Side Hustles – Making and Selling Fonts

  • On April 22, 2024 ·
  • By ·
Drawing board with stacks of hand-lettered papers, markers, and pencil sketches of lettering

As somebody with ADHD, my brain craves novelty. Ever been in the shower, rinsed out your hair, and realized you don’t remember if that was shampoo or conditioner? It’s a similar experience when I’m not fully present in what I’m doing. Even subjects I’m passionate about can be a struggle so part of how I approach things is finding ways to make them engaging. A good method I’ve found is weekend projects. Something I can dive into for 24-48 hours, low risk so it becomes creative play, different enough to satisfy that craving for shiny and new, and satisfying to wrap up in time so I can return to my regular grind feeling competent.

Why Fonts?

I have experience making handwriting fonts for my comics. The process is fairly straight forward, especially since there’s a known number of designs to make. I start from a template, create each character using whatever method best fits, bring them into the software, and spend the rest of my time testing and adjusting alignment. Fonts are great self-contained projects. I can experiment with different programs and methods, even go entirely old school and draw on paper. There’s a useable asset at the end I can use however I want. Every font is unique and helps me build up a collection to offer.


My weapon of choice is High-Logic FontCreator. It’s Windows-only, though runs fine on my Macs with Wine. At the time it was the most affordable option that vectorized images on import. I also appreciate a perpetual license.

(FontCreator – Getting Started on YouTube)

If you need free tools try FontForge or Birdfont. For browser-based options there’s FontArk, Glyphr Studio, FontStruct or Pentacom’s BitFont Maker. I’ll also throw in Metaflop if you like playing with sliders.

Calligraphr and YourFonts are sites where you download/upload a template to make a font. They’re not very robust but they are a simple starting point.

Other premium options include apps by FontLab, Glyphs, and RoboFont. Fontself offers an extension for Illustrator and Photoshop CC as well as an iPad app. There’s also iFontMaker for iPad and Apple silicon.

References for Designing Typefaces

Designing and laying out typefaces for fonts should really be its own post. For now I’ll share some useful resources. I particularly like vintage lettering books as they’re instructional and show off the craftsmanship involved. My personal favorite is the Studio Handbook: Letter and Design for Artists and Advertisers by Samuel Welo. It’s 282 pages of hand-drawn text and illustration.

(Hand Drawn Design from Cover to Cover via Printmag)

Here’s a Digital Bookshelf of Lettering Manuals and Alphabet Source Books from Typographica.

Lloyd Reynolds’ Italic Calligraphy & Handwriting

(Lloyd Reynold’s Italic Calligraphy & Handwriting on YouTube)

Where to Sell

Another subject that could really have its own dedicated post. For now I’ll strip it down to basic site categories and examples.

Dedicated Font Sites: My Fonts, Fontspring, Monotype, Fontbundles, So Fontsy

Marketplaces: Envato, Creative Market, Creative Fabrica, Design Bundles, Master Bundles, The Hungry JPG

Digital Downloads: Gumroad, SellApp, Sellfy, Payhip, Podia

WordPress Plugins: Easy Digital Downloads, WordPress Download Manager, Download Monitor, Digital Download Goods Checkout for WooCommerce


Font licenses, like all copyrights, can be complicated. I’m sure if you’ve spent any time on Fontspace or DaFont you’ve noticed the difference in selection of Personal Use vs Commercial. There can be different licenses for desktop, web, app, and ePub uses. As somebody who downloads and uses fonts regularly, I like to keep things simple. Free fonts exist for various reasons (to attract buyers to premium fonts, for altruistic causes and purposes, or because they’re an educational experience) and I think it’s a good idea to offer them. If you’re going to charge, especially if it’s more than a few dollars, then your goods need to be of outstanding quality.