Steve Matteson has designed some of the most ubiquitous typefaces in the world, and engineered the original core fonts for Microsoft, adapting Times New Roman, Arial, and Courier, which you’ve probably used for term papers or resumes or anything else you wrote in Word. He has also created some less-classic designs that he’s not too proud of, such as “ Curlz ,” which falls in the Comic Sans camp of typefaces reserved for high school yearbooks, princess-themed birthday party invitations, and mockery.

But that is the plight of a professional font designer: One day you get to make lasting letter sets, the next you have to pay the bills. “Sometimes you have to do work that you’re not really proud of,” Matteson, the creative type director at Monotype, told Fast Company. “That’s why we call it work instead of play.”

Steve Matteson

Matteson’s interest in words began as a teenager, and he set up a printing press in his basement. In college, at the Rochester Institute of Technology, he discovered rare books. He fell out of love with mass printing, and was drawn to calligraphy and lettering as an art form. “You could hold these books and page through them and really appreciate the craft from centuries ago. That really turned me on to the art of the book,” he said.

Despite drawing much of his inspiration from what he calls “old-school” Goudy-style fonts and the book arts, Matteson would go on to create some of the most lasting typefaces of the computing age. And, as we enter a new mobile-first, digital-exclusive era of reading and writing, Matteston is also at the forefront of that typeface revolution, designing for major tablet and e-reader makers.

The shape of Half Dome has beautiful soft curvature at the top and abruptly falls straight down…I used that in one of my typefaces.

While recreating the alphabet from scratch sounds like an increasingly difficult task–by now, you’d think that every possible permutation of legible letter shapes has already been created–Matteson sees more opportunity than ever to design new, better fonts. “I worried about that when I first started because back then, 25 years ago, resolutions of screens were so limited, the pixels were so coarse,” he said. “But now that we’re reading on devices, I have a whole new generation of eyeballs to design for.” Fast Company talked with Matteson about how he plans on continuing to make lasting, beautiful, and sometimes wacky fonts.

“When designing typefaces, most designers probably find the biggest challenge is exercising restraint in their kind of free thinking as a designer, wanting to just go wild. Typeface design requires so much restraint you have to reign in that impulse to go crazy to make them legible and functional.”

“I often equate type design to writing music. A lot of work I do is custom work, working with a client, mobile user interface, or a print magazine. It’s similar to going up to a musician and saying: ‘Write me a jingle. And it has to be written in this key, and it’s going to be sung by a male so it has to be low in the register, and we want it up tempo,’ and all these other sort of things they might specify for a piece of music. It is similar for specifying what they want in the typeface. That builds the structure.”