Your Stress-Free Holiday Planning Guide 👻🍗🎁🪩
Feeling stretched by invites, school calendars, and all the “shoulds”? This is your friend-in-your-ear holiday plan. Three steps, zero chaos. We’ll choose what matters, brain-dump the details, and give it all a home on the calendar—so you can actually enjoy the season you’re living, not the one the internet is selling.
We’re talking about:
✻ 3 simple steps to plan your stress-free holiday/Q4 season (Pick → Brain Dump → Calendar)
✻ Real-life examples + plug-and-play prompts (Halloween, Thanksgiving, Christmas, New Year’s) to turn ideas into dates—with margin, blackout nights, and “leave by” times
Let’s dive in. 🖤
Hey friend—welcome back to The SELF CARE Sisterhood. Quick note up front and before we dive in: I know we don’t all celebrate the same holidays. Some of us do Halloween and Thanksgiving, some celebrate Hanukkah or Christmas, some ring in the New Year big, some keep it quiet, and many honor other traditions too. This isn’t about what you “should” celebrate; it’s about helping you decide what matters in your season so you can stress less and be more present—whatever you observe.
Around here, I don’t stumble into highlight reels—I plan for the memories I want to make. Every year around this time, I sit down with my husband, Charles, and we map out our Q4 so it feels like us: simple, calm, and full of the moments we’ll actually remember. So often Q4 can feel like a whirlwind where we wonder where the time went. October thru December can be packed and happens so fast. The holidays tend to sneak up on us as we’re juggling different roles to manage our day-to-day lives. And when we add the holidays on top of your already full life, it can make things feel overwhelming really fast. Yall. The holidays don’t need more hustle; they need clarity about what matters and kindness with your capacity. So today I’m walking you through the exact process I use in our home so you can borrow it and make it yours.
How I plan our holidays every year (real life)
I’m going to walk you thru three simple steps, but before we dive into that, you’ll need a notebook, your calendar (digital or physical), and anyone with you who you want their help making these decisions. I love to do this alongside of my husband, but maybe you want your kids present for this, too. Make it a family affair and figure out what matters to everyone so the holidays feel like a way to grow closer in the process. Okay, so the three steps we’re going to walk thru to make this super simple are:
Pick what matters (the memories I want + my non-negotiables).
Brain dump the details (everything needed to make those memories real).
Put it on the calendar (with margin so we can actually enjoy it).
That’s it. No 47-step spreadsheet. Just three steps that help us soak in the season and make the memories on purpose. Alright. Let’s start with “Picking what matters.”
STEP ONE: PICK WHAT MATTERS
Goal: decide which holidays you’re planning for and name 1–5 non-negotiables for each—the memories you want to make on purpose. (This is not your to-do list; details come in Step 2.)
What you’ll need: a notebook, pen, your calendar, and—if helpful—the person who plans with you. Bonus: last year’s photos to jog ideas.
Let’s break this into two parts. First, in your notebook, write out all of the holidays you want to create an intentional plan for.
For me, the holidays that I want to intentionally plan for this year are:
– Halloween
– Thanksgiving
– Christmas
– New Years Eve
So step 01 - easy, right? Just list out all the holidays you want to plan for. I like to do this on a separate page for each bc in the next step you’ll need space to write out the details.
Then, for each holiday, define 1-5 non-negotiables.
The way I do this is I ask, “What matters to me for this holiday?” Clearly defining what matters to you for each holiday, helps prioritize these things. It can be easy to get swept up in the “do all the things” for every holiday trap but that’s stressful. I find it so beneficial to name 1-5 things that matter for each holiday so you are a better steward of your yesses and can more easily say “no” to things that don’t match up with your non-negotiables. Don’t be tempted to make this into a to-do list for each holiday – that’s coming up. This is just for you to name what is the most important to you for each holiday.
I’ll give you a few examples of my non-negotiables for each holiday that I’m planning for:
– Halloween non-negotiables:
01: Decorate the house/front porch for fall
02: Matching family costumes that involve the dogs
03: Carve Jack-O-Lantern’s with Charlie
04: Pass out candy on Halloween
– Thanksgiving non-negotiables:
01: Decorate for Christmas (I personally love to do this before Thanksgiving so it goes on my Thanksgiving non-negotiable list)
02: Sign up for + train for a turkey trot
03: Volunteer with an org (Meals on Wheels or passing out Thanksgiving meals to those in need)
04: Meal plan + cook Thanksgiving Dinner
– Christmas non-negotiables:
01: Christmas/holiday movie board
02: Cookie + Chex Mix baking night
03: Christmas Cocktail night
04: Matching family jammies
05: Gift giving to family and friends
06: Christmas/Christmas Eve Church Service
– NYE non-negotiables:
01: Plan charcutterie board + foods for NYE
02: Decide how we spend the night in (just the two of us, games with family, invite friends over?)
03: Plan when we will take down/clean up Christmas decor and reset the house.
These don’t have to be the ONLY things you do during each holiday but these are the most important to you.
STEP 2: BRAIN DUMP THE DETAILS
Goal: turn your non-negotiables into tiny, do-able pieces—so scheduling (Step 3) is basically plug-and-play on your calendar.
What you’ll need: your notebook, a pen, your calendar open, and (optional) whoever helps make plans at home.
How to brain dump (fast):
For each holiday + non-negotiable, write bullets under WHO / WHAT / WHERE / WHEN Don’t make it pretty—just dump.
🎃 HALLOWEEN (your non-negotiables)
1) Decorate the house/front porch for fall
Who: me (+ Charlie for bins)
What: mums, pumpkins, wreath, lights, doormat, fall decor, seasonal candle swaps
Where: front porch, main living spaces
When: beginning of September (1–2 hours)
2) Matching family costumes (dogs included)
Who: me (order), Charlie (approval), dogs (measurements)
What: theme, sizes, leashes/bandanas
Where: order online; try-on at home
When: decide theme by top of October
3) Carve Jack-O-Lanterns with Charlie
Who: both of us
What: pumpkin carving night + roast seeds
Where: at home
When: a week-ish before Halloween
4) Pass out candy on Halloween
Who: both; one of us on dog duty
What: candy, playlist, seating, adult beverages
Where: car trunk
When: Oct 31st 6–9pm
🦃 THANKSGIVING
1) Decorate for Christmas beforehand
Who: me on the inside, Charlie with the outdoor lights
What: tree, mantle, lights, outside wreaths/decor, inside decor
Where: main living spaces, front of house
When: early November
2) Sign up + train for a Turkey Trot
Who: both
What: register, simple 3-week plan, packet pick up
Where: local race
When: register in October/begin training
3) Volunteer (Meals on Wheels or meal distribution)
Who: both
What: choose org, sign up slot, confirm logistics
Where: local org
When: sometime around Thanksgiving
4) Meal plan + cook Thanksgiving dinner
Who: both
What: menu, grocery list, shopping/grocery delivery, prep + day of cooking schedule
Where: our home
When: plan by mid November, shop weekend before Thanksgiving
🎄 CHRISTMAS
1) Christmas/holiday movie board
Who: both of us
What: list 8–10 movies + check streaming, snack plan
Where: living room
When: Sunday evenings
2) Cookie + Chex Mix baking night
Who: both of us
What: choose 2 cookie recipes + Chex Mix, tins/bags for gifts
Where: kitchen
When: first weekend in December
3) Christmas cocktail night (mocktail option too)
Who: us (maybe another couple)
What: 2 signature drinks (one zero-proof), charcuterie board, playlist
Where: home
When: mid December
4) Matching family jammies
Who: me (order)
What: sizes for both + the dogs
Where: online
When: order by Dec 1
5) Gift giving to family/friends
Who: both (list/budget); both (ideas)
What: list names, caps, experience gifts, wrapping, shipping deadlines
Where: notes app (ongoing all year)
When: finish before mid December
6) Christmas/Christmas Eve church service
Who: both
What: choose service time
Where: church
When: pick date/time as soon as schedule drops
✨ NEW YEAR’S EVE
1) Charcuterie board + cozy foods
Who: me (shop), both (assemble)
What: cheeses/meats/crackers/fruit/dips + one hot bite
Where: home
When: shop between Christmas and NYE
2) Decide the vibe (just us? family games? friends?)
Who: us
What: invite list, start/end time, game stack/playlist
Where: home
When: decide by Christmas; send invites
3) Take down/clean up Christmas + reset house
Who: both
What: undecorate, sort broken/loved, vacuum/mop/dust, fresh bedding, swap winter decor/candles/etc
Where: whole house
When: top of January
STEP THREE: PUT IT ON THE CALENDAR
Alright, so you picked what matters and you brain dumped the details. Now we a going to look at each holiday’s prep list, assign the dates you’re going to do those tasks and put them on your calendar.
As you do this step, remember that you’re the boss of your schedule. You are doing this holiday planning early enough that you can space tasks out and not be frantically trying to do stuff at the last minute. Schedule things so that you have plenty of wiggle room in case you need it.
To do this we’re going to take each holiday’s prep list from the previous step, pair any tasks together that make sense, and write or type them into your planner/digital calendar. I’m personally a paper and pencil girl and I use the Peacefully Productive Planner, for reference.
Let’s use my Halloween non-negotiables and plug them in.
🎃 Halloween — how I’d calendar it:
1) Fall décor + porch setup (beginning of September)
FALL DECOR INSIDE September 9th: “Pull bins from garage, swap seasonal candles, ”
PORCH September 26th: “Grab mums + pumpkins from Trader Joe’s”
2) Matching family costumes (dogs included)
WEEK OF Oct 6 - 12th — “Pick theme + order costumes” (placed in other tasks list column in planner)
3) Pumpkin carve + roast seeds
BUY PUMPKINS Oct 17th w/ grocery haul — “Pick 2 carving pumpkins + tea lights”
CARVING NIGHT Oct 21st — “Carve + roast seeds”
4) Pass out candy on Halloween (trunk or porch)
BUY CANDY Oct 24th w/ grocery haul — “don’t over do it…two or three bags is fine”
BUY FALL SANGRIA SUPPLIES Oct 24th w/ grocery haul — “Red wine, apple cider, oranges, apples, rosemary, bourbon”
SET UP ~5pm OCT 31st
BONUS tips AS YOU PLAN:
Before we wrap, here are four tips to help you as you LIVE OUT your plans:
Name your “enoughs.” How many events is enough? How many presents is enough? How many non-negotiables are enough? Enough isn’t stingy; it’s protective. Know your enough and live that out.
Make white space part of the plan. One of the reasons we have so much stress over this final stretch of the year is bc we are literally STRETCHED too thin. Make margin and white space and part of this plan. This is why we are doing this now so we have plenty of time and space so the holidays don’t “sneak up” on us. Plan unplugged days. Give yourself the gift of rest so you energy and presence so you can be fully in each moment this season, bc ultimately that’s what it’s about, right?
Let what matters lead. If a new invite competes with a non-negotiable, you are allowed to say a kind “not this year.” You’re not flaky; you’re focused. Just bc other people don’t have a gameplan in place doesn’t mean they get to hijack yours.
Hold the plan loose. I have to include this for my Type A personalities listening. The plan you just created is a tool to help you live more intentionally as we wrap up the year. This is not a pair of handcuffs holding you rigid. The fastest way to bum yourself out this season is to hold too tightly to your expectations. Things will shift and things will not go as planned—kids get sick, weather changes, energy dips. It’s okay, friends. Move a date, swap an activity, scale it down, or cancel without guilt.
Alright friend— That’s it. Three steps:
PICK WHAT MATTERS
BRAIN DUMP THE DETAILS
PUT IT ON THE CALENDAR
Not you trying to keep up with Sally on the internet this year or stressing out the week before Christmas bc you haven’t done all the things you wanted to do. No. This is going to be a holiday season that feels like you bc it’s intentional and on purpose.
Alright friend—thank you for hanging out with me today. I can’t wait to see you plan a season that actually feels like you. When you finish the three steps—Pick what matters, Brain dump the details, Put it on the calendar—snap a pic of your Big Three and tag me @inspirebeautybritt so I can cheer you on. Remember: name your enoughs, leave white space, let what matters lead, hold loosely to the plan. I love you and I’m rooting for you. I’ll see you right here next week on The Self Care Sisterhood Podcast.
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