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/humanize

Makes a draft read like a real human typed it — adds asymmetry, light contractions, and (rarely) one safe typo. Use only when a draft is technically correct but reads polished beyond plausibility, when the user wants to "rough it up," "make it more human," or "less AI-clean."

From plugin
winning-writing
1431 skills
Install
$ npx -y skills add kalyvask/winning-writing --skill humanize --agent claude-code

How it fires

How this skill gets triggered: by you, by Claude, or both.

  • Fires itselfAuto-invocation. Claude auto-loads it when your prompt matches the work.Auto-invocation is when the right skill fires by itself at the right moment, driven by a FLOW.md router and a hook, instead of you invoking it by name. It is the difference between a skill being installed and a skill actually getting used.Read the full definition →
  • You can call itInvoke it directly when you want it.
  • Slash command/humanize

Context preview

The summary Claude sees to decide when to auto-load this skill.

Makes a draft read like a real human typed it — adds asymmetry, light contractions, and (rarely) one safe typo. Use only when a draft is technically correct but reads polished beyond plausibility, when the user wants to "rough it up," "make it more human," or "less AI-clean."

SKILL.md

humanize.SKILL.md
name: humanize
description: Makes a draft read like a real human typed it — adds asymmetry, light contractions, and (rarely) one safe typo. Use only when a draft is technically correct but reads polished beyond plausibility, when the user wants to "rough it up," "make it more human," or "less AI-clean." Does NOT run on high-stakes writing (see "When NOT to humanize"). Triggers on "humanize," "rough it up," "less polished," "more casual," "sounds too clean."

Humanize

Source: `points/ai-writing-rules.md` and the centaur-writer thesis. The point of this skill is the inverse of every other skill in this repo — most of them sharpen, this one *de-sharpens* deliberately.

**Operator note (2026-05-07):** Dialed back from the original aggressive setting (too many typos and missing words landed in finals), then re-tuned for a middle ground: a few safe roughening moves are still welcome even in short pieces. The bias is "fewer types of typos, but still some texture" — not "skip everything."

The premise

A perfect email is suspicious. Real people:

  • Use contractions inconsistently ("it's" once, "it is" once in the same email — humans aren't consistent)
  • Vary sentence punctuation (sometimes a period where a comma would be cleaner)
  • Use parentheses inconsistently
  • Repeat a word from the previous sentence sometimes (real attention drift)

A model output is *too clean*. This skill leaves a small amount of real-person residue in. Note: residue, not damage. Missing required words and unsafe typos are damage; do not introduce them.

Two modes

Mode 1 — Shorten + roughen (default)

Take the draft and: 1. Cut 10–20% of the words 2. Convert most "I am / it is / they are / cannot" to contractions, but mix in one full form somewhere for inconsistency 3. Drop the *subject pronoun* in one casual opener if the draft has one (never drop articles) 4. Vary one sentence's punctuation in a slightly imperfect way (a period instead of a comma; a sentence fragment) 5. Optionally combine two short adjacent paragraphs into one (or keep an aside on the same line instead of breaking) — humans don't always hit return where AI does 6. Apply at most ONE safe typo (see below). Pieces under ~150 words: max 1 typo. Pieces over 300 words: still max 2 typos total. Never accumulate.

Mode 2 — Roughen only (preserve length)

Same as above, no length cut.

Safe roughening moves (use freely, even in short pieces)

These are not typos — they are rhythm choices that read as a real person rather than a model. Apply 1–2 per piece without worry:

  • **Subject-pronoun drop** in a casual opener ("Just landed in SF" instead of "I just landed in SF")
  • **Paragraph compression** — combine two short adjacent paragraphs that AI defaulted to splitting (humans don't always hit return at every clause break)
  • **Mixed contractions** — use "I'm" most places but leave one "I am" somewhere for inconsistency
  • **One sentence-fragment** where a full sentence would also work
  • **Replace one comma with a period** (or vice versa) where both would scan

Approved typo types (use sparingly — see counts above)

Only these types qualify as safe typos. Pick ONE for short pieces, at most TWO across longer pieces.

  • **Doubled small word:** "to to" or "the the" or "and and" (auto-correct miss, classic — readers parse past it)
  • **Missing space inside a contraction or compound:** "i'll" with lowercase i (a phone-thumbs slip)
  • **Missing terminal period** — drop the period on the *very last* sentence of the piece only. Never mid-paragraph. This reads as "sent in a hurry," not as broken parsing.

That's it. The three above are the only approved typo types.

**NEVER use:**

  • Homophone slips ("your"/"you're," "their"/"there"). High-evaluation readers flag these as illiteracy.
  • Dropped period **mid-paragraph or mid-piece**. Only the very last period of the whole piece can drop; anywhere else reads as broken parsing.
  • Single-character drop ("thats" for "that's"). Reads as carelessness.
  • Misspelled common words, mangled names, mangled numbers, garbled URLs.
  • Broken capitalization at sentence start (mid-piece — lowercase opener of an email is a separate stylistic choice and is fine if the user does it consistently).
  • **Dropped articles, negations, subjects, verbs, or any content-bearing word.** Missing words are not informalisms — they are damage. The reader cannot recover the meaning.

The wrong typo is worse than no typo. **When uncertain, skip the typo (but still apply the safe rhythm moves above).**

Approved contraction rules

  • "I am" → "I'm" (always, except in formal opening)
  • "it is" → "it's" (most of the time)
  • "they are" → "they're" (always when casual)
  • "cannot" → "can't" (always — "cannot" is a corporate tell)
  • "do not" → "don't" (always when casual)
  • "would not" → "wouldn't" (always)
  • "I will" → "I'll" (most of the time, but mix in "I will" once for emphasis)

Subject-pronoun drop (sparingly — only one per piece)

Drop the subject pronoun in a casual opener, never the article:

  • "I just got back from London" → "Just got back from London"
  • "I sent you the proposal" → "Sent you the proposal"
  • "I'm thinking about a pivot" → "Thinking about a pivot"

Do not drop "the," "a," "an," "to," or any other article or function word. Do not drop the subject inside a clause that already has one.

When NOT to humanize (skip entirely — output the input unchanged)

The skill does not run on:

  • **LinkedIn About sections, bios, profile pages.** These are evaluated word-by-word by recruiters.
  • **Cold emails to formal recipients** (judges, regulators, journalism editors at top publications, senior partners at funds, hiring managers at named companies).
  • **Job application materials** (cover letters, application short-answers, follow-up notes).
  • **Op-eds and any pitch to a publication.** Editors reject typos.
  • **Gratitude notes.** They should already be in the user's voice.
  • **Six-word summaries** or any deliberately compressed
Read more
Ships withwinning-writing

31 Claude skills for cold outreach, op-eds, pitches, press inquiries, bios, exec memos, performance reviews, spoken-delivery talks, fact-checking, and reply-rate tracking.

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Repo: kalyvask/winning-writing

Other skills on winning-writing.