The pedant in us all

I love pedantry. I am currently in the middle of a lifelong campaign to reclaim that word toward more positive connotations. For years I have told people that St Andrews, the Scottish city, has no apostrophe because the town was founded before the apostrophe entered English.

Claude tells me that the real answer is more boring: British convention dropped it. St Andrews takes no period either, because traditional British style omits the point on contractions—St, Dr, Mr—where the shortened form ends with the word’s last letter. I swear I read my favorite factoid in a book somewhere though.

I find useless information like this utterly fascinating, and I’m not afraid to go deep-diving into leather-bound books to learn the details. It’s what makes me a good copyeditor and, in another life, a good typesetter.

You see, nothing would make me happier than reformatting Word documents—cleaning up paragraph spacing and indentations, researching footnotes, and fiddling with the styles pane. Fiddling is a technical term. A part of me yearns to spend a week in a cabin with nothing but an espresso machine, my MacBook Pro, an Apple Studio Display, and Adobe InDesign reconstructing medieval golden-ratio text blocks. I yearn for craft, for beauty, especially the kind AI can’t yet create. It’s the closest thing I have to a calling in life.

If you told me you’d pay me to spend two hours on a slide deck describing why the chorus of Taylor Swift’s “The Man” should have been written “If I were a man . . .” because of the subjunctive mood, I might die. I mean that figuratively, of course. It’s hyperbole.

And since I’m about to write so much about rules, I want to be clear that I’m a proper prescriptivist, not an anarcho-descriptivist, as David Foster Wallace distinguishes them in his essay “Tense Present.” He argued that mastering the fundamentals are important because the details stand out to the reader, costing attention, which is worth a whole other essay. And do note the spaced periods in that ellipsis above rather than the single-character glyph … . The spaced version is The Chicago Manual of Style’s preference, which I follow unevenly. Welcome to my brain.

Yet I find myself working through strategies, budgets, and timelines to build marketing operations. The kind that work, of course. I love bringing to life a vision someone has carried for years about their business, messaging that resonates with ideal buyers, even the technical, agentic sales implementations I wrote about yesterday.

Sometimes I struggle because I don’t always know how deep to go. With one client we’re working through breadcrumb structured data to improve their SEO—specifically what Google Search Console means by Either "name" or "item.name" should be specified (in "itemListElement"). With another we’re scaling sales assets across a team using Claude Design and Claude Code. With another I’m considering implementing a house copywriting style guide. How deep in the weeds should we get? How much time should we spend on that?

AI has a particular way of writing. You see certain phrases that show up like “quietly” or “load-bearing” or “worth sitting with.” Much digital ink has been spilled about em dashes and “not this but that” constructions. But what I keep coming back to is Does it matter? (Should I capitalize that D in Does, or put the question in quotes because I’m externally verbalizing my internal dialogue, or set the sentence in italics as Chicago would suggest, or just put a colon after is and call it a day?)

I ask because there are far subtler details like these that nonetheless separate a professional from an amateur. But I wonder if the average person knows the difference.

I can tell when a writer starts a draft in AI and edits it afterward, because AI writes straight apostrophes rather than curly ones. Google Docs and Word substitute the correct character automatically—the right single quotation mark, U+2019. Claude doesn’t do that unless you ask.

It goes back to the way type was set for centuries: The apostrophe was created in 1496, which was then turned “straight” with the advent of typewriters and, now, computers. Typewriters had a limited number of keys, so one character had to do two jobs, and modern computers kept it going. New characters had to be created to go back to curly apostrophes. See Matthew Butterick’s brilliant explanation of the difference. (Code is the exception, where straight quotes are correct and curly ones will break your build. It’s why the error message above is set the way it is.)

Claude knows these rules, but only sometimes. It uses the single-character ellipsis where Chicago wants three spaced periods. It capitalizes the first word after a colon where Chicago would lowercase it, then lowercases where two full sentences follow and Chicago would cap. I used to capitalize the word after a colon, but I found §6.61 in the 16th edition of CMOS where I highlighted that ruling years ago when I was working at a publisher. I’m really fun at parties, I swear.

Claude doesn’t always know what to follow. Knowing the difference between Claude’s output and world-class copywriting—or world-class software engineering or graphic design—requires a professional. It also requires time. Lots of it.

Marketing fascinates me because it sits at the intersection of history, linguistics, technology, business, and psychology. The best in the world synthesize those fields, taking the strongest element from each and creating a harmony that moves people to action.

The question for me nowadays is this: what matters? I’d like to zoom in on a headline and inspect its tone, its apostrophes, its terminal punctuation. But choosing what to focus on in a given day is hard for me, hence my writing last week on priorities. There is only so much time.

I wrestle with myself. Craft matters. It’s why we flock to the IMAX theater to watch Christopher Nolan’s The Odyssey in 70mm, the way it was intended, the first film shot entirely with those cameras—a detail I could not have cared less about six months ago. But now, having seen it, I get it. Or at least I want to. Nobody explained to me why shooting 70mm film mattered. Even if they did I probably wouldn’t have cared. But I felt it. 

I guess that answers my question. Nobody wants craft they haven’t experienced. We are all pedants eventually. We just have to be shown good taste first. 

So, what do we focus on? What do we use our limited marketing budgets for? In short, pay for the pedantry people will feel.