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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!
Episode Highlights:
[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 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 9 – How’s It Going? How to Take Stock of Your Holiday Prep So Farate Guide to Holiday Planning
Read the Transcript for Episode 19:
Heidi 0:00
Hey there, friends. Welcome back to the Holiday Headstart Podcast. Today, we are talking about our plans for getting ahead in 2025 and sharing a get ahead tip for organizing your planner pages.
Emily 1:02
Let’s get started with our tradition spotlight. Traditions are an important tool in building a healthy, happy, connected life. This week, we have a tradition for celebrating Martin Luther King Day. Tell us about it, Heidi.
Heidi 1:15
Martin Luther King Day falls on January 20 this year. And if you are looking for a way to add some meaning to the day, one thing you can do is to talk about Dr. King’s legacy of working for freedom and promoting peace. If you’ve got little kids, there are some amazing picture books you could read. One we really like is Martin’s Big Words.
Emily 1:35
Oh, I love that book. Then you can have your family members trace a footprint on paper and write something they can do to follow in Martin Luther King’s footsteps. You could also hang the footprints where they can be a reminder.
Heidi 1:48
In most places, there are also lots of community events celebrating the day, but because this holiday falls on a Monday, it often catches me off guard. So here is just a friendly reminder to look up the events in your area now, rather than trying to wait and do it at the last minute.
Emily 2:05
Right. Another thing you might want to do is follow Bernice King on Instagram. I know we both follow her. She is the Kings’ youngest daughter and often shares photos and sweet memories of her family. Following her has given me such a deep appreciation for Coretta Scott King. She was such an amazing woman, and she deserves recognition for all of her hard work and commitment and her dedication to Dr King’s legacy.
Heidi 2:29
She really is an incredible woman. I really have so much admiration, and I’m sad that we don’t speak and celebrate her more often. And another Instagram account that is well worth a follow is Oh Happy Danny. She’s got great, amazing, well designed resources about living a more just and hopeful life.
Emily 2:48
I love her stuff. It’s so good, and it looks good too. So win, win. We’d love to hear about your favorite traditions. Come join us on Instagram @theholidayheadstart.
Emily 2:57
While the holiday season is now behind us, it’s come and gone, and you might be wondering what on earth a holiday podcast has to talk about on January 15. But don’t underestimate our commitment to making it the holidays every day.
Heidi 3:14
We are nothing if not committed to this.
Emily 3:16
Right.
Heidi 3:18
Planning ahead is kind of our favorite sport, and we have barely scratched the surface of all of the possibilities, so stick with us for all of our best tips and tricks.
Emily 3:26
Yep, there’s so much more to come, and not to mention that there are way more holidays to consider than just Christmas. I mean, Christmas is obviously the best one, but we love a leprechaun treasure hunt and a Fourth of July fruit kebab, kebab, whichever one you call it.
Heidi 3:42
I’ve heard it both ways.
Emily 3:44
Our goal here is to support you with a little planning and a little prep, so the days that make life special all year long don’t become the days that make you stressed.
Heidi 3:54
So let’s talk a bit about what we’ve got coming up this year. We are going to look at things from a big picture perspective, so that we are making sure to address what’s important. And then we’ll zoom into smaller monthly and weekly planning, so that we make sure that we are accomplishing the tasks that we need to move us closer to those important goals.
Emily 4:13
Let’s start with our big picture plan for dividing the year into quintiles. Originally, we were working with quarters, but that came with a few hiccups. For example, having the fourth quarter encompassing October, November, December, the most hectic months of the year, put more pressure on the other three quarters to do a lot of heavy lifting. And heavy lifting can be tricky to do months in advance.
Heidi 4:36
But by breaking off November and December into their own little special corner of the planning calendar, that gave us 10 slightly saner months for the rest of our planning and prep.
Emily 4:47
And to help direct all that planning and prep, we’re giving each quintile its own theme. So quintile one is all about reflection. Of course, we’ll be reflecting on our past holiday season, but there’s also more general reflection about our hopes and dreams for our Christmas ideals and all the rest of the year.
Heidi 5:06
Our first quintile is January and February. But the nice thing about trying to squish 12 months into five sections is that the dividing lines get real blurry. That may sound like a downside, but I promise it’s a plus. That means you get to be the boss of the calendar instead of letting the calendar be the boss of you.
Emily 5:26
If you’ve got kids in school, they may have spring break in mid March. In that case, you may want to stretch quintile one to spring break and move to quintile two once the kids are back in school.
Heidi 5:37
Around here, though, Spring Break isn’t until April, so our quintile two starts in March and runs through May. We wanted to build a buffer into this quintile by giving it a full three months, because May can be so crazy with all of the end of the year demands.
Emily 5:51
Oh, May. I’m already dreading it. If you don’t have to plan around kids’ schedules, you may not need to take school year calendars into account. So adapt your quintiles to fit your own circumstances. I never thought I would be saying quintiles so many times. A word that I just learned.
Heidi 6:11
We should turn it into a drinking game, I guess.
Emily 6:13
Don’t do that, you guys will die!
Heidi 6:17
However you split up the months, we’re going to use that second quintile for our holiday dreaming. What do you wish your holidays looked like? What needs to happen to make those wishes come true?
Emily 6:27
June, July and August are our third quintile. These are the months when we’re really diving into our planning. We’ll make our gift lists, our grocery lists, and every other list we can think of. Yes, this is actually the perfect time to really get deep into your planning for the holidays.
Heidi 6:44
I mean, who doesn’t love spending their summer making lists?
Emily 6:47
I mean, clearly we do, because think about it, what’s more fun than sitting by the pool in 100 degree weather, listing all of the neighbors I want to give Christmas gifts to.
Heidi 7:00
And sitting at the pool with the neighbors might knock a few of those neighbors off your list.
Emily 7:04
You’ve received my texts about neighbors I’m ready to be done with after their behavior at the pool, so you are not wrong.
Heidi 7:13
But minus the 100 degree heat that actually does sound great to me. I love having tasks that make me feel productive while I’m able to, you know, chill on the couch or by the pool. Okay, that was a flat out lie.
Emily 7:29
This doesn’t sound right at all.
Heidi 7:32
Give me all the AC. But I do stand by the rest of it. Relaxed productivity is my favorite thing.
Emily 7:38
Yes, you can do that at home with some lemonade in a comfy chair with some air conditioning on, for sure.
Heidi 7:45
All of the best things in life.
Emily 7:47
September and October make up quintile four for us, and this is our chance to put those plans into action and prepare everything we need for the upcoming holidays.
Heidi 7:57
As we mentioned earlier, one of the benefits of quintile planning is that it makes it easier to pivot. Since I don’t have kids to get back to school and I don’t have a classroom to set up anymore, August is my gateway to the holiday season. My silly brain says that because school is starting, that must mean it’s autumn, and if it’s autumn, the year is almost over, and that means it’s Christmas. And I know that that is not rational, but I have also found that it’s really helpful for that holiday panicky feeling.
Heidi 8:26
If I use August as my launch into holiday prep, I don’t start baking or decorating yet. I’m not that bad, but it is just good for my stress to know that I have set the first week of August as my official start to holiday prep, and then I know I have plenty of time to get it all done. But I also understand that I’m a bit intense, and that August is firmly a summer month for most people. So for most of us, we’re just not gonna sweat preparing until it’s actually September.
Emily 8:54
And that leaves us with November and December for celebrating in our final quintile, or more realistically, those ones are first of celebrating and also completing all the tasks you couldn’t do in advance or didn’t get around to, and going to all the events and all of the school programs and all the things that you’re going to have to do in November and December. Can you tell that I’m still bitter about how busy I was this year?
Heidi 9:18
But we are going to do our best to keep that list of things I didn’t get around to as small as possible. And that’s where our Holly Days come in. I didn’t mispronounce holiday. It’s Holly Day.
Emily 9:31
Yes, capital H, capital D.
Heidi 9:34
We have our big picture quintile planning, and now we’re going to zoom in into our smaller monthly and weekly planning so that we can put all of those plans into practice.
Emily 9:45
In her book Outer Order, Inner Calm, author Gretchen Rubin has a saying that is unfortunately very prophetic. Something that can be done at any time is often done at no time. That is so true in my life. Months go by without seeing a friend, because you could just schedule lunch anytime, or you don’t get those pictures hung on the wall, because you’ll just deal with it later. I am at 10 years in my house, and I am still doing things that I said I was gonna do, you know, soon when I moved in, because it just it could happen at any time, and so it just didn’t happen at all.
Heidi 10:19
Right? There’s none of that urgency to get you moving. But when it comes to planning ahead for something as multifaceted as Christmas, we run into several traps. First, right, We don’t have that urgency. We’ve basically got a whole year before we really need to worry about this again.
Emily 10:35
Plus there’s the overwhelm. If I open the door to dealing with Christmas, I’m going to be buried in an avalanche of red and green, I can’t deal with that on top of the day-to-day stressors I’m barely managing.
Heidi 10:45
And maybe the biggest hurdle to planning ahead is that it is outside of your regular routine. It’s just not built into the daily flow of your life, and that makes the hurdles of procrastination and overwhelm even more challenging to tackle.
Emily 11:01
Right, so let’s solve this problem with a little thing we call Holly Days. We’re going to dedicate time every month for a Holly Day, for your holidays.
Heidi 11:11
I used to do this on the 25th of every month, as, you know, a little nod to Christmas, but I found that the variability of when the 25th fell during the week made it really hard to do any kind of holiday tasks in the middle of a workday. So instead, depending on what’s happening that month, I use the third or fourth Sunday to do a little planning ahead.
Emily 11:30
Unless you’re really diving into the nitty gritty, this won’t take all day. An hour is probably more than enough time. So I start by taking stock of where I am and what I’ve accomplished so far. Then I look ahead at what’s coming in the next month. And then I can tackle some of my holiday tasks. Maybe that’s updating my permission slips or Christmas card addresses, and then I’m done till next month.
Heidi 11:51
Now, it pains me to say this, but there are no pages for this in the Holiday Headstart Playbook. I know, I know we were just worried that we would overwhelm people if we tried to add this whole separate system to all of the Christmas specific planning. If you have the playbook, you know that’s already a lot. But if you would be interested in some sort of holiday planner, please let us know. We are trying to figure out how best to support our head starters with this type of big picture monthly planning.
Emily 12:23
And I’m sure we’ll talk more about Holly Days in the future, but for today, start by scheduling your January Holly Day, and then make sure you know exactly how you want to use that time. Start by taking stock of where you are at this point in January. Have you recovered from the holidays yet? If not, what’s your next step? Next, take a look at your February and March calendars. What’s on the horizon that you need to be aware of? Make the Valentine plans, stock up on Lucky Charms, buy the birthday gifts.
Heidi 12:50
And then consider where you are in your bigger holiday plans. Since we are in quintile one, let’s focus on reflection. If you have the Holiday Headstart reflection journal, take a peek at that. There are a lot of questions there to spark some thoughts about what worked, what didn’t work, and what to do moving forward.
Emily 13:07
And go back and listen to last week’s episode, episode 18, where we did this reflection process ourself about our holiday experiences and what we want to do differently this year. So if you need some inspiration, listening to us might help you with your own post Christmas reflections.
Heidi 13:25
So as we head off into the wild adventure that is 2025…What? Crazy! Keep these things in mind. Figure out your own quintile calendar, and if the themes of reflecting, dreaming, planning, preparing and celebrating fit your needs. Then schedule your monthly holiday so that you have an organized system for getting all of that preparing done.
Emily 13:48
We’d love to hear about your plans for getting a head start on the holidays. Yes, already. Connect with us on Instagram @theholidayheadstart.
Emily 13:52
Now it’s time for a Get a Headstart Tip. Each week we leave you with a small actionable tip to help you get a head start on your holiday planning. This week’s get a head start tip is organize your holiday files. Tell us more about it, Heidi.
Heidi 14:10
When I first started making detailed holiday plans, I did it all digitally so that I didn’t have to start from scratch each year. It saves so much time to tweak last year’s plans without having to retype everything. The problem is that I was doing exactly that. I was tweaking last year’s plans, which means I lost a lot of important information. I cleared the lists of all the gifts that I had given and who had sent me Christmas cards and all of the menu details that I actually wanted to reference.
Heidi 14:39
But after that, I get smart. In my Google Drive, I have a big folder called Holidays, and inside that main file, I have a file for each year’s holiday planner going back to 2018. So now that we are in January, I will make a folder for my 2024 holiday planner, and then I will go through and make a copy of each section of the Holiday Headstart Playbook, and I can just drag those copies to my 2024 folder, and I can start updating the playbook for my 2025 information. There’s just nothing like the magic of a new planner, even if it is just a digital one.
Emily 15:15
One thing you might want to do is download a new copy of the Holiday Headstart Playbook and copy any of the new pages we have added into your current playbook section. So compare the two side by side. Or you could go vice versa and copy the information you typed in your 2024 playbook into a newly downloaded playbook file. We have added a few new pages since we launched, and I’m sorry to say we’re probably going to keep doing that, because we just, you know, this is an evolving system. And we’ve added, like, a list of holiday events that need to be scheduled, and a family outfit planner and things like that that you probably will want to get into your version.
Heidi 15:52
Having this as a digital product is a little bit like, I don’t know, cat nippy, so easy for us to make changes every time we have a new idea. So yeah, there’s going to be more coming in the future. We can’t help ourselves.
Emily 16:06
If you prefer paper planning, this process gets much simpler. You can just put all your papers in a binder and then print off any new pages you need for 2025.
Heidi 16:15
But you do have to add all of your 2025 information by hand, so I think I’m going to stick with my Google Sheets, thank you.
Emily 16:20
Right. Me too.
Heidi 16:23
Now it’s time for what we’re working on this week. As a way to keep ourselves accountable and give you some ideas of what you can do in advance for your own celebrations, we’re sharing what we’re working on this week. Emily, what’s on your to do list?
Emily 16:34
This week, I’m working on finishing up taking down all my holiday stuff. I always have some things that linger, some intentionally, like I have my glittery holiday houses, and I tend to leave those up into January because I need the sparkle. But you know, it’s time to start getting it all put away, and then I will pull out anything that I didn’t use this year and evaluate if I still want it. So then I can donate that and have a fresh start come Christmas.
Heidi 17:04
Such an important step, so you’re not buried in Christmas boxes.
Emily 17:08
Yep. What are you working on, Heidi?
Heidi 17:11
Well, I am just focused on recovery right now. I leave it all on the field in December, so it really does take me a few weeks to bounce back, and I’m trying to be okay with that. Trying to take things slow and just be gentle with myself. My body is only going to recover as fast as it’s going to recover, and as I have learned the hard way, pushing myself just makes me frustrated and more tired. So gonna take the next loving step as it comes and try not to let the inner critic have the upper hand. It really doesn’t matter if my tree doesn’t get taken down for a while, I am repeating to myself over and over.
Heidi 17:47
To wrap up the show, we’re sharing our nice lists. Emily, what has made it on your nice list this week?
Emily 17:52
I’m putting my new favorite moisturizer on my nice list. It’s the extreme cream from INNBEAUTY Project. It has such a nice texture, and it’s especially wonderful in the winter, when my skin is so dry. Now it’s not cheap, but it is cheaper than the moisturizer I used to use, so to me, it’s a win.
Heidi 18:13
Well, that’s good to know. I just stocked up on my expensive stuff, so,dang it.
Emily 18:20
Well, just keep it in mind.
Emily 18:21
Okay, good to know.
Emily 18:23
What’s on your nice list, Heidi?
Heidi 18:25
I’m putting smart plugs on my nice list. My outside Christmas lights have been on a system from Apple, but then this year, Apple decided I needed to buy a home hub in order to keep using that system, and I did not want to spend $100 just to turn on my Christmas lights. So I got a $10 smart plug that I can use for my phone. It was so handy, and it was much cheaper than adding a whole hub for this project.
Emily 18:49
Yes, love it.
Heidi 18:51
That is it for today’s episode. Work on your quintile planning and schedule your Holly Days, and don’t forget our get ahead tip for organizing your 2024 files before you start on your 2025 plans.
Emily 19:03
Thank you so much for joining us, and stick around with us. We’re going to be talking holidays of all kinds for the rest of this year. And if you enjoyed this episode, it would be so helpful if you gave us a five star rating and a review on Apple podcasts to help us reach new listeners.
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!