From HOW to NOW: A Font Journey 

By John
 | 
September 15, 2025
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In 2016, I was awarded an all-expenses-paid trip to attend the HOW Design Conference in Atlanta, Georgia. To say I was excited would be an understatement. The speaker list was a contemporary Who’s Who of design giants: Aaron Draplin, Paula Scher and Michael Bierut of Pentagram, Pum Lefebure of Design Army, and my personal hero, Stefan Sagmeister. I registered for every session I possibly could fit into my schedule. I was determined to soak up every ounce of inspiration.

At last minute, I also signed up to see Erik Spiekermann’s talk. Obviously, I knew who Spiekermann was — Stop Stealing Sheep was required text at Syracuse, though I’ll admit I never quite finished it. By 2016, I had also incorporated his most famous font, Meta, into several design solutions. Unlike the other speakers that I eagerly anticipated, I had no expectations for Mr. Spiekermann. Within five minutes of his presentation, though, his understanding and passion for typography was apparent and nothing short of inspirational. His unapologetic stance on the importance of typography left an enduring mark on my understanding of branding and design. I left convinced that Erik Spiekermann was a genius.

A Sketchy Start
Fast forward to today, and I’m three weeks into designing my first font. It’s a display font meant to attract attention at large sizes and on packaging, which is the exact opposite of a text font like Meta. Still, I’m designing a font! It’s a passion project that has sat in the back of my mind for years. Thanks to a digital product launch class, it’s not just a possibility anymore — it is finally going to become a reality. And, like any project, I have a deadline to meet.

I began designing my font rather hastily with messy sketches. Sketching helps me get the bad ideas out early. I initially imagined a quirky, playful font for seasonal invitations or retro signage. I was trying to think of fonts that other designers would use. But, as I refined my sketches, I realized that approach didn’t align with my personal approach to design.

Instead, I pivoted toward a bold, simple geometric sans serif. As I sketched, I began to brainstorm different applications for my new font. I also thought of ways to market it to my audience. I asked myself, what if I created a font that highlights its use for a very specific use-case scenario, like pizza boxes? Connecticut is kind of known for pizza, making the cardboard they’re packaged in ubiquitous. A new creative direction emerged.

Making a Font
Designing for a defined audience helped me to focus on the tone and structure of the letterforms. After sketching a few short words like, “PIZZA,” POP,” and “HOT”, I started to build the font in Adobe Illustrator. I traced and outlined several of the most important characters. Many of defining elements from these letters can easily be repurposed for other characters, giving the font a cohesive feel. This is a lesson I recalled directly from Mr. Spiekermann, nine years ago.

To test usability, I purchased Fontself Maker, an Illustrator plugin that takes your working files and magically export working fonts. For only $40, it’s somewhat of a game-changer. Watching tutorials and referencing Fontself’s guide helped me better understand the technical details of letterspacing, kerning, and the design nuances of typography. It sure beats outlining Franklin Gothic with Rapidographs, but the process hasn’t exactly been easy. The biggest challenge so far has been psychological. I keep having to escape years of corporate typographic norms to create something unique, original, and all mine.

Moving Forward
Still, my limited experience with font creation has been self-fulfilling so far. Next up: finishing the final eight characters, designing numerals, and tackling punctuation. I don’t want to underestimate the remaining tasks. Yet to be designed is the question mark, exclamation point, @ symbol, hashtag, dollar sign, percent sign, colon, period, hyphen, semicolon, and, my personal favorite, the em dash. Each element will be tested and refined in Fontself. Licensing research and marketing strategy are also on the horizon. I’ve got a few name ideas as well, but that’s next week’s adventure.

Looking back, Erik Spiekermann’s talk at HOW wasn’t just inspirational, it was foundational. It reminded me that the subtleties of typography aren’t to be overlooked. The best typographers painstakingly consider shape, form, negative space, and rhythm, visual tone of voice, and clarity. In some ways, this font is helping me appreciate all the typographic things I took for granted go so long. It’s about time I put Mr. Spiekermann’s lessons to practice.

Download a PDF of my week three Product Development Journal.

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