Newsletters should be letters!

And maybe all writing should be epistolary, while we're at it

An advertisement Jason Polan ran in The New Yorker

Hey y’all,

I’ve been sending out newsletters for over a decade. Perhaps paradoxically, the way I keep an element of fun and spontaneity in the process is to be totally militant and rigid about blocking off every Monday and Thursday on the calendar so I can come out here to the studio and write a letter to you.

I thrive on the challenge of coming in here with nothing and leaving with something. Even if I try to plan ahead, I never know exactly what’s going to happen. I’ll often think all weekend about what I want to write, take notes, research, get it fixed in my mind before going to bed on Sunday night, and then when I sit down the next morning at my desk I’ll look up at a sticky note that says “What feels urgent?” and write something completely different than what I had planned.

People often ask me for advice on how to write a newsletter. I usually tell them some variation of what I wrote in Steal Like an Artist: “Write a newsletter you’d like to read.” 

I have a few more tips, like “Pick a repeatable format” or “Be consistent at a regular frequency.”

But my current personal motto is: “Newsletters should be letters.”

What I love most about newsletters is the letter part — the epistle, the missive, the bulletin, the dispatch! What’s going on — in the studio, in my life, in my mind — that’s worth sending out? Worth opening? Worth reading?

A favorite 45 from the melted stack Meg found (featured on my May mixtape)

Not only do I think newsletters should be letters, I’m starting to think that all writing gets better — and maybe even easier — when we simply try to sit down and write a letter.