Part 2: From Overwhelmed to Organized: My Step-by-Step Guide to Holiday Gifting and Planning

For me, the holiday season is all about gift-giving. It's my love language! But I know that for many, the sheer volume of things to do—the shopping, the wrapping, the planning—can quickly tip from joyful to absolutely overwhelming.

If you feel the mental load of the holidays starting to crush you, allow me to be your guide. I have a two-list methodology that is both cathartic and incredibly productive, designed to reduce your stress and free up your time for enjoying the season.

Step 1: The Brain Dump—Two Separate Lists

Before you buy a single gift or book a single ticket, you need to get everything out of your head and onto paper (or a screen). Think of this as your "wish list" with no initial limits on time or money.

List A: The People List (Gifts)

Write down everyone you want to give a gift to. Be inclusive! This list should cover immediate family, friends, and the often-forgotten heroes who make your life easier:

• The amazing people who collect trash and recycling

• The mail carrier

• The hairstylist/barber

• Teachers and school staff

• Your parents, siblings, and extended family

• The neighbor who always waters your plants

List B: The Experience List (Memories)

Next, create a comprehensive list of all the holiday experiences you'd like to do this season. This can include:

• Seeing The Nutcracker or a festive play

• A visit to a holiday light show or display

• Attending a local Polar Express or holiday train ride

• Hosting a special holiday dinner party

• Seeing The Rockettes (or a similar major seasonal show)

Step 2: Merge, Prioritize, and Book

Once you have your complete brain dump, it's time to merge the two lists and get strategic.

1. Match Gifts with Experiences: Look for ways to connect the two lists. For example: "Do we want to take the parents and the kids to see The Nutcracker?" If the answer is yes, that experience becomes the gift for that group. Experiences are often the best gifts, as they connect us and build relationships—from a lovely dinner out to a play or even a membership to a local arboretum.

2. Book Now and Eliminate Dates: As soon as you decide on an experience, book it immediately. Once those dates are locked on your calendar, they eliminate other potential overlapping events, automatically reducing your planning options and simplifying your schedule.

3. Cross Off the Easiest Gifts: Now, return to your People List. Quickly tackle the "cash gifts"—anyone who will receive a monetary gift, gift card, or simple token of appreciation (like a nice note on Holiday stationary or just the annual Holiday Card). Write a card, stuff the envelope, and check it off your list. You do not need to wait for the custom Holiday cards. This is a fast, satisfying win that gives you immediate momentum.

Step 3: Tackle the Logistics and Big Projects

With your experiences booked and cash gifts sorted, you can now focus on the items that require real time and energy.

• Audit Your Sightings: Realistically look at your list and determine who you will see in person versus who you want to mail a gift to.

• Mail Early: If you plan to send physical gifts that are not being fulfilled by a major retailer (like Amazon) with rapid shipping, you need to ship them in the next two weeks. Sending packages now avoids the holiday postal frenzy, reduces stress, and ensures your gifts arrive on time.

• Focus Your Energy: You now have a concentrated list of the remaining, personalized gifts—the ones that require thought, sourcing, and perhaps some patience to execute well. With nine weeks until Christmas, you can effectively use this time without feeling rushed.

This methodology helps you reduce the enormous mental load associated with the holidays, allowing you to use your remaining time and energy on crafting the perfect, meaningful gifts that matter most.

Now that you've got your plan, who is the first person on your People List that you're going to check off?