Yaay – it’s the season to join in with the Stress-Free Holiday Planning Challenge!
I know that you – like I do – love to entertain and create happy holidays for your families and friends! But in the past, maybe it’s been as stressful for you as it was for me. There was never enough time to get it all done.
So this year, let’s join forces and start early for a stress-free holiday season! Great planning. Effective Time Management. More Organization – Martha Stewart would be proud.
We’ll take it in small bites – an email a day for 10 days – with easy prompts to guide us through the planning and organizing. And a ready made workbook to take away the guess work.
When we’re done, we’ll not only have a master plan for all our 2023 holidays, we’ll have gotten the long lead time things finished! We’ll be able to enjoy the holidays the way we always want to! And it doesn’t cost a fortune. In fact, you get to choose your own price!
How it all started
Back in my younger days, there was no such thing as a stree-free holiday! I ran around like the infamous chicken with no head. I worried so much about all the things I wanted to do, that I couldn’t get organized enough to do any of them!
But then I decided I wanted to be as great a hostess as my mom (that’s another story!) And I figured out a planning strategy that I’ve used and refined ever since. Now it’s so easy to see what I have time for, choose the most important things, and let go of the rest.
Late summer/early fall is usually when I start planning our holiday season, and this year I thought I’d share that planning with you!
Any job is more fun with friends! Just an hour or so each day for 10 days gets the season off to a great – and relaxing – start.
How to have a stress-free holiday season
The whole point of the Stress-Free Holiday Planning Challenge is to PLAN, of course. To get a jump on your holidays so you can enjoy them, knowing that you’ve got everything under control. Lots of people tell you to “plan ahead,” right? But if you’re like me, that advice doesn’t really help too much.
“HOW do I plan ahead?” is the question I ask, and maybe you do too.
So our planning challenge walks you through exactly what to do. We’re going to focus on the long-lead time items first
And just so you know, our mantra for a stress-free holiday season is “Excellence Over Perfection.” And you get to decide what excellence is. Use these bite-sized challenges to make your holidays exactly what you want!
How it works
The planning challenge opened on Monday, October 9, 2023, and you can join anytime. As soon as you sign up, you’ll get your welcome email and binder pack link.
Then you’ll get an email with each new challenge. It will have a link to the instructions and your workbook, with all the pages you’ll need for the day’s planning.
(If it’s after the 9th when you join us, you’ll have immediate access to the previous days.)
So let’s look at what we’ll do each day.
10 Days to a stress-free holiday
Pre-Challenge Prep
This is the day to create your Challenge binder, where you’ll keep everything for Holiday 2023 together in one central location. When you sign up for the planning challenge, you’ll be able to download your binder pack – the cover & spine, note pages, and calendars; and links to the binder itself, tabs, and other things to make your planning easier.
Your binder is where you’ll put each day’s workbook pages. Any ideas come to you while you’re out and about? Write them in the binder. When we’re done, you’ll have your master plan right here.
Holiday Season Overview & Preliminary Plan
On Day 1, you’ll create the big picture overview of each of your holiday celebrations this season – from October right through the end of the year. You can customize for whichever holidays you celebrate.
This will give you a great idea of how they all fit together, who you’ll be sharing them with, and what you want to do for each one. Additionally, you’ll choose your style, theme, and color-scheme, and get familiar with your shopping lists!
Budget
Day 2 is budget day. This might not sound too thrilling, but I have a custom budget sheet for you that makes it so much easier, and fun too! You’ll confidently know how much you want to spend on a little (or big) Halloween party, for instance. And you’ll still have the right amount set aside when your New Year’s Eve dinner shopping comes around.
No more guessing and crossing your fingers that you don’t go into too much debt by Jan 1! At this point, it’s not set in stone, it’s just a general starting place. And honestly, there’s nothing that reduces holiday stress more than knowing you’re organized and your money is under control.
Guests & Travel
On Day 3, you’ll look at who you’ll be sharing these celebrations with. You’ll find out what their availability, needs, and preferences will be during the times you’ll be together. And if there’s any travel for them or you, you’ll look at that too. As you know, it’s always best to nail down transportation as soon as possible, and “as soon as possible” starts now!
Gatherings & Activities
What will you do to celebrate each of your holidays this season? On Day 4, you’ll go deeper into the details. You’ll decide what you need to prepare – especially the long lead time items. Do you want to see the Nutcracker ballet? The light parade? Have an elegant meal out? Host a gingerbread house-making party? Create a new family game? You’ll plan for those arrangements today.
And what do you not want to do? You’ll look at scheduling just the right amount of celebrating that will make you and each of your family members happy. A plan that includes enough down time really helps!
Gifts
Day 5 is for thinking about what gifts you want to give. What would your friends and family members love? Who else do you want to acknowledge at this time of the year? What do you want for host/hostess gifts? You’ll make your list of who and what, your gift budget, and your plan to shop or DIY early!
Holiday Cards
Day 6 is all about staying in touch via holiday cards. If you send them at all, what kind do you want? Photos or non-photos? Do you write a family letter? Who are you sending to? When do you want them to arrive? Here’s where you plan it all out and get your cards ordered or created in plenty of time.
Current Inventory
We set aside Day 7 for taking inventory. What do you already have that will help you implement your plan? Are the items in good shape or do they need repairs? What needs to go on your acquisition list, and where will you buy, get, or make it?
Meals
Day 8 is Meal day! Food is often a big part of our celebrations. Here’s where you get to plan what you want to serve, or what you’re contributing for each gathering. If anything needs to be sourced or ordered early, it’ll show up in today’s task.
Table Settings
And of course, you have to eat the food somewhere! On Day 9, you’ll think about what you want your table settings to be like. You’ll consider your style, theme, and color-scheme, and look at your inventory. Add any items you need to your lists, and if you want any long lead time items, you’ll get them ordered.
Home Cleaning & Prep
And Day 10 our of stress-free holiday pre-planning challenge, will be devoted to your home and what, if anything, you want to do to get it ready too. Do you want to make any little – or big – repairs or updates? Does it just need its regular cleaning before guests arrive? Do you simply want to put a seasonal potpourri on the stove, and get out the holiday music? Today you get to make that plan and add house tasks to your calendar. No more hoping you’ll have time, then finding out you really didn’t. This year you’ll be prepared and love the season!
Making it happen!
Doesn’t that sound organized and fun?! I can’t wait to start! Click the big green button to join us and start enjoying your relaxed and stress-free holiday!
Pin the Stress-Free Holiday Planning Challenge for later!
Wow this challenge is sure to relieve some holiday stress. Ask anyone who knows me and they’ll say I’m a planner. I truly love a good plan. I have to mention that I had quite a giggle from the “Martha Stewart without the jail time comment ” . Pinned to my stress relief board xo
Haha – yes, I’m still laughing about that one! 🤣 I’m right there with you on being a planner – it’s so rewarding! Thanks so much for stopping over and for the pin, Katherine – I really appreciate it! Happy Wednesday!
This is brilliant, Barbara! You are truly the hostess with the mostess! (or as my daughter likes to say “Martha without the jail time” LOL)
Hahaha! Tell your daughter I laughed out loud right in front of my colleagues at that one! 🤣 I’m grateful Martha and I are different in that way! But in the entertaining way, I’m honored at the comparison – thanks! 😊 We’re having a great time with the planning, and I’m getting so excited for the first holiday party of the season! Thanks so much for stopping by, and take care over there!
Barbara, this all looks so fabulous and timely!! As Jenna says, you have thought of everything (of course you have lol). Could I join next week as it’s a bit of a busy long weekend here? Thanks so much!
Oh of course Kim! I’m so happy you’ll be joining us! Hope you have a fabulous Thanksgiving my friend! 🦃
This is awesome, Barbara! I was drafting something similar earlier this week 😆
Yes – tis the season! 😊 I’d love to see how you organize your planning too – there’s always so much fun stuff to learn! Hope you have a great week!
I am very impressed Barbara, you have thought of everything! You are the Martha Stewart of entertaining!
You’re so sweet Jenna – thanks! 😊 It’s going to be so much fun!