Mark Simonson

There is a problem with that approach. Many apps have a small caps button or command. If the font includes small caps, they are used. If they don't, the the caps are scaled down. Your users will need to know to ignore the small caps function and change fonts instead.

Thanks for posting these, James. Peckolick was one of my heroes.

Persistence and constant striving to improve my skills. Being obsessive helps. Don't underestimate the luck factor, but the skills are a prerequisite.

First, just to clarify the terminology: A typographer is someone who specializes in working with type, not someone who designs typefaces. It used to be an actual job position in publishing houses and advertising agencies. Nowadays, the computer has turned us all (especially graphic designers) into de facto typographers. Because the term is now rather obsolete, it seems to have been taken up by newcomers as a synonym for type designer. It's not. Please stop. The proper term is type designer.

The number of people doing type design full time is very low. Probably in the hundreds globally.

I support myself solely from retail fonts, which is unusual. Not only does it require skill, it also depends a lot on luck. If you want to follow this path, release lots of stuff, but keep your day job. If you get lucky, it might become full time. 

Other ways I haven't tried:

Get a job with a company that has in-house type designers. This seems to be a frequent path for people studying type design at Reading or KABK.

Do commissions as well as retail fonts (with primary income from the commissions) is probably the most common model for independent type designers. Better odds for success than only doing retail. I can't advise on how to follow this path since I haven't done it much.

As far as school goes, I studied commercial art for two years back in the seventies, but as a type designer I am mostly self-taught over several decades. Better to take a course if you're in a hurry.

I keep each font/font family in its own folder.

Within that folder, I have a folder for banners and other images needed by distributors and for my own site. I have a master Adobe Illustrator file that contains all the different sizes needed. I export required images into separate folders for each distributor.

I have another folder that contains specimens and user guides, both the source documents and PDFs for distribution.

I also make a folder for each new version of the font/font family containing the source documents, finished fonts, and anything else related to that version.

There are a few other folders for keeping information or documents relating the the font/font family as a whole.

I have a completely separate folder in which I put copies of the latest version of each font, organized by family and also by package (some distributors require preassembled sets). Whenever I need to send font data to a distributor, it comes from this folder.

I'm not sure if this is the best system, but I've developed it gradually over a couple of decades and it seems to work for me. I continue to tweak it. It was much less organized even ten years ago.