Newsletter Mania?

How I ended up publishing four(+) different newsletters every week

I mentioned to someone recently that I publish four separate newsletters. Two publish weekly, one twice a week, and one daily. They asked how I did that.

Well. It’s not something I set out to do. It’s more of a journey.

Ask Leo!

My weekly Ask Leo! newsletter – Confident Computing – is part of what I semi-facetiously refer to as “the day job.” It’s Ask Leo! that pays the bills.

The process is simple: throughout the week I write or update four articles on the Ask Leo! website, and record a video for each. Those, then, plus a “best of” article, become the meat of the newsletter sent out every Tuesday. I add a little bit of an intro, but the newsletter is really about the five articles I’d posted throughout the prior week.

That newsletter is coming up on 20 years old, and as I type this, the most recent issue is number 1,076. It’s sent to a little over 26,000 subscribers weekly.

I have help. I have a real live human editor who makes my articles look like I’m a better writer than I really am, and I have an assistant who performs the mechanics of pulling the newsletter together and queueing it up to send.

Not All News is Bad

NANIB, as I refer to it, is a newsletter I started for purely selfish reasons.

At the beginning of 2017, I was feeling affected by the constant flood of negative news. It was the beginning of the first Trump administration, and the news and socials were filled with so much negativity that it flooded out anything and everything else. (This hasn’t changed.)

I tasked myself with finding one piece of good news every day. I knew it was out there. I just had to motivate myself to find it.

I shared links on Facebook for a short while, but then decided what I really needed to make a genuine commitment was to set up an email newsletter. That way I forced myself to ensure that there was something not just for myself, but for some number of readers, every single day.

The first of what is now a collection of over 3,000 good news items went out on February 18, 2016, and I haven’t missed a day since. 1,400 subscribers are along for the ride.

It takes maybe five minutes every day to scan the sources I pay attention to and make a selection. It’s worth it. NANIB is a solo effort; it’s just me.

7 Takeaways

7TA is another newsletter I started for purely personal reasons: to force myself to consume better content.

I’ve resolved to read something of substance each day — a chapter, an article, whatever — and identify one idea to “take away”. That takeaway, and my reflection on it, gets saved here on 7 Takeaways. Each week I publish that week’s collection on the site, and send it out in email.

Less doom scrolling, more reading. And the public commitment of a weekly newsletter becomes my motivation to actually make sure it happens. I started in December 2020, and here we are 236 issues later, being sent to ~850 subscribers.

This takes a little more time throughout the week. I actually need to read, but that’s the point. Once I come across something of iinterest, it takes maybe 10 minutes to write up its entry. But it’s the reading that takes the time.

After reading a few of the typos that slipped through, my wife now acts as my editor for most issues.

HeroicStories

HeroicStories has a long and complicated lineage.

Randy Cassingham of This is True fame started it in 1999. I became involved as a supporter (and eventual tech support, of course) after a fundraising drive. From its manifesto:

Thus, HeroicStories’ mission is to use the power of the Internet and existing media to bring diverse, international voices to the world to explore the idea that people are good, that individuals and individual action matter, and that regularly showing examples of people being good to each other will inspire similar actions in others.

Randy handed the reins of HeroicStories to Joyce Showalter in 2003. Unfortunately, she passed away in 2014. That’s when I returned and took it on.

The original mechanism of HeroicStories was to be a place where ordinary people could write and share their stories. We’d provide polish and platform, but the stories themselves came from the readers. Over time, new story submissions have slowed to a bare trickle. One reason is that while in 1999 getting your story published to a wide audience was a struggle that HeroicStories could help with, today, social media and other platforms have made it trivial place your stories online.

As a result, HeroicStories has republished its collection of 850 stories multiple times (with an additional editing pass one cycle, and the addition of a podcast the next), while only occasionally adding a new story.

We’re now in the third and final cycle of republishing HeroicStories stories. Once complete, the twice-weekly newsletter will stop, though all the stories will remain archived on the HeroicStories website.

The majority of HeroicStories is handled by an assistant who manages the stories on the website, and the tech to ensure that they’re published on schedule.

But wait, there’s more!

I said four newsletters, but there are a few of others worth mentioning as well.

• The Ask Leo! Tip of the Day publishes 5 times a week for Ask Leo! patrons at the Bronze level of patronage.
• The Best of Ask Leo! is a once-a-week newsletter that contains the complete text of a hand-selected Ask Leo! article.
• Ask Leo! new article notification, as its name implies, is an email notifying the recipient that a new article has been posted on Ask Leo!.
• My personal blog also publishes to an email list whenever I post something new. Perhaps you’re reading this because of that.

OK, so maybe it’s more than four. I count … eight? Yikes!

Automation, and why it’s good to be a geek

It’s the tech that saves me. Except for Confident Computing, the publishing process for all the other newsletters is super-simple:

• Post the content to a WordPress blog.
• Magic happens.

Seriously, all I really do is create new entries on an assortment of WordPress blogs. I’ve configured my newsletter sending service, Aweber, to notice when something new has been posted (via an RSS feed), and then send what it finds to a list. Automatically.

For some, it really is just that simple. For others (like Ask Leo! individual articles), I’ll have created a custom RSS feed to filter on special criteria or perform some custom formatting, but the mechanics are the same: hit publish in WordPress, and eventually email gets sent to a corresponding newsletter.

The flagship newsletter, Confident Computing, is slightly more complex:

• I publish my articles on askleo.com
• Once a week I write up a short introductory blurb for the newsletter
• My assistant runs a custom script (a web page written in PHP) which assembles the content of the newsletter, formatting it all appropriately.
• That content is then copy/pasted into Aweber, and scheduled to be sent.

It’s a journey

You can see that it’s been a lengthy journey. None of this happened overnight. Almost all of the assitance and optimizations have been incremental refinements. As I’ve learned, I’ve optimized, and as I’ve optimized I’ve made it possible to publish a lot.

It’ll change, of course. I may pull back on some and tweak others as time goes on.

But for now, yeah. Four newsletters. Or eight. Depending on what and how you count.