Type, politics, philosophy, and digital tenancy; my reading backlog

Reading through a large backlog of articles I’ve had open. Here are some notes and observations, mostly for my own benefit.


The history of web design can be seen as a set of tensions between designers wanting things to be positioned with utmost precision, and the web pushing back on some of that control. 

Type in the digital era is a mess

Fascinating look into the history of type, leading up to problems surrounding line-height on the modern web.


it’s too easy to conflate the h4 style—intended to be shorthand for “the fourth largest heading style”—into actually meaning “use an <h4> element.” After all, <h2 class="h4">is a bit of a mindbender and seems wrong at first glance. I’ve seen those who don’t understand the power of HTML and CSS—whether that’s designers that aren’t very familiar with front-end code or full-stack developers who focus more or back-end or DevOps than front-end—feel forced to choose between appropriate styling and semantic code. They’ll pick an inappropriate element because it looks visually looks right or pick what visually looks right at the expense of semantics and accessibility, defeating the inherent advantages that HTML and CSS have out-of-the-box.

Typography in Design Systems

A breakdown of a couple different methods for creating type systems, and their various pitfalls. Mall comes up with a couple different fun ideas based on guessability, then demonstrates they are all insufficient, before going into what he things the most flexible system could be.


For those who think it trivializes our political process to judge candidates by their typography—what would you prefer we scrutinize? Qualifications? Ground into dust during the last election. Issues? Be my guest. Whether a candidate will ever fulfill a certain campaign promise about a certain issue is conjectural.

But typography—that’s a real decision candidates have to make today, with real money and real consequences. And if I can’t trust you to pick some reasonable fonts and colors, then why should I trust you with the nuclear codes?

Typography 2020: A special listicle for America

Intersection of politics + type = this post is my jam. Butterick’s sharp and witty take on campaign design has breathed new life into my sad, tired bones. I felt my skin clear as I laughed my way through each campaign website. 10/10 would read again.

Also, can’t wait to dive into this even deeper dive mentioned in the footnotes.


Trump didn’t have great design, but he was saying things to the right audience. Design is just one part of it.

Josh Higgins: Obama’s former design director on the new wave of political branding

Relevant, given my work on campaign assets. A lot of his advice and takeaways I’ve experienced on a much smaller scale.

Aside: wouldn’t it be cool if I wrote a book interviewing people who worked on presidential or high-profile legislative campaigns? I think it’d be cool.


Today, we may think we own things because we paid for them and brought them home, but as long as they run software or have digital connectivity, the sellers continue to have control over the product. We are renters of our own objects, there by the grace of the true owner.

We Are Tenants on Our Own Devices

I’ve been feelin’ this lately, especially with my video game collection. For the past couple years I’ve all about digital downloads — they save physical space, can load faster, are easier to acquire, etc. However, if something catastrophic were to happen to my account, that’s… hundreds of dollars and years of games, gone.

I’m a voracious Kindle reader, but I’m also afraid to get rid of books I own digital copies of, in case my Kindle account is ever locked. Owning physical books feels like a luxury I don’t have the privilege for anymore, but I’m keenly aware that each new Kindle purchase is just renting.

I need to get more serious about indie tech.


…in the tech industry, with our motto of “strong opinions, loosely held”, we’ve glorified overconfidence. 

Strong Opinions Loosely Held Might be the Worst Idea in Tech

I disagree a little with the author’s premise — I don’t think “strong opinions, loosely held” has to mean belligerent overconfidence — but the advice around adding a degree of uncertainty to your statements feels sound.


It’s okay to love a hobby the same way you’d love a pet; for its ability to enrich your life without any expectation that it will help you pay the rent. What would it look like if monetizing a hobby was downgraded from the ultimate path to one path? What if we allowed ourselves to devote our time and attention to something just because it makes us happy? Or, better yet, because it enables us to truly recharge instead of carving our time into smaller and smaller pieces for someone else’s benefit?

The Modern Trap of Turning Hobbies Into Hustles

As a “creative,” this whole article resonates with me. Now that I’m in my 30s, I’ve started allowing myself to embrace creative hobbies for the hell of it, though I still struggle with the tension of “I’m spending all this money on my hobbies, so surely I need to, well… get some of that money back?” But what’s the use of having a job that fulfills more than my basic needs if I can’t spend that money on enriching my life through music and art?


Because the problems at hand are complex systems problems – where the root causes are not the actors themselves, but the ill-designed structures and incentives that dictate their actions – we should think about redesigning the rules and incentives of social, political, and economic systems as the path forward.

History of the Capital AI & Market Failures in the Attention Economy

This article spoke to the political theory fan in me (it was my college major, after all) and while I didn’t completely understand everything, I was able to follow the general themes and found myself nodding along with the author’s proposed solutions. It’s a good exercise in potential solutions for our fucked up mess of a country, but I wonder how we’d go about actually implementing said solutions. It feels like in order to implement the solutions, we’d need… to have already implemented some of the solutions. Or at the very least, someone needs to unseat Mitch.


Ideas ride us into battle like warhorses. We can witness, participate in, and even lead these battles, but their true meaning eludes us. We don’t really know where ideas come from, nor how to control them.

The tyranny of ideas

Somehow or another I subscribed to Nadia Eghbal’s newsletter, The Internet is a City. This post she mentioned writing in her latest email caught my eye: “I wrote about how the world is run by ideas, not people, and how reputation can become a blessing and a curse for creators.” This is a good one sentence summary of the post, and I’m not sure what else to mention, other than I enjoyed her philosophizing on the topic.


I have come to regard [subtlety] as something of a dark art, a force of nature that can be summoned but never fully harnessed, and can backfire at the slightest misstep. Anyone can pick up a bullhorn and make her intent clear to all, but to attempt something subtle is to step blindfolded into the unknown. You are always teetering on the brink of insanity. You are always walking on a wire strung across an abyss, hoping to make it from one end to the other without losing your balance, or your mind.

On Subtlety

There are thoughts brewing here, inside my head, but they need time to steep.

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