40-Day Christmas Challenge | Day 39: Reach Out Before the Rush Is Over • Everyday Cheapskate

There are people we think about far more often than we talk to. You know the ones.

You see something that reminds you of them. Their name crosses your mind. You remember something funny they said 20 years ago.

And you think: I really need to call her.

Then life keeps moving.

Christmas has a way of bringing those people to mind. So today, we’re going to stop thinking about reaching out.

We’re going to do it.

Today’s Challenge

Choose one person you’d genuinely like to connect with and contact them today.

Call. Text. Send a voice message. Write an email. Drop off a note. Knock on the door. Whatever makes sense for the relationship. The method matters a lot less than actually doing it.

Do This Today

1. Think of one person.

Not your entire Christmas card list. One person.

Maybe it’s a friend you haven’t talked to in months. A relative who lives far away. An older neighbor. A former coworker. Someone who used to be part of your everyday life. Someone you simply miss.

Who came to mind while you were reading that?

There’s a good chance that’s your person.

2. Don’t wait until you have time to do it properly.

This is where good intentions get stuck.

You think calling means you need an uninterrupted hour. Writing means finding the card, the stamp and the right words. Catching up means explaining everything that’s happened since the last time you talked.

Maybe not. Send the text.

I’ve been thinking about you. How are you?

Or:

You crossed my mind today and I realized it’s been too long. I miss you.

That’s enough to open the door. If a longer conversation happens, wonderful.

If not, you’ve still made the connection.

3. Make it personal.

Give them one sentence that could only be meant for them.

I was thinking about the Christmas we __________. That still makes me laugh.
I saw __________ and immediately thought of you.
I’m really glad you’re in my life.

One specific sentence changes the whole message. It says: This isn’t a broadcast. I meant you.

Quick Win

Open your phone. Find the person. Type:

You crossed my mind today, and I decided I should actually say hello. How are you?

Send. Day 39 complete.

A Text Counts

So does an email. So does a voice message.

I know there’s a temptation to rank forms of communication. A handwritten letter is meaningful. A phone call is personal. A text is, well, a text.

But you know what’s better than the beautiful handwritten note you never get around to sending?

Thinking about you today.

Sent.

Don’t let the perfect method prevent the actual connection.

Don’t Turn This Into Catching Up With Everyone

Please resist. Today’s challenge is not:

Contact every person I’ve neglected since 2019.

We’re not creating a guilt tour.

One person. That’s enough.

If you made a connection list back on Day 12, you can certainly look at it. But you don’t have to work your way through it. This isn’t another list to finish. It’s one person to notice.

Some Relationships Need Boundaries

There may also be someone you miss whom you should not contact. That’s okay.

Christmas does not require you to reopen a relationship that is unhealthy, unsafe or better left alone.

Missing someone doesn’t automatically mean contacting them is wise.

Choose somebody else. Today’s challenge is about connection, not obligation.

Maybe Your Person Is in the Next Room

The person you need to reach out to may not be far away at all.

We can become very good at assuming the people closest to us know how we feel. Tell them anyway.

I’m glad you’re here.
Thank you for everything you’ve done.
I love doing Christmas with you.
You made this year easier for me.

There are gifts that don’t need wrapping. This is one of them.

Why It Matters

We’ve spent 39 days talking about Christmas.

Money. Food. Gifts. Calendars. Guests. Decorations. Traditions. All useful. But none of those is really the point.

The point is people. People we love. People we miss. People sitting across the table. People far away. People whose names still make us smile.

We’ve spent all this time making room for Christmas.

Today, use a little of that room for someone who matters. Tell them you thought of them.

Your Turn

Who is someone you’re always happy to hear from, no matter how long it’s been? No names required. Tell us in the comments what makes that relationship one you can pick right back up.