7 things on my November holiday checklist

Yes to connection, no to frantic energy

Psst: we have another AMA podcast coming up soon! Submit your questions for John and/or me here or just leave them in the comments. You can listen to the first one here!

When a reader (hi, Molly!) learned that we were moving in October, she commented that we’d chosen the best time of year to move. Despite the fact that we definitely didn’t set out to move in the fall, I agreed with her reasoning: this season tends to be about tradition, family togetherness, and cozy rituals — all of which can be soothing in a new environment. Parents usually have time off to ease the transition and provide closeness. The holidays offer a distraction from dwelling on any tough feelings. You’re making a lot of new core memories in a short span and can start a new year in a new place. It all feels a little more exciting and a little less scary for kids!

As if I needed another reason to love the cascade of fall/winter holidays :)

Like many of you, my attention has turned to Thanksgiving and Christmas now that Halloween is behind us. Mine is not a frantic energy, and I bet yours isn’t, either: we’re not looking to rush the season, but we do want to get ahead in a few small ways so that we’re freed up to enjoy the best parts of December — attending events, wrapping gifts, baking treats, welcoming family, or simply reading a stack of picture books by the tree — without feeling the press of execution.

As we work through holiday logistics, I want to encourage us all to plan for the emotional moments, too. As Molly pointed out, the holidays are such a rich opportunity for connection, warmth, modeling, and helping our loved ones to feel seen and known, but these chances can be missed if we overcommit and overwhelm ourselves in the name of good things. With a little advance preparation, we can free ourselves up to be mentally and physically available when it really matters.

With all that in mind, I thought we could chat through a few things I like to do in November to set myself up for a peaceful and joyful Advent. Your list will likely look different than mine, but I hope it sparks an idea or two — or, at the least, gives you some permission to go slow, focus on what matters, and leave the rest behind for the next few weeks.

1. I name (or confirm) what matters most.

This is hard — because there are SO MANY things I and my family love about the holidays — but because what matters most to us is feeling peaceful, relaxed, and able to enjoy our very favorite events and traditions, it’s a must-do. When we’re forced to choose between options or RSVP, we can refer to the thoughtful hierarchy we’ve already made and the choices become a bit easier.

2. I plan our calendar.

It’s easier to do when we know what matters most! There are several pieces to this:

— I confirm any dates we’ll have houseguests, or that we’ll be traveling. I make sure we’re clear on holiday plans for both sides of the family.

— We decide where we’re going to go for our end-of-year celebration dinner and make a reservation. Weekends in December book up fast, and so do babysitters!

— I look up the dates of any “external” holiday activities we want to do and make sure they’re on our calendar. I've also been known to proactively text friends who usually host things in December (like a caroling party) to check on the dates so I can block them off.

(I learned the importance of making space for our must-dos the hard way when a birthday party bumped up against the firehouse pancake breakfast a few years ago. We made it to both, but not without tears and some whisper-yelling between me and John. In the aftermath, I decided to mark the breakfast date on our calendar early and schedule nothing else that morning, and we’re all happier for it.)

— With all of these top-tier things in place, I can see how full our month is and better judge what else we have room for. Finally, I’ll make a loose list of other things we want to fit in and tentatively schedule them, knowing they’re easy to flex (things like baking sugar cookies or an evening drive to look at lights).

3. I start labor-intensive projects.

For me, that means ordering Christmas cards and beginning to paint my children’s book ornaments. Because I like to send a newsletter with our card, it’s a more involved process than just choosing a photo and design. While I usually save the stuffing, addressing, and stamping until the first week of December or so (it’s cozy to do in front of the fire with a Christmas movie on!), I order our cards and send our newsletter to print in November so they’re ready when I am.

For the ornaments, I choose the book for each child, print out the artwork, and gather all of my supplies into a kit so they’re easy to reach for. I also put brush to wood in at least a simple way — maybe painting the base layer — which banishes the pre-project nerves wonderfully.

4. I clear the decks.

Before I add Christmas decor to the mix, I like to pare our home back to a clean slate. I clear surfaces and remove extra decor. I tuck away any furniture we don’t need for the month. I clean anything that needs it. If there are persistent trouble areas, like a particular closet or a spot on the counter that consistently attracts papers, I’ll try to tackle them now. I want the Christmas version of our home to be the most peaceful, lovely, and cozy, so a little extra effort in November goes a long way.

This year, on the heels of our move, my main goal is to unpack the rest of the boxes before we bring our Christmas tree home!

5 I choose a devotional or faith focus.

This could be a book I’ll read, a study I’ll do, a podcast I’ll listen to — something that takes me deeper into my faith. I’ll also think through what faith formation looks like for our kids in this season.

6. We draw names.

These days, we are doing “secret Santa”-esque gift exchanges amongst the siblings instead of everyone giving everyone a gift. I like to have our picks nailed down in November, which leads me to my last to-do…

7. I make a gift plan — and do some shopping.

As much as this flies in the face of certain circles of the internet, I actually like to do some of my Christmas shopping in December! It feels festive and celebratory and happy to me. However, I like to make a general plan for as many gifts as I can early in the season, and I particularly like to knock out the hardest gifts (and any custom gifts) in November. To me, the hardest gifts are usually my parents and in-laws (and they often end up getting custom gifts, so extra time is usually required!). Kid gifts are easy and fun, so I’ll often leave those til December, hitting up my favorite local spots to round things out. And then I get to wrap — whee!

While this list is more tactical and less focused on relational moments, I find that they’re connected: when the logistics are handled, it’s easier for me to be present for and enjoy the sweet/tender/hilarious moments, whenever they might find me.

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For some of you, this process might seem obvious and basic. Maybe you’re a pro planner, and you’ve been honing your own version of this list for years.

But for others, this might be all new. In the Articles Club text chain, one gal recently asked if we could share pics of our bathroom counters and drawers, expressing a bit of shame that she didn’t intuitively know how to organize things. To which wise Pressley (Baird) Frevert responded, “Zero shame for not knowing how to do this. I believe this is a real skill you have to learn and practice.”

I’d say the same thing for orchestrating a holiday season that unfolds as you hope it will. It’s something that comes more naturally for me, and I’m happy to share what works in our home. If you’re earlier in the learning curve, how encouraging that you’ll grow a little more experienced each year! ❤️

Friends, feel free to share where you are on the holiday planning curve, a task you like to complete in November, or any other thoughts that are bubbling. And maybe click over to this post by my dear friend Lisa Kirk for another dose of solidarity on the things we thought we’d know more about by now. xo!

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