What is a Newsletter, Anyway?

And how is it different from a blog?

When I sent out feelers at my first Substack newsletter, in August of 2020, I barely knew what a newsletter was. All I knew was that everyone was doing it and it looked like I needed to jump on that bandwagon. I had just started another newsletter for my now-defunct Medium publication, Indelible Ink, but that one made sense. It was there to promote the works of the writers I was publishing. Nothing more.

When I began my first newsletter (which had to go through three names before I settled on Constant Commoner, the name of an old blog of mine), I had no idea what I was doing. Or even why. What was a newsletter going to do that a blog or a Medium page couldn’t? I didn’t know, but I liked what I saw in other newsletters, and I wanted to try it.

I struggled most with the tone. Everything seemed ‘off’ and I couldn’t find a way to settle in. Since it wouldn’t be a newsletter unless I found subscribers, it didn’t feel like a blog, though that’s how I was writing it. It felt like an email, and I couldn’t get past that. Who were these people who were subscribing, and what did they want that would be different?

At first they were friends and family, and that was hard enough, but then I began to get subscriptions from people I didn’t know. I was glad they were there, but how was I going to keep them?

Constant Commoner had no real focus at first, since I saw it as a place to move pieces from my other blogs into a new neighborhood where they might have a chance to be seen again—and that was a problem until Substack began allowing sections. Before that it was all over the place.

Now I try to think of it as a magazine with something for everyone. But it’s still a newsletter. Its main function is to appeal to subscribers, and I can only guess, from my own experience on the other side, that they’re a fickle bunch.

My second newsletter, this one, Writer Everlasting, has more focus. It’s about writers and writing. But it took me a while to get the tone right here, too. I often re-post pieces I’ve published before, and I’m fine with that—I only post the ones I’m proudest of—but I write now with greater ease than I did with some of the earlier pieces. Maybe nobody else can see it, but I can.

What changed? I think I can safely say it was because of E. Jean Carroll. E. Jean made a name for herself years ago as an advice columnist at Elle Magazine, but she was fired in February 2020, after she made a bit of a national fuss by accusing Donald Trump of raping her in a dressing room at Bergdorf’s and then suing him for defamation—a case that’s still ongoing.

I knew a little of her case, but I sat up and really paid attention after I read a piece she wrote in The Atlantic that shouldn’t have been hilarious—but definitely was!

So some time after Elle fired her, she moved her operation over to Substack, where I found her again, and she’s as delightful and delicious and naughty as she’s ever been. While I don’t write like her, and couldn’t if I wanted to—I mean, come on! That’s her. This is me!—the bells went off.

As I read E. Jean’s newsletter week after week, I marveled at her colossal confidence, at her ability to engage, to make me feel as if I belonged there and I was part of her circle and she was happy to see me.

And then I’m thinking, YES! That’s exactly what this is. It’s friends talking to friends. It’s you clicking on my newsletter link in your inbox, not because you have to, but because you want to. You’ve been to my place before and you want to come over again. And that makes us not strangers.

So why would I treat you like one? I wouldn’t. Not anymore. But, you ask, what about all those other newsletters? Those newsletters that aren’t like mine or E. Jean’s or maybe yours? You’ll notice I’ve filed this under the section called ‘Creative Writing’. That’s because I have my creative writing cap on at the moment, and I want my newsletters to be, if anything, creative.

If your goal is to be successful by publishing a serious, important newsletter, (like Heather Cox Richardson, who writes newsletters with boring titles, long paragraphs, and no pictures, but has subscribers up the wazoo), you might want to slide past everything I have to say here. I don’t know how to do that.

But if bells went off for you, too, let’s talk a little about how to do this. I’ve been reading tons of Substack newsletters lately, after spending time at Substack’s Thursday Office Hours Shout Out Thread, where I find mountains of newsletters to link to and read. I love when they do Office Hours (every Thursday between 1 and 2 PM EST), and especially when they do a Shout Out (once a month or so).

I’ve found some truly awesome newsletters to subscribe to, but I’ve also found some truly awful newsletters.

Now, nobody writes an awful newsletter on purpose, so I chalk it up to three things: Fear, ego, don’t-give-a-shit. So in the interest of expediency let’s abandon the last two and move along to the first one: fear. In every stilted, stunted newsletter I sense fear. I know it when I see it because I’ve been there. Many times. And I’m still not immune.

I saw one the other day where the writer was trying desperately to appear loose and friendly, but then spoiled it all by talking about someone ‘with whom I’m acquainted’.

Does that seem like a small thing? It wasn’t. It was as if the writer had pushed a hidden button and ‘loose and friendly’ went right out the window, to be replaced with ‘dry and dull and whatever…’. I wanted to tell him to relax. To remind him that he’s talking to people who’ve willingly signed up for his emails after reading something that spoke to them. They’re no longer strangers just happening by. They’re friends.

I’m going to end this in a minute, but here’s something else I see as a problem, even with the friendlier newsletters I’m talking about here: paragraphs as long as chapters. OMG, break them up! They go on and on and on. One look at the page tells me this is going to be more work than fun. I don’t want to read all of that! You can’t make me!

The other thing—the last thing for now—is fancy formatting. That may work well in a presentation, but we’re all friends here. No need to bat me over the head with the obvious. You want me to pay attention to that particular thing there. I GET it. I’m not stupid. I don’t need dotted or numbered lists, or paragraph headings, or separate quotes in a HUGE FONT stuck in the middle of the page, where I’ll be sure to see it, even though I’m about to read the very same thing right below. (What IS that, anyway?)

Just think about it. What do you want your newsletter to be? Even if you’re advocating for something near and dear to you, wouldn’t it be better if it were friendly? If we could just read it as if we were in the same room and we were talking?

Or am I all wet and you’ve got a better idea? We can talk right below in the comments section. (I would thank you, but I read a piece at Medium yesterday where the author went after anybody who thanked people for commenting. She thought it was lame and pathetic and some other things I’ve forgotten now. So I’m going to have to think that one over, too…)