1. Working with AI

    Build your skill from a source that has not changed in decades

    Pick a framework or workflow that has not changed in decades, such as the Eisenhower matrix, point an AI at it, answer its questions one at a time, and you have a first version of a skill you can test and tweak.

    4 min read Interactive

  2. Agents & Tooling

    Plan big, do small

    A big model should plan the work and find the tools, libraries and free databases that already exist. Smaller models, or programs on your own computer, do what I like to call the donkey work.

    5 min read

  3. Agents & Tooling

    The Infinite Sandwich and the Made Bed

    Why Systems Thinking Is Your Real AI Superpower

    5 min read

  4. Working with AI

    Hey, That's Not the Real Batmobile!

    Why "You Are A Marketing Expert" Isn’t A Prompt

    4 min read

  5. Agents & Tooling

    Gems Are Becoming Skills, but I Can Find My Gems, Not My Skills

    I am using Gemini more and more for editorial and creative work. I like it for developing ideas and roughing out illustrations, while I tend to use other tools for purely operational jobs. That has meant spending quite a bit of time playing with Gems.

    2 min read

  6. Working with AI

    Five words for the same thing

    The jargon is doing less work than it looks.

    8 min read

  7. Working with AI

    SoN 2.30: Which of your AI's rules are still doing a job?

    Last week's advice and Anthropic's both hold. The test is one question you can ask about any rule you've written.

    12 min read

  8. Working with AI

    From Custom Code to Conversational Prompts

    Who's allowed to build software has changed hands three or four times in a decade. Grok Build is the latest handoff.

    7 min read

  9. Working with AI

    Tell AI What You Want and Who You Are

    Two takes on the same idea — the ASD-STE100 controlled-English standard and the i-have-adhd Claude Code skill — on giving your AI a writing system.

    3 min read

  10. Working with AI

    SoN 2.28: "That's good, how can we make it better?"

    When I think about AI and automation, I see an opportunity opening up that goes well beyond the chatbots everyone’s being handed — well beyond prompting, too. One of the most…

    6 min read

  11. Working with AI

    Paperwork Shot List

    A shot list for the paperwork This week I’ve spent five hours or more in the car, driving between schools to move our kid from one to another for the new school year. It’s a mixed…

    3 min read

  12. Working with AI

    What I Automate with AI

    What I Automate with AI I went looking today for a list of everything I’ve got automated since I started this AI journey back in 2024. Every tool I’ve wired Claude into, every…

    4 min read

  13. Agents & Tooling

    SoN 2.22: How do you choose "the best" AI tool?

    How do you choose "the best" AI tool? A friend asked me this week to explain how to use “all the different AI tools” — ChatGPT, Gemini, Claude, the lot. She wanted, in her words,…

    5 min read

  14. Agents & Tooling

    SoN 2.16: Ask your AI what it can already do (Free Edition)

    You don't need more AI tools (Free Edition) Ask your AI what it can already do Last Friday, Maya and I spent an hour delivering a post-lunch workshop with about thirty-five people…

    2 min read

  15. Working with AI

    SoN 2.15: Ask your AI to Ask You Questions (Free Edition)

    Ask Your AI To Ask You Questions (Free) Ask your AI to ask you questions Last Saturday morning I sat down to write the weekly digest for my build-log site — seven posts from the…

    4 min read

  16. Working with AI

    SoN Vol 2, Issue 10: Same Prompt, Different Model, Worse Results (Free)

    Same. Prompt,Different Model, Worse Results Dear Reader, New LLM models drop every few weeks. Features change between updates. The prompting advice that was best practice six…

    2 min read

  17. Agents & Tooling

    SoN Vol 2, Issue 6: The Talking Wrench

    Three conversations you should be having with your AI tools Dear Reader, I had coffee with a friend this week — who’s trying to solve a practical problem. He needs a better way to…

    8 min read

  18. Working with AI

    SoN Vol 2, Issue 2: The Art of Breaking Things Down

    Last week I introduced the idea of "programming your gaps" — the mental shift from asking "how do I prompt better?" to "what friction in my life can I systematize?" Today's the…

    9 min read

  19. Working with AI

    SoN Vol 2, Issue 1: Stop Prompting Better. Start Programming Your Gaps.

    Something shifted over the holidays. Since Claude Code Opus 4.5 launched in November, a pattern has emerged among knowledge workers using Claude Code with their Obsidian vaults…

    6 min read

  20. Working with AI

    SoN 30: Four Questions That Fix Your Prompts

    Most prompts fail before you hit enter. Not because of the AI model nor because of token limits or temperature settings. They fail because you haven’t actually figured out what…

    6 min read