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Holiday Season Planning: Give Each Month a Job
Do the last three months of the year feel like an avalanche you just get swept up in? We plan for January. We plan for back to school. We even plan for Maycember. But when October arrives, most of us simply brace ourselves and hope for the best. In this episode, I’m sharing a simple approach to holiday season planning that gives October, November, and December each their own job. That way, you can enjoy the busiest season of the year instead of just getting through it again.
Key Takeaways
- Plan for the last 90 days of the year with the same intention you give January.
- Use October to get your calendar in order so the season doesn’t sneak up on you.
- Decide in November what matters most, before December starts making decisions for you.
- Protect your December so you can be present and say yes to what you truly want.
- Reflect on this year and set up the next one so you don’t start January feeling behind.
Why Holiday Season Planning Starts in October
December is going to be busy. That part isn’t changing. But the way you approach October and November decides what kind of December you get.
When we skip planning, the last 90 days build like an avalanche. One work deadline, one school event, and one holiday party at a time, it piles up until you’re swept away. Then it’s December 31st, and you’re wondering where the season went.
That’s why the busiest season deserves the best plan. And the simplest way to make that plan is to give each month a job.
October’s Job: Get Your Calendar in Order
First, zoom out. Before the holidays get loud, find one place where you can see the rest of the year at a glance.
Next, mark what’s already set in stone:
- Work deadlines and year-end commitments
- School breaks and events
- Travel dates
- Birthdays and parties you already know about
Once everything lives in one place, you’ll start to notice the collision weeks. For example, you might spot a week with a work deadline, a school event, and out-of-town guests all at once. Seeing it now gives you time to adjust, ask for help, or say no.
November’s Job: Plan the Holidays Before They Plan You
If you don’t decide ahead of time, December decides for you. That looks like last-minute gifts and rush shipping. It looks like saying yes to every invitation without asking which ones you actually want. And it looks like ending the month exhausted.
So in November, start by deciding what matters most this year. Which traditions light you up? Which gatherings are non-negotiable, and which could be simpler?
Then, move a few December to-dos earlier. Shopping for a handful of gifts or locking in travel plans now takes so much pressure off later. Above all, give yourself permission to simplify. A calmer holiday isn’t about doing everything. It’s about doing what matters, on purpose.
Looking for more ways to slow down this season? Listen to Ep. 58 – From Holiday Hustle to Silent Night: 5 Ways to Slow Down and Savor the Season.
December’s Job: Be Present, Then Reflect and Plan Ahead
December is full. There are holidays, parties, and events. For many of us, there are also evaluations, employee reviews, and year-end wrap-up at work.
However, when October and November do their jobs, December becomes much less of a scramble. As a result, you get to be present. You can say yes to what you truly want to be part of, and no to what doesn’t align.
December’s second job is to reflect and set up the year ahead. If you step into January without a plan, you’ll start the year already feeling behind. So take a little time to look back. What worked? What drained you? What do you want more of?
Then look ahead with a big picture view of next year. Figure out when you want to take vacation, identify your busy months, and set themes for your year. It doesn’t need to be a massive planning session. In fact, that’s exactly why I turn it into a party with the Big Picture Year Planning Party, my annual planning workshop happening this December.
Episode Links + Resources
- 2027 Big Picture Year Calendars: Coming Soon!
- Sleigh the Season: My 5-day holiday planning challenge this November.
- Big Picture Year Planning Party: My annual planning workshop, happening this December. More details coming soon.
- Free time management coaching session: Apply at freetimecall.com
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