February 16, 2026
Typos are the new power suit
Privilege Is Bad Grammar
CEOs say “pls,” interns sweat spellcheck — is sloppiness a flex
TLDR: The article argues that leaders often write sloppy emails because power lets them skip polish, and the crowd is debating whether that’s smart efficiency or privilege. Commenters called it countersignalling, flagged unfair pressure on non‑native speakers, and joked that “Sent from my iPhone” is the ultimate corporate shield.
The internet is clutching pearls and cackling over one spicy thesis: when you’re powerful, bad grammar becomes a power move. After recent chatter around leaked emails in high places, the community piled on with receipts — from bosses typing “K let’s circle back” to CEOs replying with lone 😂 emojis. One commenter swore those blunt messages were myth until they saw them up close, while another confessed they could spot a true CEO email by the telltale “pls.”
The hottest take? Countersignalling. As StevenWaterman put it, sloppy emails are the text equivalent of wearing holey sneakers to a board meeting — you’re so established no one dares question you. robmusial called it a “shibboleth,” the modern not-wearing-a-suit move. But not everyone’s laughing: swe_dima sparked a mini culture war, noting non‑native English speakers grind over grammar while native speakers “whip out half‑baked sentences” and get praised as efficient.
Jokes flew fast: “Sent from my iPhone” was dubbed the new corporate shield, and “cryface emoji” got crowned the most “professional” emoji. Some defended brevity as productivity, others saw privilege — a messy message is fine when you can’t be fired. With memories of the Sony hack and viral screenshots, the crowd’s verdict is split: is sloppy writing ruthless efficiency, or just power showing off?
Key Points
- •The author contrasts carefully crafted junior-level emails with terse, typo-prone responses from bosses, sometimes containing emojis.
- •The piece notes that shared screenshots of Epstein-related emails, involving Elon Musk, Bill Gates, and Richard Branson, reveal informal grammar and formatting.
- •The 2014 Sony Pictures hack is cited as another instance where executive emails appeared sloppy and unprofessional.
- •The author argues that senior power can reduce the need to demonstrate professionalism through polished writing, calling this dynamic “grammar privilege.”
- •Mobile-origin email signatures like “Sent from my iPhone” are highlighted as common markers of brief, informal executive emails.