From Halloween to Christmas: Planning Ahead for a Less Stressful Holiday Season

As soon as the pumpkin spice chai hits Starbucks, that's my signal ... it's time to start decorating for Halloween!

I love Halloween, and I LOVE Christmas.

But as much as I love the holidays, I also know how quickly those wonderful weeks between Halloween and Christmas can become overwhelming.

There are decorations to put up, parties to attend, gifts to buy, cards to send, meals to plan, guests to prepare for, and somehow we're supposed to enjoy ourselves, too!

My solution is to start early and make a plan.

You don't need to do everything at once. By spreading the work over several weeks, you can get the necessary tasks out of the way and leave more time in December for the things you actually enjoy.

So, grab your calendar and let's get started!

SEPTEMBER & OCTOBER

Start With the Big Picture

Yes, we're starting Christmas planning while the Halloween decorations are still out!

You don't have to start Christmas shopping or pull out the tree. We're simply getting organized.

Where Are You Spending Christmas?

This is the first question to answer.

Are you staying home? Hosting? Traveling? Visiting family?

If you're traveling, start making arrangements early. Think about:

• Flights or driving plans

• Hotels or accommodations

• Pet care

• Time off from work

• What you'll need to pack or ship

• Gifts that will need to travel with you

Once you know where you'll be, the rest of your holiday planning becomes much easier.

Create Your Holiday Calendar

Put every confirmed event and tradition on your calendar.

Include things like:

• Family gatherings

• School events

• Office parties

• Neighborhood parties

• Church events

• Holiday performances

• Cookie exchanges

• Travel

• Christmas traditions

• Holiday photos

• Parties you're hosting

If you're planning to host a holiday party, start planning it now.

Once everything is on the calendar, look at each event and ask:

What will I need for this?

Maybe you need a new outfit for the office Christmas party.

Maybe the kids need clothes for Christmas pictures.

Maybe you're hosting a party and need additional serving pieces.

Add these things to a Holiday To-Buy List.

I keep food and gifts on separate lists. Otherwise, one enormous holiday shopping list becomes overwhelming very quickly!

Decide on Your Christmas Budget

Before you start shopping, decide how much you want to spend for Christmas.

Consider more than just presents.

Your holiday budget might include:

• Gifts

• Decorations

• Christmas cards

• Stamps

• Food

• Entertaining

• Clothing

• Travel

• Activities

• Teacher and neighbor gifts

• Shipping

Then create your gift list and decide on a budget per person or per present.

Having a plan before you start shopping makes it much easier to avoid those impulse purchases that can add up quickly.

Create the Family Wish Lists

Sit down together and have everyone in the family create a Christmas wish list.

This is especially helpful when grandparents, aunts, uncles, and friends start asking:

"What does everyone want for Christmas?"

Instead of trying to remember ideas on the spot, you've already got them.

You can even create online wish lists or registries through retailers such as Amazon or Target so extended family members can easily see ideas.

And don't forget to create a list for yourself!

Get a Head Start on Christmas Cards

Create or update your Christmas card list early.

I find the easiest option is to choose a favorite family photo and have photo cards printed. I always have a message printed directly on the card—that's one less thing I have to do later!

If you want something more personal, you could include a family Christmas letter.

Another fun idea is to create a little update for each member of the family—just a few sentences about their year—and print those on labels to place on the back of the card.

Once you've finalized your list:

• Purchase or order the cards

• Update addresses

• Print address labels

• Buy stamps

• Purchase shipping and packing supplies if you'll be mailing gifts

One more December errand has just disappeared from your list!

NOVEMBER

Get the House Holiday-Ready

Before bringing out the Christmas decorations, I like to declutter the house.

Christmas decorations add a lot visually, so removing some of the everyday items makes the house feel much less cluttered.

This is also the perfect time to have children go through their toys.

Have them choose toys they've outgrown or no longer play with and donate anything that's still in good condition.

You're making room for the gifts that will arrive at Christmas while teaching children the wonderful habit of giving to others.

My Christmas Decorating Trick

I have a cabinet that I use specifically for this purpose.

When I decorate for Christmas, some of the pictures, knickknacks, and everyday décor around my house go into that cabinet.

That leaves room for my Christmas decorations without making the house feel overcrowded.

When Christmas is over, the decorations go away and my everyday pieces come back out.

Everything has a temporary home.

Start Your Holiday Meal Plan

Think through all the meals you'll be responsible for during the holidays.

That includes more than Christmas dinner.

Consider:

• Christmas Eve

• Christmas morning

• Christmas dinner

• Overnight guests

• Parties you're hosting

• Appetizers

• Desserts

• Drinks

• Cookie baking

• Teacher and neighbor treats

Start your grocery list now.

I like to divide mine into nonperishable and fresh items.

You can begin buying nonperishable ingredients as you see them on sale instead of purchasing everything during one giant grocery trip right before Christmas.

Also look at your recipes and ask:

What can I make ahead and freeze?

Anything you can prepare ahead is one less thing you'll need to do during Christmas week.

Start Christmas Shopping

Now it's time to start working through that gift list.

The important part?

Stick to the list!

Keep track of what you've purchased and what you've spent.

If wrapping as you shop works for you, that's a wonderful way to stay ahead.

Personally, I can't do that!

I like to see everything I've purchased for each person before I wrap. It helps me make sure I've kept things reasonably even and haven't forgotten anything.

So I shop by my master list and then, once I've finished shopping for someone, I wrap all of that person's presents at once.

Find the method that works best for you.

MID-NOVEMBER

Cards & Gifts That Need to Travel

By mid-November, I like to focus on anything that needs to leave my house.

Finish ordering your Christmas cards and start purchasing gifts that will need to be mailed.

This gives you plenty of time for orders to arrive, gifts to be wrapped, boxes to be packed, and packages to be shipped.

My Goal: December 1

I always try to have everything that needs to be mailed out of my house by December 1.

Once those boxes are gone, I can cross an entire category off my Christmas list!

MID-NOVEMBER TO DECEMBER 1

Time to Decorate!

I personally start decorating around mid-November because I have a LOT of Christmas decorations! 😊

If you don't decorate quite as enthusiastically as I do, December 1 is a great goal.

Here's one of my favorite organizing tricks:

Clean as You Decorate

Before you decorate an area, clean it.

This is the time of year when the top of my entertainment center finally gets its deep cleaning! 😊

Dust the shelf, clean the surface, vacuum behind the furniture—whatever that area needs—before putting the decorations in place.

I try to use Christmas decorating as my holiday deep clean.

Once the house is decorated, I can spot-clean throughout December instead of worrying about major cleaning projects when things get busy.

DECEMBER 1

Christmas Is Coming!

December 1 is a great deadline for several holiday tasks.

By now:

• Mailed gifts should be on their way

• Christmas cards should be ready to send

• Most decorating should be underway

• Your gift shopping should be well underway

• Your holiday meal plan should be taking shape

This is also a good time to order your turkey, ham, roast, or other special meat for Christmas dinner.

If you're buying a frozen turkey, you can purchase it now—just make sure you have enough freezer space first!

Getting a Real Christmas Tree?

If you prefer a real Christmas tree, this is a great time to get one.

Before bringing it into the house, give the tree a fresh cut at the base if needed and place it in water promptly. Once it's inside, keep the tree stand filled with water throughout the season.

Then decorate and enjoy that wonderful Christmas-tree smell!

SECOND WEEK OF DECEMBER

Finish Shopping & Wrapping

My goal is to have Christmas shopping finished and wrapped by the second week of December.

This gives me breathing room.

Finish:

• Your gift list

• Your regular Holiday To-Buy List

• Any remaining nonperishable grocery shopping

• Party supplies

• Stocking stuffers

• Teacher gifts

• Hostess gifts

• Wrapping

At this point, you're no longer preparing for Christmas.

You're getting ready to enjoy Christmas.

ONE WEEK BEFORE CHRISTMAS

Prepare the House & Kitchen

Now we're getting close!

This is the week to get the household caught up.

Around the House

• Get laundry completely caught up

• Make guest beds

• Put fresh towels in guest bathrooms

• Stock toiletries

• Check toilet paper, paper towels, soap, and other household necessities

• Do your final spot-cleaning

• Clear space in the refrigerator

In the Kitchen

Finalize your Christmas meal plan and review your grocery list.

This is also when we bake Christmas cookies.

We love giving cookies to teachers, neighbors, friends, and others we want to remember during the holidays.

I make extra and freeze some of the cookies so my family can still enjoy fresh-tasting Christmas cookies when Christmas arrives.

This is also the perfect week to prepare and freeze any recipes that can be made ahead.

2–3 DAYS BEFORE CHRISTMAS

Fresh Food & Final Prep

Now shop for your fresh ingredients.

Because you purchased the nonperishable ingredients earlier, this grocery trip should be much more manageable.

Then start preparing anything you can ahead of time.

Chop vegetables.

Make desserts.

Prepare casseroles.

Make sauces.

Set up serving pieces.

If possible, set the Christmas dinner table early.

It's one more job you won't have to think about on Christmas Day—and I love walking past a beautifully set Christmas table while we're waiting for the big day.

If you're using a frozen turkey, make sure you've allowed enough refrigerator-thawing time based on its weight.

Don't Forget the Little Things

Some of the smallest forgotten details create the biggest Christmas-morning frustrations.

Before Christmas Eve:

• Check batteries for children's toys and gifts

• Buy extra batteries if needed

• Charge phones

• Charge cameras

• Charge video cameras

• Charge portable speakers

• Make sure you have chargers available for guests

• Assemble complicated children's gifts ahead of time when possible

• Have trash bags ready for wrapping paper

And then...

Stop.

You've planned.

You've shopped.

You've wrapped.

You've cooked.

You've cleaned.

You've decorated.

Now it's time to enjoy what all that preparation was for.

The Chaos Managed Holiday Philosophy

The goal of planning Christmas early isn't to create a picture-perfect holiday.

It's not about having the most beautifully decorated house, making every recipe from scratch, or checking every possible tradition off a list.

The goal is to make room for Christmas.

When we spread the work over several weeks, December doesn't have to become one giant to-do list.

You have time to bake cookies.

Watch Christmas movies.

Drive around and look at lights.

Go to the party.

Sit by the tree.

Spend time with the people you love.

And maybe—just maybe—you'll get to Christmas Eve and realize something wonderful:

There's nothing left to do except enjoy it.

— Samantha

Professional Organizer | Chaos Managed