What makes a great newsletter?

What makes a great newsletter?

On Monday I sent out my first newsletter and have received a lot of great feedback and encouragement to continue. It was a pre-newsletter really, because in it I mention that it’s new, that it’s the first time I’ve opened up a mailing list to the public, and that I admittedly have no idea what kind of content it will contain or how often it will go out.

If my newsletter is to be successful, then I guess I better start thinking about these things.

  • Do I want to commit to a frequency?
  • If so, what can I reasonably manage?
  • What kind of content will I send? And how much?
  • Who am I writing it for?
  • Will I publish the same content to my site?
  • Will I link to third-party content?
  • What else should I be thinking about?

So, I’ve got newsletters on the brain.

Not everyone likes email, but I do. I love it. I love that it comes to me; I don’t have to go looking for it. I keep trying to implement feed readers or bookmarking apps like Pocket, but they’re just not working out for me. They’re extra work and require me to develop new habits that I’m not ready for.

Where am I online? I’m on Facebook, Twitter and my inbox. This is where I consume the most content, linking through when I want more.

Newsletters are easy to subscribe to and easy to ignore or get rid of if you change your mind.

So in thinking about the value I get out of newsletters—convenience, ease of use, good content—I decided to turn toward some favorites for inspiration.

Paul Jarvis’ Sunday Dispatches

Paul Jarvis is a writer and entrepreneur who, after years of freelancing, has turned the bulk of his energy toward product development. He’s the author of a number of books, some online courses and several WordPress themes, among other things.

His newsletter, the Sunday Dispatches, goes out once a week—you guessed it, on Sundays—except at the end of the year when he takes time AFK.  He’s very consistent with his mailings, each containing one article usually no more than a 5 min read. He then publishes the article the next day on his website, or sometimes on Medium.

I don’t think I have ever not read one of his emails. What I love about his writing is his no-bullshit style, fantastic analogies and sheer simplicity. Sometimes it feels like he’s in my head, expressing things that I haven’t yet been able to put into words. I also like that the newsletters are short and focused; they don’t try to do too much or disperse my already very low attention span over more than one topic.

Sara Rosso’s Newsletter and Special News

Sara Rosso is the Director of Marketing at Automattic, and also a writer, speaker, photographer, foodie and well-seasoned traveler. Her monthly newsletter is as eclectic as she is, full of news about what’s she been up to and what’s been on her mind.

My favorite part is the section called “Tickle your Neurons”, where she curates a list of interesting links divided into two categories:

  • Left Brain: On technology, business, productivity, and self.
  • Right Brain: On food, travel, design, music, and photography.

These are always refreshing and fun and she makes a point to share content here that she doesn’t share elsewhere.

Brian Krogsgard’s Post Status Notes

Brian Krogsgard is a WordPress developer and the creator of Post Status, a news site dedicated to “informing WordPress professionals and enthusiasts about the industry.” While he provides both free content and a personal newsletter for the general public, the good stuff happens behind a pay wall. For $99 / year, club members get access to premium content including a regular podcast, partner discounts, access to the community slack and my favorite, Post Status Notes, his (mostly) daily newsletter.

Post Status Notes is chocked full of content, and presented in a very keen and digestible way. They always open with a brief, personal introduction from Brian, then go on to present his main articles of the day. These are often well developed, analytical pieces, which include quotes and references to outside sources.

The last section is Footnotes, where he lists news briefs full of external links. These are a great way to get a quick overview of what’s going on in the world of WordPress. I often skip down to this part first, then scroll back up.

Post Status notes are usually waiting for me when I get up in the morning, perfect for sitting on the couch with a cup of coffee and a quick read. I mostly only scan these because they are long and, oh, did I mention my limited attention span? Although I save every single one in my archives and refer back to them from time to time.

Dave Pell’s NextDraft

I don’t like the News. I find it boring, depressing and often lacking in journalistic integrity when it comes to mainstream media. Dave Pell has managed to get me to read the news with his daily NextDraft.

He curates news links to external sites by topic or theme, rewriting the headlines in his own clever and often hilarious way. In addition to his writing style, what I appreciate about his approach is that he seeks out multiple sources, and I feel like I can trust that they are the best ones to look at whatever the subject is from different angles.

These quick briefs highlight the news making it digestible and well-rounded. And sometimes silly and quirky, which is good too.


My favorite newsletters are weeklies, monthlies and dailies. They have both very generalized and very specific audiences. Some have original content while others publish elsewhere, or are made mostly of curated links. It’s a smorgasbord.

So, what will I take away? Only one way to find out (it will be a surprise for us both).