Your Holiday Head Start: Simple Things to Do Now for a Less Stressful Christmas

Is it just me, or does December have a way of sneaking up on us?

One minute we’re putting out pumpkins and planning Thanksgiving dinner, and the next we’re frantically searching for Christmas stamps, wondering where we hid that perfect gift we bought in July, and asking ourselves why we thought hosting three holiday gatherings was a good idea.

Sound familiar? 😂

Now, before anyone panics, I’m NOT suggesting we skip Thanksgiving. That poor holiday deserves its moment in the spotlight, too. Pass the stuffing, please!

But over the years, I’ve learned that taking care of a few little things ahead of time can make a BIG difference when the holiday season gets into full swing.

And believe me, I’m not writing this from some perfectly organized, color-coded Christmas command center. Between working full-time, keeping up with this little blog, family, church, and everything else life throws our way, I know how quickly the calendar fills up.

So consider this your gentle nudge to give yourself a little holiday head start.

No pressure. No deadlines. And definitely no expectation that you’ll tackle everything on this list.

Just a few simple things you can do now so you have more time to enjoy the magic later.

1. Get a Jump on Those Christmas Cards

Let’s start with one of those little projects that always seems to take longer than we expect.

If sending Christmas cards is part of your holiday tradition, now is a great time to get a few things checked off your list.

  • Update your address list. Any friends or family move this year? New marriages or additions to the family? Make those changes now.
  • Buy Christmas stamps. The holiday designs are already available, so why not pick them up before the post office gets crazy?
  • Start looking through your photos. If you send photo cards, scroll through this year’s pictures and start narrowing down your favorites.
  • Order your cards early. Already have the perfect photo? Go ahead and order them! One less thing to think about later. (Keep a look out for early bird discounts, too!)

And if you’re an old-school Christmas card sender like me, there’s something especially satisfying about getting those little envelopes ready to go.

Now, actually getting them in the mail? That’s another story. 😉

2. Start Your Gift List (And Shop Your Own Stash!)

I’m a big believer in keeping a running gift list. Not only does it help me stay organized, but it also keeps me from forgetting what I’ve already purchased.

Because there’s nothing quite like finding a gift you bought months ago…after you’ve already bought another one.

A few easy things to do now:

  • Make a list of everyone you’ll be shopping for and establish a budget that works for you.
  • Check your gift stash or gift closet before buying anything new.
  • Start asking for wish lists, especially from those hard-to-shop-for family members.
  • Order personalized or custom gifts that may require extra time.
  • Keep an eye out for sales on things you already planned to purchase.

And don’t forget those smaller gifts for neighbors, teachers, coworkers, and holiday hostesses.

Need a little gift inspiration? I’ve rounded up plenty of ideas in my Stocking Stuffers, Favorite Things Party Gift Ideas, and Hostess Gift Ideas posts. Sometimes the hardest part is just figuring out what to buy!

3. Give Your Holiday Calendar a Little Attention

Before the invitations start rolling in, take a few minutes to look at your calendar.

Holiday concerts, church celebrations, family gatherings, school activities, parties…you know how quickly it all adds up.

If you’re planning to host something this season, consider choosing a date now and giving your guests a little heads-up.

You don’t need to plan the menu, polish the silver, or start making place cards. Just getting the date on the calendar is a win.

And while you’re at it, think about the things you really want to make time for this year.

A favorite holiday concert? An evening looking at Christmas lights? A quiet night watching a Christmas movie?

Put those on the calendar, too.

The fun stuff deserves a spot right alongside the obligations!

4. Take a Peek at Your Holiday Supplies

Notice I said peek. I’m not suggesting you haul every Christmas bin out of the attic before Halloween!

But a little inventory can save you from buying things you already own—or discovering you’re out of something when you need it most.

A few places worth checking:

  • Wrapping supplies: Paper, ribbon, tissue, gift tags, tape, bags, and boxes.
  • Holiday entertaining supplies: Candles, napkins, serving pieces, table linens, and glassware.
  • Decorations: Anything you already know needs replacing, repairing, or replenishing.
  • Holiday baking basics: Check your pantry before making that first big baking supply run.

This is also where my little habit of taking notes from the previous Christmas comes in handy.

Every year, I try to jot down what worked, what didn’t, what I served, what I purchased, and what I want to remember for the next holiday season.  Because as I’ve said before, memory is a liar! 😂

I shared more about this in my Next Christmas Prep (Because Future-You Deserves a Break) post.  Turns out, last year’s me occasionally has some pretty good advice for this year’s me!

5. Think About Your Favorite Holiday Traditions

Now for the fun stuff!

We all have those little traditions that make Christmas feel like Christmas. And sometimes, in the rush to get everything done, they’re the very things that get squeezed out.

So think about what makes the season special for you and your family.  Maybe it’s an Advent calendar, making an Advent wreath, baking cookies together, or gathering your girlfriends for a Hallmark Christmas Movie Night.

Perhaps it’s visiting a favorite Christmas display, attending a special church service, or simply spending a quiet evening at home with the tree lights on.  Whatever those traditions look like for you, give them a little thought now.

A few things, like popular Advent calendars or tickets to holiday performances, are worth ordering or booking early.

But the rest? They can wait.

And if you’re looking for inspiration, I’ve shared some of our favorite traditions here at Fun with Fun-Size, including my Advent Calendar ideas and Hallmark Christmas Movie Night.

Because at the end of the day, these are the things we’re making room for in the first place.

A Little Holiday Head Start (Without the Overwhelm!)

Here’s the thing: You don’t need to tackle this entire list today. Or this week. Or even this month.

Maybe you update a few addresses while watching television. Pick up stamps while running errands. Start a gift list while waiting for an appointment.

Little things. Bite-sized pieces. No holiday marathon required.

And because I know how easily those little mental notes disappear (or is that just me?), I’ve created a simple Holiday Head Start Checklist you can print and keep handy.

You’ll find it in my Resource Library, along with other little extras I’ve created to make life a bit easier.

Pick a few things, check them off when you can, and give yourself a little pat on the back.

Final Thoughts: More Joy, Less Juggling

The goal isn’t to have Christmas completely planned before Thanksgiving. Good grief, where’s the fun in that?

It’s simply about getting a few of those pesky little tasks out of the way so there’s more room for the good stuff.

The twinkling lights. The traditions. The gatherings. The laughter. The people we love.

And if life gets busy and some things don’t get done?  What doesn’t get done, doesn’t get done.

The holidays aren’t about checking every box on a list. They’re about being present enough to enjoy them.

So here’s to a little preparation, a little less scrambling, and a whole lot more holiday joy.  And maybe, just maybe, knowing exactly where the tape is when we need it. 😉

Happy holiday prepping, my friends!

Love finding little ways to make the holidays easier?

Subscribe to Fun with Fun-Size for easy entertaining ideas, thoughtful gifts, holiday inspiration, and everyday reasons to celebrate. You’ll also get access to my Resource Library, including the Holiday Head Start Checklist.

Because celebrating life should be fun—not another full-time job!

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