1
Foundation
Days 1–30
Build the skeleton: argument structure, summarizing others fairly, staking your own view. Core book: They Say / I Say.
Week 1
Reading heavy
Representing others' views
Summarizing without distorting. Quoting with purpose. Filling every blank with real content.
Week 2
Read + write
Staking your own position
Agreeing, disagreeing, mixed views. Keeping your voice distinct from the voice you're responding to.
Week 3
Writing heavy
Cohesion + so what
Transitions. Handling objections. Answering "who cares?" Starting to loosen the templates.
Week 4
Writing heavy
Self-diagnosis
Catch your own errors before anyone else does. Rewrite your Day 1 passage and compare. Set goals for Phase 2.
Phase 1 checkpoint
You can write a 300-word structured argument and self-diagnose its weaknesses before anyone else sees it.
2
Critical Thinking
Days 31–60
Add the thinking layer. Forming strong opinions, stress-testing them, reasoning from evidence. New books enter.
Week 5
Reading heavy
How opinions form
Read: Thinking, Fast and Slow (Part 1 — cognitive biases). Write daily: one opinion + three reasons it might be wrong.
Week 6
Read + write
Steel-manning
Read: Paul Graham essays (Putting Ideas into Words, How to Think for Yourself). Write: argue the opposite of what you believe.
Week 7
Read + write
First principles reasoning
Read: A Mind for Numbers (chunking + understanding). Write: take a belief about AI or work — break it to its assumptions.
Week 8
Writing heavy
Apply it to your topics
Write three 300-word opinion pieces on topics you care about (AI, productivity, project management). Strong claims, not observations.
Phase 2 checkpoint
You can form a genuine opinion, name three counterarguments, and explain why you still hold the view.
Thinking, Fast and Slow — Kahneman
Paul Graham essays (free online)
A Mind for Numbers — Oakley
3
Voice + Publishing
Days 61–90
Find your voice. Write like you talk. Publish your first blog posts. Study the writers you admire.
Week 9
Reading heavy
Study your writers
Read 10 essays each by Clear, Graham, and Sivers. For each: what's the structure? What makes the opening work? How do they end?
Week 10
Read + write
Voice experiments
Read: On Writing Well (Zinsser) ch. 1–5. Rewrite one Phase 2 essay in the style of each of your three writers. Notice what changes.
Week 11
Blog prep
Draft your first three posts
Pick three topics (AI, productivity, project management). One draft per day, 400–600 words. Apply Graham's filter: read aloud, rewrite anything that doesn't sound like you.
Week 12
Publish
Revise and publish
Revise all three posts over three days. Publish by Day 90. The bar is not perfection — the bar is "I would say this to a smart friend."
Phase 3 checkpoint
Three published blog posts. A voice that sounds like you. A writing habit that doesn't depend on motivation.
On Writing Well — Zinsser
James Clear essays (jamesclear.com)
Derek Sivers essays (sive.rs)