Holiday Planning in October: 5 Do-Ahead Steps For a Simpler Season

The holiday season may seem distant right now, even a little out of focus. But as we’ve all experienced, once it hits, that distant vision can turn into a blur fast. I picture lit candles, festive foods, friends and family, and a little time to relax. The reality of those five or six weeks is often something else entirely. Menus to plan, gifts to buy and wrap, events to host and attend. But holiday planning in October can help. Here are 5 do-ahead steps for a simpler season.

I first wrote about getting ahead of the holidays last October. I’d decided to try the approach I wish I’d taken years ago: small, intentional steps in the fall, so December didn’t swallow me whole. Not frantic, not overachieving. Just smart preparation that frees up time and sanity when it matters most.

So how did it go? A few wins. A few not-so-much.

What worked and what didn’t

Things like organized holiday wrapping start off great. Then the kids return home and it turns into a blizzard of paper and ribbon. Honestly? We love having them home so much I no longer care!

But that doesn’t mean I’m abandoning my list. This year I’m doing it again, with one change. Before I touch a single bin or start a single list, I’m deciding what the season is actually for. For me, that’s family. In all its messiness. And that includes tolerance for a disorganized wrapping station.

Start with the season you want, then the tasks

Here’s what I noticed last year. The do-ahead steps helped. They really did. But getting organized earlier only solves half the problem. If your list is too long, starting it in October just means you’re busy for three months instead of one.

Somewhere along the way, the holidays became a season of more. More gifts, more parties, more decorations, more baking, more everything. All packed into the same six or eight weeks, on top of a life that was already full before any of it started. And more was never really the point. Connection was. Meaning was. A handful of moments that felt like they mattered.

Not everything we do this time of year is worth the same amount of us. Some of it is real. Some of it is habit, obligation, or the fear of doing less than last year. So before the five steps, I take one honest pass at three questions:

• Who do I actually want to give to, not everyone on a list built out of guilt?
• Which decorations genuinely make our home feel like the holidays, not just the ones I’ve always put up?
• Which events do I look forward to, and which do I dread the minute the invitation arrives?

My answers become my real list. Everything else in this post gets filtered through it, and you’ll see those questions show up in every step below.

Want a place to write your answers down? Your Simple Season is my free guide to deciding what matters this holiday season, and then protecting it once you have. Three short sections: Name What Matters, Guard What You Choose, and Step In Simply. A shorter list. A fuller season.

1. Taking stock of my holiday decor (and letting go of what I don’t love)

One of the fastest ways to make December easier is to know what you actually have. Decorations multiply over time. Think candles tucked in boxes, garlands that have lost their sparkle, ornaments whose hooks have mysteriously disappeared. Every year I used to promise myself I’d sort through it all “after the holidays.” But by January, I was too tired to care, and everything got stuffed back into the bin it came from.

• So in early October, I pull out my bins and boxes and spread it all out. I pick a slow Saturday morning, make a pot of coffee, and treat it like a treasure hunt. The question I ask now is simple: which of these actually make our home feel like the holidays? If you’ve moved, you’ll probably find the garland that perfectly circled your old staircase has no place to go in your new home. Or maybe it’s just the sheer volume that’s overwhelming you and your storage space.

• Fewer decorations, but the right ones, make the whole house feel peaceful instead of chaotic. For me, that’s the Santa pillow my grandma sewed and stuffed decades ago. And the spinning musical Santa, rotating to “Santa Claus is Coming to Town.” Those stay, every year. A lot of the rest is negotiable. Here’s the permission I didn’t give myself for years: you’re allowed to decorate less than you did last year. Nobody is keeping score. If hauling out every bin feels like a chore rather than a pleasure, that’s worth noticing.

• While everything is out, I jot a quick list of what needs replacing, like a string of lights or a missing wreath hook. I still vividly remember the Covid year when I could not, at any price, find tinsel for our tree. There simply was none. So order what you need now, while shelves are fully stocked. By Halloween, everything is packed and labeled again. I’m definitely not an early decorator. Nothing comes out until after Thanksgiving. But when it’s time, I know exactly where my favorite pieces are.

• When our kids were young, we’d pick a day after school to start decorating. They all loved helping. Decorating isn’t quite as exciting as it once was, but I put on some music and begin. When I can do it without digging and sighing and wondering what I’m missing, it’s a much more fun experience.

2. Getting a head start on gifts

• Few things unravel our calm faster than last-minute gift shopping. Between long lines, shipping delays, and trying to guess what people might want, the whole thing can feel more like a marathon than a pleasure. So I start in October.

• My first step is the list, and this is where the real list matters most. I write down the people I genuinely want to give to this year. Not everyone I’ve ever exchanged gifts with. Not the coworker I feel I “should” include. The people I’d actually love to surprise. Then I add a few ideas next to each name. I don’t need the perfect idea for everyone right away. Just a direction. It’s not a fancy spreadsheet. Just a note on my phone, which works well because I can save links to things I’m considering.

• My second step is one I skipped for years: I set a real number for gifts, and I say it out loud, before the sales start. To my husband, to myself, written at the top of the list. A budget I’ve said out loud is so much harder to drift past one “perfect find” at a time. My fully updated Gift Guides are out soon. Click here to get an update when they publish.

• October is a smart time to shop. Sales start well before the big holiday promotions, as retailers try to win early shoppers. Prices and shipping times have been unpredictable lately, too, and buying early takes that pressure off. Spacing purchases out also avoids the December crunch, when every shopping cart seems to fill at once. If I’m shopping online, I check shipping times and availability now. If I’m buying locally, I note the small businesses I want to support and plan a couple of November visits, before the stores get crowded.

• And one trick I’ll never give up: a small bin or closet shelf that serves as my holiday gift station. As gifts arrive, they go straight there, along with wrap, tissue, tags, and tape. By the time December rolls around, much of my shopping is done, and all that’s left is wrapping and enjoying it. Starting early isn’t just practical. It changes the emotional tone of giving. There’s time for real thoughtfulness, and less pressure to check boxes. For me, it’s about finding things that will truly delight the people I love.

3. Holiday menu plans and prep (yes, in October)

• It might sound early to think about holiday meals, but food is the heart of so many gatherings, and it’s also one of the biggest stressors. Every year I used to find myself running to the store for last-minute ingredients, or realizing I was out of the one spice I needed for a favorite recipe.

• I start by jotting down the meals I’ll likely host or contribute to: Thanksgiving dinner, a December brunch, Christmas Eve appetizers, a New Year’s Eve dish. Nothing is set in stone. It’s a loose sketch of what’s coming. And it’s a good moment to ask whether every one of those meals needs to be homemade, or whether some can be simpler this year.

• With that list in hand, I pull out my favorite recipes and check the pantry. October is a great time to restock shelf-stable staples like flour, sugar, baking powder, spices, nuts, canned pumpkin, and chicken broth. Doing this early saves money before prices climb closer to the holidays, and it avoids crowded stores. I even prep a few make-ahead items, like homemade cranberry sauce or cookie dough that freezes beautifully.

• I start baking Biscotti in late October, so it’s ready from Thanksgiving through New Year’s.

• A friend of mine starts a “Holiday Freezer List” every October, a sticky note on her freezer door that lists what’s prepped and ready. I borrowed that idea last year and it’s a keeper. By December, the goal is a few things waiting, a plan in place, and the peace of mind that dinner doesn’t depend on a last-minute grocery miracle.

4. Scheduling the holidays before they schedule me

The holiday season has a sneaky way of filling itself with parties, concerts, gatherings, and errands. I’ve noticed that anyone I haven’t seen in a while suddenly feels the need to get together before the holidays. Lovely, in theory. But it adds up. And if you went to their house last year, guess whose turn it is this year.

By the time December arrives, it can feel like we’re living someone else’s calendar. So I set the pace before the invitations start rolling in.

• I keep two kinds of plans. A paper planner for menus and baking, because I like seeing it all on one page. And my digital calendar for everything with a date and time. In early October, I plug in the big events I already know about: friend dinners, the kids’ breaks and travel, and any larger family gatherings. Then I block off a few white space weekends, days I keep free on purpose to rest, bake cookies, or simply enjoy the season without rushing.

• I also book appointments that fill up fast, like salon visits or a home cleaning before kids or guests arrive. October is early enough that schedules are still open. The bigger part of this step is deciding what kind of December I actually want. Do I crave slow evenings with lights and music, or am I energized by gatherings and outings? For us, the answer is somewhere in the middle. Knowing that makes the next decision much easier.

• Here’s the decision: I sort invitations in advance. A few things get an automatic yes. The family gathering, the friend dinner we’ve done for years, [add one or two of your own real automatic yeses]. Everything else gets a considered maybe, not an automatic yes. That doesn’t mean no. It means I check it against my real list and my white space before I answer.

Protecting my calendar isn’t about restriction. It’s about making sure the things I actually chose don’t get crowded out by the things I didn’t. The calmest Decembers don’t happen by accident. They’re built one early decision at a time. The reward is more moments that feel meaningful, and fewer that feel like obligations.

5. Ordering holiday cards (and gathering addresses) early

Holiday cards used to sneak up on me every year. I loved sending them, but they were a mini-marathon. The outfits for the kids, the photo shoot (or shoots), the editing, the card design. It always seemed to land right when everything else peaked.

These days, we only send holiday cards every few years. I’d rather stay in touch with the people on that list more often throughout the year than rely on one annual family update. But there’s a time and place for every approach, and if cards are on your real list this year, October is the month to make them easy.

• Start by updating your address list. A quick text or email to friends confirms new addresses before the rush. Then decide on the type of card you want, photo cards, classic designs, or something handmade, and order now while discounts are plentiful. Printers are faster in October, and you can take your time writing personal notes.

• If you send cards digitally, it’s still worth setting up the list early. Draft your message, choose a design, and schedule the send. A little organization now turns a stressful December chore into something meaningful.

• I also use this step as a prompt to refresh wrapping supplies: tape, tags, ribbon, and paper. These are easy to forget until it’s midnight and you’re out of tape. Restocking now means I’m ready for spontaneous wrapping sessions, or for when the kids get home, arms full of gifts that all need wrap and ribbon.

Why October is the month to begin holiday planning

The beauty of doing these things in October isn’t just that December feels lighter. It’s that November and December get to be more fun. The season unfolds instead of unravels. There’s room for spontaneity because the essentials are already handled.

A simple season isn’t a smaller season. It’s a clearer one. When you walk into December already knowing what you’re keeping and what you’re letting go of, there’s room left over. Room for the moments you can’t plan, and for actually being present at the ones you did.

I think many of us reach midlife realizing that our peace of mind matters as much as any tradition we uphold. We’ve hosted, baked, shopped, and stayed up late making everything magical for everyone else. This stage of life offers a different kind of wisdom. Joy and ease are worth planning for, too.

Making space for what matters

If you’re reading this and already feeling behind, don’t. The point isn’t to do everything perfectly or early. It’s to remember that peace of mind is built in layers, and October offers us the perfect layer of calm before the cheer.

Maybe you start with one thing, like sorting your decorations or sketching your menus, and let the rest unfold from there. Or maybe you start one step earlier, with those three questions about what this season is really for. The smallest early efforts often make the biggest difference later.

Choose your list. Protect it. Let the season be what you decided it would be, not what everyone else’s calendar talked you into. December doesn’t have to be chaos. It can be beautiful, simple, and bright. And that begins now, in October, with a cup of coffee, a good list, and the comforting promise that we’re creating a holiday season we’ll actually have time to enjoy.

Your Simple Season walks you through it: name what matters, guard what you choose, and step into December with a shorter list and a fuller season. It takes about the length of one cup of coffee.

I’ve learned that the calmest Decembers don’t happen by accident. They’re built with intention, one early decision at a time. The reward? More moments that feel meaningful, and fewer that feel like obligations.