Hello. I've been fonting since Y2k was a concern, but there's just a barrier to progress I can't break. The problem is that my background is in literature and linguistics, not art... I just don't see the things the rest of you see. Can somebody point me towards something remedial? I know I'll never be great, but surely adequacy is a realistic goal?
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Instead of applying the elements of typical art education to the problem, consider your adapting your literary/linguistic strengths to the task of creating typefaces. Create difficulties for yourself and try to solve them to develop your design muscles uniquely. For example, take a literary work that you’re very close to and adapt it into a typeface where every concern is solved in a way that relates to an aspect of the story, setting, or character. During this process, learn about the works of artists and designers that relates to the task at hand. Having experience in a field outside type design can be quite valuable because, there’s a danger of arriving at the same conclusion as someone else. If you're okay with that, that's a legitimate strategy too, but it sounds like you want to go beyond that. In other words, instead of looking for a new tool, build with the one you have to develop your own unique abilities.
That means if you've only got one letter, you can figure out the vertical and horizontal stems and then you can create the H, I, E, F, T and some mathematical symbols. Find the pieces you can reuse to create what's missing.
For my money, there's no better guide that Leslie (now Zavier) Cabarga's Font, Logo and Lettering Bible and there's usually a used copy for under $5 bucks at Amazon.
The ABC of Custom Lettering by Castro
Lettering for Advertising by Leach
The Logo, Font, and Lettering Bible by Cabarga
Fonts and Logos by Young
Theory of Type Design by Unger
Anatomy of a Typeface by Lawson
The History and Technique of Lettering by Nesbitt
How to Create Typefaces by Henestrosa, Meseguer, and Scaglione
Designing Fonts by Campe and Rausch
Designing Type by Karen Cheng
Some of these are out of print and expensive so ask your local librarian to help you find them.
Look. Look at classics, look at forgotten masterpieces, look at the most highly regarded work of your contemporaries. Really look and try to understand why the shapes are the way they are, and why it wouldn’t make any sense for them to be other. Look at the relationships within a style, at how one shape informs another, or how shapes diverge systematically and try to describe the system to yourself.
There are techniques and analytical models that you can employ to help you understand what you are looking at—practicing making shapes with different tools, reading up on Noordzij’s theory of the moving front and applying it to the things you look at—, but what you’re ultimately trying to do is come up with your own internal language of design, your own way of understanding what you see and what you make.
Next, make a font of your own design that will achieve the same character count, with similar proportions but in a slightly different genre, so that you are not tempted to copy. Now, the trick is to make your design look as good, as big, and as smooth.
This process is remedial, as requested, in that it is practical, rather than based on principle, or analyzing the proportions of individual letters according to convention and authority, which is how critique is usually done, but only takes one so far. It also has the merit of giving due accord to the “colour” of body text, which to my mind is the heart and soul of typography. Don’t use kerning, that’s cheating!
Despite the tedium, by the end of the year, we had learned to really look at and analyze the many subtleties of various typefaces rather than just reading the words the letters spelled. In the critique sessions, the instructors would point out this or that in our tracing to make a point or two about those subtleties.
I doubt anyone would have the patience to do this on their own, and without the benefit of the subsequent group critiques, doing so might not achieve much. However, I suppose my relevant point is that carefully analyzing typefaces that work well, then figuring out what makes them work (or not) seems to be an obvious avenue to improving one's own type designs.
I would add to what Ray says and don't ever discount what skills you have. Sure you don't look at things in the normal way. Sure you might not know the formal term for a thing or two. Sometimes, as my wife (a trained classical artist and art historian) says, it's the formality that will trip you up and I constantly notice things she does that she doesn't, because she's been trained not to notice it.
Learn what you can, but don't feel that it's holding you back. If you've been designing fonts for years/decades, you're far more ahead of the game than the person who can name every little detail there is about font design and has never in a day done one at all.