Every year it happens the same way.
You blink and it’s October. You blink again and it’s December. Somewhere in between the gift list got out of control, the budget got blown, and the season that was supposed to feel magical just felt exhausting.
Sound familiar? I thought so.
That’s exactly why I created the 100 Days to Christmas Challenge — and why I think this year is going to feel completely different for everyone who joins us.
So What Exactly Is the 100 Days to Christmas Challenge?
The 100 Days to Christmas Challenge is a free holiday planning community that walks you through the entire holiday season one simple step at a time — starting September 16th and going all the way through to Christmas Day.
Every single day inside our free community you’ll get one small, doable planning task. Not a giant to-do list. Not an overwhelming project. Just one thing — the right thing at the right moment — so that by the time December arrives you are not starting from scratch. You are just executing a plan you already made.
We cover everything — fall traditions, Halloween fun, Thanksgiving prep, Christmas gifts, cards, budget, menu, decorating, cookies, and all the little things that make the season feel special instead of stressful.
Why Does It Start in September?
I know what you’re thinking. September feels early. You can’t even think about Christmas when it’s still warm outside.
But here’s the thing — September is exactly when you need to start if you want December to feel calm. The families who sail through the holiday season without losing their minds are not the ones with more time or more money. They are the ones who started earlier.
September gives you breathing room. It gives you time to compare prices before everyone else is panic buying. It gives you time to plan handmade gifts before there are no more weekends left. It gives you time to think about what traditions actually matter to your family instead of just defaulting to whatever happened last year.
July is basically the last exhale before the rush begins. September is when we start moving — but gently, one step at a time, with zero pressure.
What Do We Actually Cover in 100 Days?
This is not just a Christmas planning challenge — it is a full holiday season guide. Here is a peek at what we walk through together:
Starting in September we tackle the big picture planning — setting your holiday budget, starting your gift lists, getting your planning binder set up, and thinking about handmade gifts while you still have time to actually make them.
As we move into October the focus shifts to fall fun and Halloween — fall traditions, Halloween costumes and parties, fall baking, family outings, and all the cozy seasonal things that make October magical. And yes, we are also quietly getting ahead on Christmas in the background.
November is all about Thanksgiving and the pivot to Christmas — menu planning, cleaning prep, gratitude, and making sure Christmas shopping is well underway before the turkey even hits the table.
And December? December is for enjoying the season you planned. Decorating, cookies, cards, advent activities, and actually being present for all of it instead of scrambling to catch up.
How Does the Community Work?
The 100 Days to Christmas Challenge lives inside a free Skool community. If you have never used Skool before don’t worry — it takes about a minute to set up and it is completely free to join.
Once you are inside you will get daily planning prompts posted right there in the community. You will also get access to your free Pumpkins to Presents Planning Binder — a set of printable binder covers and dividers to keep all your holiday planning organized in one place.
And the best part? You will be doing this alongside a whole community of people who get it. People who are done letting the holidays happen to them. People who want to actually enjoy the season this year.
Plan together. Survive together. 🎄
Want to Go Even Deeper?
The free community gives you everything you need to walk through the season one step at a time. But if you want the full toolkit, I also have two printable packs available inside the community:
The Christmas Planning Pack includes every printable you need to plan your entire Christmas — gift lists, budget worksheets, wishlists, card lists, mailing addresses, gift wrap inventory, advent calendar planner, cookie planners, Christmas menu planner, and more.
The Holiday Season Pack covers everything else for the journey along the way — fall baking bucket list, Halloween checklist, candy signs, You’ve Been Booed pack, family Halloween movie bingo cards, Thanksgiving planner, cleaning planner, and gratitude reset.
And if you want the full live planning experience, Get Your Sh!t Together — Christmas Planning is our live weekly community where we plan the season together on Zoom every Sunday from September 16th through December 20th. It is the most supported way to do the challenge and honestly the most fun.
All of these are available inside the free community — you can explore them once you are in.
Ready to Join Us?
The 100 Days to Christmas Challenge starts September 16th and it is completely free to join. All you need to do is sign up, join the community, and show up one day at a time.
