Explore the archive

Topics

Browse recurring questions across the writing, with the latest useful entry point in each thread.

Engineering

Software practice, technical judgment, and delivery.

LatestThe Org Chart, the Tube Map, and Models That Are Wrong on Purpose

Technology & Systems

The tools and structures behind modern work.

LatestThe Org Chart, the Tube Map, and Models That Are Wrong on Purpose

Work & Productivity

The mechanics of attention, planning, and execution.

LatestEverything Says Urgent, So Stop Sorting on Arrival

AI & Agents

Building and working alongside intelligent systems.

LatestEverything Says Urgent, So Stop Sorting on Arrival

Leadership & Organizations

How teams, managers, and institutions work.

LatestEverything Says Urgent, So Stop Sorting on Arrival

Personal Essays

Notes from lived experience.

LatestBeing Wrong in Public

Writing & Communication

Clear thinking expressed through language.

LatestEverything Says Urgent, So Stop Sorting on Arrival

Decision Making

Better choices under pressure and uncertainty.

LatestEverything Says Urgent, So Stop Sorting on Arrival

Culture & Ideas

Research, history, and arguments worth carrying forward.

LatestA Third of Feedback Makes Performance Worse

leadership

A connected set of ideas from the archive.

LatestThe Ratchet on Your Wrist

artificial-intelligence

A connected set of ideas from the archive.

LatestYou Probably Need a Scorer, Not Another LLM Call

Food & Home

Useful pleasures away from the desk.

LatestAdding People Reduced Output

management

A connected set of ideas from the archive.

LatestThe Ratchet on Your Wrist

software-development

A connected set of ideas from the archive.

LatestYou Probably Need a Scorer, Not Another LLM Call

engineering-mangement

A connected set of ideas from the archive.

LatestYour First Month Leading a New Team, Week by Week

software-engineering

A connected set of ideas from the archive.

LatestYour AI Model Has a Retirement Date

behavioral-economics

A connected set of ideas from the archive.

LatestThe Ratchet on Your Wrist

data-science

A connected set of ideas from the archive.

LatestYou Probably Need a Scorer, Not Another LLM Call

machine-learning

A connected set of ideas from the archive.

LatestYou Probably Need a Scorer, Not Another LLM Call

productivity

A connected set of ideas from the archive.

LatestIn Defense of the Simple Checklist

technology

A connected set of ideas from the archive.

LatestYour AI Model Has a Retirement Date

accessibility

A connected set of ideas from the archive.

LatestFewer Wrong Exits: The Wayfinding Method Behind DC Metro’s New Signs

apple-watch

A connected set of ideas from the archive.

LatestThe Ratchet on Your Wrist

books

A connected set of ideas from the archive.

LatestAlchemy, Read by Someone Who Manages Engineers

career-advice

A connected set of ideas from the archive.

LatestYour First Month Leading a New Team, Week by Week

design

A connected set of ideas from the archive.

LatestFewer Wrong Exits: The Wayfinding Method Behind DC Metro’s New Signs

engineering-management

A connected set of ideas from the archive.

LatestYour AI Model Has a Retirement Date

Essays

Observations that resist a narrower label.

LatestReading list

goal-setting

A connected set of ideas from the archive.

LatestThe Ratchet on Your Wrist

programming

A connected set of ideas from the archive.

LatestYou Probably Need a Scorer, Not Another LLM Call

public-transit

A connected set of ideas from the archive.

LatestFewer Wrong Exits: The Wayfinding Method Behind DC Metro’s New Signs

saas

A connected set of ideas from the archive.

LatestFour Hours to Build, Five Years to Own

teamwork

A connected set of ideas from the archive.

LatestAgents Raise the Price of a Big Team

ux-design

A connected set of ideas from the archive.

LatestFewer Wrong Exits: The Wayfinding Method Behind DC Metro’s New Signs

work

A connected set of ideas from the archive.

LatestIn Defense of the Simple Checklist