way up from 28 percent the year prior. Money, family friction, and grief topped the list.

You can’t fix all of that. You can fix the part where none of it was planned.

Thanksgiving is Thursday, November 26. Christmas is a Friday this year. That gives you eight weeks of runway right now, and about four before the defaults lock in.

One meeting. Ninety minutes. You and your wife, or you and whoever runs the household with you. No kids, no phones, ideally somewhere outside the house where neither of you will get pulled into laundry or email. A booth at a diner works great. So does a long walk with a notepad.

Put it on the calendar this week. Treat it like a board meeting, because it is one. The board just happens to be the two of you.

Here’s the agenda. Six items, in this order.

Get a printed calendar for November 20 through January 4. Paper. You want to see the whole season at once.

Mark everything that’s already fixed. School breaks. Office closures. Concerts, recitals, games, parties you’ve already said yes to. Your business deadlines. Her business deadlines. Any travel already booked.

Most couples have never looked at the whole season on one page. It’s always a shock. You’ll see collisions you didn’t know were coming, and you’ll catch them now instead of at 4pm on the day of.

This is the big one, and it’s where most of the old fights live.

Each of you writes down, separately, before you talk: Where do you want to be for Thanksgiving? For Christmas Eve? For Christmas Day? For New Year’s? Then compare.

Some of these will match. Lock those in. For the ones that don’t, here’s a framework that keeps it from becoming a referendum on whose family matters more:

Pick one approach for each holiday. Then agree on one thing that matters more than the location: how long you’re staying, and when you’re leaving. “We’ll head out around 7” said in October is a plan. Said at 9pm on the day, it’s an argument.

Most of the money stress in December comes from never setting a number in the first place. You spend whatever the season pulls out of you and find out the total in January.

Set three numbers:

Then agree on the rule for going over. Something like: anything over $200 that isn’t on the list, we talk first. Simple, and it eliminates the “you spent how much?” conversation in January.

Here’s where you need to be honest, because this is where most men blow up the holidays without meaning to.

Look at the calendar together and decide, out loud, which days are work days and which are not. Specifically:

Then tell your team and your top clients your schedule before Thanksgiving, in writing. “I’m offline December 24 through 27. For anything urgent, contact Jen.” When your clients know you’re off, they plan around it. When they don’t, they text you on Christmas Eve, and you answer, because you didn’t set it up any other way.

Your wife has watched you “quickly check something” at every holiday for years. That schedule is mostly for her. She needs a reason to believe you this year.

Each of you names one thing that makes the season feel like the season. Be honest about it, even if it sounds small.

Maybe it’s the morning walk on Christmas Day. Maybe it’s the dinner with just the four of you before the family stuff starts. Maybe it’s driving around looking at lights with hot chocolate in the car. Write them down and put them on the calendar like appointments, because if they’re not on the calendar, they’re the first things the season eats.

Then each of you names one thing you’d happily never do again. The party that nobody enjoys. The gift exchange with forty dollar limits and fifty people. The 6am drive. You don’t have to kill all of them this year. But naming them out loud is how they stop being mandatory.

Somebody’s going to be disappointed by item two. Probably a parent. Decide now who makes which call, and make them in October, not the week of.

This is the script I’ve used, and you can steal it:

“Mom, wanted to give you a heads up early so you can plan. We’re doing Thanksgiving at Sarah’s parents this year and we’ll be with you for Christmas Eve through Christmas morning. We’re really looking forward to it. What can we bring?”

Notice what it does. It leads with the plan, not an apology. It gives her something to look forward to. And it ends with a question that moves the conversation to logistics, not feelings. Make the call. Don’t text it. And make your own family’s call yourself. Your wife shouldn’t have to deliver bad news to your mother.

One move will change your December more than anything else here: buy the gifts in October.

At least the ones for the people who matter most. It works because you’re not tired yet, you have time to think about what each person actually wants, things are in stock, and shipping is free and normal.

The hard part is remembering what people want. Your brother mentioned a book in June. Your mom said something about her garden in August. Your kid’s teacher has a thing for a certain coffee shop. You heard all of it, and you remember none of it on December 19th.

I keep all of this in Clay. It’s where I keep notes on everybody in my life, family included. When somebody mentions something they want, or a kid’s name, or that they just moved, it takes ten seconds to add a note. Come October, I open it and the gift list is basically already written. It’s also why I remember birthdays now, which my wife has noticed, and which has been worth more than the subscription.

If you’d rather use a note on your phone, fine. Just start it today and write down everything you already know.

“My wife handles the holidays.”

She does. And she’s tired of handling them alone. Showing up to this meeting with a printed calendar and a pen is one of the most attractive things a man can do in October. I’m only half joking.

“Our families won’t go for this.”

Your families don’t get a vote on whether you plan. They get a vote on how they react. Most of them will be relieved. The ones who aren’t would have been upset no matter when you told them. Telling them early is a kindness.

“I can’t commit to days off. The business needs me.”

Then the business has a problem bigger than the holidays, and the holidays are just where it shows up. If three days without you is a crisis, you’ve got a single point of failure, and that point is you. Fix it this quarter, and use the holidays as the deadline.

Three things, this week:

One meeting in October buys you a December where you’re actually there.

Friday, we’re back to work, with a tool every pro athlete uses and almost no business owner ever touches. You’ve been in hundreds of sales calls. You’ve never once watched yourself in one.

Refined. Relentless. Unapologetic.

Marcus