In the Inbox

Thinking About Newsletters

Given my hatred of email, I’ve been rather confused recently. You see, I’ve found myself subscribing to things. Things that are delivered to my inbox. Yes, I’ve asked for more things to be placed into my inbox. On purpose.

Newsletters.

The email newsletter is obviously nothing new. In fact, while it may not be as old as email itself, it was one of the earlier, more evident use-cases. Then user groups came around. Then the world wide web. Blogging. RSS. Facebook. Etc. Such newsletters should have faded with newer technology.

And yet, they’ve endured.

That newsletters have made a strong comeback in recent years isn’t some huge revelation — folks have been noting the trend for years. But it sure feels like the ball keeps on rolling. And again, given how much I dread email, that they’ve come back into my life has surprised me.

But after several months of subscribing to a few, I think I get it. The email newsletter is one of those things that perhaps on paper (even digital paper) doesn’t seem different from what the aforementioned newer technology allows for. But it is different. Likely because of the delivery mechanism, email newsletters tend to feel a lot more personal than a blog post. And maybe it is because you allow them to come into your inbox, an increasingly sacred place when it comes to space and time.

Talking to a number of people in my network recently, this resurgence does feel very real. But it’s more interesting than people simply subscribing to everything they can and using email as a catch-all (as people may have done in the past with RSS). It’s a much more curated experience. Most people I’ve talked to seem to subscribe to only a couple or a few or at most, a handful of newsletters. And they read them religiously as a result.

A few common ones I hear about these days include theSkimm, Ben Thompson’s Stratechery, Matt Levine’s Money Stuff, Dan Primack’s Term Sheet, and Jason Hirschorn’s REDEF. But there are, of course, many more.¹

Medium has offered a similar functionality with “Letters” for some time — and publications like Backchannel seem to use it to good effect — but I’m not sure it’s quite right. Maybe it’s the tiny creation box, or maybe it’s the fact that they’re all sent from the same generic @Medium account, or maybe it’s that everyone opts-in to get the letters when you follow a publication — I’m not sure.² It doesn’t feel quite newsletter-y enough (which I think may be on purpose, but still, something feels a little off from what it should be, IMO).

Then there are the newsletters which are basically an aggregation of a service’s content. Nuzzel comes up time and time again here (though a newer functionality allows people to curate their own). Medium’s Daily Digest also comes to mind here as well. A conversation with my father this past weekend revealed that he loves reading Medium, but mainly does so through this morning digest email. And he’d love one more granularly tailored around the authors/publications he wants to read (namely, me).

Anyway, just been thinking about this a lot recently because I’m finding myself now a far more loyal reader to the newsletters to which I subscribe versus content I find via any other means.

¹ There’s been a lot of intrigue recently over the hand-off of Politico’s Playbook newsletter — namely because the same person, Mike Allen, has written it (nearly) every day for the past nine years. And now a new group of folks will be writing it going forward. For something so personal, that’s likely to be quite jarring.

² So I’ll send this as a “Letter” and see what happens!