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. 

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.