Sending a perfectly-written email? That's so low-end.

• CEOs and powerful people love sending short, typo-ridden emails.
• With the rise of AI tools, a hand-crafted email is more meaningful — a luxury item.
• So unleash those typos, I say! Or "typoes," as I purposely typed in the headline. (Did you notice?)

I come bearing great news for my kind of people (horrible typists): Typos are the new status symbol. Garbled spelling, a missed space, improper capitalization — those are all the new and best ways to signal to others that you are powerful and elite.

The Wall Street Journal, a place that employs editors to do more than just catch typos, wrote about how the rich and powerful are, in some cases, abandoning perfect prose. The examples they cite include Jack Dorsey's all-lowercase memo announcing layoffs at Block and David Ellison texting David Zaslav and somehow writing their shared first name as "Daivd" (as someone who typos their own 5-letter name not unfrequently, I find this relatable).

The most notable recent example of how the rich and powerful have abandoned the bourgeois veneration of proper writing is in the Epstein Files, which are full of Jeffrey Epstein's awful typing in emails. Of course, Epstein isn't aspirational. Please do not mistake me here. But if you look at just his typing — and some of the replies he got from rich and powerful friends — you can gather my point: It seems that if you're rich and powerful enough, one of the many things people are willing to overlook is god-awful written communications.

I have written before about "emailing like a CEO" — replying to emails immediately, often with just a few words, or sending a message with just a subject line and no body. For the most important person at a company, some of the pleasantries of formal email style aren't required. I even tried emailing like a CEO myself as an experiment. Hammering through my inbox like Paul Bunyan made me feel invigorated.

The problem is that when you're not the boss, sending emails like a boss can come off as rude. Or maybe not? As the WSJ story points out:

Disregarding spelling and grammar in a written conversation can be a power move or a sign of friendliness, or perhaps both at the same time, said Deborah Tannen, a linguistics professor at Georgetown University.

It conveys: "I'm important, you're not so I don't have to bother," or "We're so friendly, I don't have to worry, we don't stand on ceremony," she said.

Handcrafted emails can show you're not AI

There's been a big change in written communication since I last tried emailing like a CEO, back in 2017. That's AI.

AI tools have made super-polished text easy to produce for anyone — either because you used ChatGPT to completely write an email, or a tool like Grammarly to polish up your own writing.

In general, giving more people access to well-written emails is a good thing. But in a world of perfect AI-written (or assisted) text, how do you stand out? How do you signal you're operating on a higher level than the hoi polloi? That's right — with typos.

Typos, sloppy grammar, and downright hostile capitalization: They're all signs of hand-crafted, AI-free writing. And when AI writing makes text cheap, the value of real writing goes up.

A typo-free email is workslop. Send an AI-assisted email with perfect prose, and the recipient feels you made no real effort. Send a bespoke, finger-typed email, and it shows you care enough to send your thoughts directly — without an AI filter. It's intimate, special, precious. Mistakes and all.

So if you want to send a really important email to someone, make sure you've got a few typos in there. And tell 'em Kaite sent you.

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