Originally published on October 24, 2022
When it comes to holiday planning, one thing I’ve learned over the years is this: Waiting until the last minute to complete (or start) the various tasks associated with the holiday season is not a gift to me. Instead, I’ve found that setting the groundwork early in the season helps me create truly personal experiences—and actually savor them while they’re happening. By taking the time to plan and prepare in advance, I’m able to infuse the holiday season with an extra touch of magic, ensuring that every moment is thoroughly enjoyed.
If you tend to find yourself more stressed than usual throughout the holiday season, these are some of the holiday planning tasks you can do now to make life easier for yourself over the next couple of months. These ideas are, of course, dependent on the specific holidays you personally celebrate. Whether it’s Thanksgiving, Christmas, Hanukkah, Diwali, Kwanzaa, or any other festive occasion, I hope everyone can find some helpful insights in the list below.
How far in advance should you start your holiday planning?
It is recommended to start preparing for the holidays at least one to two months in advance. This allows you enough time to make a thorough holiday planning checklist that’s personal to you, set your budget, purchase gifts, and make any necessary travel arrangements. Starting early helps reduce stress and ensures a smoother holiday season. By preparing for the holidays now, you can avoid that last-minute panic that sets in and robs us of the holiday spirit come December.
7 Holiday Planning Tasks to Do Right Now
1. Make a checklist of holiday tasks you need to complete.
Make a checklist of any tasks you need to do related to the holidays (particularly if you’ll be hosting at any point). Some tasks may be in this blog post and others will be personal to you. This can include anything you need to purchase, anything you need to clean, any invites you need to send, etc. While you don’t necessarily need to start checking off every task right now, you’ll be glad you already have the list made once the time comes to begin holiday preparation. If you can, give yourself dates or deadlines for these tasks and group like tasks together (e.g., purchases, decorations, party planning).
For a recent party we hosted, Joe and I created a shared doc of tasks that needed to be completed beforehand. We could both check things off over time and easily split the responsibilities. It was immensely helpful!
2. Design and order your holiday cards (if you’re sending them).
The thoughtful act of sending holiday cards can become a chore if you wait until the very last minute to order them (I know from experience). It can be frustrating to scramble through limited options and rush the process. Save yourself the stress later on and order holiday cards early this year. I would suggest ordering them by mid-November and sending them in the first week of December. Plan ahead, choose the perfect design for you, and make this year’s holiday card-sending experience a delightful one!
We’ve used Minted for our holiday cards for the past couple of years. What I like about Minted is that there is a style option for everyone. I also love that I can store my address book in my Minted account and have the addresses added to each envelope—this saves me a ton of time.
If you are planning on including a family photo in your cards, I highly recommend getting your photos taken in early September or October. While I am by no means always this prepared, we had ours taken in September this year and it felt so nice to have it checked off the list extra early. If you didn’t have a chance to get family photos taken this year, consider setting a digital reminder for yourself for late next summer to schedule a fall family photo session.
3. Decide on the holiday decor you want to get this year (if any!).
The reality is that some of the best decor (especially decor at more budget-friendly prices) tends to sell out early. This doesn’t mean you need to rush out to buy everything right this second. However, having a holiday decor list ready to go will mean that if you do see something you need at a price you’re willing to pay, you can purchase it in the moment with the assurance that it was already on your list.
Dig out your box(es) of holiday decor from last year and assess what you need (if anything) for this holiday season. I highly recommend investing in pieces that you can reuse year after year. If you are just beginning to collect your holiday decorations, I would recommend starting where you get the most bang for your buck, which in my opinion is greenery. Whether it’s a lush wreath on the front door, garlands draped along the staircase, or a beautiful centerpiece for the dining table, it instantly adds a holiday vibe to any space, with or without additional decorations.
4. Buy a few wrapping supplies.
There will be plenty of wrapping supplies available throughout the holiday season, from gift bags to wrapping paper to gift tags. But if you’re going for a specific aesthetic and want wrapping accouterments from certain collections that tend to sell out (I’m looking at you, Heath & Hand With Magnolia), consider buying it early. I like to shop for ribbons at party supply stores like Litin’s because you can often get a ton of them for a low price!
5. Stock up on decorating essentials.
While they’re not the star of the show, having tools like Command Hooks on hand will be very helpful when you decide you want to decorate your house for the holidays (and don’t want to have a last-minute Target run involved). We use them for hanging garlands and wreaths all throughout our house.
Not having the proper decorating tools can make decorating super aggravating. While it’s not the sexiest thing to spend your money on, it’s going to save you the headache of falling wreaths and precariously-palaced garland… I speak from experience!
6. Start making gifting lists.
To ensure you find the perfect gifts for friends and family members, set aside a few minutes to brainstorm gift ideas for each person on your list, considering their hobbies and personal interests as you do. If you find yourself coming up empty, do not hesitate to reach out to the giftee! I think it’s perfectly okay to send them a short Q&A to help get your wheels turning. By gathering more details, you’ll have a better chance of coming up with thoughtful and personalized gift ideas. Questions could include:
- What’s a hobby you want to pick up?
- What’s your favorite color?
- What’s your favorite indulgence?
- How do you unwind?
- Or, if they’re comfortable sharing exact links, simply ask them, “What’s on your wish list?”
7. Make your own wish list.
While some people frown upon this, I see no problem in proactively sending a wish list of items you want to people you know are going to give you a gift. Send a small variety (so they still have the option to choose) with exact links. With all of the talk of reducing clutter and donating items in our homes, I think there is something particularly helpful about getting gifts you truly want and will keep over time.
There you have it, folks! A few surefire holiday planning ideas to steer clear of headaches and sail smoothly into a stress-free holiday season. Remember, it’s all about thoughtful gestures and creating experiences that resonate. So go ahead, pour yourself a hot cup of cocoa, cozy up by the fire, and check one (or a few) of these items off your holiday planning checklist.
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Kate is the founder of Wit & Delight. She is currently learning how to play tennis and is forever testing the boundaries of her creative muscle. Follow her on Instagram at @witanddelight_.
