40-Day Christmas Challenge | Day 14: Solve the Holiday Logistics Now • Everyday Cheapskate

There are Christmas plans.

And then there are all the little plans required to make the Christmas plans actually happen.

Who’s watching the dog? Who’s picking up Mom? Where is everybody sleeping? Do we need a sitter? Wait. Did anyone actually ask Sarah if she could feed the cat?

These are not particularly festive questions.

They are, however, considerably more pleasant to answer before they become emergencies.

So that’s what we’re doing today.

Today’s Challenge

Look at your Christmas calendar from Day 5 and find anything that depends on another person, reservation or arrangement.

Then take care of one of those arrangements today. That’s it.

We’re not solving every logistical detail of Christmas. We’re getting ahead of the one that’s most likely to cause trouble if we wait.

Do This Today

1. Look for what your plans depend on.

Scan your calendar for plans that can’t happen without something else falling into place.

Childcare for an event.
Pet care while you’re away.
A ride to or from the airport.
A hotel or other place to stay.
Transportation for someone who doesn’t drive.
A comfortable place for an overnight guest.
Help for an older family member or someone with mobility or accessibility needs.
Someone checking the house while you’re gone.

You may have several.

You may have none. Wonderful. Enjoy your unusually short Day 14.

2. Pick the one you don’t want to solve at the last minute.

That’s today’s target.

Maybe it’s arranging for the dog. Maybe it’s asking your brother, “Are you still able to pick Mom up?” Maybe you need to find out where your out-of-town guests are actually staying instead of assuming someone somewhere has handled it.

Don’t leave important details living in the land of I thought we had that figured out.

3. Confirm it.

This part matters.

“I mentioned it a few weeks ago” is not a confirmed plan.

Send the text. Make the call. Make the reservation. Get the answer.

Then put the agreed-upon details where you’ll find them later.

If another person is involved, make sure they know they’re involved. A surprisingly important detail.

Quick Win

Find one event on your calendar that depends on somebody else and send:

“Just confirming our plan for ________. Does ________ still work for you?”

Done. That’s Day 14.

Ask Before You Assume

Holiday logistics have a funny way of turning people into volunteers without anyone actually volunteering them.

The teenager will watch the little kids. Your sister will pick Dad up. The neighbor will feed the cat.

Maybe. Ask.

And if someone is doing you a genuine favor, make it easy for them. Give them the information they need: times, phone numbers, keys or codes when appropriate.

A sincere thank-you wouldn’t hurt either. Christmas cheer improves considerably when nobody feels ambushed.

Put the Details Where You’ll Find Them

Once you’ve confirmed something, add enough information to your calendar that you won’t have to hunt for it later.

Not: AIRPORT

More like: Pick up Mom — Flight 123, Terminal 4, 2:15 p.m.

Future You shouldn’t need to search six weeks of text messages to figure out what Present You arranged.

Paper calendar? Write it there. Digital calendar? Add it to the event.

Why It Matters

Waiting doesn’t always make holiday logistics more expensive. It does tend to give you fewer choices.

The person you hoped could help may already have plans. The convenient option may no longer be available. And a small arrangement that would’ve taken one phone call suddenly requires six.

Handling one important detail now gives you something we’ve been trying to create throughout this Challenge: options.

Options are very nice to have at Christmas.

Your Turn

What’s the holiday detail you’re most likely to forget until the last minute? Pet care? Airport pickup? Childcare? Where everybody is sleeping? Tell us in the comments. There is great comfort in discovering that other competent adults have also forgotten who was supposed to pick someone up.