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One Year of Newsletters: Lessons Learned

Last year I had an idea: Create a really, really high-quality newsletter. Reading technology-related news is a daily and rigorous ritual for me, so why not take that effort and synthesize it into a curated list of “What to Read“? Many others are doing this, of course, but I felt the value for readers was to get it from your trusted technical advisor (I manage technology for a number of small and medium-sized businesses). For many years this voracious appetite for news and information was only for me, but I knew it was time to change that. Time to share this with the world.

And, this was only logical for what I do. There was a time on this blog when I chased the news, writing pieces on various different new developments (almost as if I was reporting on them). This made for some very interesting writing on my part, but it was difficult to keep up with, and these articles never seemed to resonate. The more popular among almost 700 articles are those conceived of in a longer, more measured process. Articles with weight and usefulness, like The EASY Way To Move Your Microsoft Office 2011 For Mac License Between Computers.

The very first CWL Newsletter

At first, I sent out one edition on weekdays. It was an ambitious goal, but one I knew was possible given all the information I regularly consume. This would give way to the reality that I couldn’t keep this up while still travelling and working. I pared back the frequency to once a week (on Fridays) and made the body longer with more categories. The categories themselves evolved from simple ideas describing what was in the links, to describing topics. I started to learn more about the Avant-guard and interesting versus just news. Looking for new tools, versus talking about old problems.

Even today, the categories I use are in flux. Sure, there will always be a “News”, but I have branched out into things like “Security” and “Finance” based on reader feedback and experiences in the field. In some cases, links and information I provide are directly tied to experiences, not just the news cycle. I also envision categories could become seasonal (as  “Finance” might be at tax time).

There have also been challenges with my newsletter service, too. I chose free Tinyletter as a start. The web interface for editing is WYSIWYG, but it blocks right-clicks in the browser, cancelling out spell-checking. For someone who sucks at spelling, this has forced me to type slower and more accurately. When I can’t spell a word and I know it’s wrong, I take a trip outside the page to Google or a dictionary. Tinyletter also sucks on mobile. Their interface essentially renders the same as on desktop, making any sort of editing brutal. On occasion, I’ve used the interface on my phone only to send out messages when I can’t get to a computer. Their SPAM filtering of links is rather mystical also. Most links I run through my newsletter have to be checked on their choice of sites. Add it all up, and it’s clunky, cumbersome, but free. At least it would get this out there to subscribers.

Then, a little over a month ago, I made the move to MailChimp (Tinyletter’s parent company). This would allow for more control of the visuals, as well as making a layout that I felt like an improvement. I also wanted to give this thing a better name than “What to Read”. It felt like people were seeing this email and weren’t really aware that it was coming from me. I settled on the name of THE PROTOCOL and worked on a layout that looks much like this now.

The Protocol Newsletter

And, subscriber growth has been slower than I had hoped. Thankfully, the list of users continues to grow, albeit slower than I had hoped. I’ve found the challenge of making the content well is not a match for getting the word out. The next step is to look at growing subscribers. I’m open to suggestions on how to get this out to a broader audience. Let me know in the comments if you have any ideas.

Here’s to another good year of evolution. I know that this needs to expand, and with it, the very platform I’m using is going to need to expand too. I’m in it for the long haul folks, you can depend on that. In fact, let me do something for you: When my newsletter reaches 250 subscribers, I will give away a gift. I’ll ship the 250th subscriber (in North America, contest rules) a pair of brand new Apple earbud headphones or an iPhone charger, on me. We’re not there yet, so I’m depending on you, a good reader to help me out.

So, get everyone to subscribe to “THE PROTOCOL“, you’ll like it I promise. Everyone can use a spare set of headphones.