The Holiday Headstart

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. 

Planning ahead for Christmas can feel overwhelming, but small steps now can make the holiday season smoother and happier. In this episode, we’re sharing five practical ways to get ahead on holiday planning in March. From crafting a personal recovery kit to selecting a holiday decoration theme, we’ve got loads of actionable tips to prevent stress from stacking up in December. 

Episode Highlights:

[00:00:44] - Tradition Spotlight on gentle April Fools jokes

[00:04:20] - Task 1: Stock a personal recovery kit

[00:07:40] - Task 2: Pick a decorating theme

[00:11:47] - Task 3: Organize your garage before it gets hot

[00:12:32] - Task 4: Edit your Christmas card list

[00:13:46] - Task 5: Search for ideas of traditions you might like 

[00:14:34] - What’s on our to-do lists this week

[00:16:55] - Our Nice Lists

What's Next?

Need motivation to get started? Try scheduling a Holly Day this month to focus on holiday prep!

Resources Mentioned:

• The Fall Risk by Abby Jiminez
• Paperian Brilliant Weekly Scheduler
• 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

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.  

Hey friends! In this episode of Holiday Head Start, we’re sharing a fun roundup of St. Patrick’s Day ideas—some from our own childhood traditions and some fresh inspiration from others. The beauty of celebrating smaller holidays like this one is that there are no big expectations—just fun little touches to add a little sparkle to the day!

We chat about our favorite traditions, like a leprechaun visit that leaves behind tiny footprints and a pot of gold, plus an easy festive punch and a creative take on “Irish” haystacks. We also share a fun printable dice game to use up leftover candy and a sweet shamrock-shaped pretzel treat.

If you’re looking for simple ways to celebrate, we’ve got you covered! Tune in for all the details, and be sure to connect with us on Instagram @theholidayheadstart to share your favorite St. Patrick’s Day ideas.

Resources Mentioned in This Episode:

• Rainbow Haystacks from SoFestive
• Shamrock Dice
• Prequel Skin Utility Ointment
• Grab The Holiday Headstart Playbook
• Take the Holiday Profile quiz
• Follow on Instagram @theholidayheadstart 
• Leave us a review on Apple Podcasts!

What’s Next:

Choose something festive to add surprise and delight to your St. Patrick’s Day!

If You Enjoyed This Episode, You’ll Love These Too:

• Episode 22 – Easy Valentine’s Day Traditions to Start With Your Family This Year

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. 

Ever feel like you need permission to set boundaries, take up space, or just be yourself in tough situations? In this episode, we’re diving into one of Brené Brown’s most genius ideas—permission slips. No, not the kind you signed for field trips, but the ones you write for yourself to navigate emotionally vulnerable moments.

From work meetings to holiday gatherings, permission slips are a powerful tool for claiming your agency and setting your own rules. Join us as we explore how writing these simple notes can help you manage expectations, reduce stress, and show up as your best self—especially during the holiday season.

Highlights from the episode:

[00:00:53] - Tradition Spotlight on personal whimsy

[00:07:31] - What Are Permission Slips

[00:09:38] - Permission Slips You Might Want

[00:14:57] - Writing Your Own Permission Slips

[00:18:00] - This week’s Get A Headstart Tip for Grocery Lists

[00:20:06] - What’s on our to-do lists this week

[00:21:41] - Our Nice Lists

What’s Next:

Take a moment today to write a few permission slips for yourself. Need help getting started? Try these prompts:

👉 I give myself permission to feel…

👉 I give myself permission to do…

👉 I give myself permission to not…

Whatever it is, write it down. Make it real. And most importantly, give yourself permission to embrace the life you want. 

Resources Mentioned:

• Brene Brown talks about permission slips
• A Jane Austen Year podcast
• Cheese grater
• 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 24: How to decide if your holiday traditions still work for you

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. 

Traditions make the holiday season feel magical, but they can also lead to stress and overwhelm. In this episode, we’re taking a step back to evaluate which traditions are truly meaningful and which ones might be more hassle than joy. Just because you’ve always done something doesn’t mean you have to keep doing it! Using six key questions, we’ll walk through how to assess your traditions—considering their purpose, who’s involved, the opportunity cost, and whether small adjustments could make them more enjoyable.

Now is the perfect time to reflect, long before the holiday rush, so you can make thoughtful changes without pressure. Our goal? A holiday season focused on connection, not stress. Tune in to learn how to simplify your traditions in a way that keeps the meaning but ditches the overwhelm!

Highlights from the episode:

[00:00:57] - Tradition Spotlight on bedroom picnics

[00:02:35] - Why February is the perfect time for reflection

[00:06:13] - Reflecting on what matters

[00:11:53] - Is this tradition worth continuing?

[00:13:07] - Where to start with reflection

[00:15:08] - This week’s Get A Headstart Tip for managing wish lists

[00:17:10] - What’s on our to-do lists this week

[00:18:35] - Our Nice Lists

What’s Next:

• Choose a tradition that’s causing some headaches, and use the guiding questions to help you decide if your tradition needs to be tweaked or retired.

Resources:

• The Traitors
• Severance
• 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 - 10 easy steps to create a new holiday tradition for your family 

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 January, we shared five simple ways to get ahead on your Christmas prep (check out Episode 20 if you missed it). Today, we’re continuing the momentum with five simple tasks you can tackle in February to make your holiday season smoother and less stressful. 

The key to a stress-free Christmas is starting early. Taking small, manageable steps each month can spread out the workload and avoid last-minute panic. Whether it’s getting ahead on gift planning, organizing storage spaces, or preparing for DIY projects, this episode will help you take proactive steps now that your future self will appreciate. Tune in as we break down each task and share practical tips to make your holiday preparations more effortless and more enjoyable!

Highlights from the episode:

[01:03] - Tradition Spotlight on simmer pots

[03:12] - Tip 1: Start gift idea lists

[06:26] - Tip 2: Find hiding places for gifts

[08:50] - Tip 3: Organize photos

[10:55] - Tip 4: Organize crafts

[11:42] - Tip 5: Start DIY gifts now

[16:06] - This week’s Get A Headstart Tip for identifying your holiday stressors

[17:00] - What’s on our to-do lists this week

[19:06] - Our Nice Lists

What’s Next:

• Schedule your February Holly Day and add these tasks to your to-do list.

Resources Mentioned:

• Canopy humidifier
• 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 Holiday Headstart Episode 20 - 5 Things You Can Do in January to Get Ahead for Next Christmas

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 back to Holiday Head Start! Today, we’re sharing a roundup of Valentine’s Day traditions—some we’ve loved for years, and some fun new ideas we’ve gathered along the way. From Secret Cupid exchanges to heart-y pizza, we’re sharing our favorite ways to use Valentine’s celebrations to foster love and connection.

Highlights from the episode:

[00:00] - Secret Cupid

[7:15] - Planning a new Valentine tradition

[15:45] - Valentine’s Day gift tradition

[17:58] - Valentine candy letter boxes

[20:28] - This week’s Get A Headstart Tip for making playlists

[23:31] - What’s on our to-do lists this week

[26:36] - Our Nice Lists

Resources Mentioned:

• So Festive Blog
• Ember Mug
• Fijn Cocoa
• 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 - Crafting your Holiday Values for a More Meaningful Christmas
• Episode 11 - 10 Easy Steps to Create a New Holiday Tradition for Your Family

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.  

Every year since 2001, we’ve been knee-deep in the joys (and chaos!) of holiday class parties. After two and half decades, we’ve collected invaluable insights to help make class parties fun and manageable. In this episode, we’re sharing our top 10 tips for hosting a successful class party that keeps kids engaged without the chaos.

If you’re someone who’s ever felt overwhelmed by trying to entertain 25 energetic kids, this episode is for you! We’re sharing practical advice for planning, organizing, and running a party that’s enjoyable for kids, stress-free for you, and appreciated by teachers.

Highlights from the Episode:

[00:00] - Tradition Spotlight on half birthdays

[00:04:43] - Communication is Key

[00:10:34] - Deal with the Details in Advance

[00:17:07] - Keep it Simple

[00:23:51] - This week’s Get A Headstart Tip for

[00:24:30] - What’s on our to-do lists this week

[00:27:01] - Our Nice Lists

Resources mentioned:

• Oriental Trading Valentines
• Target Valentines
• Mindware Valentines
• Paper Source Valentines
• 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 like these too:

• Teacher Approved Podcast Episode 33
• Teacher Approved Podcast Episode 34
• Teacher Approved Podcast Episode 96

More about the Holiday Headstart:

Do you want to make the holidays magical and memorable but life gets in the way and things end up feeling stressful instead of special? You’re in the right place. Co-hosts Emily and Heidi are two sisters and former elementary school teachers who have cracked the code on how to keep up with all the annual holidays, events, and day-to-day to-dos. 

They’ve learned how to bring their experience and planning in the classroom into their personal lives - and now they want to share their best tips with you. Tune in weekly to learn how to work just a little at a time so the days that you look forward to most don’t get sacrificed to the busyness of daily life. They’ll talk holiday planning (hello, Christmas!), traditions, and ordinary days too…because those should feel just as significant!