Okay Type: Normal stuff, just done really well
  This headline is set in Okay by Okay Type. Get it on Fontstand for only €4.50/month.

Okay Type is Jackson Showalter-Cavanaugh, a one-person (plus cats) type design studio and foundry in Chicago, USA. Apart from a well-curated retail catalog and custom type design projects, they are specializing in fancy home-made pizza and Laugenbrezel. Indra Kupferschmid interviewed Jackson in the slowest way possible (2/2020 to 11/2023) about life as a graphic designer and type maker.
This headline is set in Okay by Okay Type. Get it on Fontstand for only €4.50/month.

Photo: Jackson Showalter-Cavanaugh

Jackson Showalter-Cavanaugh started the company in 2009 by quitting his job as a graphic designer at a large agency in Chicago and deciding to focus on type, not really knowing yet how exactly.

“I did not have a plan when I quit my job to be a full-time type designer. As a student, I didn’t really understand graphic design. I thought it was the most practical thing to do at art school, but I never really felt like I knew what I was trying to do. Then at some point I remember learning that there were people who just drew typefaces. Behind the scenes of all of the cool graphic design things I was struggling to care about was this secret world of super obsessive, hyper-detailed nerds who specialized entirely on drawing letters. I was instantly hooked and wanted to learn all I could. I also learned how freaking hard type design was and realized I was not ready to do it.

“So I went to work as a graphic designer at a big design agency. It was a great experience, I learned a ton about how the design world works, developed a strong design point-of-view, all that stuff. But after a few years the 60, 80, 100 hour work weeks caught up and I burnt out.”

What frustrated you most about agency life?

“It’s a little hard to remember, and it’s not really fun to think about that stuff. I definitely remember that I did not fit in. Like, at all. I didn’t even know what clothes a graphic designer was supposed to wear. I showed up on my first day dressed in my wrinkliest IT Department business casual. I was a total slob, not the typical smartly-dressed graphic designer with one quirky detail like ‘I always wear something orange’ or whatever (still true).

“The most frustrating thing was how little I was able to deal directly with clients. I get it, huge companies have layers of management. And the decision makers’ time is more valuable than everyone else’s. But it always seemed like the intermediates were always reinterpreting things to make them more palatable to whoever they were talking to, and that leads to a lot of misunderstandings. No one wants to redo a week of work because they were told the VP wanted a ‘warmer’ design.”

“I still really wanted to try doing the type design thing and thought I should spend a year exploring that full time. Finish a typeface just to say I did it. I honestly didn’t know what to expect financially or professionally. Hopefully it would lead to more interesting font-related work because I didn’t want to have to put together a new graphic design portfolio.”

That first typeface to finish was Alright

technologickému Richard Danielpour 507 Small Arbor verschwörerisch

Le Petit-Quevilly Calle Mederos 330-65 skeiðarársandur comercializador

forstwirtschaft Torsten Brandes West Valley City Wienring 96

Casas de Bárcena nepremišljenost Ernst Wilhelm Wolf 646 Cold Stead

The Alright Sans family consists of four widths: Normal, the slightly more compact Narrow (shown here), Condensed and Compressed

Alright, released in 2009, came out at a good time for digital fonts. It filled the then-void of semi-friendly, semi-serious typefaces that don’t outright hug you but are also not as stiff and impersonal as Helvetica et al. Available at MyFonts at its heydays, Alright saw quite the success. With webfonts starting to gain traction, it was chosen by large companies for their corporate design with the need for more styles and variation. After several rounds of expansions initiated by custom adjustments, Jackson released Alright v2 in 2019 as a replacement.

“Alright was my first typeface and it had a lot of ‘first typeface’ issues. I didn’t know what to expect when I released it but people actually started buying it and using it. Customers started requesting a condensed version but by then I was so embarrassed by those ‘first typeface’ issues that I couldn’t think of sinking any more time into it. So instead of doing the healthy thing like moving on to draw my Helvetica-killer or jumping on the Geo-sans bandwagon, I decided to turn a simple Alright expansion into full-on, from the ground-up, Alright revival. The new version looks much better so I guess it was worth it.”

Speaking of first-typeface syndrome – how did you pick up what is needed to draw and get a typeface to work? Do you sometimes regret or miss that you didn’t attend any formal type design program?

“Every single day. But that’s just imposter syndrome. Pointless self-doubting insecurity. I’ve been making type as my job for 15 years. School might have helped me get somewhere in my career sooner, but that place wouldn’t be where I am today. And I’m pretty happy how things are going with my tiny slow type business.

“I always think I could do a better job though. I could draw this thing better or know more about that topic. Self-doubt can be an excellent motivator. I can’t get better if I don’t know where there’s room to improve.”

Almost every single day, I think about a quote from a 2014 interview with Jackson on the blog Workspiration (very 2010s): “I sincerely want everything to be better. Everything. There is too much shit in the world and most of it exists only because someone didn’t try hard enough to make something as good as possible. I fucking hate that. Why make something that isn’t great? So instead of crapping out a dozen half-baked shit fonts I try to concentrate my efforts into making just a few things as good as I possibly can.”

It was the booming period of “move fast and break things” and “better done than perfect” and he wasn’t having any of it. Someone (US-American) actually concerned about and striving for quality, workmanship and high standards? Hear, hear! I still have a note with it on my office wall.

A slightly wrinkled piece of A5 paper with the quote “Why make something that isn’t great. I fucking hate that” stuck to a wall with clear tape, to the left a yellow post-it note with the text PW: 123”. Slightly blurry in the distance a bookshelf and a pile of papers on an untidy desk

Jackson’s quote on my office wall

What in fonts or what kind of fonts were you missing while working as a designer?

“Corporate design is usually very boring. Sure, there are ‘concepts’ and things need to stay interesting enough to appear just the right amount of fresh and contemporary. But it’s all weighed down by the need to appear trustworthy and authentic. A good investment for the shareholders. Which means the most interesting parts of a design are handled cautiously. In my experience, fonts are usually the first thing to get the red X for being too ‘out-there’. Corporate typography always errs on the side of being a little too safe. So my design goal has always been to make something that hits that sweet spot. Interesting to a designer but not particularly noticeable to any middle-management non-creatives looking for opportunities to justify their existence in the process with a red pen.”

I want to imagine this is the brief Jackson designed his typeface Harriet to. Something he would have liked to use as a graphic designer: an extensive, versatile Scotch-style serif family in Text and Display variants. With all the bells and whistles you’d want for editorial and advertising design, sharp detailing in the Display and excellent, calm readability in the Text styles. Not too crazy but sophisticated and adaptive.

Roger, Elizabeth Anspach and Khartoum-Omdurman’s nice

Pip & Richard Krämer, 91 Chaussée Caroline Landry multiprocessors Villenave-d’Ornon

Harriet Display is one of two optical sizes of Jackson’s Harriet typeface, “a contemporary reimagining of Baskerville with a dash of Scotch Roman”, as he describes it. Below, the less sharp and detailed Harriet Text styles

Sonnenuntergang Nizhny Novgorod saltvandsområde Franz Ignaz Beck

Luigi Castellacci Villar de Olmos Sabrina-Heinrich-Markt 88 skeiðarársandur

Baixada Santista Via d’Ausiàs Marc 11 saltvandsområde verhältnismäßig

constructivisms Dammarie-les-Lys skeiðarársandur Jan Václav Voříšek

Leaving agency life also meant leaving Chicago for New York City, albeit briefly. After a couple of years, he’s back in Chicago – a city with perhaps not a large type scene or many type events but a lot of type history. Printers Row, Marder and Luse / Chicago Type Foundry, Bertsch & Cooper …

Does the glorious past type scene of Chicago inspires or influences your work?

“Oh, yes, I really enjoy researching Chicago’s design and printing history. It’s a shame how much of that has been lost to the graphic design historians. Try to talk to a young designer about R. H. Middleton or Ray DaBoll. A lot of that is because almost all pre-Helvetica graphic design has been forgotten. But it is also because those designers didn’t do a lot of self-promotion. The bulk of the work done in Chicago was for every-day stuff. They weren’t making fine books or extravagant posters. They were lettering newspaper ads for cars and designing packaging for food. Normal stuff, just done really well. I’d like to think my sensibilities are similar. I want to make practical, useful things. I want them to be made really well. And I’d prefer it if people not really know that I exist.”

Oops 🙊

What if Gill Kayo didn’t look so weird? Kinda humanist but always extra bold

Richard Leveridge 91 Chaussée Caroline Landry multiprocessors Villenave-d’Ornon

Okay, this typeface name may sound confusing here, is the extra bold display sans from Okay Type. The three widths and italics set a punchy, black headline

The fonts mentioned in this article are available to rent by the month for a fraction of their retail price on Fontstand.