Get Ready for the Holidays: Create a Plan and Calendar for the Season

It probably doesn’t surprise you that I feel strongly that getting organized upfront is the best thing you can do to ensure a smooth and enjoyable holiday season.  I believe being organized is the best way to make the most of your time, money and energy, so that you can spend all of it how you truly want. Being organized helps to make sure you’re not wasting any of those things.

It doesn’t matter the form of how you get organized upfront; you can use a calendar, to-do apps on your phone, or a collection of checklists, whatever works for you. You should consider a format that works with sharing with anyone else who needs to see it, whether you share electronically or hang a large calendar on the fridge for all to see.

As you build your plan, you should both step back and see the whole season at a glance, and also start to put in your own obligations and plans in and around the master plan, such as:

  • Parties, concerts, school events, cookie swaps, bazaars and craft fairs (and fingers crossed, you’re not double-booked!)

  • Baking days

  • Shopping days

  • Travel

These should all be added to the season-full of activities I’ve outlined here to help get you started. In the coming weeks, you’ll see me post more about many of these activities I outline below, and I hope that all of them give you ideas on how to make sure you’re spending the season the way you want to this year!

Make a plan

Key Dates to remember:

Thanksgiving: Thursday, November 28

First night of Hanukkah:  Thursday, November 28

Christmas: Wednesday, December 25

First Half of November:

  • Review your budget. Figure out what you plan to spend for gifts, decorations, any events you host or attend.

  • Unearth your holiday card list from last year. Check to see who can come off, and think through whom to add.  Anyone move since last year? Get their new address, ready to go.  Buy your stamps (and buy extra… before stamps go up three cents each in January.)

  • Start your gift list, and try using an iPhone App for keeping it all straight this year!  Don’t forget the people like teachers, mail deliverer, doorman, day care, paper deliverer  or the charity opportunities at your school, place of worship, business, etc.  When you’re finding great deals on gifts and toys, don’t forget the ones less fortunate than the rest of the people on your list.  (Remember to have cash on hand for tips as the holidays approach).

  • Review your pantry staples that you might need for baking or other recipes this season. Replace your baking soda and baking powder if it is a year old. Now is the best time to start stocking up on those kinds of ingredients.

  • Clean out your refrigerator and your freezer! You’ll need the space, and better to do it when you don’t have the stress of cooking and needing space RIGHT NOW.   (also, keep some space in case any guests you have coming to stay with you need a bit for medication.)

  • If you bake goods as gifts, go check out the dollar store in your area to select trays, tins, plates, etc. They already have the inventory out there; get in while the variety and quality is at its best… not the day before you bake, and there are only 3 dented tins left.

  • Menu plan for Thanksgiving and for Hanukkah. (Because Thanksgiving is so late this year, you can kind of wait until mid November, if you must.)  Gather the recipes and make the shopping list.

  • Finish up your Hanukkah gift shopping and wrapping. With TWO holidays falling on the same day, there’s no time to waste!

  • Book your appointments that you’ll want for hair, nails, etc. before big events or parties.

  • Line up babysitters for those events or parties now.

Second Half of November:

  • Think about the holiday outfits you’ll plan on wearing (or have your family wear) this year. Get them together and review them. Make sure everything fits, that you have the right stockings, socks, shoes, etc.   Get anything dry-cleaned that needs it.  This includes any ugly sweater you’ll need for such an occasion!

  • Complete the shopping for Thanksgiving and arrange to do any “make ahead” dishes that you can.   If you’re hosting or if you’re bringing food, select all your serving pieces.  For hosts, set the table on Wednesday.

  • If you are putting out a menorah for Hanukkah, check your candle supply (probably can’t run out last minute before the first night of Hanukkah, because it will be Thanksgiving and many stores will be closed…. well, until the Black Friday sales start after sundown).

    Peanuts characters  © Charles M. Schulz

    Peanuts characters © Charles M. Schulz

  • Enjoy your Thanksgiving!  Family, Friends, Food and Football! What could be better? Remember to treasure old traditions, and create new ones along the way.   And for those of you celebrating Thanksgivukkah, you have even more to celebrate!!

  • If you’re a Black Friday shopper, make sure you set out your plans in advance of the big day (which this year start right after Thanksgiving Dinner for many stores).

  • Start menu planning for any events you host in December… Keep an eye out for deals to stock up.

  • Set up a gift-wrapping station in your home, and designate where wrapped gifts will go. Make sure you have a good supply of wrapping paper (don’t forget your leftovers from last year!), tape, tags, pens and at least one extra pair of scissors, for when someone else swipes the first one.

  • Are you an “Elf on the Shelf” house?  Find your elf, and make a plan for what you’ll do every day with the elf.  You’ll have a much better chance of remembering to check in with the elf every morning if you’ve got a plan in place for daily adventures (but you should probably still go ahead and put a daily reminder in your phone, anyway…. Just in case).

December 1-7:

  • Start decorating!  Plan a day for inside decorating and another for outside decorating.  You can decorate inside at night, but need daylight for outside!

  • You should be making a decent dent in your gift shopping list by now. Don’t forget any hostess gifts or “just in case someone stops by with a gift for us” gifts purchased and wrapped.

  • Wrap as you receive gifts, but keep a list of gifts that you wrapped… if your memory is like mine, you can find yourself unwrapping a gift, just because you forgot what the heck it was.

  • Take advantage of the stores that offer you free gift wrapping whenever you can.

December 8-14:

  • Get as much of your gift shopping done by this week as you can.  Anything you order online can be delayed in shipping if you order much later than this (even if you’re willing to pay for overnighting, you still can’t control the weather around the country, which can impact delivery).

  • Finish up and mail your holiday cards.

  • Any packages that need to be mailed to a US destination and arrive before Christmas should be mailed by this week.

  • If you are traveling for the holidays, finish your packing list, and mail ahead any gifts you can.

December 15-22:

  • Get the house ready for guests. Treat yourself to a deep clean from a cleaning company if you’re having guests for Christmas.

  • Hit any last-minute gift shopping

  • Menu plan for any non-holiday meals for which you’ll have guests over  the holidays.  Try  not to go to the grocery store after the 21st if you don’t have to do so.

  • Make sure there are plenty of batteries in the house, for the gifts, the video games, for whatever comes up while your guests are around.

  • If you’re traveling for the holidays, finish your packing this week and be ready well in advance of your departure.  Millions of people will be on the road and in the air with you at the same time.  Don’t add the stress of last-minuteness to the craziness that is already part of traveling at Christmas.

  • Watch a Christmas movie or two with the family… don’t forget that all this work you’re doing is about spending time with your family and making memories! Take a break for a bit and enjoy these moments.

December 23:

  • Create a cooking timeline for your Christmas Eve or Christmas Day meals. Review your ingredients one last time.

  • Do any prep work on the food or the decorating that you can.

  • Set the table for Christmas Eve or for Christmas Day

December 24:

  • Make sure your camera has space and a charge for all the great memories you’ll capture tomorrow!  (Same goes for phones.)

  • If Christmas morning is at your house, set up the pot of coffee and find the garbage bags for wrapping paper before you go to bed.  Oh, and don’t forget the milk, cookies and carrots!

December 25:

  • Enjoy the holiday all day long!

  • Don’t forget the camera and the holiday music!

  • Clean up before going to bed.  Those dishes will look awful tomorrow.

December 26:

  • Head out and take advantage of the great pricing for next year – Holiday cards, decorations, wrapping paper, etc.

Rest of December and early January:

  • Find spots for your new treasures. Be okay with returning or exchanging unwanted gifts, and sell or donate what you can’t. Don’t make space in your home for the things you don’t need or love!

  • Pack up the decorations, and give a critical eye to the things you didn’t use (and probably won’t use again), the things that were more trouble than they were worth, and don’t pack them back up; let go of them.

  • After the holidays end, write a letter to yourself about what worked well, what didn’t, what you’d change next year, and keep it in an ‘Open This First’ envelope with your decorations.  Start with the clearest memories of the season, not the, “oh yeah… now that I have this up, I remember why I didn’t like it” sensation that comes with memories of regret.

  • Capture all the photos from the holidays, and put them in some order.  Get some prints made of the ones you’d love to have or share with others.  Consider making a photo book of your favorite memories of the season.

  • Write and mail your thank you notes, and return anything you borrowed from friends and family this season.

norman rockwell

Photo from
Norman Rockwell’s “Santa Napping” © 1922 Farm and Fireside



1 Comment

  1. Rebecca Stapler

    It is so important for my sanity to be organized during the holiday season! Thanks for the guidelines. 🙂


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