When I hear “holiday newsletter,” I think, “Here are the life milestones that each of my seven children reached this year!” That’s what the Times uses as their example of a good year-end newsletter. But end-of-year newsletters are for everyone. Especially if you don’t have children.
A year-end newsletter is a way to check in with old friends and distant acquaintances—it’s more intentional than a Facebook post but easier than making twenty phone calls. It is private, it is platform-free, it is a treat to receive. It doesn’t even have to summarize your year.
You should probably send it by email. A printed letter is touching but too much work, and people are more likely to reply to an email.
Your newsletter can look radically different from any you’ve received. It could be:
A listicle of the times you threw up this year
A drawing of something that happened each month
The story of your biggest fight this year, told as if you are a contender for the coveted Iron Throne of Westeros
What you imagine each of your recipients did this year, ending with a request that they reply with what they actually did
A one-page screenplay of the funniest moment that happened to you
Links to some tweets you really liked
A full-on family newsletter but it’s about you as if you were a little kid, as if you were your own partner, and as if you were your dog
Your favourite albums/movies/podcasts of the year—but you have to write something about how they made you feel, or an idea expressed in them, so you can start a better conversation than “Oh, I liked that too”
Or! If those all sound too try-hardy or stupid to you, just write one normal-arse email to one specific person: a friend you used to be close to, whom you follow on Instagram, but don’t really talk to as much as you’d like. Then see if you could send that same email, maybe with minor tweaks, to, like, ten other friends.
Then write an email to someone you have kept in touch with, and dig deeper. They already know about your job and your dating life and your family, so build on that, take stock of the year, or tell them a detail you hadn’t before. Now see if you can send that email to some other friends.
Yes, I’m suggesting multiple emails for your different friend tiers. But you can quit at any point. You can quit after you write one email to one person! That’s still pretty cool!
Just write the very first one—honestly, it can be like five sentences that amount to “I’m still alive, hope you are too,” and it will make someone feel nice. A lot nicer than a Facebook post or a tweet, and if you throw a pic in there it’s even nicer than an Instagram post.
Because each person you sent it to will feel special that they were included. And when they reply, you’ll feel special too, as if you’ve finally won the coveted Iron Throne of Westeros.