Typefaces for Writing

It took three attempts before inspiration finally struck for this essay. First, there was a conversation among a few friends describing terminal windows and typefaces, particularly how their form inspired creativity.

Then John Gruber wrote this, when linking to an essay from Jason Kottke:

Being able to apply italics or boldfacing to words is somewhat more expressive than being limited to un-styled plain text. Talented writers don’t need italics, but they can make good use of it if it’s available.

Considered together, they took me down a path of introspection. About my choice of typefaces, and the many forms my words assume as they funnel through my writing process.

Writing is a lot like photography. Most take pictures, but never become photographers. That’s not to say photography is hard or requires professional training. Consider the difference between a relative bombarding you with vacation photos and a professional photographer featuring their work at an art gallery. Your relative might show you hundreds of photos, with no organization or reason. You might only see a dozen photos at the gallery.

A photographer uses the process of selection to choose only their best photos, and discard the rest. It can be difficult to get rid of photos, particularly if you capture photos for memories. However, the art of selection is the essence of photography, and critical to your evolution as a photographer.

This same principle grounds my writing process. I became a writer the day I focused on improving what I write. And to improve, I committed to edit and redraft prose before I publish. Accordingly, each step of the process has been carefully considered.

Noto Sans & EB Garamond

Any serious effort for an essay begins on my reMarkable Pro tablet, using the type cover. Formatting options are delightfully limited, which keeps me focused on words. A fellow type enthusiast might glance sideways at the two typefaces used by the reMarkable. There are numerous devices and iOS apps dedicated to drafting. Most of the iOS options let me customize my choice of typeface, so why the reMarkable?

I’ve found a lot of debate and thinking online about the art of drafting. Many focus on “silencing your inner critic” and getting your words out as quickly as possible. I was looking for a way to get beyond an initial thought and work the problem. If the first draft is a stream of loose thoughts, the first edit helps me determine if I have anything. And that is the breakthrough feature of the reMarkable.

The challenge was avoiding a feeling I call writer’s debt. This feeling is similar to technical debt, for any fellow programmers reading. Early on, I struggled with editing large bodies of text because it was so tedious to edit using a keyboard.

Before the reMarkable, I experimented with printed copies of my drafts. I would mark them up with a pen, and it made the process feel wonderful¹. If you’re familiar with the reMarkable tablets, you can see where this is going. Their tablet², paired with a type cover, is the digital replica of a typewriter and red felt pen. I type my drafts into narrow columns of text, then use the attached stylus to add red corrections over it.

There are less dead trees involved, and the slender tablet is more convenient to carry than a folder of loose paper. Every page I create on the reMarkable hardware is automatically synced to a cloud service, and there is an app to view them on my Mac³. The reMarkable is an improvement to my drafting process in many ways.

But I was still accruing debt that required tedious keyboard work. The process was difficult to restart after breaks, and it was error-prone. Instead of a single editing pass, I required multiple passes to find any errors introduced during the update.

SF Mono

Any writing I want to publish goes through Ulysses: my preferred editor for Markdown. It is configured to use one of the best monospaced fonts available⁴. Before I used the reMarkable for drafts, everything started in Ulysses. However, starting in Ulysses led me towards updating existing drafts in place. As I’ve already mentioned a few times, it was tedious.

I found a new way to edit, not in hardware, but with a process called trash drafting. Each draft gets re-written from a marked-up version of the prior draft.

The theory of trash drafting is that by reflowing text through the keyboard, you prevent errors that can occur in sentences when you select and replace parts of it. In practice, I’ve found this reduces the need for additional edits. Trash drafting is why I felt comfortable using the reMarkable for first drafts. If I’m going to re-type a subsequent draft on the Mac, why not take advantage of a device that lets me develop the original idea?

While re-typing, it’s also easier to consider typographic details and style. Ulysses and SF Mono are ideal tools for considering emphasis, hierarchy, and section breaks.

Essays on this site are typically written across three drafts, where the second is typed into Ulysses. Fiction often requires several more drafts. Fortunately, Ulysses allows me to export Markdown to various formats, including PDF. I can always return to the reMarkable for markup, by exporting a PDF from Ulysses and syncing to the tablet. Once it’s marked-up, I re-type the marked up version back into Ulysses.

Trash drafting sounds time-consuming, but I’ve found it a more efficient approach to editing. I can take breaks during editing and always know where I left off. I’m a faster typist than I realized, and the extra typing keeps me in the flow.

Trash drafting is the glue that brought my writing process together.

Equity & Bild Compressed Light

The third form of review uses the typefaces chosen for this page. I copy exported Markdown from Ulysses and paste it into Nova, my preferred editor for web development. All of my published writing is kept in a GitHub repository, alongside the Jekyll configuration files for the site.

In Nova, I preview a replica of my published site, then check my writing for any artifacts in its final typesetting. Even during this review, I will make final tweaks to language to minimize widows and ensure a smooth typographic flow.

For essay titles, I selected a compressed style of Bild, a typeface from Jonathan Ross. I first saw Bild in his font-of-the-month club, where its bolder variants reminded me of the gothic sans common to German street signs. The lighter weight was well-suited for my essay titles.

Equity is a lovely text face designed by Matthew Butterick, which I favor for its newspaper looks. The masthead of a prior version of this site was set in generously kerned small-caps, which is a treatment that originally drew me to Equity. There are two body presentations set in Equity. Essays use a traditional web layout, where paragraphs are separated by an extra line space. For fiction, I use a slightly larger size, forgo the additional space between paragraphs, and indent the first sentence⁵. This style is a nod to Agatha Christie. Her style used paragraph breaks for dialogue, using a new paragraph when the speaker changes.

In addition to a nice typographic texture, this allowed her to avoid speech verbs and use short paragraphs to convey the actions of her characters. Taking inspiration from her style has helped me avoid needless exposition, by focusing on punchier dialogue and character action that provides movement within a scene.

Three Forms

In all, my writing is transformed into three forms during its evolution from raw idea to published piece. The typefaces selected for each phase serve a purpose, but the contrast between them is the largest utility. I’ve found my words can lose feeling after repeated reviews. It can be difficult to keep the ideas fresh while I edit. Each time my writing transitions between forms, it feels and reads different. I use each form as an opportunity to reintroduce myself to the composition.

Experimentation is an important part of growth, and I hope I’ve convinced you to consider your process more. The reMarkable Pro, Ulysses, and typefaces mentioned above are all opinionated choices. They work for me because they best support what I’m trying to accomplish at this moment. I expect to continue experimenting.

After all, writing—like photography—is a pursuit of continuous improvement.