September 4, 2026 Read on daringfireball.net
5.3

Writing With Unnatural Constraints

Design & UIMedia & JournalismWeb & Standards

Gruber examines a remarkable Super Metroid FAQ from the late 1990s that achieves full text justification through careful word choice alone, with no extra spaces or hyphenation. While technically impressive, he argues the result is subtly stilted because fitting words to line length necessarily overrides choosing words for clarity and meaning. He connects this to lipograms β€” writing that avoids specific letters β€” using Gadsby, a 1939 novel without the letter 'e', as the canonical example of a technically astonishing but unreadable result. The key principle he extracts: writing within any unnatural constraint necessarily compromises prose quality, because the constraint displaces meaning as the highest priority in word choice. He applies this directly to AI text watermarking through word choice β€” even if the effect is subtler than avoiding 'e', it must produce some stiltedness. He closes by pushing back on the premise that monospace typesetting is unpleasant, citing Markdown as an example of the satisfaction of plain-text formatting.

Any writing constraint that competes with meaning for priority in word choice necessarily degrades prose quality β€” a principle that undermines AI text watermarking as compatibly with good writing.
  • 7

    It's sophistry to argue that one can write within a constraint without the constraint affecting the quality of the writing.

  • 6

    The gimmick necessarily becomes the highest priority of your word choices, not clarity or meaning.

  • 5

    It's stilted, as though written by someone for whom English is their second language.

  • 6

    That's a hell of a trick, but there's a reason why Gadsby is almost unheard-of, and Fitzgerald's The Great Gatsby remains famous.

  • 7

    I couldn't get through more than two paragraphs before deciding that my point was proven.

  • 3

    He tried something very difficult and pulled it off with aplomb.

  • 3

    When you format something in plain text, you know exactly how it's going to look everywhere.

opinionated, analytical, literary