Automate when it makes sense.

All parts of the newsletter process can be automated, not all should be.

Years ago, I use to write essays weeks ahead of time. I'd plug them into Mailchimp and schedule them to go out at regular intervals. When published, the final version of that newsletter (sometimes I'd jump in and make small edits at the last minute) would be captured by email automation in Evernote, tagged and filed appropriately. That was a pretty sensible automation for the time.

Now, just about anything is possible. Each reader can have a different experience based on their preferences. You can publish to RSS and have your posts pulled into the newsletter, summarized, and formatted with a template you touch once. The reader can subscribe via RSS and read the newsletter in any way they want.

A signup form can identify where a reader signed up, offer them a different welcome message based on that interest, time of day, region of the world, etc.

You can set your newsletter to arrive in an inbox at the exact time in the correct time zone when a specific segment of readers is most likely to read.

You can bookmark an interesting link in a web app, add a comment on the fly, and it will automatically trigger an automation that appends that link and commentary to your newsletter.

I can go forever, and so can the automations. But a good newsletter is human, relatable, and trustworthy. There's an uncanny valley that far too many newsletters enter with complex automation schemes. Plus, the more complex the scheme, the more you begin to rely on apps to tell you who your readers are, rather than your conversations.

It's best to keep it simple for as long as possible. In fact, as paper and television journalism becomes more and more automated, cutting out more humans every year in the creation process, two of the most popular journalistic newsletters, NextDraft and Reliable Sources, are famously hand-made, one day at a time. They're both researched, written, edited, and published over the course of a single day, in the voice of their creators. And their readers love them for it.

Properly-placed automations should occur to you over time and should never come at the cost to the relationship you have with your readers or the quality of the content.

Check out the rest of this month’s posts on creating email newsletters.