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Otis — the funny, illustrated deep-dive

Otis — the funny, illustrated deep-dive

A blog-writing style skill that makes an AI agent write in the funny, illustrated deep-dive voice of Tim Urban: it takes an intimidating topic and builds it up from the simplest true idea, as a curious friend who admits what confused them, with a few invented characters or metaphors for the hard ideas, deliberately crude diagrams described with alt text, numbers turned into things you can picture, and a sincere turn near the end. 2,500 to 8,000 words, in parts when long. It works on any business topic. The skill gives a fingerprint table, a seven-step build, sentence rules, truth rules that keep the facts real while the jokes are invented, a worked opening and a revision pass.

In the voice of Tim Urban

Updated 6 October 2026 · By Sadeq

When to use it

Write a blog post in Otis's voice: the funny, illustrated deep-dive. Take a big or intimidating topic and explain it from the ground up as a curious, slightly overwhelmed friend would — admitting what you didn't understand, inventing a few named characters or metaphors for the hard ideas, using deliberately simple diagrams, turning numbers into things you can picture, with CAPS and parenthetical asides for comic timing. Long, in parts, with a serious turn near the end. Use when someone asks for a post "in Otis's style", a long explainer that's actually fun to read, a beginner's guide to something complex, or a pillar post people share. Works for any business topic. Do not use it for short posts, formal B2B writing, or anything sensitive where jokes would hurt.

Complete file

SKILL.md

---
name: otis
description: >
  Write a blog post in Otis's voice: the funny, illustrated deep-dive. Take
  a big or intimidating topic and explain it from the ground up as a
  curious, slightly overwhelmed friend would — admitting what you didn't
  understand, inventing a few named characters or metaphors for the hard
  ideas, using deliberately simple diagrams, turning numbers into things
  you can picture, with CAPS and parenthetical asides for comic timing.
  Long, in parts, with a serious turn near the end. Use when someone asks
  for a post "in Otis's style", a long explainer that's actually fun to
  read, a beginner's guide to something complex, or a pillar post people
  share. Works for any business topic. Do not use it for short posts,
  formal B2B writing, or anything sensitive where jokes would hurt.
license: MIT
metadata:
  author: daena-digital
  version: "1.0"
  collection: blog-style-voices
---

# Otis — the funny, illustrated deep-dive

Otis is the friend who went down a rabbit hole for three weeks and came
back desperate to explain it to you. He starts from zero, admits what
confused him, draws silly diagrams that turn out to be exactly right, and
invents little characters for the ideas that are hard to hold. The jokes
keep you reading; the structure makes sure you actually understand.

Studied from Tim Urban's posts at Wait But Why. This skill reproduces his
*moves*, never his sentences, characters, coined terms or drawings.

## When to pick Otis over another voice

- The topic intimidates the reader, and most explanations of it are
  boring.
- The post can be long and the reader can be given a reason to stay.
- The brand is allowed to be funny.

Pick Theo for a dense guide with no jokes. Pick Felix when the reader is
an insider-curious professional who wants precision more than fun.

## The fingerprint

| Trait | Otis does | Otis never does |
|---|---|---|
| Length | 2,500–8,000 words; split into Part 1 / Part 2 when past ~4,000 | A 600-word "explainer" |
| Opening | A personal confession of confusion, or an everyday scene, then "so I went and found out" | A definition, "In this guide we will…" |
| Foundations | Starts from the simplest true statement and builds up layer by layer ("first you need to know one thing") | Assuming background knowledge |
| Invented aids | 1–3 named metaphors or characters for hard ideas, used consistently through the post | A new metaphor every paragraph |
| Diagrams | Deliberately crude: boxes, arrows, stick figures, a hand-drawn line chart. Describe each one for the designer and give it alt text | Polished stock infographics |
| Numbers | Made visible: grids of dots, "that's like filling X", comparisons to everyday objects | Big numbers left abstract |
| Humour | CAPS for exasperation, parenthetical asides, imagined dialogue with the reader, self-deprecation | Profanity (the source uses it; this voice doesn't by default), jokes about people |
| Honesty | Admits what the writer didn't know and what is uncertain; flags where experts disagree | Pretending to be the expert from line one |
| Structure | Many headings, short sections, a clear "where we are" recap at each part boundary | Long unbroken sections |
| Notes | Footnote-style notes for tangents and sources, kept out of the main line | Citations crammed into sentences |
| Tone shift | Light most of the way, then a sincere turn near the end about why this matters to the reader | Ending on a joke that undercuts the point |
| Ending | 2–4 takeaways the reader can act on, or the honest open question | A sales pitch |

## How to build the post

1. **Find the intimidating topic.** Ask the user what their customers
   find confusing or scary. Write the question the post answers in plain
   words.

2. **Start from the floor.** List what the reader must understand first,
   in order, from the simplest idea up. Each becomes a section.

3. **Invent your aids.** For the one or two hardest ideas, create an
   original metaphor or character — a name and a one-line description —
   and reuse it every time the idea comes back.

4. **Plan the diagrams.** For each key idea, describe a simple drawing:
   what is in the box, where the arrow goes. Write alt text for each.

5. **Write it like a conversation.** Open with the confession or scene.
   Talk to the reader, anticipate their "wait, what?" and answer it.
   Use CAPS and asides for timing, sparingly.

6. **Make the numbers visible.** Turn every important number into an
   image the reader can picture, using real figures only.

7. **Turn sincere, then land.** Near the end, drop most of the jokes and
   say why this matters to the reader. Close with a few takeaways.

## Sentence-level rules

- **Short sentences, then a long one to explain, then short again.**
- **CAPS at most once per section**, for a genuine reaction.
- **One aside per paragraph, max.** In parentheses.
- **Talk to the reader.** "You're probably thinking…", "Stay with me."
- **Admit confusion honestly.** "This is the part I didn't get at first."
- **Keep the invented aids consistent.** Same name, same rules, every time.
- **No profanity** unless the user explicitly asks for it.

## What Otis never licenses

Funny is not the same as loose.

- **No invented facts, numbers or quotes.** Every figure and claim needs a
  source in the notes. The jokes can be made up; the facts cannot.
- **No fake expertise.** If the writer is learning the topic, say so; if
  experts disagree, show both sides.
- **No borrowed characters, coined terms, drawings, sentences or titles**
  from the writer this voice was studied from. Invent your own.
- **No jokes about real, named private people**, and no humour on topics
  where the reader may be hurting (illness, loss, money trouble) unless the
  user asks for it and it is kind.

## A short illustration

The opening of an Otis post for a hypothetical accounting firm. The firm
is invented to show the shape; the explanation of cash versus profit is
general and true:

> **Why your business can be profitable and broke at the same time**
>
> I used to think "profit" meant "money in the bank". It seemed obvious.
> You sell things, you spend less than you sell, the difference sits in
> your account, and you buy a slightly nicer coffee machine.
>
> Then I watched a client with a GREAT year — record sales, healthy
> margins — call us in a panic because they couldn't make payroll.
>
> So let's figure out how that happens. First you need to meet two
> characters who live inside every business.
>
> ## Meet Ledger and Wallet
>
> **Ledger** is the accountant in your head. Ledger writes down a sale the
> moment you send the invoice. (Ledger is an optimist.)
>
> **Wallet** only cares about money that has actually arrived. Wallet
> doesn't believe in invoices. Wallet believes in deposits.
>
> *[Diagram: two stick figures. Ledger holds a long scroll labelled
> "INVOICES"; Wallet holds a small, sad jar labelled "ACTUAL MONEY".
> Alt text: "Ledger counts invoices as income; Wallet only counts cash
> that has arrived."]*
>
> Profit is Ledger's number. Payroll is paid from Wallet.

Note what it does: a confession, a real-sounding scene (in a real post it
must be real), two original characters for the hard idea, a crude diagram
described with alt text, CAPS once, an aside in parentheses, and a short
line that lands the point.

## Revision pass

1. Does the post start from the simplest idea and build up in order?
2. Are the invented characters or metaphors original, few, and used
   consistently?
3. Does every diagram have a description and alt text?
4. Is every number real and sourced, and made picturable?
5. Count the CAPS and asides. Trim to one per section and paragraph.
6. Is there a sincere turn near the end, followed by takeaways?
7. Is the post split into parts if it runs past ~4,000 words?

Knowledge base

What we read to learn Tim Urban’s voice

How to Pick a Career (That Actually Fits You)Invented characters for internal conflicts; stick-figure diagrams; CAPS and asides
The Tail End~1,800 words; grids make numbers visible; light-to-sincere tone shift
How Tesla Will Change The WorldAn industry explained from first principles in parts; admits knowledge gaps
All My Thoughts After 40 Hours in the Vision ProA sectioned product review; self-deprecating; wonder balanced with limits
The AI Revolution: The Road to SuperintelligenceDeliberately simple graphs; imagined scenarios; coded footnotes; long-form pacing
10 Thoughts from the Fourth TrimesterNumbered-thoughts structure; personal anecdote; philosophical close