Skip to content

Trails

Curated reading paths — pieces ordered by how the thinking builds, not when they were published. Start anywhere.

Engineering

Architecture, craft, and what happens to the discipline when the tools change.

Constraint Architecture

The theoretical layer — what changes when machines are on the other side of the interface.

  1. Design Physics: When Interfaces Meet Agents

    Traditional UX has a hidden assumption: humans on both sides. That assumption is breaking.

  2. Code Owns Truth

    We obsess over prompt engineering when we should obsess over constraint engineering. The prompt is a request. The constraints are the physics. The code is what ships.

  3. Pervasive AI: What Happens When Your Assistant Never Logs Off

    I've spent a month running a personal AI agent on a Mac Mini. The technology works. The promises don't — at least not the way we were told they would.

  4. The Multi-Agent Moment

    A technical breakdown of multi-agent orchestration: Claude's Agent Teams, OpenAI's Agents SDK, Google Antigravity, Gas Town, Beads, and the community alternatives.

  5. Your Vault, Your Rules: Password Managers, Sovereignty, and Agents

    On the quiet ethos connecting Buttercup, Enpass, pass, and VeraCrypt — and why it matters more now that AI agents need your credentials too.

  6. The Context Engineering Stack

    I built an internal context engine for our 1,765-doc knowledge base. My teammate independently found a better one. The difference was a reranking step I hadn't thought of. Here's what the emerging context engineering stack actually looks like — and why no single tool gets it right yet.

Frontend Physics

The mechanical truths about how browsers render, scroll, and stream — and how to test what AI agents can't see.

  1. The Frontend Testing Gap

    Backend testing is a solved problem. Frontend testing for stateful, streaming, visual UIs is not. That's exactly where AI coding agents are generating the most code.

  2. Rapid Generative Prototyping: Design in the Post-Figma Era

    Design is no longer artifact creation—it's constraint architecture. The three-layer model for the agentic economy.

Agentic Engineering

What engineering looks like when agents write the code and humans define the constraints.

  1. What's Left: Software Engineering in the Agent Era

    When anyone can spin up a coding agent and ship something workable, what actually matters? Not the word soup — the real answer.

  2. I Don't Know How to Interview Engineers Anymore

    What interviewing looks like when AI can write the code but not make the call — and why the same break is happening in every field that used output as proof of understanding.

  3. Your Infrastructure Spec Already Moved Into Your Code

    Infrastructure config is collapsing into application code — the same pattern as build tooling a decade ago. Void showed us the destination. The question is whether you want to ride the platform or steal the pattern.

  4. Kipple at Scale

    Large engineering orgs already solved coordination for thousands of humans. How much transfers to thousands of agents — and where does entropy win?

Systems & Epistemology

How systems know what they know — event sourcing, truth, distributed state.

  1. Self-Healing Systems: The Holographic Event Pattern

    Every event must carry everything a repair bot needs to act without asking questions. Don't scatter breadcrumbs — ship holograms.

  2. Proof, Not Truth: Epistemic Humility in Knowledge Systems

    We don't sell answers. We sell receipts. The receipts are what earn the right to call something true.

  3. Convex and the Reactive Database Paradigm

    How Convex challenges our mental models of databases—not relational, not NoSQL, but something new.

  4. The SaaSpocalypse

    Anthropic wiped $285 billion off software stocks this week. The market is panicking about AI replacing tools. But the real disruption is what it means for the people who build them.

  5. The Fork in the Stack

    The agent era is splitting infrastructure into two camps: those building new primitives and those retrofitting old ones. The bet you make reveals what you think agents are.

Life & Identity

What you optimize for, what you're actually aligned with, and how to tell the difference.

  1. Why Everyone Should Have a SOUL.md

    The case for documented identity in an AI-saturated world. Not just for agents — for humans too.

  2. The Funeral Test for Your Digital Self

    From Covey's funeral visualization to company codexes to personal test harnesses — the throughline is intentional identity.

  3. Learning to Take Up Space

    On the difference between disappearing and controlling — and the third thing that isn't either.

  4. Named Things: A Glossary of Compressed Wisdom

    The named laws, razors, and principles that keep showing up in engineering and strategy. Each one is a concept compressed into a name — human-language embeddings, built over centuries instead of training runs.

  5. Raising Humans in an AI World

    What do you teach a three-year-old when the ground is shifting under everyone's feet?

  6. What Are Test Scores Actually Worth?

    I built a school data product for parents. What I built, how my thinking evolved, what an axiom actually is, and where the data runs out.

  7. Why AI Can't Shop for You Yet

    The properties that matter most in fashion aren't properties of the product — they're properties of the relationship between the product and the person. No protocol fixes that.

Seeing & Making

Cameras, constraints, craft — the thing itself, not the optimization of it.

  1. What Cameras Taught Me About Software (and Life)

    The arc of creative tools: diverge to learn, converge to create. Why more gear made me worse, and what that means for building software.

  2. Photography as Interface

    What camera mechanics teach us about designing for attention, perception, and control.

  3. Photography After AI

    What's the value of photography when AI generates pixel-perfect images in seconds? The same thing that's valuable about code when AI writes it: not the output, but the seeing.

Building in Public

Speed of thought, rent a human, and what it feels like to make things right now.

  1. Building at the Speed of Thought

    Your brain processes 10 bits per second. Your WiFi does 50 million. We built entire workflows around pretending the gap didn't exist.

  2. Rent a Human

    A marketplace where AI agents hire humans for physical tasks. The inversion is here.

  3. Working With AI

    How I think with AI, where I don't trust it, and what co-authorship means.

  4. When Do We Stop Talking About AI?

    The specific exhaustion of a generation that can feel the stitch where human thinking and machine fluency got sewn together.

  5. Memory and Journals

    AI agents have perfect memory within a conversation and total amnesia between them. What can human journaling teach us about what memory should actually be?

  6. Toward AI-Native Analytics for Personal Publishing

    An RFC for a small, legible analytics system — privacy-first, edge-native, AI-queryable — built on Cloudflare Workers.

  7. Trails: A Pattern for Navigating Ideas

    Why I replaced a knowledge graph with curated reading paths, and what I found when I looked for prior art.

  8. Hello World

    First post. Why I built this blog and what I hope it becomes.