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Jackson Cavanaugh is a typeface designer in Chicago. He spends his time drawing letters, making fonts and managing his small type foundry, Okay Type. His typefaces Alright Sans and Harriet Series have won awards from Communication Arts and the Type Directors Club. Sometimes he makes fonts for clients like 3st, Converse, Crosby Associates, IDEO, Motorola, NewPage, Ogilvy, Otto Group, Potbelly, Starwood, Trek, Uppercase magazine, and VSA Partners.


As Perfect as Possible

How did you get started in typography? Originally I went to school for graphic design. At some point I read a type book and something clicked. I wasn’t all that interested in design briefs or audience research or even color, but holy shit, was I interested in type. I read every type book I could get my hands on and turned every project into something type-related. Except I wasn’t good enough to be paid. So I got a normal graphic design job out of school and continued my type obsession on the side.

What personal experiences or circumstances have most influenced your work or style? The handful of years I spent as a graphic designer were invaluable. Working with clients, vendors, design directors and project managers doing high-level branding and corporate communications taught me how design actually happens. More importantly, it showed me what designers and clients want from typefaces, what features they look for and what it takes to get something approved and out the door.

What’s something that people misunderstand about typeface design? Beyond the general lack of understanding that actual people spend actual years actually drawing every single character of a font? I’d say the biggest misunderstanding is about quality. For every good new release there are a hundred worthless ones, and there’s so much marketing fluff around each release it’s hard for designers to process the actual quality, usability and originality of a design.

What is the strangest assignment or project you’ve ever worked on? A few years ago I wrote some OpenType code to swap sets of alternate-width characters inside a monospace font. For instance, a normal monospace font has an unpleasantly wide letter I and a cramped, narrow letter M, so a word like SLIMMINGLY looks kind of bad. Our code found instances where we could cheat narrow letters narrower and wide letters wider without breaking the overall monospace block of text.

What would be your dream assignment? I watch a lot of hockey and baseball and I spend a lot of time obsessing over the typography on the uniforms. It’s sad to see so many baseball teams, even the well-dressed ones, use the same exact chamfered lettering on the back of their uniforms. I’d love a chance to work on fixing something like that.

What is your biggest challenge as a type designer? Most of my projects are very long, painfully slow and usually self-initiated. It’s a challenge to stay focused enough to actually finish them, but it’s a good form of self-editing—if I’m not interested enough to finish a typeface, it’s probably not interesting enough to sell to designers.

Which type designers do you most admire and why? Matthew Carter. He has worked in every phase of typesetting technology: metal, photo, digital. He knows type history better than just about anyone. But his work isn’t stuck in history; it builds off it and combines seamlessly with the present. He’s struck an amazing balance.

What other profit centers could type designers explore besides commissioned work? There’s a reasonably large but competitive market for lettering and editorial illustration right now. I draw logotypes occasionally. I know a few people who do excellent typographic consulting for agencies and publishers, and there are retail sales of desktop licenses (and webfont licenses, e-pub licenses, app embedding licenses, etc.).

Do you have any advice for people just entering the profession? Do you really want to do it? Seriously? Learn to spend way too much time working on a project. Type design is about getting every detail as perfect as possible. It’ll take years to learn the craft before you should consider releasing anything to the public.

What’s one thing you wish you knew when you started your career? I wish I’d spent more time learning the business side of things: How to negotiate licenses and commissions, what details of distribution agreements are good and bad, how and what to charge and when to get help from people smarter and more talented than me.