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.