The Biggest Holiday Planning Mistake I Used to Make
For years, I made the same mistake when it came to holiday planning: I waited until the holidays felt close enough to start thinking about them. September was definitely too early. October still felt like fall. There was school and sports and Halloween and everything else happening in our lives, so Christmas planning could wait until November. Except, of course, the holidays weren't actually waiting. The calendar was already filling up. Gift ideas were already being mentioned. Events were being announced. There were things I wanted to make, traditions I didn't want to forget, and little pieces of information starting to pile up in the back of my brain. I simply wasn't doing anything with any of it yet.
Then November would arrive, and suddenly everything felt urgent. Instead of casually thinking about a gift idea in September, I was trying to buy it, wrap it, ship it, and stay within my budget in December. Instead of noticing an event when it was first announced, I was trying to squeeze it onto an already crowded calendar. And every year, I seemed to have the same conversation with myself: Why didn't I think about this sooner?
I finally realized that my biggest holiday planning mistake wasn't procrastination. It was that I had completely confused planning early with doing early.
I'm Not Doing Christmas in September
When I say that I start holiday planning in September, I don't mean that I'm putting up my Christmas tree or wrapping presents while everyone else is buying pumpkins. I'm not trying to skip fall, and I certainly don't want to spend four months actively preparing for Christmas. In fact, the whole reason I want to start thinking about the holidays now is because I don't want them taking over my life later.
September gives me something November and December don't always have: perspective. I can think about the season before everything feels urgent. I can ask myself which traditions really matter to our family this year, what events we already know about, who we'll be shopping for, what I might want to make, where we're going, what we're hosting, and what caused unnecessary stress last year. None of those questions requires me to actually do anything today. I'm simply capturing information while I have the time and mental space to think about it.
And honestly, that's one of the biggest shifts I've made in the way I think about planning in general. Planning isn't always about creating a giant list of things to accomplish. Sometimes planning is simply taking something out of your head and putting it somewhere you know you can find it later.
Start With a Five-Minute Holiday Brain Dump
If the idea of holiday planning in September makes you immediately picture a 14-page Christmas checklist, I want you to forget that completely. You don't need a detailed plan right now. You don't even need a planner. Start with a blank piece of paper and five minutes.
Write down whatever is already floating around in your head about the upcoming season. Maybe someone has already mentioned a gift they'd love. Maybe you know you'll be hosting Thanksgiving. Maybe there's a family tradition you skipped last year that everyone really missed. Maybe you've already seen an event you'd like to attend or remembered that you need to order something that always takes forever to arrive. Don't organize the list and don't turn everything on it into an immediate task. Just get it out of your head.
That's essentially how I begin using my Holiday Headquarters Insert. I wanted one place where all of those scattered thoughts could eventually find a home. It includes sections for my holiday vision, calendar and events, budget, gifts, home plans, and the other information I want to reference throughout the season. Instead of having twelve unrelated lists, screenshots, notes, and reminders, I can slowly build one holiday resource as our plans take shape.
Give Your Future Self a Little Help
I joke a lot about “Future Elisa,” because apparently I have spent years believing she is going to be far more capable than Present Elisa. 😂 She will have more time. She'll remember everything. She'll magically know what I meant when I wrote a cryptic note three months earlier. She'll have no problem figuring out Christmas while juggling work, kids, school schedules, activities, family commitments, and normal everyday life.
Unfortunately, Future Elisa is usually just as busy as Present Elisa—sometimes busier. The kindest thing I can do for her is stop handing her things that I could easily take care of now.
That doesn't necessarily mean completing a task. If I write down a gift idea today, I've helped her. If I add a known event to my holiday calendar, I've helped her. If I make a note that we definitely don't need to buy wrapping paper this year because I discovered six unopened rolls in a closet, I've helped her. 😂 Tiny decisions made without urgency can remove a surprising amount of mental clutter later.
That's really the idea behind my complete Holiday Planning System, too. Holiday Headquarters helps me plan the season, my Daily Dashboard helps me manage the especially busy days and projects as they arrive, and Memory Keeper 2.0 gives me somewhere to capture the stories and photos along the way. I think of the three pieces as Plan the season. Live the moments. Remember the memories.
Holiday Peace Starts Now
My goal isn't to have Christmas completely planned by the end of September. I don't want to know exactly what we're doing on December 18th or have every gift purchased before Halloween. I simply want to enter the busiest part of the year with a little less clutter in my head and a little more clarity about what matters.
Because the real benefit of planning ahead isn't checking things off sooner. It's creating breathing room later. I want space for the spontaneous Christmas movie night, the evening when everyone ends up hanging out in the kitchen longer than expected, and the traditions that matter enough that I actually want to be present for them instead of mentally running through tomorrow's to-do list.
The goal isn't to get ahead of the holidays. It's to create enough breathing room to enjoy them when they arrive.
And sometimes that starts with nothing more than five quiet minutes and a blank piece of paper in September.
Ready to give your holiday plans a home? Explore the Holiday Headquarters Insert and complete Holiday Planning System.
