CT No.52: In the middle of the morass

What a life this year has been

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.

What I’m trying to say, whether it’s through reviewing software very piece of the content ecosystem matters, whether we’re talking news or entertainment or technology or information hierarchy or academic research. From creation to discovery, from the medium’s message to the effects of algorithmic reading and rendering to how the audience uses the information they receive, it all plays a part in how our culture communicates.

Defining the new normal for digital content

My favorite part of any TV show about the content creation business is when an executive or salesperson walks into a room of professional creators and says, “Give me all your best ideas!” Then, inevitably, the executive or salesperson takes the ideas and fucks them up in practice.

Succession is a very good show about the media business because it is not about content creation at all.

The scene is such a beautiful fantasy because it implies that professional creators are being asked for their ideas, ever. In my experience executives never ask for your ideas. They read some non-idea sentence online like “Humans prefer video to photos to text” and that becomes the foundation for a “pivot to video” strategy, and commercials are sold against it as they always have been, and we have the same content but made shittier, again!

I read “Humans prefer video to photos to text” in a very famous newsletter this week. The man who wrote that sentence makes a living writing a text-based newsletter, providing high-level business analysis for venture capitalists. The man who wrote that sentence boiled down the success of TikTok, YouTube and Instagram Live to “humans prefer video to photos to text.”

How do we take this conversation back from something so massively reductive? How do we actually introduce new ways of thinking into that environment?

Here are all my best ideas, which I intend to explore in the next year’s worth of newsletters. If you are an executive, you can take them and fuck them up, so we can make the next iteration.

  • For content to be valued, we need to focus on the craft of content through the lens of technology. It’s a multidimensional process, and the impact of the creativity within a medium cannot be reduced to the medium itself. Creative process is often reduced to “inspiration” or “storytelling” rather than clear description of craft or operations. I was on a webinar the other day for marketing professionals to learn about an established content network, and sales executives reduced the success of the creative project to “it creates empathy.” The format does not create empathy. The craft creates empathy. The idea directs the craft. The operations create circumstances for the content to succeed.

  • Digital marketers should spend time thinking critically about the ideas and intent of content, rather than just the presence of content. Publications aimed at digital marketers and the tech industry need to incorporate more critical thinking into their content calendars and production processes. Content needs to be questioned at the level of the idea — who is helped by this idea? Who is left out? What externalities do we need to consider?

  • Content is only growing more collaborative — and editorial feedback needs to be a part of the process. There are no auteurs, and there are all sorts of methods for creating. Content creators have to be open to new methods that they didn’t learn in school or in the workplace. Businesses must be open to understanding the length, methods and impact of the process on final outcomes.

  • Content discovery algorithms need to be evaluated, heavily. Academia can not be solely responsible for monitoring tech’s impact on publishing. If you work with the technology—buy, sell, or optimize content for a specific medium— find the time to dissect how that algorithm works, what that algorithm implies. We need more critical thinking, especially in the world of organic content discovery.

  • Ad-supported media needs to scale down, significantly. We need models where ads are more specific to the content they support. More closed ad networks, old-school classifieds, etc. Creative partnerships need to look more like partnerships and less like ad factories. Programmatic scale should be thrown out the window — seriously, if your ad doesn’t have impact without scale, then the ad doesn’t have impact. And we need models where sales reps are rewarded for understanding the craft of the content, rather than just the audience that the content is reaching.

  • Especially in the U.S., we are still in significant crisis mode, and all our processes need to acknowledge that.

Speaking of business models

I’m figuring mine out for the next year. If you have a website redesign, content strategy, SEO/UX or content operations project you’d like to work through, reply to this email. I’d love to work with you.

But in the meantime, if this newsletter has helped you this year and you’d like to support I’m doing, you can leave me a tip.

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The hand that feeds: Substack review

You know what Substack does. Like Blogger and Wordpress and Tumblr, Substack is a way of life. It’s the natural extension of blogging, combined with Medium’s uniform design and writing experience. By oversimplifying the authorship, publishing and discovery experience, Substack makes the practice of writing a newsletter easy.

It’s also currently the best platform for individual content-driven newsletters by leaps and bounds. It does not provide the audience management and insights of a Mailchimp or other robust marketing automation platform — but that’s not the purpose of the technology.

Substack at a glance

As a WYSIWYG editor with minimal customizations, Substack works best for the subject matter expert, the beat reporter, the thought leader who actually thinks but who is also not a graphic designer.

Designing email templates is a pain in the ass, and Substack fixes that problem, as long as you’re cool with how Substack looks.

Setting up payment systems and business models is a pain in the ass, and Substack fixes that problem, as long as you’re cool with the massive cut they’re taking.

What I’ve enjoyed about Substack: it works. It rarely breaks. They add new features only after they’ve clearly been tested. The features intentionally make the authorship experience better, which enhances the reader experience. It’s not the first CMS that prioritizes the author, but it’s one of the best.

Also I can drag and drop gifs into the body of email newsletters without a thought, so.

I would like more list management options, like the ability to remove users who have not opened an email in 6 months. But they’ll get there I’m sure. And then one day there will be too many features and it will gradually start sucking because that is the content tech cycle.

But I’m enjoying the glory days. I’m cool with Substack.


I’ll be back in a few weeks with a cleaned up process and a clear head. In the meantime, here are the top five most popular Content Technologist newsletters from the past year.


And once more: here’s the tip jar. It helps keep me independent so I can think about the content of the newsletter and also give back to my community. It’s not necessary but it’s appreciated.

See you in a few weeks.


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