In this episode, we're breaking down exactly how to tackle your holiday planning so you can stop white-knuckling your way to January. And we're starting with something that might surprise you—we're celebrating what you've already done.

Then we'll walk you through our full system: from making your Ta-Da List, to creating your Tackle List for those tasks you dread, building an intentional to-do list, and timing everything so you're not cramming it all into the last two weeks of December.

Plus, we're sharing bonus lists that will save your sanity—like Early Bird Tasks you can knock out now, "one and done" decisions that eliminate decision fatigue, and our favorite TV Tasks for productive relaxing.

Highlights from the episode:

[00:55:00] - Tradition Spotlight on annual Christmas ornaments

[00:07:00] - Make your Ta-Da List

[00:11:20] - Make your Tackle List

[00:14:04] - Make your To-Do List

[00:15:48] - Other helpful lists

[00:20:49] - This week’s Get-A Headstart Tip for preparing for guests

[00:21:49] - What’s on our to-do lists this week

[00:27:52] - Our Nice Lists

Resources:

• Miss Mouth’s Messy Eater Stain Treater Spray
• Jacquie Lawson Advent Calendar
• 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:

• The 5 Step Action Plan for Traditions [Episode 6]
• Unlock the Power of the 3 Cs: Your Ultimate Guide to Holiday Planning [Episode 7]
• How to Use a Task Docket to Make Managing Your Holiday To-Dos Easy Peasy [Episode 12]

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.  

Halloween can sneak up on you fast, so let’s walk through our 10-step system for planning a Halloween that feels magical instead of manic. From figuring out your budget to mapping your trick-or-treat route, we cover everything you need to know to stay ahead of the chaos. If you want to actually enjoy Halloween this year instead of just surviving it, this episode is for you.

Highlights from the episode:

[00:01:14] - Tradition Spotlight on Joy Lists

[00:05:11] - Planning Halloween step 1 - Identify your purpose

[00:07:03] - Step 2 - Budget

[00:08:35] - Step 3 - Activities and Traditions

[00:11:07] - Step 4 - Calendar and Coordinate

[00:11:53] - Step 5 - Food

[00:15:46] - Step 6 - Costumes and Photos

[00:18:52] - Step 7 - Home Prep

[00:19:25] - Step 8 - Logistics

[00:21:09] - Step 9 - Halloween Night Details

[00:22:00] - Step 10 - Lists

[00:24:48] - This week’s Get A Headstart Tip for inventorying gift stock piles

[00:26:20] - What’s on our to-do lists this week

[00:27:45] - Our Nice Lists

Resources:

• Joy Lists
• ClayMoo
• 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 4: How to Craft Your Holiday Values For A More Meaningful Christmas Season
• Episode 6: The 5 Step Action Plan for Traditions

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.  

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

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

• 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!)

• 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

• 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

• 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!)

• 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.  

August is the sweet spot for getting ahead without the pressure. This month, we're sharing five practical tasks that will make your December so much smoother: from coordinating gift exchanges early to booking photographers before they're booked solid. Plus, we'll help you tackle DIY gifts before the last-minute panic sets in and make sure those fall birthdays don't get lost in the holiday shuffle. If you've been following along with our monthly prep series, you're already ahead of the game—and these five tasks will keep that momentum going strong.

Episode Highlights:

[00:01:05] - Tradition Spotlight on back-to-school pencil cookies

[00:04:50] - Task 1 - Draw names now for gift exchanges

[00:05:55] - Task 2- Start shopping for advent calendars

[00:07:38] - Task 3 - Buckle down on DIY gifts

[00:09:25] - Tip 4 - Book your family photographer 

[00:10:49] - Tip 5 - Plan any birthdays from September to January

[00:13:07] - This week’s Get A Headstart Tip for using Miss Freddy’s tips to organize and store kid memories

[00:16:19] - What’s on our to-do lists this week

[00:20:24] - Our Nice Lists

Resources Mentioned:

• Allermi Allergy Spray
• Grab The Holiday Headstart Playbook
• Take the Holiday Profile quiz
• Follow on Instagram @theholidayheadstart 
• Leave us a review on Apple Podcasts! 

If you enjoyed these episodes 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

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.  

What if instead of white-knuckling your way through supply lists and schedule changes, you could actually feel prepared, maybe even excited, for the new school year?

We're taking our proven 10-step holiday planning framework and applying it to back-to-school season. Because just like Christmas, back-to-school isn't a single day, it's a season with its own rhythms, demands, and thousand tiny decisions.

In this episode, we're giving you a roadmap to approach this season with more clarity and way less chaos, even when you can't hit pause on regular life to deal with all of the changes coming your way.

Highlights from the episode:

[00:00:24] - Tradition Spotlight on Backwards Back-to-School Dinner

[00:03:25] - Starting with what matters

[00:08:57] - How to make back-to-school feel special 

[00:10:36] - Figuring out logistics

[00:18:43] - Making a game plan to get it all done

[00:22:55] - This week’s Get A Headstart Tip for connecting with your child’s teacher early

[00:24:39] - What’s on our to-do lists this week

[00:26:33] - Our Nice Lists

Resources Mentioned:

• 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 4: How to Craft Your Holiday Values for a More Meaningful Christmas Season
• Episode 7: Unlock the Power of the 3 Cs: Your Ultimate Guide to 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.  

In this episode, we're sharing five gentle ways to get ahead on holiday prep while you're still enjoying those pool days and popsicles. From stocking up during back-to-school sales to finally starting that wishlist you always forget about, these low-key tasks are all about making December feel more joyful and way less stressful.

No tinsel required—just a little July planning that will make your future self want to send you a thank-you card.

Episode Highlights:

[00:00:22] - Tradition Spotlight on a summer picnic

[00:01:02] - Tip 1 - Stock up on school supplies for stockings

[00:02:03] - Tip 2 - Start making your gift lists

[00:04:55] - Tip 3 - Make your own wish list

[00:06:37] - Tip 4 - Think about how you want to spend the week after Christmas

[00:09:22] - Tip 5 - Inventory the supplies you have for hosting guests

[00:11:56] - This week’s Get A Headstart Tip for starting your planning in the right place

[00:14:50] - What’s on our to-do lists this week

[00:19:03] - Our Nice Lists

Resources Mentioned:

• Splendor Duel
• Somebody Feed Phil on Netflix
• Grab The Holiday Headstart Playbook
• Take the Holiday Profile quiz
• Follow on Instagram @theholidayheadstart 
• Leave us a review on Apple Podcasts! 

If you enjoyed these episodes 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

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.  

We're six months out from the holidays. It’s too early for tinsel, but we’re just in time for some smart prep! In this episode, we share five simple tasks you can tackle now to make December feel a whole lot lighter. From freezing cookie dough to drafting a household "Minimum Upkeep Plan," these June-friendly ideas are all about giving your future self the gift of breathing room.

Trust us—your December self will thank you.

Episode Highlights:

[00:00:20] - Tradition Spotlight on Choosing Your Song of the Summer

[00:03:22] - Tip 1 - Make and freeze cookie dough

[00:05:32] - Tip 2 - Draft holiday menus

[00:06:23] - Tip 3 - Plan non-holiday meals that fall near the holidays

[00:08:05] - Tip 4 - Schedule your Elf antics

[00:09:26] - Tip 5 - Make your household’s Minimum Upkeep Plan

[00:12:13] - This week’s Get A Headstart Tip for cleaning berries

[00:14:27] - What’s on our to-do lists this week

[00:18:02] - Our Nice Lists

Resources Mentioned:

• Guide to freezing dough
• Guide to cleaning berries in hot water:
• NY Times
• The Kitchn
• Grab The Holiday Headstart Playbook
• Take the Holiday Profile quiz
• Follow on Instagram @theholidayheadstart 
• Leave us a review on Apple Podcasts! 

If you enjoyed these episodes 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

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.  

Welcome to the 100 Days of May—also known as May-Cember, the month that feels like it never ends! In this episode, we’re talking TV Tasks—easy, screen-friendly activities you can do on your phone while relaxing on the couch.

We’ve rounded up a handful of low-effort, high-payoff tasks you can tackle during your downtime. If you’re looking for calm, cozy ways to get a little head start, this episode is here to help.

Episode Highlights:

[00:01:02] - Tradition Spotlight on planting pumpkins

[00:04:37] - Tip 1 - Organizing Pinterest

[00:07:40] - Tip 2 - Look for new holiday recipes 

[00:09:23] - Tip 3 - Find holiday playlists

[00:12:45] - Tip 4 - Track down addresses

[00:14:36] - Tip 5 - Find book titles for December

[00:08:04] - This week’s Get A Headstart Tip for making a TV Task List

[00:20:28] - What’s on our to-do lists this week

[00:23:20] - Our Nice Lists

Resources Mentioned:

• Holiday Romcom List 
• Grab The Holiday Headstart Playbook
• Take the Holiday Profile quiz
• Follow on Instagram @theholidayheadstart 
• Leave us a review on Apple Podcasts! 

If you enjoyed these episodes 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

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.  

In this episode of Holiday Headstart, we dive into how understanding yourself through Gretchen Rubin’s Four Tendencies framework can completely change the way you plan for Christmas—and reduce your stress while you're at it. We break down each of the four tendencies—Upholder, Questioner, Obliger, and Rebel—and explore how your response to expectations shapes your ability to plan, prep, and actually enjoy the holidays. Whether you love a checklist or resist all structure, this episode will help you create a holiday planning system that works with your natural tendencies, not against them.

We’ll share personalized tips for each tendency, including how to build in flexibility, avoid analysis paralysis, use accountability to your advantage, or embrace your inner maverick. If you’ve ever felt like your holiday prep always falls short or leaves you burnt out, this episode might just be the mindset shift you need. Plus, check the show notes for a link to Gretchen Rubin’s quick Four Tendencies quiz so you can discover your own type and start planning smarter today!

Episode Highlights:

[00:01:03] - Tradition Spotlight on a Today’s Your Special Day plate

[00:02:51] - Introduction to the 4 Tendencies

[00:08:26] - Using your tendency to thrive

[00:10:16] - Tips for Upholders

[00:12:38] - Tips for Questioners

[00:15:49] - Tips for Obligers

[00:19:07] - Tips for Rebels

[00:21:37] - This week’s Get A Headstart Tip for getting holiday tasks done in advance

[00:24:37] - What’s on our to-do lists this week

[00:27:47] - Our Nice Lists

Resources Mentioned:

• Gretchen Rubin’s 4 Tendencies Quiz
• Kitchen Shears
• You Are Special Today plate
• 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 this too:

• Episode 25 - Why You Should Write Yourself a Permission Slip for the Upcoming Holidays

We’re back with five more simple tasks to help you chip away at holiday prep throughout the year! Whether you’re just joining us or have been following along, these tips are designed to make the holiday season less overwhelming and more enjoyable.

In this episode, we share five simple tasks you can complete in April to prepare for the holiday season. By tackling these small, manageable tasks throughout the year, you can reduce the stress and overwhelm that often comes with the holiday rush. This month's tasks include creating a wrapping station, listing fourth-quarter grocery needs, completing a holiday values exercise, inventorying winter items, and assembling a "Need-to-Know Box" for essential holiday items. 

Let’s break the holiday chaos into manageable pieces and give ourselves the gift of a calmer, more joyful season!

Episode Highlights:

[00:01:01] - Tradition Spotlight on the Shepherd Supper

[00:04:38] - Tip 1 - Make a wrapping cart

[00:09:28] - Tip 2 - List your fourth-quarter grocery needs

[00:12:35] - Tip 3- Complete the holiday values exercise

[00:14:51] - Tip 4- Inventory winter items

[00:16:16] - Tip 5- Assemble a “Need to Know” box

[00:18:44] - This week’s Get A Headstart Tip for storing wrapping paper

[00:20:38] - What’s on our to-do lists this week

[00:22:18] - Our Nice Lists

Resources Mentioned:

• Gramercy Cart from Michaels 
• 4-section file organizer
• Mail holder
• Slap bracelets
• Emma M. Lion Series
• 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 You Can Do in January To Get Ahead for Next Christmas
• Episode 23: 5 Easy Tasks to Do in February to Get Ahead for Next Christmas
• Episode 27: 5 Things for March
• Episode 4: Holiday Values Exercise
• Episode 6: The Need-to-Know Box

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.