Christmas may feel far away, but it’s never too early to start getting ahead. In this episode, we are bringing back our five easy tasks you can tackle in January to set yourself up for a smoother, more joyful holiday season. Plus, we’ve got creative tips for celebrating lesser-known holidays like Groundhog Day, and we’ll reveal the magic of reflecting on your past holiday experiences to make future celebrations even better. So grab your notes as we give you the tools to stay stress-free and joyous all year round!

[01:04] – Tradition Spotlight on Celebrating Groundhog Day

[03:20] – Getting Ahead for Next Christmas

[04:01] – Tip 1: Reflect and Record

[05:55] – Tip 2: Savings Strategy

[06:42] – Tip 3: Stocking Solutions

[09:13] – Tip 4: Undecorate with Purpose

[10:25] – Tip 5: Recipe Roundup

[14:27] – This week’s Get A Headstart Tip for saving for back-to-school expenses

[15:49] – What’s on our to-do lists this week

[16:51] – Our Nice Lists

1. Join us next week for more tips on holiday preparation and planning!
2. Check out the Holiday Headstart Playbook for more tools and inspiration.

1. Grab The Holiday Headstart Playbook
2. Follow on Instagram @theholidayheadstart
3. Leave us a review on Apple Podcasts!

1. Episode 5 – Making a Plan for Gift Giving
2. Episode 8 – Make Your Christmas Baking Game Plan with the Holiday Headstart

While there’s so much to manage right now, there’s a gift of slower paced days heading your way. But if you don't think about it even a tiny bit ahead of time, it just... disappears. And then you get to January wondering what happened and why you still feel exhausted.

Since there’s not room to add anything heavy to your plate, we’re keeping things light. In this episode, we're walking you through five different "resets" you might be craving after the holiday rush—recovery, connection, catch-up, fun, or closure—and helping you build a bare minimum plan so that the week between Christmas and the new year actually gives back to you.

You could literally make your whole plan while you listen. So grab your headphones, finish wrapping those gifts, and let's make sure the week after Christmas doesn't slip away.

Highlights from the episode:

[00:01:06] - Tradition Spotlight on sibling gift exchange

[00:03:35] - A gentle post-holiday plan

[00:06:50] - Post-holiday reset 1: recovery

[00:08:08] - Post-holiday reset 2: connection

[00:08:42] - Post-holiday reset 3: catch up

[00:09:29] - Post-holiday reset 4: fun

[00:10:12] - Post-holiday reset 5: closure

[00:11:17] - Bare minimum plan

[00:19:11] - Make your own plan

[00:21:25] - This week’s Get A Headstart Tip for making a Christmas lost-and-found box for lost decor items

[00:22:48] - What’s on our to-do lists this week

[00:25:20] - Our Nice Lists

Resources:

List any resources mentioned in the episode first, and then the evergreen links below them.

• 🔥 Wish Papers for New Year's Eve: https://www.amazon.com/s?k=wish+papers
• 📚 Jolabokaflod (Icelandic Book Flood) tradition idea
• 🎄 My Minds Eye Glitter Christmas Village pieces
• 📺 The Merry Movie Club on Instagram: @themerrymovieclub
• 🎬 Merry Christmas Ted Cooper (Hallmark movie recommendation)
• Grab The Holiday Headstart Playbook
• Take the Holiday Profile quiz
• Follow on Instagram @theholidayheadstart 
• Leave us a review on Apple Podcasts! 

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.  

Stockings are such a given that most of us never stop to think about whether they're actually working for us. We just keep doing what we've always done—until the stress piles up or disappointment creeps in.

In this episode, we're walking you through six key areas to consider when it comes to stockings—from clarifying your "why" to setting boundaries around cost and expectations. We're also tackling something that doesn't get talked about nearly enough: what to do when everyone else's stocking is overflowing… and yours is empty.

Whether you're trying to simplify your holiday prep, get everyone on the same page, or just make sure you feel included and cared for this season, this conversation will help you approach stockings with intention instead of stress.

Highlights from the episode:

[00:01:12] - Tradition Spotlight on kazoo caroling

[00:04:04] - Step 1: What matters about stockings?

[00:05:05] - Step 2: Who’s included?

[00:05:57] - Step 3: Style & setting

[00:08:28] - Step 4: What’s the stocking budget?

[00:10:52] - Step 5: Stocking timing and traditions

[00:11:43] - Step 6: Managing stocking disappointment

[00:16:59] - This week’s Get A Headstart Tip for ordering PJs

[00:19:38] - What’s on our to-do lists this week

[00:22:33] - Our Nice Lists

Resources:

List any resources mentioned in the episode first, and then the evergreen links below them.

• 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 11 - Creating New Holiday Traditions
• Episode 12 - Managing Your Holiday To-Dos

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 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.