The Holiday Headstart

The Holiday Headstart

Heidi and Emily, Holiday Planning

Episodes 41
Avg. Duration 23m
Activity Declining
Apple Rating 5.0 (10)
Since Apr 2024
Latest Episode Jan 2026

Publishing Details

Schedule
Every 2 Weeks
Format
Episodic
Consistency
50%
Hosting
feeds.captivate.fm

About This Podcast

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! Whether you’re a mom or not, this podcast will give you the headstart you need to not only plan unforgettable moments, but enjoy them too! Follow along on Instagram @theholidayheadstart.

Podcasting 2.0 Features

episode medium

Social Media

Explore Statistics

Recent Episodes

40. 5 Things You Can Do in January to Get Ahead for Next Christmas (Seriously!)

Jan 24, 2026 20m

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,…

39. A Gentle Plan for the Week After Christmas

Dec 14, 2025 28m

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…

38. Before You Stuff a Single Stocking, Listen to This

Dec 01, 2025 25m

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…

37. The Holiday List System That Actually Works

Nov 06, 2025 31m

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…

36. How to Do Halloween Right (Without Doing Everything)

Oct 24, 2025 31m

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…

35. Your September Holiday Reset: The 5 Tasks That Matter Most

Sep 10, 2025 23m

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…

34. 5 August Tasks to Make Your December So Much Easier

Aug 26, 2025 23m

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…

33. The Back-to-School Roadmap for Busy Moms

Aug 12, 2025 29m

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…

32. 5 Tasks for July to Save Your Sanity in December

Jul 30, 2025 22m

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…

31. 5 Holiday To Dos You Can Check Off in June

Jun 28, 2025 21m

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…

30. The Easiest To Do List: 5 Ways to Plan Christmas from Your Couch This May

May 28, 2025 26m Transcript

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…

29. How Knowing Yourself Better Can Bring More Joy to Your Holiday Planning

Apr 26, 2025 30m Transcript

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…

28. 5 Tasks To Do in April to Get Ahead for Next Christmas

Apr 09, 2025 26m Transcript

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…

27. Do These 5 Easy Things in March to Get Ahead for Christmas!

Mar 19, 2025 19m Transcript

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…

26. Easy Festive Traditions You Can Try For St. Patrick's Day [Episode 26]

Mar 05, 2025 20m Transcript

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…

25. Why You Should Write Yourself a Permission Slip for Upcoming Holidays

Feb 26, 2025 24m

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…

24. How To Decide if Your Holiday Traditions Still Work For You

Feb 19, 2025 22m Transcript

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…

23. 5 Easy Tasks To Do in February to Get Ahead for Next Christmas

Feb 12, 2025 21m Transcript

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…

22. Easy Valentine's Day Traditions To Start With Your Family This Year

Feb 04, 2025 29m

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…

21. Top 10 Tips for Planning a Holiday Class Party

Jan 29, 2025 31m Transcript

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…

Frequently Asked Questions

How many episodes does The Holiday Headstart have?

The Holiday Headstart has published 41 episodes since April 2024, covering topics in Education, How To.

Is The Holiday Headstart still active?

The Holiday Headstart is currently declining with new episodes every 2 weeks. Average episode length is 23m.

Similar Podcasts