Continuing the theme of software fixes for hardware problems, here’s an essay I wrote in 2016 about a broken computer display that I “fixed” as a teenager, just because I wanted to play Civilization.

It remains one of my favourite things I’ve ever written.

One of the small things I added to Medium in early 2016 was a change to the favicon:

It came from an observation about the writing process. When writing on Medium, you are likely to have a bunch of Medium tabs open with other posts, yours or otherwise, for reference… but you usually only have one tab you’re writing in. Why not make it extra visible so that you can easily come back to it?

But there was a second, more emotional reason. Writing is hard. Many people never touch the “New story” button, on Medium or otherwise. I wanted the writers to feel extra amazing, with the interface itself giving them a nod of recognition. (Visually, the hollow draft icon was also meant to be a “scaffolding” of the published story icon.)

I’d love to hear more about websites or web apps that are using favicons in a particularly useful or delightful fashion. If you have examples, I would appreciate a note!

When I was at Medium, over a decade ago, I really enjoyed going deep on typography.

People seemed to generally enjoy what we did. Writers really loved automatic em dashes and range dashes, discovered the beauty of hanging punctuation, and as funny as it might sound today, the smart quotes were a huge hit, too. I was proud of the tight drop caps, the underlines brought me some notoriety, and we even supported ligatures at a time when not only this wasn’t the default, but it also had some mildly scary performance consequences.

But for every two things that worked well, there was also something that in retrospect proved to be me trying too hard, and had to be quickly undone.

I was really excited about resurrecting pilcrows, but many users saw them as rendering or escaping errors.

I briefly added vulgar fractions to all the places where Medium rounded numbers, but that made those numbers confusing and weird in practice.

(And I already mentioned the strange, rare bug with system fonts, although I suppose there are always bugs.)

It was an interesting calibration process. And somewhere in between successes and failures was one thing that I have never mentioned before, and one nobody ever brought up.

I recently shared the story of 2015’s typographical redesign of Medium. As we were exploring the candidate typefaces, we fell in love with one in particular: Charter, a font designed by the industry legend Matthew Carter – and no, this is not a bug, Google Search switches to using Carter’s own Verdana to honor him.

Charter had this perfect balance of “casual” and “refined” we wanted for Medium at the time. Unsurprisingly, it also came with a bunch of typographical niceties – among them lowercase (old-style) digits, which I really wanted:

But there was a problem. Those lowercase numerals came with a “medieval 1,” a particular style of a lowercase digit 1 that resembled an uppercase I. People hated it and were confused by it, thinking indeed that a bug caused a letter I to make its way to the numbers.

No amount of pleading would get us to push that digit through. The backup plan was going with uppercase numerals, but I hated the idea; those digits felt so ugly and pedestrian to me – they were not just uppercase, but also monospace! It was a frustrating situation, being so close and yet separated from a warm Charter embrace by one glyph that it didn’t happen to have.

And so… I drew one.

I, someone who has never ever designed a typeface, decided to vandalize Matthew “The Most Widely Read Man In The World” Carter’s typeface and plop in a new digit 1 of my own creation.

The internal complaints stopped. Weeks later, we launched the new fonts, Charter front and center, my fresh non-medieval 1 attached. I don’t remember the exact details, but we found a way to do this that was compatible with the font’s licensing – and yet I never talked about it because… well, I think you can understand why.

I believe my rogue 1 lasted until a subsequent redesign in 2022, long after I left the company. A decade in, I still don’t know how to feel about it. Did I save Charter as a candidate for Medium by mutilating it a bit, am I writing this post just to launder my own ego, or is this the equivalent of a perp coming back to the scene of the crime? Was I ambitious (laudatory) or ambitious (derogatory)? Maybe you can tell me. But I hope either way it makes for a fun story.

Speaking of remastering (and diacritics), I grabbed my older Medium deep dive called The curious case of the disappearing Polish S, and put it on the new site.

It looks so much better than on Medium and while I was at it, I’ve redone all the visuals, and updated it a little bit.)

It’s still probably one of my favourite bugs to encounter. I hope you enjoy!

I just published a new photoessay about the history of the Fn key, and particularly what Apple has been doing with it recently.

Do we need yet another person crashing out about Apple’s design decisions? Am I doing it only because it’s fashionable to be on Apple Design Hate Train these days? I’ll be honest: I don’t know.

But I have been bothered by Apple’s approach to this aspect of its keyboard design for a while, because it starts breaking what I think is really important in using a computer well: keyboard shortcuts.

I hope it’s also a fun visual history of the most tricky of modern modifier keys.

(And if you like it, I linked to a few of my other keyboard essays in the footer.)