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!

Christmas may feel far away, but it’s never too early to start getting ahead. In this episode, we’re sharing five easy tasks you can tackle in January to set yourself up for a smoother, more joyful holiday season later this year. 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!

Highlights from the episode:

[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

What’s Next?

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

Resources:

• Holiday Headstart Reflection Journal
• 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 5 - Making a Plan for Gift Giving
• Episode 8 - Make Your Christmas Baking Game Plan with the Holiday Headstart

Show Notes: https://www.secondstorywindow.net/hh-podcast/christmas-planning-in-january/

The holidays may be behind us, but that doesn’t mean the work stops. We're here to keep the holiday spirit alive while planning ahead for a stress-free and joyful year. From meaningful, memorable traditions like celebrating Martin Luther King Day to low-key fun with half-birthday parties, we're here to make every season shine.

In this episode, we share tips for organizing your annual files, scheduling monthly holidays, and making relaxed productivity your new favorite thing. Let's make every holiday special, stress-free, and a little more magical together. Don't miss out on transforming your holiday prep into a year-round celebration!

Highlights from the episode:

[01:15] - Tradition Spotlight on Martin Luther King Day

[04:13] - Big picture quintile planning

[09:17] - Planning ahead with Holly Days

[12:50] - Reflecting in quintile 1

[13:52] - This week’s Get A Headstart Tip for transitioning files from 2024 to 2025

[16:23] - What’s on our to-do lists this week

[17:48] - Our Nice Lists

What’s Next?

• Subscribe to the podcast for our upcoming deep dive into holiday reflections and practical takeaways.
• Let us know if you'd be interested in a dedicated Holly Day planner—we’d love to support your year-long holiday journey!

Resources:

• 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 9 - How's It Going? How to Take Stock of Your Holiday Prep So Far

Show Notes: https://www.secondstorywindow.net/hh-podcast/plan-the-year/

Christmas is officially behind us, but before we get too far into January, we're pausing to reflect on the holiday season we just experienced. In this episode, we share our highs and lows, lessons learned, and plans to enhance our future holidays. We discuss how we balanced holiday tasks with self-care and how we aligned our actions with personal goals. Join us on this reflective journey full of practical advice and holiday insights, so you can make your next holiday season the best one yet!

Episode Highlights:

[00:01:09] - Tradition Spotlight on Lunar New Year

[00:02:49] - 5 Rs of post-holiday reflection

[00:05:30] - Our highlights of the season

[00:07:00] - When did your efforts contribute to our holiday celebrations?

[00:10:05] - What did you learn about planning and preparing this year?

[00:14:58] - What aspects of the season caused you the most stress?

[00:20:28] - What is your plan for saving for Christmas this year?

[00:22:10] - How could next year’s holidays more closely reflect your values?

[00:28:18] - How did you practice self-care during the holidays?

[00:32:42] - What advice would you give your future self as you move toward another holiday season?

[00:37:06] - This week’s Get A Headstart Tip for post-holiday Ta-Da! Lists

[00:39:19] - What’s on our to-do lists this week

[00:40:39] - Our Nice Lists

Resources:

• Luminette Glasses
• 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:

• Holiday Headstart Episode 9: How’s It Going? How To Take Stock Of Your Holiday Prep So Far

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.  

Can you believe we’ve stepped into a brand-new year? As we kick off this year, we’re here with a pep talk that skips the pressure to reinvent yourself and instead invites you to start from where you are.

Sit back, take a deep breath, and let's journey into the new year with grace and gratitude, armed with small steps for meaningful progress. January isn’t magic; it’s just another month. Let's start this year not by transforming who we are but by building on the strengths that make us unique. Join us as we continue the conversation on embracing imperfect progress, adding a dash of joy to everyday moments, and sticking together on this exciting journey ahead.

Episode Highlights:

[00:47] - Happy New Year!

[02:06] - Fresh Start Framework

Resources Mentioned:

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

What’s Next?

The new year isn’t about a complete overhaul—it’s about continuing your beautiful, imperfect story. Stick with us, because we’ve got big plans for 2025:

• More traditions to explore
• Practical tips to simplify your life
• And, of course, plenty of lists to make!

Whatever this year holds, we’re here to cheer you on every step of the way. Let’s make it a great one—together.

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

• Episode 15: Holiday Pep Talk: What's Important Now?
• Episode 16: Holiday Pep Talk: The Magic of the Week After 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.  

Merry Christmas! You did it! We're here with a special post-Christmas pep talk to help you embrace the sweet, quiet magic of the time after the holidays.

Now, you’ve arrived in the quiet, magical in-between—the week after Christmas. In today's episode, we'll explore how you can give yourself permission to rest, savor the joys around you, and let the joy of the season settle in before life picks up again. So grab a cozy blanket, settle in, and let's dive into how you can be intentional and gentle during this slower-paced week.

Episode Highlights:

[1:56] - Slowing down

[2:50] - Embracing the pause

Resources Mentioned:

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

What’s Next?

As we look ahead to the new year, take time to savor this slower pace. Reflect on the joys and lessons of the season, and think about how you want to step into January. We’ll be back soon with tips to help you transition into the new year with intention and peace.

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

• Episode 15: Holiday Pep Talk: What's Important Now?

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.  

It’s the week before Christmas, and the whirlwind is real. Your to-do list is long, your time is short, and the pressure feels intense. But here’s the truth: Christmas isn’t about perfection. It’s about connection, joy, and being present for the moments that matter most. 

Today, we’re here with a pep talk to help you find peace in the chaos. Join us as we share helpful strategies for slowing down, focusing on what really matters, and finding those precious pockets of joy. So tune in, take a deep breath, and let's navigate this holiday season together with intention and calm.

Highlights from the episode:

[1:53] - Slow down and breathe

[3:33] - Write it all down

[5:46] - Find pockets of joy

Resources:

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

What’s Next?

• Plan Your Reset: Set aside time after the holidays to reflect, recharge, and gently ease back into your routines.
• Reflect & Learn: Jot down what worked well this season and what you’d like to adjust for next year. Use tools like the Holiday Headstart Playbook to capture those insights.

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

• Episode 12 - How To Use a Task Docket to Make Managing Your Holiday To Dos Easy Peasy
• Episode 14 - Top Christmas Tip: Use a Script to Save Your Sanity on the Big Day

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.  

Do you feel overwhelmed trying to keep track of everything during the holidays? Today, we’re sharing one of our best-kept teacher secrets: creating a script for big days like Christmas. A script is more than a plan—it’s a minute-by-minute outline that acts as your safety net, support system, and freedom-giver during hectic events. Listen in as we unpack how this simple tool can help you stay organized, enjoy the holiday, and preserve your energy.

Highlights from the episode:

[01:04] - Tradition Spotlight on Christmas Night adventures

[05:09] - 3 Reasons you need a script

[08:16] - How to write your Christmas Day script

[13:19] - This week’s Get A Headstart Tip for making a Christmas Morning basket

[15:59] - What’s on our to-do lists this week

[17:42] - Our Nice Lists

Resources:

• 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 12 - How to Use a Task Docket to Make Managing your Holiday To-Dos Easy Peasy
• Episode 13 - Holiday Housekeeping: How a December Upkeep Plan Will Save Your Sanity

Show Notes: https://www.secondstorywindow.net/hh-podcast/holiday-planning-script/

In this episode, we tackle the stress that comes with the holiday season and explore proactive strategies to manage overwhelm. Instead of waiting for the inevitable meltdown, we’ll discuss how to build a plan that simplifies your responsibilities while ensuring your home stays functional and festive. From revisiting your personal holiday values to crafting a Minimum Upkeep Plan (MUP), you’ll walk away with practical tools to navigate the season with more joy and less chaos.

If you have the Holiday Headstart Playbook, grab it now to follow along. Don’t have it yet? Download it here.

Highlights from the episode:

[01:00] - Tradition Spotlight on Grinch Dinner

[09:43] - What a Minimum Upkeep Plan (MUP) is and why it’s essential during December

[13:54] - Cleaning styles: Beat-the-Buzzer, One-and-Done, and Bespoke Cleaning 

[14:57] - Tools and pages in the Holiday Headstart Playbook to streamline your routines

[16:31] - This week’s Get A Headstart Tip for planning for Winter Break

[17:37] - What’s on our to-do lists this week

[18:49] - Our Nice Lists

Resources:

• Muslim man celebrates first Christmas
• Grinch Playlist
• Book Club Hotel
• MDesign Shower Caddy
• 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

Show Notes: https://www.secondstorywindow.net/hh-podcast/holiday-housekeeping-december-upkeep-plan/

In today's episode, we are diving into the festive yet sometimes daunting task of holiday planning. From managing the expectations and potential pitfalls of putting up your Christmas tree to smart strategies for tackling your gift lists and holiday checklists, we've got you covered. Learn how to streamline your holiday tasks with our unique approach to task dockets, helping you to turn overwhelming lists into manageable actions. Plus, discover a fun tip for getting a head start on next year's plans. Get ready to embrace an organized and joyful holiday season with practical tips and ready-made strategies!

Highlights from the episode:

[01:09] - Tradition Spotlight on decorating the tree

[04:38] - Introduction to the Task Docket

[09:22] - Filling out your to-do lists

[16:05] - This week’s Get A Headstart Tip for getting ahead on your decorating

[18:05] - What’s on our to-do lists this week

[19:34] - Our Nice Lists

Resources:

• 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 6 - The 5 Step Action Plan for Traditions
• Episode 7 - Unlock the Power of the 3 Cs: Your Ultimate Guide to Holiday Planning

Show Notes: https://www.secondstorywindow.net/hh-podcast/holiday-tasks-docket/