Your September Holiday Reset: The 5 Tasks That Matter Most [Episode 35]

Click below to hear the full episode:

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 place.

But here’s the twist: you don’t need to tackle all 40. Instead, your challenge this month is to choose the 5 tasks that will have the biggest impact on your December. Think of it as holiday triage—focusing on what will matter most to you and your family. Whether you’re just starting now or you’ve been following along all year, this episode will help you prioritize, simplify, and move into fall with confidence and clarity.

Episode Highlights:

[00:01:04] – Tradition Spotlight on an apple cider bar

[00:01:43] – Tasks for September

[00:03:54] – Money and Planning Tasks

[00:05:40] – Systems and Organization Tasks

[00:09:27] – Food and Entertaining Tasks

[00:10:56] – Gift Tasks

[00:12:28] – Experience and Traditions Tasks

[00:14:19] – Logistical Tasks

[00:16:08] – Your Top 5 Tasks

[00:18:19] – This week’s Get A Headstart Tip for making holiday prep time more enjoyable

[00:19:26] – What’s on our to-do lists this week

[00:20:37] – Our Nice Lists

The Complete List: Holiday Prep Tasks by Category

Money & Planning

  • Set up automatic savings transfer for Christmas fund
  • Inventory winter clothing needs (coats, boots, gloves)
  • List 4th quarter grocery needs and extra expenses

Systems & Organization

  • Write yourself notes for what to do differently next time
  • Update your Pinterest boards
  • Set up stocking bags for year-round gift collecting
  • Stock up on discounted school supplies for stocking stuffers
  • Create hiding places for presents (try moving bags!)
  • Sort holiday decoration bins 
  • Organize holiday items in the garage/attic while weather is nice
  • Donate holiday items you don’t use anymore
  • Plan strategic un-decorating for next year
  • Choose decorating theme and color scheme
  • Make a wrapping station
  • Create a Need-to-Know Box for essential holiday items
  • Declutter crafting area before DIY projects
  • Buy advent calendars early (best selection available now!)

Food & Entertaining

  • Gather all holiday recipes in one place
  • Make and freeze cookie dough
  • Draft holiday menus (including non-holiday meals around Christmas)
  • Find and test new holiday recipes

Gifts

  • Start gathering gift idea for everyone
  • Start working on DIY gifts NOW (seriously!)
  • Create gift lists for loved ones and yourself
  • Draw names for gift exchanges

Experiences & Traditions

  • Reflect on last holiday season (what worked/didn’t work)
  • Stock a personal recovery kit for post-holiday recuperation
  • Dream about traditions that support your holiday purpose
  • Complete the holiday values exercise
  • Find holiday playlists and book lists
  • Plan the week after Christmas (Twixmas!)

Logistics

  • Organize holiday photos into albums
  • Edit Christmas card list and track down addresses
  • Book family photographer before they’re completely booked
  • Plan for fall and winter birthdays
  • Prep guest room/space for holiday visitors
  • Figure out Elf plans (if applicable)
  • Create household Minimum Upkeep Plan

Resources Mentioned:

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Read the Transcript for Episode 34:

HH 35

Heidi: [00:00:00] Welcome to the Holiday Head Start Podcast, where we get intentional about kicking overwhelm to the curb and bringing the joy back to your holidays and every day.

Emily: I’m Heidi. 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: And we are 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: You can check out the show [email protected]. Ready to get a headstart on your holidays.

Let’s go.

Heidi: Hey there friends. Welcome back to the Holiday Head Start podcast. Today we are revisiting all of the get ahead tasks that we have talked about so far this year. So buckle up. But first, we have a tradition Spotlight Traditions are an important tool in building a [00:01:00] healthy, happy, connected life. And this week we have a tradition from Heidi.

Well, if you are looking for a fun fall celebration, why not try an apple cider bar? Think hot chocolate bar, but fallier and fruitier. Just grab some apple cider and some simple mix-ins like whipped cream or cinnamon, and you are all set for a festive drink experience. In the show notes, there is a link to two blog posts, one from My Homier Home, and one from Eleanor Rose Home that both share.

Recipes, photos, and lots of amazing tips and tricks. You’ll definitely wanna check those out. Oh! I love this. It’s so cute. And if you try it out, let us know. We would love to hear how it goes. You can join us on Instagram at the holiday headstart. I can’t believe we are in the middle of September already.

Yeah, this year it’s flown by. But the scary truth is that from this point forward, the calendar is just going to start moving even faster. And before you know it, we’re gonna be in the holiday rush. So with that in mind, [00:02:00] instead of giving you five brand new tasks for September, we’re taking a step back and we are looking at the bigger picture.

If you have been following along since January, we’ve now shared 40 different holiday prep tasks with you. Whoa, 40. That’s a lot. And we are guessing that unless you are some kind of holiday planning superhero, you probably didn’t get to all 40 of those things, and that is totally okay. That was never the expectation. The whole point of spreading these tasks across eight months was to give you options not to create the giant to-do list that was going to stress you out. Definitely not. So this month we’re doing a strategic reset. We’re going to walk through all the tasks we’ve covered from January through August, and we’re not trying to dump 40 tasks on you, but instead we’re going to help you choose five key tasks that will make the biggest difference for your specific situation.

We are all about being strategic with our time and energy, and the secret to staying [00:03:00] sane during the holidays isn’t doing everything. It’s focusing on the few things that matter most to you and your family. Yeah. This is kind of your holiday prep triage. So with just four months left until Christmas, what are the tasks that will actually move the needle for you?

And rather than recapping month by month, Emily and I have organized all 40 tasks into categories that make this easier. Some are about money and budgeting. Others about organizing and systems. And of course we’ve got food and experiences all worked in there too. And don’t feel like you have to write all of this down.

We put the whole list in the show notes. You can reference it easily. As we go through this list, if you notice yourself feeling overwhelmed, try to reframe it. This isn’t a menu, it’s a buffet, and if you try to sample everything, you’re just gonna end up sick. So limit yourself to just the five things that matter most to you and your family.

So let’s just rip the bandaid off and dive into the tricky stuff. By taking a [00:04:00] look at the money and planning category, oh, this is my least favorite part, but these are the tasks that help you avoid holiday, financial stress, and get your logistics sorted out. Early in January, we suggested making a savings goal, setting up that automatic transfer so that you aren’t putting everything on credit cards in December.

And I actually did set up an automatic transfer each week, so. I feel like I took a big grownup step. Wow. Good job. If you are like me and you are just thinking about savings now, it might be too late in the year to build a huge Christmas fund, but any amount saved now is an amount. Your January bills will thank you for.

Another way to save some money is to inventory your winter clothing and make a list of who needs new coats and boots and gloves. We talked about doing this in April when you packed away your winter items, but if you didn’t do it, then do it now. That way you will be ready to snag any good bargains that cross your path.

In April, we suggested listing your fourth quarter [00:05:00] grocery needs so you know exactly what extra food expenses are coming. That’s something that could be a huge lifesaver if you haven’t tried it before. And I did not start my grocery list yet, so I better get on that. This, this is the task that gets me every year.

I keep saying I’m going to be on top of this one, and somehow it always catches me off guard. Oh yeah. This is exactly why we need this reset episode and a reminder. We’re just giving you ideas. You don’t have to do all of these. We’re not even gonna do all of these, and I’m behind on many, many of my tasks, so we’re just gonna tackle what we can.

But if money, stress is your biggest holiday concern, those three tasks that we just shared could make a massive difference. Our next category of Get Ahead tasks is systems and organization. These are the tasks that make the actual execution of the holidays smoother. January gave us setting up stocking bags.

You can collect little gifts all year, and September is definitely not too late to start that, and you would still be way ahead of the game. Plus, [00:06:00] there is still time to use this tip from July and stock up on school supplies for gifts. Keep an eye out for any clearance sections that might have some hidden gems perfect for stocking stuffers. I saw someone online who found a huge box of markers for like a dollar 99, so that was a definite steal. Whoa. In February we talked about creating hiding places for presents because nothing ruins Christmas Eve. Like realizing the gifts are in three different closets and you can’t remember which ones.

Yes. So grab some moving bags now you can stash your gifts in the basement or garage. Just make sure you make a note of what is stashed where, and while you’re stashing gifts, use this tip from March to work in your garage or crawl space while the weather is nice. Related to that, in January we talked about undecorating with next Christmas in mind.

It makes redecorating so much easier down the road. Now obviously this task is going to be a bit tricky to do in September unless you’re crazy enough to unpack all of your holiday decorations just to repack them. No, please do [00:07:00] not do that. But you could also schedule a reminder for December 27th or whenever you usually start thinking about un decorating and remind yourself that you want to pack up your bin strategically.

So next December is a little easier. Or you could start sorting through those holiday bins and tossing or donating the stuff that you don’t love anymore.

Another get ahead tip you could try is to commit to a decorating theme and color scheme, which saves both money and decision fatigue. This will save you from wasting money on a darling pink reindeer that totally clashes with all of your other Christmas decorations.

And that’ll save you a lot of money and decision fatigue if you commit to your plans. Now in April, we recommended making a wrapping station and your need to know box. Both of these tasks are helpful because they give you a designated space for items that might normally be scattered all over your house.

Oh yeah. If you have to track down the tape and the scissors in different rooms, you will be stressed before you even get to wrap a single gift. So save yourself [00:08:00] that headache by getting all of your wrapping materials in one spot Now. And use that same logic to set up your need to know box. This is a hack from our teacher lives.

At the end of the school year, teachers often pack up a box of things they’ll need first when setting up their rooms. So this is where they put materials for bulletin boards, labeling, supplies, staplers, scissors, first day activities, anything they know they’re going to need right away when they get in there.

So let’s apply that to Christmas and do yourself a favor and set up a holiday. Need to know box. This is the home for anything that you need to know exactly where it is. It might be something you need early in the season, like an advent calendar for December 1st. Or it might be the cookie plate you need for Christmas Eve.

Anything that you absolutely need to have at a certain time, but that might not have a clearly defined home goes in your need to know box. September’s a great time to pull all those odds and ends into a central place. And while you’re organizing, maybe declutter your crafting area.

It’s especially [00:09:00] helpful to get this out of the way before you dive into any handmade gifts. And don’t forget August task about getting Advent calendars early. If advent calendars are part of your tradition, buying them early, like this week early means you get the good ones instead of whatever’s left in November.

If you’re someone who feels scattered during the holidays, like you’re always searching for supplies, uh, guilty, focusing on these organization tasks could be just the game changer you need. Our third category of get ahead tasks is food and entertaining, because after money, I think food is often the most stressful part of the holidays.

A good place to start with food tasks is gathering all your holiday recipes in one place. Think how nice it’ll feel to know exactly where grandma’s stuffing recipe and your famous fridge recipe are when you need them. Yeah, just don’t combine the stuffing with the fudge. No one needs that. No. In June we suggested making a freezing cookie dough, but if you didn’t do it, then you will still be months ahead of the game if you take that on soon.[00:10:00]

Yeah, that would be a nice cozy fall, afternoon, weekend activity if you want. Enjoy some cozy baking, but also get ahead and the cool thing is that you can bake and freeze most cookies . But if it’s still too hot to have your oven going like it is here, just mix up the dough and freeze it.

You’ll be so happy to have that much of the task already done when December rolls around. In June, we also talked about drafting holiday menus. A huge lifesaver can be planning those non-holiday meals that happen around Christmas. Like, what are you gonna feed everyone on December 27th when nobody wants to cook?

But everyone still insists on eating so annoying. If you haven’t looked for any new recipes yet, September is a great time to tackle this task because you’ve still got the time to test things out when the pressure’s off. Right. The last thing you want on Thanksgiving is to find out that the new corn casserole recipe turned out to just be flavorless yellow mush.

Our next category, category four, is gifts. This is where a [00:11:00] lot of the emotional weight and a lot of the hassle of Christmas lives. In February, we talked about setting up gift idea lists so you can collect ideas throughout the year. If you haven’t done that yet, this might be the perfect holiday task to start with.

I was just adding something to my lists a couple hours ago. So smart. This year we talked about DIY gifts multiple times because they end up taking so much more time and more energy and often more money than you might expect. Oh yeah, this is pretty much a guarantee. So start now if you haven’t yet, or even better, start now on any DIY gifts for next year’s Christmas and just buy this year’s gifts.

Don’t back yourself into a corner if you can avoid it. July was when we talked about starting gift lists for your loved ones and yourself. And in August we suggested drawing names for gift exchanges, ASAP. And I know we said you should choose the five Get ahead tasks that will have the biggest impact for your holiday. But I am putting on my bossy big sister hat [00:12:00] right now and saying. If you haven’t started your own gift list yet, open your notes app and start it right this second. Yeah. Even if you don’t have any ideas to add to it yet, at least now you’ll have some place to write down any future ideas instead of telling yourself, oh, I’ll remember that I want this.

’cause probably you won’t remember. And then when people are asking you what you want for Christmas, you have nothing to tell them. Yes, you deserve to have nice things. So write down every idea that crosses your mind. And then our fifth category of get Ahead tasks is experiences and traditions. These tasks are about making sure that you can actually enjoy your holidays instead of just survive them.

Back in March, we talked about stocking a personal recovery kit for after all the holiday craziness is over ’cause you’re gonna need to recover. So why not make it as restful as possible? Think how great it will feel on Christmas night to pull out your recovery kit with some fuzzy socks or a head massager or a magazine that you love, but don’t normally buy and [00:13:00] note, this could be the perfect gift for a friend because who wouldn’t want a basket of little pres to pamper themselves with after a stressful holiday?

Another suggestion from March is to think about ideas or traditions that support your holiday purpose. Basically dreaming about what you want your holidays to look like and something that can help with that is to complete the holiday values exercise that’s in the holiday Head Start playbook. We talked about this in April, and also in much more detail back in episode four.

Even if you have already done this task, you might wanna give your values list a little peek to make sure that it reflects how you are feeling about this upcoming holiday season. May had several tasks that were all about creating atmosphere, finding holiday playlists, looking for book titles to read in December, tidying up your Pinterest boards.

Checking off a few of these to-dos now can really elevate your holiday experiences and bonus. These types of tasks are usually very easy to do from your phone and probably your couch as well. [00:14:00] In July, we recommended planning the week after Christmas because that weird limbo time deserves some intentional thought.

If you want to actually enjoy that slower time instead of just drifting through it, consider making a few simple plans now before you are too exhausted to deal with one more decision. And finally, our last category of get ahead tasks is logistics. These are the less glamorous tasks that prevent future headaches.

February had us organizing holiday photos, and this is another great TV task that you can start now. Next time you’re scrolling your phone on the couch, just set up some albums for last year’s Christmas and look at that. You are on your way to having all of your photos organized. And you can also get a jump on this task from March to start editing your Christmas card list.

Figure out who you actually want to send cards, and start tracking down any addresses you need. Another great task that you can do in front of the tv. These are our favorite tasks. Yeah, relaxing and being productive at [00:15:00] the same time is kind of my favorite way to actually relax. Mm-hmm. And while we were thinking about cards, this is a gentle nudge to schedule your photographer before they are completely booked up this fall.

If you want a family photo for your cards, this is a task that really cannot wait.

And, and speaking of those time sensitive tasks, this might be the moment to plan for all those fall and winter birthdays. It’s so easy for these special days to get swallowed up by the holiday hustle. Plus, nobody wants to be that person who wraps a birthday gift in reindeer paper ’cause they didn’t get the right wrapping paper.

Yep. Another headache you wanna avoid is being unprepared for guests. So take inventory of your guest room or guest space if you host overnight visitors during the holidays. We talked about this back in July. If you want more ideas. And let’s go ahead and close out this list with two tasks from June that might not sound fun, but can definitely save your December sanity.

First, figure out your ELF plans if you have a little visitor from the North Pole and make [00:16:00] your household’s minimum up. Keep plan so you know exactly what cleaning needs to happen to keep your house livable during the holiday chaos. Now, hopefully we did not scare you off with that list. You are not going to do all of those things.

There’s no expectation that you will take on all of those tasks. You’re just gonna pick five. Just pick five and then also make your list for yourself. I. So how do you choose those top five tasks? Well, we started January with reflecting on last holiday season, what worked, what didn’t, what we wanna repeat and what we wanna leave in the past.

So this is the perfect place to start as you look ahead to this year’s celebrations. And you can start by thinking about what typically stresses you out most during the holidays. Is it spending feeling disorganized? The gift giving pressure. And then take a look at our categories, money, organization, food and entertaining gifts, traditions and experiences and logistics.

Identify the [00:17:00] category that matches your biggest stress point, and then pick one to two tasks. From there, the full list of tasks is in the show notes. So for your remaining three to four tasks, think about your bandwidth. If you’re already overwhelmed with life, focus on the simpler tasks you can do from your couch, like tracking down addresses.

But if you have got more energy right now, maybe tackle some of the bigger tasks that will really pay off later. Like making gift lists, or doing that holiday values exercise. And remember, you can always come back to this episode and check out this list. Maybe you focus on three tasks in September, and then come back and pick two more in October.

Just pace yourself so that you don’t burn out on holiday prep before the season even starts. The whole point of talking about this is so that we can work smarter and not harder. You don’t need to do everything. You just need to do the things that will make the biggest difference for your specific situation.

So your homework for September is pick your top five tasks or spread it out over a couple months, [00:18:00] and then write them down somewhere where you will actually see them. And then give yourself permission to ignore all the other tasks on this list for now. We would love to hear which five tasks you are focusing on.

Come share with us on the Holiday Headstart Instagram. It might help other people to see how they want to prioritize their own lists. 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 started on your holiday planning. This week’s get a Head Start tip is give yourself a reward. Tell us more about it, Heidi.

Well, we just shared a huge list of get ahead tasks, and even though you’re definitely only choosing five tasks to focus on this month, that can still feel overwhelming. So one way that we can ask more of ourselves is if we give more to ourselves. If you are putting off these prep tasks like, you know, figuring out your grocery needs for the next few months, find a way to make that test more enjoyable.

Give yourself a little treat as a reward for finishing team up with a friend so that the two of you can knock out your tasks together [00:19:00] or pair work time with something more pleasant like binging reality tv. Yeah. ’cause unfortunately these tasks aren’t going anywhere, so we can either deal with them when they show up or when they blow up.

So find a way to make this process something you enjoy instead of dread. If you want some more personalized ideas, go back to episode 29 where we talked about how to leverage the strengths of your personality type to get ahead. All right. As a way to keep ourselves accountable and give you some ideas of what you can do in advance for your own celebrations.

We are sharing what’s on our to-do list this week. Emily, what are you working on? Uh, we’re starting to do some planning for our upcoming Harry Potter dinner that we do to kick off October. I read a new Harry Potter book with my kids every year, and we kick that off with a fun. Dinner. So I’m just starting to make some planning about that because I think we wanna change up a little bit about what we did with dinner last year.

And also we’re on book seven, so I don’t know what we’re gonna do next year if we’re [00:20:00] going to, I don’t, I don’t think we’re gonna start ’em over, so we’ll see if we still want the, the dinner next year. If we, it would be sad if we stopped it, so I bet we’ll still keep the dinner even if we’re not. Using it as a reading kickoff.

But anyways, just doing some planning for the dinner. Well, I can’t wait to see how it comes together. That’s always a fun night. What are you working on, Heidi? Well, I guess I am committed to doing grocery lists now. I think you are. I will have to find a way to make it more enjoyable because I hate I, that’s kind of task I hate.

But maybe I will bring my laptop over to your house. Emily and I can work in your kitchen. Well come on over. All right, to wrap up the show, we’re showing our nice list. Emily, what’s on your nice list this week?, On my nice list is the puzzle that you gave me for my birthday. Oh. Um, it is nineties theme.

It’s my favorite kind of puzzle that has a bunch of little details in it that you can enjoy. And so this is just a puzzle that is covered with nineties ephemera, like, movie posters, CD [00:21:00] covers, TV shows, and yes, toys. Was fun from the nineties pointing out all the things we remembered from our childhood.

Yeah. So that was a fun surprise. So thank you for that. You’re very welcome. I’m glad you’re enjoying it. What’s on your nice list? Well, this is way less exciting. So I follow Tabitha Brown on Instagram, who is a delight. If you don’t know her, you’re missing out, definitely follow her. But she was dealing with like a cold recently, and her doctor told her to do a Neti Pot.

Mm-hmm. And she got on Instagram, she looked like she had been through a war and she said, do not mess with people who do Neti Pots. They’re a different kind of person. I don’t know how anyone does this. And I was like, no. Tab, tab. You need the Neil Med bottles. And thankfully, her comments were full of so many people saying, no, don’t do the Neti Pot.

Do a Neil Med bottle. So I’m gonna share this here. ’cause I thought this was more common knowledge maybe. So if you also, if it deal with allergies or. Even if you’re just sick, the NEOMED bottle is so [00:22:00] nice. It’s a squeeze bottle, so you fill it with warm water. Not too hot. I have learned this the hard way.

Oh yes. Don’t go hot. I’ve done that too. Because scalded sinuses are exactly as fun as they sound like they would be. You also don’t want it too cold, you know? Gives you a brain freeze. Yeah. You really, you got a real, real small window. Think like baby bottle. Baby bottle. Yep. And then it has like a special salt.

packet so that it doesn’t feel so burny like you got pool water up your nose. Yep. And I always do it in the shower ’cause it’s just easier that way, but Oh yeah. That’s the only way to do it. Yeah. I’m someone who really, like, I hate having my face wet. Even in my, I’m in my mid forties and I still, like, I’m a 2-year-old that, uh, swim lessons for the first time we won’t get in the water.

But I can manage this, so I believe in you if you also need some. I’m really out. I haven’t done it in years, but I used to do it pretty regularly, so I might have to start it up again ’cause my allergies have been bugging me. But I do think with the Neil Med or I’m sure with the Neti pot too, that the more you do it, the easier it gets.

Oh [00:23:00] yes. It feels so. Yes, definitely. Yeah. Yeah. So I’ll stick with it at, yeah, if I don’t do it, I wake up with a sinus headache every morning, so it is worth it to me. That’s for sure. Well, that is it for today’s episode. Choose the five key. Get ahead tasks that will have the biggest impact on your holiday happiness, and then find a way to make getting those tests done a little more fun.

Thank you so much for joining us and we hope to see you here next week.

Thanks for tuning in today. Use this week to get a headstart 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 Podcast and leave us a review. We’ll see you here next week.

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!

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