Holiday Planning: How to Actually Enjoy the Season

Don’t you love the holidays? I do, especially because there are so many wonderful things to do! Host a beautiful dinner. Go to a concert. Send cards. Bake cookies. Find thoughtful gifts. Invite friends over for cocktails. Go see lights. Set a gorgeous Christmas table. Decorate the house.

And that all sounds fabulous in July – even in September. But when the season actually starts , it doesn’t seem quite so doable anymore. Over the years, I discovered that the secret isn’t trying to do everything faster, it’s deciding ahead of time what I actually want the season to look like. Then I make a plan.

How All My Holiday Planning Started

Back in my younger days, there was no such thing as holiday planning! I ran around like the infamous chicken with no head. I worried so much about all the things I wanted to do, that I couldn’t get organized enough to do any of them!

But then I decided I wanted to be as great a hostess as my mom (that’s another story!) And I figured out a planning strategy that I’ve used and refined ever since. Now it’s so easy to see what I have time for, choose the most important things, and let go of the rest.

“Plan Ahead” – But What Does That Actually Mean?

The whole point of holiday planning is to PLAN, of course. To get a jump on your holiday season so you can enjoy it all, knowing that you’ve got everything under control. Lots of people tell you to “plan ahead,” right? But if you’re like I was, that advice doesn’t really help too much.

“HOW do I plan ahead?” is the question I asked. If you’re asking that too, here’s the plan I created and have used for years.

The basic idea is this:

Look at the whole season first. Decide what matters. Then create a plan to make those things happen.

It’s simple – but so powerful!

I plan what needs to happen in October and November so I’m not scrambling in December. Then I know how parties, travel, gifts, meals, decorating, and regular life all fit together.

How It Works

I like to start with the things that affect everything else — dates, people, commitments, and anything that needs advance reservations or ordering. Then I work my way down into the details.

Here are the ten areas I consider when I’m planning our holiday season – and you can use them too.

1. Start Holiday Planning With the Big Picture

First, take a look at the season as a whole – October through December.

• Which holidays or occasions are you celebrating?
• Where will you be?
• Who will you be with?
• Are you hosting anything?
• Are there traditions you definitely want to keep?
• Is there something new you’d love to do this year?

Put the major pieces on your calendar first. Once you can see the whole season, it’s so much easier to see what realistically fits into it.

And just as importantly – what doesn’t fit into it.

You don’t need to do what other people do, or what you think the holiday is “supposed” to be. Some of our best holidays have been when we just did whatever we wanted, whether it was traditional or not.

2. Think About Your Holiday Budget

Not the most romantic part of holiday planning, but definitely one of the most helpful.

Think about the big picture at first.

Gifts, entertaining, travel, food, decorations, special activities, clothing, tickets, postage — whatever tends to be part of your holidays.

You don’t need to know exactly what everything will cost yet. The point is just to make deliberate choices instead of starting the new year wondering where all that money went!

3. Guests and Travel

Who will you be celebrating with this year? If you’re hosting overnight guests, now is a good time to find out their schedules and any particular needs they have.

If you’ll be traveling, start thinking about transportation, reservations, pet care, and all those other practical details.

Anything that needs to be booked early belongs at the top of your holiday planning list.

4. Gatherings and Activities

Now we get to the fun part!

What do you actually want to do this holiday season? Any of these?

• Maybe you want to host a dinner party.
• Go to The Nutcracker.
• Meet friends for cocktails.
• Have a cookie-decorating afternoon.
• Go to a favorite restaurant.
• Drive around looking at Christmas lights.
• Have people over for a casual soup supper.
• Or just stay home one evening – or more – and drink hot chocolate, look at the tree, and listen to holiday songs.

Choose the things that will make the season feel like your holidays — rather than automatically saying yes to everything that comes along.

5. Gifts

Make your gift list early so you have choices.

Think about who you want to give to, what they might like, and whether anything needs to be ordered, shipped, commissioned, or made.

And remember hostess gifts and those little unexpected gifts that always seem to pop up during December.

You don’t necessarily have to buy everything right now, but knowing what you want to give to whom is the first step toward giving gifts your people will love.

6. Holiday Cards

First, decide if you even want to send cards this year! If you do want to, decide what kind.

• Do you need a family photo?
• Are you writing a letter?
• Do you need to update your address list?
• Will you order cards or make them yourself?

Working backward from the date you’d like them to arrive makes this one much easier.

7. Take Inventory

Before buying anything, see what you already have.

• Decorations.
• Wrapping supplies.
• Candles.
• Serving pieces.
• Table linens.
• Holiday dishes.
• Pantry supplies.
• Or anything you use specifically at this time of year.

Taking a little time to look through what you already have can inspire ideas for the season, as well as save you from buying something twice.

8. Think About the Food

Holiday food is another fabulous part of the season! Start sketching out menus for the meals or gatherings you already know about. You don’t need final recipes yet.

Just think about what you’d like to serve, what you may be asked – or offer – to take to someone ele’s gathering, and whether there are any specialty ingredients or foods that need to be ordered ahead. This is also a great time to identify anything you can make in advance and freeze.

And it’s not just the big holiday meals. If you’ll have houseguests, for instance, think about breakfasts, lunches, snacks, and dinners for the other days they’ll be with you too. Planning those ahead means you can shop once and then have a leisurely breakfast with your guests instead of suddenly remembering that you don’t have enough pastries for twelve!

9. Plan Your Tables

You knew I was going to get here eventually! If you’re hosting holiday meals, start thinking about how you’d like your tables to look.

You might already have everything you need, or maybe this year you want to treat yourself to a new piece or two. Or maybe use your grandmother’s china that usually stays in the cupboard. Or maybe add a different color napkin, bring out the silver, or create a centerpiece around something you already own.

Planning early gives you time to play with ideas instead of trying to invent a whole table twenty minutes before everyone arrives.

10. Get the House Ready

Finally, look at your home. Does anything need attention before the holidays?

Maybe there’s a repair you’ve been meaning to make. Or the guest room needs a little work.

Or maybe all you really want is a good cleaning, the Christmas music playing, candles glowing, and something that smells wonderful simmering on the stove.

Decide what “ready” means to you. Then be realistic about the time, energy, and money you have available. The holidays probably aren’t the moment to launch a major home improvement project. Sometimes the smaller version of a project will make you just as happy – and leave you more time to enjoy the people you’re getting the house ready for.

Now Turn All Those Ideas Into a Plan

Making these decisions ahead of time is what makes the whole season more relaxed and fun. Instead of being totally stressed out – or even mildly frantic, which is still annoying – you already know that you’re prepared for what you’re doing. And what you’re NOT doing!

Start your shopping lists, and actually put events, shopping, and prep time on your calendar. Then you know exactly what happens when.

And when you have your plans already on the calendar, you’ll easily see when you can fit in a spontaneous gathering or last minute fun thing to do. Joining the carolers, maybe?! (AI made this picture for me but seriously – doesn’t it look like it should be on a puzzle?!)

The Art of Holiday Planning

A few years ago, I first shared my holiday planning process here on Mantel and Table as a 10-day planning challenge.

Since then, I’ve taken that process and turned it into The Art of Holiday Planning — a complete system you can work through on your own schedule.

It walks you through the things we’ve talked about here, and helps you turn all those holiday ideas floating around in your head into an organized, workable plan.

In the 10 step-by-step lessons, you’ll work through your whole holiday season — your schedule, budget, guests and travel, gatherings, gifts, cards, meals and table settings, decorating, holiday inventory, and getting your home ready. And you can choose the planning style that works best for you. We have either a beautiful printable workbook or an Excel spreadsheet that helps you keep all those moving pieces organized in one place.

And as you work through it, the pieces build on each other. Things you decide about guests affect your meals. Your gatherings create tasks. Your decorating plans create shopping list items. Long-lead-time purchases get moved forward. And by the end, you don’t just have a random collection of holiday ideas — you have an actual plan for making them happen.

Come learn the system for making your holiday season beautiful, welcoming, and exactly the way you want it!

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