DHH Writing Resources
Source material and further reading for mastering the style.
Overview
DHH Writing Resources
Source material and further reading for mastering the style.
Primary Sources
DHH's Blog (world.hey.com/dhh)
Essential posts that define the style:
On Remote Work:
- "Remote work is the future" (2020)
- "The presence prison" (2021)
- "Escape the hustle" (2022)
On Product Philosophy:
- "On writing software well" (series)
- "The Majestic Monolith" (2016)
- "Reconsider" (2015)
On Business:
- "It's always a good time to lower prices" (2023)
- "Why we don't negotiate salaries" (2019)
Books
REWORK (2010) Co-authored with Jason Fried. The manifesto for small business.
- Short chapters (2-3 pages each)
- Contrarian takes on common business advice
- Punchy, declarative style
Remote: Office Not Required (2013) The case for remote work before it was cool.
It Doesn't Have to Be Crazy at Work (2018) Against the hustle culture.
Shape Up (free online) Basecamp's development methodology—and a masterclass in clear technical writing.
Style Elements to Study
Sentence Structure
DHH's typical patterns:
The Declaration:
"We don't have meetings."
The Three-Beat:
"Build less. Charge more. Sleep better."
The Reversal:
"Move fast and break things? How about move deliberately and build things that last?"
The Question-Answer:
"What's the best meeting? The one you don't have."
Paragraph Structure
Most DHH paragraphs follow:
- Bold claim (1 sentence)
- Brief elaboration (1-2 sentences)
- Concrete example or evidence (1-2 sentences)
Total: 3-4 sentences max. Often 1-2.
Post Structure
Typical DHH blog post:
- Hook: Contrarian statement or strong opinion
- Context: Why this matters now (brief)
- Thesis: Clear statement of position
- Evidence: Experience-based examples
- Objection handling: Address counter-arguments
- Close: Quotable conclusion
Word count: Usually 300-800 words. Rarely over 1000.
Contrast Study
Understanding DHH's style by contrasting with others:
| Writer | Style | DHH Difference |
|---|---|---|
| Paul Graham | Exploratory, building arguments | DHH arrives at conclusions faster |
| Seth Godin | Metaphorical, inspirational | DHH is more concrete, less abstract |
| Hacker News | Technical, qualified | DHH is opinionated, unhedged |
| Corporate blogs | Safe, buzzword-heavy | DHH is risky, plain-spoken |
Practice Exercises
Exercise 1: The Conversion
Take a corporate announcement and rewrite it in DHH style.
- Cut word count by 60%
- Remove all hedge words
- Add a contrarian frame
- End with a strong line
Exercise 2: The Thesis Test
Write 10 thesis statements. For each one, ask: "Could someone disagree?" If everyone would agree, it's too weak.
Exercise 3: The Sentence Diet
Take a paragraph you've written. Target 12 words per sentence. Cut everything that doesn't need to be there.
Exercise 4: The Callback
Write a blog post that opens with a question and ends by answering it decisively. The last line should be quotable.
Quotes to Remember
"I'm not particularly prescient. I just have a low tolerance for bullshit."
"Startups don't die from running out of money. They die from running out of time."
"The best way to predict the future is to build it. But only if you actually ship."
"Meetings are toxic. They chop up the day into small bits."
"Simple is good. Good is simple. Don't mistake complication for sophistication."
Warning
The DHH style is powerful but risky:
- It's easy to be contrarian without being insightful
- Strong opinions require strong evidence
- Punchy doesn't mean aggressive
- The goal is clarity, not controversy
The best DHH-style writing is brave, not reckless. It takes positions because they're true, not because they're provocative.