Having intentions to make the holidays feel special and actually bringing your ideas to life are two very different things! Whether you tend to leave things to the last minute, let overwhelm take over, or struggle to be present for the moments that matter most, we can relate.

There was a time where we resisted the need to plan ahead for holidays, but now we want to help you learn from our mistakes. Just like we created our own curriculum for the classroom when we saw a need, we’ve mastered the art of systems for holiday prep. 

In today’s episode, we’re sharing how we discovered a need for step-by-step holiday prep that keeps stress levels down. Plus, you’ll hear how to utilize Pinterest for getting organized without getting overwhelmed.

Episode Highlights:

[01:03] - Why we care so much about planning and preparing for the holidays

[02:42] - How we learned to keep stress levels down during holiday planning

[07:43] - A “get a headstart tip” for using Pinterest to get organized

[11:09] - What’s on our to-do list this week

Links & Resources:

• The Unselected Journals of Emma M. Lion, by Beth Brower
• Somebody Feed Phil on Netflix
• Follow on Instagram @theholidayheadstart 
• Leave us a review on Apple Podcasts!

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

Heidi 0:04

Welcome to the holiday Head Start podcast where we get intentional about keeping overwhelmed to the curb and bringing the joy back to your holidays, and every day. I'm Heidi.

Emily 0:15

And I'm Emily. We're 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.

Heidi 0:27

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.

Emily 0:39

You can check out the show notes at theholidayheadstart.com. Ready to get a head start on your holidays? Let's go.

Heidi 0:50

Hey there, friends. Welcome back to the Holiday Headstart Podcast. Today, we are talking about how we came to be the holiday planning powerhouses that we are, and we're sharing a get ahead tip for organizing your ideas.

Emily 1:03

Since our podcast is brand new, we thought that in this episode we would take the opportunity to share a little about who we are and why we care so much about planning and preparing for the holidays. Why don't you tell us how you got started, Heidi?

Heidi 1:20

Well, for a long time, I resisted the idea that I needed to plan ahead for the holidays. I, this is so silly, but I was deeply in denial that I even had holiday stress, right? Being child free, I don't have to deal with the biggest source of holiday stress, which is, of course, making a memorable, magical Christmas for small humans. So naturally, that had to mean that I shouldn't have any stress at all, like somehow I was exempt, because Santa doesn't visit my house. And, right? I know that's not rational, but that's where I was.

Heidi 1:55

Emily 2:41

That's a good description.

Heidi 2:42

And obviously nobody wants to feel that. So I decided to tackle this like I would a teaching problem. I consulted every resource I could find that talked about how to plan for the holidays. There's surprising lack of experts in the field, much more in teaching I found, but, you know, I did what I could. So I bought the books, I read blogs, I listened to podcasts, and I found lots of really good ideas, but no real clear steps to implement them in my own life.

Heidi 3:13

So I just started piecing together my own plan for how to prepare for Christmas in advance, in the hopes that, you know, the last minute rush didn't send my stress into overload every year.

Emily 3:25

And that is 100% how we tackled teaching problems as well. The two of us taught second grade at neighboring schools, and then we taught preschool together for several years, and we found that as teachers, the curriculum we were provided was often subpar. So we figured it out. We asked ourselves, what does best practice look like in this area? And we started researching and compiling resources. From that, we built our business Second Story Window.

Heidi 3:52

And if you have used any of our second story window products, you may have noticed that we don't have very many one time use activities. Instead, we tend to be more like, Here, let's roll out a year long program so you have the exact thing you need for each day of school.

Emily 4:12

Yes, we are very good with a system. That probably stems from learning the hard way that if we don't have a standardized way to implement a good idea, it does not happen. I think of all the fun things I wanted to try in my classroom, but because they didn't have a set time in my schedule, or didn't lend themselves to being a part of a routine, they just didn't happen. Either I couldn't figure out when to do them or I completely forgot they existed.

Heidi 4:37

Yeah, when your schedule is already full, it's hard to add extra things, even if they're things that you're excited about. And this was 100% the problem I was having with Christmas. I wanted to send the cards and buy thoughtful gifts and bake cookies, but when, right, normally, I'd wait to be panic motivated. You know how it goes. It's the third week in December. So if I don't make myself sit down and stuff envelopes right this second, these cards will not arrive before Christmas.

Emily 5:08

And panic is a very powerful motivator, but maybe not the best use of time, and definitely not the most healthy, especially if you're trying to avoid an autoimmune flare up, Heidi.

Heidi 5:18

Emily 6:03

Yeah, that's definitely a win, besides not damaging anyone's health, preparing in advance allows us to be present for the moments that matter. There have been plenty of family get togethers or holiday traditions that I attended but couldn't enjoy because I was managing my crushing to do list at the same time.

Heidi 6:22

Right? We only get one Christmas each year, and we deserve to enjoy it as much as the people that we're doing all this work for. For me, I have learned that I need to create a plug and play system as much as possible. So one thing we like to do is do a Grinch dinner every December, and Emily and her kids come over, I have everything I need in one central place. I pull out the food that I bought ahead of time, so there's no last minute grocery runs. I have a timeline for setting everything up, and then when Emily and the kids arrive, I can just be pulling the last few things out of the oven, and we have a fun, low stress night together.

Emily 6:59

I love our Grinch dinner, especially because you host it.

Heidi 7:02

And you do the dishes.

Emily 7:04

Yes, that's true. There are still a few hiccups. That's just how life goes. But because we've done most of the heavy lifting in advance, the hiccups don't derail the whole night.

Heidi 7:15

Because we have learned so much over the past seven years, we want to help you apply the same tips and tricks to your holiday planning. We hope you will join us here each week as we share all the nitty gritty details for how to plan ahead for all of the celebrations in your life.

Emily 7:32

Not just Christmas! We're gonna be talking about lots of fun things.

Heidi 7:36

And you can find us on Instagram at The Holiday Headstart. We would love to hear how you get a head start on your holidays.

Emily 7:43

Now it's time for a get a head start 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 use Pinterest to get organized. Tell us more about this, Heidi.

Heidi 7:59

So Pinterest can be an incredible tool in organizing your holiday plans. It gives you a central place to put all your notes and recipes and ideas. I love Pinterest, but it can quickly become overwhelming. I think the key to making Pinterest useful is to keep your boards very specific. If you have one giant board for Christmas, you will never find what you need.

Emily 8:25

Oh, I've made that mistake.

Heidi 8:26

Yes. But we start out not knowing how many pins we're going to need, and then suddenly there's 200 and you can't find a single one. So narrow categories are much more useful. I'm not going to pretend that I'm a Pinterest expert, but one thing that has helped me is to give all of my related boards similar titles. Emily, I think you gave me this idea.

Emily 8:47

Yes, I do do that.

Heidi 8:48

Yeah. So all of my Christmas boards start with Noel. So I have Noel: recipes, Noel: decorating ideas, Noel: Christmas Eve dinner. And my other holiday boards are, Celebrate: Easter, Celebrate: Halloween. It's very, very creative, but the more focused the board, the easier it is to find things.

Emily 9:10

So why didn't you call your Christmas boards Christmas? Why do you call them Noel?

Heidi 9:14

Because I'm weird. I have a ton of Christmas boards, as you might imagine, as someone who has a podcast about holiday planning. And because my boards are organized alphabetically, I didn't want a huge log jam of boards so early in the alphabet as C, because then I'd have to scroll through them anytime I needed a board that started with, you know, E, F or G. And really, I wish N was a little later in the alphabet, but it works. Okay? I persevere through the hardships in life.

Emily 9:42

I guess you could switch it to Yuletide. Then it'd really be at the end.

Heidi 9:46

That's a good idea. Except I have got, I think I have even more preschool boards than Christmas boards.

Emily 9:52

So then you have to scroll through the preschool board.

Heidi 9:55

Yeah, that is a bummer.

Emily 9:56

Maybe preschool could be, um... I'll keep thinking about that one.

If you don't want dozens of holiday boards, another way to organize your pins is to add sections to your board. So you can just have a single Christmas board and then a section for recipes and a section for gift wrap ideas and anything else you need to refer to.

If you haven't added a section to a board before, it's super easy, just open one of your existing boards or create a new board, and then at the bottom of the window, there's a big plus sign in the middle of the screen, so click that and then select section and add a name. Now when you pin stuff to that board, it will give you the option to pin right into that section so it's already organized.

And if you already have pins on that board, you just hit organize, and then you can select all the pins you want to move to a new section. It is really easy. Once you get the hang of it, you will be just flying through and it's really such a relief to know exactly where to find that one cookie recipe that you have to make every year is. You can just pull it up without having to think about it.

Well, one of my upcoming what we're working on is going to end up being organizing my Christmas Pinterest board.

Oh, I love it. I want to see them all.

Speaking of what we're working on, as a way to keep ourselves accountable and to give you some ideas of what you can be doing in advance for your own celebrations, we're sharing what we're working on this week. Emily, what is on your to do list?

I'm getting ready for our holiday season delivery driver basket.

That is impressive that you were doing it so early.

I know I've never ever been this early before, and I'm sure we'll talk about it in a future episode. But both Heidi and I like to put a basket of treats for drivers out on the porch during the holiday season. I noticed that the boxes of candy bars that we get from Costco are on sale for the best price that we like to get them at. So I'm gonna grab them now, and I may stick them in the freezer, or I'll just store them in a cool place, and it will just be so nice to know that I'm already ready to go for that so far in advance, and it spreads out some of the holiday expense to buy that so early. What are you working on, Heidi?

Well, I'm going to take credit for you getting the delivery driver treats, and check that off my list.

I'm glad I could help.

And we can put them in my basement closet, because it stays pretty cool down there. It's really nice that candy bars keep for a long time. And just to take it a step further, I went ahead and set up a little bin with the rest of my delivery driver supplies. In the past, I had things in different closets, and so I could never find them at the same time when I was trying to put them out on the porch. So now it's all in one central location. It has a label on it, and I put it in the, quote, unquote, holiday closet that I have not really organized yet, but it's shoved in there and the door shut. So we're calling it a win.

Good job. I should do that. I'm not sure if my sign and my basket are in the same place, so I will have to check on that. Yeah, that's the tricky part. And if you are someone who likes to give out full size candy bars at Halloween, this could be a way to get ahead for Halloween too. So if you're a Costco member, take a look. There was like a big manufacturer coupon on the big boxes of full size candy bars of like Snickers, m&ms, Twix, etc. So check that out. That could be a good way to get ahead for Halloween too.

And they really do stay good for a while. So don't feel like you're they're going to expire before you can use them.

Nah.

To wrap up the show, we are sharing our nice lists. Emily, what has made it on your nice list this week?

I am adding The Unselected Journals of Emma M Lion.

So good.

So Heidi gave me the first book in this series for our Christmas book lunch, again, something I'm sure we'll talk a lot about later. And I have been reading this series ever since, but trying to kind of go slowish, because I don't want it to be over.

It's just the most charming, witty laugh out loud, truly, I was literally laughing out loud the other day, funny series I've read in the longest time. Emma M Lion keeps a faithful journal of her unexpected adventures in 1883 in her London neighborhood of St. Crispians. And there's a full cast of quirky characters that you will fall in love with, including a friendly ghost of a Roman centurion who steals things from one house and leaves them in another.

It's like, I've been trying to describe this to people. I think it's like Gilmore Girls meets Pride and Prejudice with a dash of Parks and Rec. What do you think, Heidi?

I think that's a really good combo, but it also kind of has the tone of, if you're familiar with Cold Comfort Farm, or To Say Nothing of the Dog, where it's just so funny and so dry.

Mm-hmm.

It's just, yeah, just so clever and witty.

I love it so much. So if you like a period piece with charm, this series is for you. And if you have Kindle Unlimited, it's free on there too. So that's an added bonus. But there are also paperbacks.

Yeah, I just had to renew my Kindle Unlimited so I can finish this series. I just started the fourth one today.

Every time I finish a book, I'm like, Oh, I'm getting closer to being caught up to it, because she's still releasing books. So I think there's seven out and I'm in book five.

Oh no.

But she's saying eight is coming soon, I hope. What is on your nice list, Heidi?

Well, I am adding the new season of somebody feed Phil on Netflix. Oh, I love Phil. If you have not seen it before, it is so fun. Phil Rosenthal travels around the world meeting people and just eating yummy food, which sounds like a pretty great job. Well, most of the time, some of the food, I don't know, he says it tastes good. We'll trust him.

But Phil is the creator behind Everybody Loves Raymond. And so if you like that show, I think you will definitely like this. It's got kind of that same level of humor. This show originally started on PBS, and that's where I was introduced to it. I happened to catch the middle of an episode when he's in a gelato shop in Italy, and he's, like, getting emotional because the gelato was so good, and so he's just like, hugging all the workers, and they're like, What is the American guy doing? And I'm just hooked. I've been hooked ever since. So it is such a sweet show. I pace myself when a new series comes out, and I save it for the days when I just I need the reminder that really, life is not the dumpster fire that it feels like it is sometimes. There's still gelato and that that goes a long way.

I love it.

That is it for today's episode. Remember to set up your Pinterest boards. Send us a screen shot if you get it, we would love to see that. And thank you so much for joining us, we hope that we can see you here next week.

Thanks for tuning in today. Use this week to get a head start on planning for what's ahead. And remember, don't get it perfect. Get it going.

Come follow along on Instagram at The Holiday Headstart. We would love to hear from you.

If you liked this episode, head to Apple podcasts and leave us a review. We'll see you here next week.