In July 1998, the Internet Society held INET ‘98, “The Internet Summit”, at Palexpo in Geneva. The University of Geneva provided about 250 computers for the conference, and I was a student there. I wrote much of the conference network’s website, www.inet98.ch, and the launcher that ran on the public...

In January 1998, a classmate and I wrote a game. It was called “Bolongas zBalls”, and it was a Java applet. You click to start, then move the mouse, without clicking. Touch the dark ball to blow it up, and the next ball turns dark. Clear them all and the next level doubles the number of balls. Touch...

Before GNU Autoconf generated configure scripts, there was a DOS program called Autoconf. It let you keep one CONFIG.SYS and one AUTOEXEC.BAT, then choose among boot configurations by pressing a key. You did not have to wait for a menu. The PC BIOS kept early keystrokes in its keyboard queue, so you...

In his Rails World 2026 keynote DHH talks about one-shot apps built almost instantly with an agent as part of Omarchy. His canonical example is Omacalc, a dead simple calculator. It’s a good demo and not a hard problem. Let’s take it further and rewrite a more advanced calculator in Rust that we can...

I write a lot, and I use AI a lot. But AI does not write my blog posts. Mostly. AI is useful for making some of my writing less tedious. Recently, I asked GitHub Copilot CLI to read a few dozen posts from this blog and derive a VOICE.md to assist my writing. The result is now checked into this repo ...

Back in January I wrote Serving Markdown for AI Agents: for every page on this blog, there’s also a .md version at the same URL, discoverable via a <link rel="alternate" type="text/markdown"> tag, so AI agents can fetch clean Markdown instead of parsing HTML. It also made me $360, via referral conve...

I spent five and a half years at AWS before moving (back) to Microsoft, where I work today. At Amazon, many meetings began with silent reading. Instead of presenting a document, the author gave everyone time to read it before the discussion started. There was a small facilitation trick that made thi...

Slava (slack-strava) connects a Strava account to a chat and posts a card for every activity, complete with map, pace, and elevation, plus commands like connect, disconnect, stats, and leaderboard. In 2023 I ported Slava to Discord by hand, evening by evening over about three weeks, and it took most...

While reviewing dozens of PRs from ericproulx optimizing Grape’s internals recently, I noticed that the bare raise ArgumentError, "..." calls scattered across the codebase were inconsistent: some messages were capitalized, some ended in a period, most were not. Longtime readers know where this is go...

distance_of_time_in_words is a small Ruby gem that turns two Time objects into a human-readable string like “3 days and 4 hours”. Two separate bug reports against it this year turned out to be variations on the same theme: computing a duration between two timestamps is not the trivial subtraction it...

My previous post walked through four bugs in ruby-enum, a gem I maintain, all stemming from the fact that class-level instance variables aren’t inherited by subclasses. The third fix, #59, made keys, key?, value?, key, value, to_h, parse and each walk up superclass and merge in a parent’s enums, so ...

The ruby-enum gem is a small library I maintain that adds enum-like behavior to a class via include Ruby::Enum and define :KEY, value. Four pull requests landed against it recently, each fixing a different symptom, and all four turned out to be the same underlying bug: class-level instance variables...

The slack-ruby-client library, an open source Ruby gem I maintain, runs a scheduled GitHub Actions workflow that regenerates code from Slack’s API definitions and opens a pull request with the diff. The commit message and CHANGELOG entry used to be a generic “Update API (2026-08-11)”, which told a r...

AI-first Engineering is now the operating default in many organizations, including mine. Developers have kept up. Vibe coding became agentic engineering, and the race towards truly autonomous engineering isn’t slowing. But what are we, managers, to do? A manager job continues to include recruiting a...

In April 2025 I wrote Apologizing for My Obsessiveness Over Punctuation, a post about my various organizational compulsions. Near the end, almost as an aside, I mentioned that I obsessively categorize expenses in Monarch, a personal finance app, linking it with my referral code. That post earned me ...

Before AI coding assistants, a typical engineering team built expertise with the years: new team members joined, contributed small bug fixes, then were given more ambitious tasks over time as they became more comfortable in a codebase, to ultimately become experts. This process took years. In contra...

Yesterday I described AI-generated code as “plausible-looking, locally coherent, globally wrong.” Here’s a concrete example from my own codebase. I needed a cleanup job to close old Slack group DM conversations in my slack-sup2 app. The AI-generated solution looked perfectly reasonable: def close_ol...

Before AI coding assistants, a typical engineering team of 8-10 people might have been lucky to have one or two “10x engineers”, or “workhorses”, the kind of engineer that both keeps project quality and feature velocity high. AI tools have solved the workhorse half of this equation, enabling massive...

In today’s shocker, Meta is to “create a new applied AI engineering organization aiming for an ultra-flat structure of up to 50 employees to one manager”. Like all software engineers I, too, tend to apply a data‑driven, mathematical approach to every problem in the world. Yet I would have chosen a m...

Dries Buytaert recently wrote about The Third Audience. For decades, websites have targeted two audiences: humans and search engines. AI agents are now the third audience, and most websites aren’t optimized for them yet. AI agents prefer clean, structured content over HTML. Markdown is ideal - it’s ...

I’ve written and talked extensively about Hypermedia APIs for about a decade. The HATEOAS constraints in representing resources for a RESTful API has numerous advantages in API design, readability, discoverability, and performance over a hand-rolled REST API. Unfortunately, adoption of Hypermedia AP...

One of the negative side effects of having any top-down command structure is that every additional layer risks introducing a new level of bureaucracy, which then actively subtracts value. Consider the Politburo of the USSR with dozens of offices of skilled bureaucrats. Because most produced no actua...

The most abused principle in dysfunctional organizations is “Disagree and Commit”. In Don’t Tell Engineers What to Do I said that “telling people what to do, especially if they are in your direct reporting chain, must not be mistaken for “Disagree and Commit”. So, what is a healthy “Disagree and Com...

A famous example where telling Engineers what to do backfired was the Space Shuttle Challenger disaster in 1986. Engineers at Morton Thiokol, the contractor responsible for the shuttle’s solid rocket boosters, warned NASA management that the O-rings in the boosters could fail in cold weather. The ni...

Let’s get Claude Code to connect to Google Sheets. We’ll use this Google Sample Spreadsheet. Go to the Google Cloud Console, create a new project, and enable the Google Sheets API on it. Install the Google Cloud CLI. brew install google-cloud-sdk Choose the newly created project on the command line....

Six months ago I failed a basic coding interview at a FAANG. Yes, I was a Principal Engineer, and yes, I was paid absurd amounts of money, yet I couldn’t implement a diameter of a binary tree as a “warm up” exercise, 10 lines of code. The interviewer was very nice about it, and was equally surprised...

One of my colleagues wrote a pretty awesome tool called claude-swarm that orchestrates multiple Claude Code instances as a collaborative AI development team. At Shopify, we are attempting to use it to generate Ruby unit tests at some scale with an army of AI test agents (think a “Ruby Expert” paired...

There’s much written about becoming a first time Engineering Manager (I recommend Camille’s book), but little about the second time. To my own surprise, I am back to being a manager after almost 6 years of writing code as an individual contributor (IC). Two months ago I joined the Developer Producti...

Last week, my team at Shopify released a new tool called Roast, a convention-oriented framework for creating structured AI workflows. Our vision is to enable A.I. agents to solve developer productivity problems at scale. Imagine continuously improving unit tests, or optimizing test performance acros...

You may have landed here because I had just apologized for my obsessiveness over punctuation in a GitHub comment and requested changes to your pull request, or you noticed me adding periods to a sentence in the otherwise excellent document you have authored. This is not the first time, and my condit...