Cultivate Your Calendar: Fun, Easy, and Meaningful Holiday Traditions

Cultivate Your Calendar: Fun, Easy, and Meaningful Holiday Traditions

What are you doing now to celebrate the holidays well?

Yes, I know it's the heat of summer and you have a few other things on your mind (back to school and, you know, whatever you're having for dinner tonight!). 

No, I'm not saying you should have every hour of your days scheduled from Halloween through Christmas. 

But, we say it often: a little forethought goes a long way. It's the keystone of our "cultivated calendar" concept: how can you do a little bit of prep NOW to really cultivate what matters when those busy, precious weeks hit at the end of the year? 
Three steps from our recent webinar (listen to the replay if you haven't already!):

—Define what matters and what DOESN'T matter! Answering this question will help you create boundaries in your life and fight comparison. What we plan time for becomes our priority and what we spend time on grows! 
—Prepare and put your yearly calendar on autopilot (yes, it's possible!). Look ahead in your calendar and choose what will anchor your days, weeks, and year. Make time for what matters to you in the big picture and mark them down!
—Live it out! No perfection required here. Life typically doesn't go the way we think it will—but if you use the gift of a little intentional forethought, you can still live out the things that matter and have flexibility.

So, what can you do in the last few days of August to set yourself up for a fun, easy, meaningful holiday season?

Make a reservation?
Call to confirm the date of a yearly event?
Send an invitation?
Buy supplies?
Block out days or evenings on your calendar?

Pick just a few things that will really matter, and make the most of them! And if you need a few ideas for new traditions to start, look no further than the PowerSheets Facebook group
—it's an amazing repository of sweet, simple ideas, no matter your age or stage! A few favorites...

We make chili for our Halloween dinner (our go-to recipe is Eat Yourself Skinny's Turkey Chili), pass out candy, and watch a Harry Potter movie! Lisa K.

We serve in some way each day for the 12 days leading up to Thanksgiving. They can be little things: taping quarters to vending machines, returning carts to their stalls, giving care kits to the homeless. Littles can definitely help with service, and it makes it easier when they get older. For me, when I really work to cultivate gratitude in November, there is an easy blossoming of joy in December. My kids ask for less, we love being together more, and Christmas is way less stressful.—Becca R. 

We go on a hike and have Thanksgiving dinner with our dear friends and their parents. It's a reminder of our story (moving far away from family and making a life in a new place, all on our own!) and a reminder that family is more than just the people you're related to!  —Emily T.
I always had sparkling juice for my kiddos for all special occasions, and I always let them use the stemware (it’s inexpensive, and I was okay with them breaking it). At 15 and 18 they still love that aspect of holidays. The fancy glass is part of what makes it special. —Kristin H.

On Thanksgiving night we get a package filled with Christmas pajamas, a Christmas book for each kid, a Christmas movie, popcorn, and hot cocoa. We put on our pajamas, watch our Christmas movie, eat the popcorn and drink hot cocoa, and then read our books before bed! —Lauren B.

On December 1st, we all go out for Christmas pancakes at a local spot that has pumpkin pancakes. We brainstorm and plan all the Christmas activities we want to do... a caroling party, secret Santa gifts on friends' and neighbors' doorsteps, sending gifts to our sponsored kids, Christmas Eve service, gingerbread house contest, etc. That first day of planning sets us up for success and starts the season off in a fun way! —Courtney H.

I'm terrible at traditions, so I try to find really simple things to repeat each year. For example, we always eat Party Mix while we decorate our Christmas tree. It sounds trivial, but my kids look forward to it because they now associate those two things together. (And I do, too!)  —Susan H.

My nephews and I decorate gingerbread houses every year together. My brother and his wife know that this is special just for us, and save it for me on a night that I'm babysitting! I love it, and the kids look forward to it. —Lissa S.

My family puts on our pajamas, picks up dinner from Sonic, and drives around to see the lights while listening to the same Burl Ives Christmas album every year. I’m a senior in college now, and I still look forward to it when I come home for Christmas! —Jeanna C.

One of my kids’ favorites still (they’re 13 and my twins are 12) is to have a Christmas tree picnic. Years ago I bought a Christmas (easily wipeable!) tablecloth, and one night before Christmas each year we set it by the tree and have dinner on the floor with all the Christmas lights on. Our tradition is to have chicken nuggets and French fries :) —Kelly B.

My daughter and I bake and decorate gingerbread cookies together on Christmas Eve. I always wished for this tradition as a little girl, but my mom wasn't much of a cook or baker. (She was wonderful, though!) She's 11 years old now and we love it! And of course, Santa gets freshly baked cookies. —Kim O.

My mom passed on the tradition of giving new pajamas every Christmas Eve (and my grandma made my Mom a quilt with parts of the pjs as she grew out of them—amazing!). My sister and I are 27 and 24, and the tradition continues still. My husband receives matching pajamas with us now, which he’s less thrilled about :) —Holly M. 

With both my husband and I working in retail and no kids, we always took the late shifts Christmas Eve so the people with children could go home. When we got home, we had wine and fondue for dinner.  —Pam C.

On New Year's Eve I make bags for every hour. We open them starting at 6pm, then one every hour until midnight. Each bag holds an activity: fireworks, silly string, Minute to Win It props, a new game, etc. I started when the kids were 1,2, and 3 and now they're 11, 12, and 13, and they still look forward to it each year!  —Chrissie T.

We'd love to hear: What's a simple and sweet tradition you have for Halloween, Thanksgiving, Christmas, or the holiday of your choice? 

P.S. Do you have kids? Our Parenting Goal Guide is filled with suggestions for cultivating what matters in the life of your little ones! Download it here and get started today!

Leave a comment

Emily Thomas

Emily Thomas

Emily Thomas

Emily Thomas is Cultivate What Matters' Content Strategist and Writer. With over a decade at Cultivate, Emily loves helping women uncover what matters, set good goals, and live them out with joy. Her free time is spent with her high-school-sweetheart husband and three young kiddos.

Cultivate What Matters Podcast

If you are ready to get unstuck, say goodbye to wasted days, and feel your life adding up to something more—you are in the right place! The Cultivate What Matters Podcast will help you uncover what truly matters in your life and give you the tools to start acting like it today. Whether you're feeling overwhelmed, lacking motivation, or simply looking for a little joy and delight, you'll find exactly what you need right here. We are so excited to walk alongside you!

Goal School

Get access to premium content to help you stay on top of your goals all year long!