🎄🎄🎄 This is Day 9 of the 100 Days to Christmas challenge. Sept 16–Dec 25, we’re taking one small step a day to a lighter, happier holiday season. Join the free community 🎄🎄🎄
If you followed along with yesterday’s task, you already know who’s getting a card from you this year. Today we’re tackling two things that pair naturally together: gathering everyone’s mailing addresses, and getting your holiday photo on the calendar before the good time slots — and the fall color — disappear.
Part 1: Gather Your Mailing Addresses
This is one of those small tasks that’s easy to put off, but a little prep now means no scrambling for addresses when your cards are actually ready to send.
Why Gathering Addresses Early Matters
- You’ll have time to confirm anyone who’s moved or changed names
- You can double-check spelling and zip codes before printing labels
- If you plan to send cards right after Thanksgiving, you’ll already be prepared
Where to Find or Update Addresses
- Pull out last year’s card list or planner pages
- Check your phone contacts, email address book, or group chats
- Look through last year’s cards for return addresses
- Send a quick text or message to confirm updates for friends and family
Don’t forget people who might not be saved in your phone — teachers, neighbors, coworkers, or your kids’ coaches. If you have a large extended family, it can help to ask one relative to collect everyone’s updated addresses in one place and share it back with the group.
Rather skip the DIY version?
The Christmas Planning Pack includes a ready-made Mailing Address printable to keep everything in one spot — already designed, already formatted — plus everything else you’ll need to plan the season: budget breakdown, gift lists, card list, gift wrap inventory, and more. Want it all, fall through Christmas? The Complete Holiday Collection bundles this with the Holiday Season Pack too. Both are available inside the free 100 Days to Christmas community — sign up below to grab yours.
[IMAGE: Mailing Address printable mockup/flatlay]
Part 2: Plan Your Holiday Photos
Here’s why this belongs on your radar now instead of in November: the leaves are starting to change but haven’t completely fallen, giving you that mix of autumn color and cozy sweater weather. The light is soft and golden this time of year, and photographers haven’t hit their December rush yet.
This isn’t about how to take the perfect photo — it’s about making sure it actually happens this year, on purpose, instead of turning into “we’ll get one soon” and then quietly becoming next year’s problem.
Decide What Kind of Holiday Photo You Want
There’s no single right way to do this — just the version that fits your family’s style, budget, and energy level:
- Professional photo session — polished, frame-worthy shots that look great on cards
- DIY at home — relaxed, budget-friendly, flexible for busy schedules
- Lifestyle or candid — real personality caught in natural moments: decorating cookies, playing outside, snuggled on the couch
- Pet-focused — a seasonal collar or cozy blanket goes a long way for the furry family members
- Photo collage — if a full shoot feels like too much this year, gather your favorite photos from the past year into one collage-style card. People love genuine moments, and it’s one of the easiest ways to personalize a card
Think about how you’ll actually use the photo — cards, gifts, framed prints — and let that guide which option fits this season of life.
Book It Now, Not Later
If you’re hiring a photographer, now is the time. Calendars fill fast by early November, and some photographers offer early-bird or weekday discounts for booking ahead. If you’re doing it yourself, treat it like a real appointment anyway — pick a date, put it on the calendar, and plan a backup day in case of bad weather.
The biggest mistake people make is waiting too long. Commit to a date now — future you will be glad when it’s time to send those cards.
Choose Your Location
- Outdoors — natural light and fall color: a park, a tree farm, or your own backyard
- Indoors — cozy and intimate: your living room, kitchen, or a decorated front porch
- Public spaces — check whether a photography permit is needed for parks or downtown areas
- For pets — somewhere calm and familiar so they’re comfortable
A Few Things to Think Through Before Photo Day
Backup plan — wipes, a lint roller, and maybe a spare outfit, because spills happen
Outfits — coordinate, don’t match. Pick 2–3 complementary colors that fit the location. Order early to avoid shipping delays, and schedule any haircuts a week or two ahead
Kids and pets — plan around nap times or feeding schedules, bring snacks and a little patience, keep it short and playful
Props and décor — a cozy blanket, string lights, or a mug of cocoa add festive warmth without going overboard
Timing — late afternoon light tends to be the most flattering
When to Send Out Holiday Cards
- The ideal mailing window is between Thanksgiving and December 10th
- Sending earlier risks your cards getting buried in early mail; sending later may mean they arrive after the holidays
- Two other things worth a quick mental note now: your Christmas card order has its own deadline, and if you send a family newsletter, that takes writing time too — both get their own full checklist later in the challenge, so no need to solve them today
Optional: Prep for Mailing Day
- Order holiday stamps early — the fun designs go fast
- Create or order return address labels
- Stock up on envelopes or photo sleeves if you’re including pictures
- Mark a “Mail Cards Day” on the calendar for late November or early December
Today’s To-Do’s
☐ Start a rough idea of outfits and location
☐ Review your contact list and fill in what you already have
☐ Text or message anyone you’re missing an address for
☐ Decide where you’ll store your completed address list
☐ Decide what kind of holiday photo you want — professional, DIY, lifestyle, or collage
☐ Pick your photo date and add it to the calendar
☐ If hiring a photographer, reach out this week to check availability
You’re Not Late — Jump In Anytime
Join the free 100 Days to Christmas community to get a new prompt every weekday, right where you are in the season.
Ten minutes today saves you hours later. Go grab those lists, pass them around, and let future you enjoy the payoff.
