40-Day Christmas Challenge | Day 1 • Learn from Last Year • Everyday Cheapskate

You wouldn’t add a family room without a plan, knit a sweater without a pattern, or head out on a cross-country trip without a map. Yet when it comes to Christmas, many of us dive in headfirst the day after Thanksgiving… no plan, no map, just a swirl of good intentions and glitter.

And before we know it, we’re sprinting through December, juggling wrapping paper, wish lists, and a half-eaten cookie for breakfast.

Winston Churchill once said, “Those who fail to learn from history are doomed to repeat it.” I can confirm. Plans not written are only daydreams.

Day 1: Learn from Last Year

Let’s start this challenge by giving our future selves a gift: a calmer, more intentional holiday season.

Think back to last Christmas. Was it full of joy? Or mostly full of lists? What moments truly mattered? Which ones you could’ve skipped and never missed?

Get the family involved, too. Sometimes their memories (good or otherwise) help us see things we might overlook.

So grab a notebook or open a note on your phone and let’s reflect before we rush.

Action Step

Set aside a few quiet minutes to think about the past few Christmases.
Write down what you loved, what caused stress, and what you wish had gone differently.
Ask yourself: What do I want this year to feel like?
Use your answers as a starting point for a simple plan… a practical roadmap for a joyful, balanced season.

If you want a head start, jot down your top three holiday wishes, the things that make the season truly special to you. Need help reflecting? Download our Holiday Reflection Worksheet to guide you through this step →

Why It Matters

A little reflection now saves a lot of scrambling later. When you plan with purpose, you protect your time, energy, and joy. It’s not about doing everything. It’s about doing enough to make the season meaningful.

Making thoughtful choices today sets the tone for a smoother, happier December… one filled with memories that last longer than the leftovers.

More Ways to Participate in #EC40DayChallenge:

Question: What did you love most last Christmas and what are you skipping this year? Share your thoughts in the comments! Your reflections might inspire someone else to find a little more peace this season.