Handwriting is so last century. These days, when we write, we type—which might help explain two recent documentaries on typography: 2007’s Helvetica and 2009’s Typeface. But where do fonts come from? To find out, we turned to one of the world’s few full-time typographers. Jackson Cavanaugh spends his days in his Logan Square apartment with his cat, A’postrophe, scrutinizing how his lowercase g looks alongside his r and, since a font should work in some 60 languages, how his Icelandic edh looks alongside his thorn. It’s a tedious job, but Cavanaugh’s first endeavor, Alright Sans, has been a bestseller on MyFonts.com for two years and was named one of the best typefaces of 2010 by Communication Arts (the typographical equivalent of an album going platinum and snagging a Grammy). In advance of the January release of his second effort, Harriet, we quizzed him on the evolution of an alphabet.

“A friend wanted to know what font a fashion magazine—something like Vogue Paris—was set in. The font was Baskerville, which is gorgeous, but when I’ve tried to use it, it didn’t work. Either the italic was too flourishy and floral or the bold got wonky and wide. So I started drawing Harriet, and it really quickly stopped being a Baskerville.”

“Baskerville, from the 1730s, set the stage for Bodoni, which evolved into Scotch Roman, which turned into Century. Century is the cleanest, most mechanical typeface, but it has almost no personality, whereas Baskerville has way too much personality. I took what works about Century and the personality of Baskerville and tried to turn that into Harriet.”

“My favorite magazine right now is Bloomberg Businessweek. It’s set in a custom version of Helvetica, which is the most boring typeface, but they redrew it to look awesome. It feels really refreshing and contemporary.”

“I tend to start with a mixture of simple letters, like an o or an n, and letters that have a lot of personality, like an r or a g. You have to make the interesting letters work with the boring letters.”

“Why does the a have a tail when nothing else does? Look back at the last few hundred years: The a has always had a tail. You can only change a very tiny bit about the way a letter looks before someone either can’t read it or notices it. You don’t want to notice details. You want to feel details.”

“My eyesight has gotten worse; I just got glasses for the first time. I have astigmatism, which makes me see an F like an E. When I went to the eye doctor, I thought, Wow, I’m going to be twice as productive!”

Choose your words

The typical computer comes loaded with around 200 fonts, but there are thousands more out there. MyFonts.com offers 89,000, ranging from free to $100 (Alright Sans runs $40 for the regular text version, $300 for all 16 varieties, from extrathin to ultraitalic). In January, Harriet will be available solely through Cavanaugh’s website, OkayType.com ($50 for the regular text, $450 for all 20 varieties).

Know your type

For blogs and e-mails, Cavanaugh recommends Georgia: “It’s superlegible—the best serif face to read onscreen.” He calls Cambria “a solid text face, good for resumés and documents.” For something “with a little more tooth and personality”—say, a birthday party invite—try Constantia or Candara.