Buying a font may be better left to professionals. That’s because font licenses are a minefield, and buying a font is a bit like buying a DIY computer thirty years ago.

I’m a huge fan of Matthew Butterick’s Typography for Lawyers, which has helped me make big improvements to my personal and professional documents and websites. Butterick also has me convinced I ought to be using better fonts than those that came with my copy of Microsoft Word. But whenever I’ve tried, I wind up deciding that Georgia is good enough.

That’s because fonts, as it turns out, are a great example of how to take something simple and straightforward and make it a royal pain to buy and use.

Font licensing is a minefield

Chances are that if you buy a font and use it like you normally use fonts, you are probably violating the license.

For example, one of the fonts Butterick recommends as an alternative to Georgia—the font I use for most text—is his own font, Equity. I happen to like Equity, but the license would make it practically impossible for me to use it.

Even though the license is short, it makes my head spin. First, it looks like if I purchased the font for my firm, I wouldn’t be able to use it for personal documents. That’s a problem, because like most solo practitioners I know, I use the same computers for my firm and for personal use (not to mention Lawyerist and Bitter Lawyer). So I’ve either got to buy two licenses (maybe four, in my case), or think about that license every time I start a new document. (Update: Says Butterick “You’re a solo attorney, right? So if “your firm” buys you a license, you can use it on personal documents. That’s not a hair I’m going to split with any solo attorney.” So that partially resolves this issue.)

Let’s say you use Equity for everything. You probably just make it the default font in Word so you don’t have to think about it. Then you need to write a personal letter—to your auto insurer, perhaps, or your bank. Don’t forget to change the font.

Or let’s say you are a member of the Lawyerist LAB or a local email list, and you want to share your client intake checklist or your flat fee retainer. Better remember to change the font before you share it, or turn it into a non-editable PDF, because you’re only allowed to share an editable document with fewer than 20 people.

What if you write a blog and decide to embed Equity in your blog, as Butterick recommends? Be careful with those landing pages; you only get three domains. And make sure you don’t get too popular. At 100,000 monthly pageviews across those three domains, you’ll have to remember to contact Butterick for a bigger license (which isn’t identified on his website).

And the thing is, the Equity license is better than most other font licenses I have come across, and it still rules out some fairly normal usage.

What is a font, anyway

It turns out that, even if you get past the license, a font is a much more complicated thing than you might think.

I looked into buying Futura because I thought it would be a good display font for one of my websites. My Google search led me to Linotype, where the page for Futura lists twenty-two different styles, all sold separately. You want to be able to use italics or boldface—or both? They don’t come together, and the “value packs” aren’t much help.

So even if you know what font you want to buy, you still may not be able to figure out what you actually need to purchase.

Fonts are for designers, not normal people (and lawyers)

In the end, I’m beginning to realize that fonts are not meant to be purchased by normal people (or normal lawyers). They are meant to be purchased by typographers and graphic designers. Unless you speak fluent typographese, you are probably better off sticking with the fonts that came with your software, no matter how much Butterick trash talks them.

But definitely get a copy of Typography for Lawyers. Even if you can’t put the font advice into practice, the rest is well worth the $25 purchase price. Edit: I just bought the Kindle edition so I would have a copy on my iPad.

By the way, I am hoping Matthew Butterick stops by to tell me I’m just being a dummy and this is all very user-friendly and I’m reading the licenses wrong and shopping at the wrong websites, or something. I really do want to take his advice and use better fonts, if I can.

Update: Butterick did stop by, and you should read his comments below. He thinks I have misinterpreted some of the terms of his license, but since I’m not convinced, I will let him speak for himself.