Your September Holiday Reset: The 5 Tasks That Matter Most

Feeling behind on your holiday prep? Don’t worry—you’re not alone, and September is the perfect month to hit reset. In this episode of The Holiday Headstart Podcast, we’re taking a step back from our usual “5 tasks” format and reviewing everything we’ve covered so far this year—40 holiday prep tasks in total! From budgeting to baking, from gift lists to game plans, we’re laying it all out in one place.

But here’s the twist: you don’t need to tackle all 40. Instead, your challenge this month is to choose the 5 tasks that will have the biggest impact on your December. Think of it as holiday triage—focusing on what will matter most to you and your family. Whether you’re just starting now or you’ve been following along all year, this episode will help you prioritize, simplify, and move into fall with confidence and clarity.

Highlights from the episode:

[00:01:04] - Tradition Spotlight on an apple cider bar

[00:01:43] - Tasks for September

[00:03:54] - Money and Planning Tasks

[00:05:40] - Systems and Organization Tasks

[00:09:27] - Food and Entertaining Tasks

[00:10:56] - Gift Tasks

[00:12:28] - Experience and Traditions Tasks

[00:14:19] - Logistical Tasks

[00:16:08] - Your Top 5 Tasks

[00:18:19] - This week’s Get A Headstart Tip for making holiday prep time more enjoyable

[00:19:26] - What’s on our to-do lists this week

[00:20:37] - Our Nice Lists

The Complete List: Holiday Prep Tasks by Category

Money & Planning

• Set up automatic savings transfer for Christmas fund
• Inventory winter clothing needs (coats, boots, gloves)
• List 4th quarter grocery needs and extra expenses

Systems & Organization

• Write yourself notes for what to do differently next time
• Update your Pinterest boards
• Set up stocking bags for year-round gift collecting
• Stock up on discounted school supplies for stocking stuffers
• Create hiding places for presents (try moving bags!)
• Sort holiday decoration bins 
• Organize holiday items in the garage/attic while weather is nice
• Donate holiday items you don’t use anymore
• Plan strategic un-decorating for next year
• Choose decorating theme and color scheme
• Make a wrapping station
• Create a Need-to-Know Box for essential holiday items
• Declutter crafting area before DIY projects
• Buy advent calendars early (best selection available now!)

Food & Entertaining

• Gather all holiday recipes in one place
• Make and freeze cookie dough
• Draft holiday menus (including non-holiday meals around Christmas)
• Find and test new holiday recipes

Gifts

• Start gathering gift idea for everyone
• Start working on DIY gifts NOW (seriously!)
• Create gift lists for loved ones and yourself
• Draw names for gift exchanges

Experiences & Traditions

• Reflect on last holiday season (what worked/didn't work)
• Stock a personal recovery kit for post-holiday recuperation
• Dream about traditions that support your holiday purpose
• Complete the holiday values exercise
• Find holiday playlists and book lists
• Plan the week after Christmas (Twixmas!)

Logistics

• Organize holiday photos into albums
• Edit Christmas card list and track down addresses
• Book family photographer before they're completely booked
• Plan for fall and winter birthdays
• Prep guest room/space for holiday visitors
• Figure out Elf plans (if applicable)
• Create household Minimum Upkeep Plan

Resources:

• Apple Cider Bar: My Homier Home
• Apple Cider Bar: Eleanor Rose Home
• Remarks 1990s Puzzle 
• Neil Med Sinus Rinse
• Grab The Holiday Headstart Playbook
• Take the Holiday Profile quiz
• Follow on Instagram @theholidayheadstart 
• Leave us a review on Apple Podcasts! 

If you enjoyed this episode, you'll love these too:

• Episode 20: 5 Things for January
• Episode 23: 5 Things for February
• Episode 27: 5 Things for March
• Episode 28: 5 Things for April 
• Episode 30: 5 Things for May
• Episode 31: 5 Things for June
• Episode 32: 5 Things for July
• Episode 34: 5 Things for August
• Episode 4: How to Craft Your Holiday Values for a Meaningful Holiday Season
• Episode 29: How Knowing Yourself Better Can Bring More Joy to Your Holiday Planning

More About The Holiday Headstart:

Welcome to The Holiday Headstart podcast, where we get intentional about kicking overwhelm to the curb and bringing joy back to your holidays (and every day). We’re Heidi and Emily, two sisters and former elementary school teachers, who’ve taken the simple strategies and practical tips we mastered in the classroom and put them to work in our personal lives. 

And we’re here to help you do the same! Join us each week as we share how, with a little planning and a little prep, you can ensure that the days that make life special don’t become the days that make you stressed.