Christmas card etiquette question

In My Humble Opinion
1

I’m a tutor. I’d like to send Christmas/holiday cards to families I’ve worked with. (It felt nice to get cards from some of my families last year, so I’d like to send out cards this year.)

I haven’t done this before, and I’m not quite sure how to do this. Is it appropriate to send Christmas cards to people I’m currently working with? People I worked with last year but want to stay in touch with? People who are done working with, but with whom I’m going to have ongoing contact?

I have a family I’ve finished working with, but they still owe me money. I’m going to have to bill them again in December, and probably in January. But I still like them a lot and am looking forward to working with their younger kid. Do I send them a Christmas card, or is reminding them of me (and, thus, of their unpaid bills) at the holidays kind of tacky?

Or should I just send cards to everyone? Am I overthinking this?

The cards I got last year were from families I’d finished working with by the time Christmas came around.

2

Your reasons for sending Christmas cards are all reasonable, friendly and kind, even sending one to the client. Sending cards to clients is something that many businesses do. I get one from my insurance agent every year, for example.

So I say, send on!

Merry Christmas!

3

Send 'em, man. Send 'em even if they don’t send one back. I send about 50 each year and get about 20 in return. But I still enjoy it because I like spreading cheer and spending time each year to specifically sit down and think about each person/family as I make out their card. It’s like sitting down to specifically pray for each one without the religious thing.

Nobody will be thinking “Bob sent us a card because we owe him money!” Business is business, they know they gotta pay you.