The Holiday Headstart

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 futur...

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...

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 tacklin...

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...

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 epi...

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 p...

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....

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 decisi...

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 fu...

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 Dec...

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...

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 actuall...

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 throu...

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 Highligh...

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 vi...

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...

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—consideri...

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...

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 Valen...

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 entertai...

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...

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, schedu...

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 p...

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 star...

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...