Insights from writing a weekly newsletter for exactly 1 year

A version of this post originally appeared in the July 16, 2020 issue with the email subject line "In the middle of the morass" and a review of newsletter platform Substack.

Hello, issue 52. I have written this newsletter every week for the past year.

Last summer, I planned my issues early. I’d begin writing on Sundays, crafting my essays, thinking deeply about the flow of the essay, testing ideas in writing, discarding the ones I didn’t like so much. Then I got more clients, pushed the writing back to Tuesday afternoons, then Wednesday evening. These days I’m lucky if I begin writing at all before Thursday.

Now it’s time for a short break and a recalibration.

From a year of writing newsletters, I’ve learned:

• This newsletter wouldn’t leave my head if I didn’t love writing it. Although it is the content marketing for my business, it is also a labor of love. And therapy. I gave up on making my living from writing a long time ago, but I am stoked that my current approach works. Newsletter = how clients find me.
• My single creative constraint — keep it acceptably professional — produced better writing and kept me focused.
• Reviewing software has been more difficult than I thought, mostly because I only review software I like. I do not like a lot of the software! I’m going to focus on better systems for me to discover better software, moving away from marketing and more into content creation.
• In reality this newsletter has been years in the making. It draws from every job I’ve ever had, my education, every link I read, every snarky Tweet I like, every conversation I have with my friends. People have asked “how do you maintain your voice” and it’s like: it’s my voice. Also, I have been blogging my whole life, so I did come into this with an idea of how to write regularly, and at some point… I’ll tease that out.
• You know what doesn’t work? Mass ad-supported digital content as it stands today! Content marketing as a tactic and not a business approach! Measuring any marketing or content effectiveness based solely on “reach” or “impressions” or even “leads”! And a whole slew of other commonly accepted digital marketing and content assumptions.
• You know what does work? Respecting your audience. Respecting your audience when they question your established norms. Remembering your audience’s humanity when you write to and about them. Understanding that there are many unheard ideas that have as much value as the established ones. Understanding that the ideas alien to you may have as much historic and human value as the norms you hold dear. Respecting the ideas that both Silicon Valley tech and established media provide as solutions as we’re figuring out digital content, and then learning how to question and change them. Accepting that they will be changed.

We’re in the middle of the sea change, kids. To quote the character of Angelica Schuyler, Look around, look around at how lucky we are to be… figuring out new business models in the midst of a global pandemic and the ongoing failure of no-holds-barred neoliberal capitalism.