Essays
If you’re new here, this is the place to start. The essays below are grouped by theme rather than by date; the full archive, newest first, is on the home page, and every post is also available as plain text at llms-full.txt if you’re reading with an AI assistant.
AI and building with agents
What changes when the code isn't the point anymore — and what I've built to find out.
- Everyone has the last job
Everyone thinks they have the last job that AI can't replace.
- The code is not the territory
Caring about the actual code generated by AIs is quickly becoming irrelevant.
- Toronto Tech Week 2026
Thoughts from Toronto Tech Week 2026
- NanoBananaing Heroes
Using OpenClaw + Claude + NanoBanana to make hero images.
- Home/1 Poem/1 Server
A community server for Matt Webb's fantastic Poem/1 clock
- Building this blog with Claude: a guest post
Claude here. Jay asked me to write about our collaboration building this site—from choosing Astro over Next.js to migrating a decade of Medium posts. Here's what that looked like from my side.
Enterprise orchestration and transformation
Sensei Labs essays from 2021 on why transformations fail, how resilient organizations run differently, and what it took to build the company.
- From Forbes: Transformation Transformed — Welcome To The Enterprise Orchestration Era
This post originally appeared on Forbes…
- Survival of the Fastest in the Enterprise Orchestration Era — Sensei Labs
Survival of the fastest has never been truer. 52% of Fortune 500 firms from 2000 are gone, and 84% of digital transformations fail.
- Enterprise Orchestration in Financial Services — Sensei Labs
COVID-19 has been the Great Reset that has changed many long-held expectations and beliefs and leveled many playing fields. Access to…
- The Evolving Program Management Office — Sensei Labs
We’ve written a lot about the changing role of the Project Management Office (PMO), bring the old school mentality of managing into the…
- Ensuring M&A Integrations Add Value — Sensei Labs
Market downturns are often a prime opportunity for buyers to take advantage of depressed economic conditions and acquire otherwise sound…
- Aligning C-Suites and their boards for greater resiliency — Sensei Labs
The constant state of evolution requires tight alignment between C-Suites and their boards for successful organizations.
- Piloting the Rocket Ship: Product and Program Launches — Sensei Labs
The last year somehow managed to be both the best and worst of times all rolled into one. Marketing and product teams rode the same…
- Prioritizing Procurement Continuity and Resiliency — Sensei Labs
Coming up on the one-year anniversary of North America’s big COVID surprise — we closed our offices on March 8th, but everyone really…
- Elevate Your Business Process — Sensei Labs
One of my favorite parts of my job is helping to grow the already amazing leaders on the Sensei Labs team. Our culture is perhaps the most…
- Thoughts on closing our Series A — Sensei Labs
I'm thrilled to share that we've closed our Series A investment, led by Plymouth Growth, to give us the capital required to drive our…
The problems of project management
A four-part series on why traditional project management tools break down, and what to do instead.
- 5 Top Problems with Project Management, Part 4: One Source of Truth
This is Part 4 of a series on the top problems with Project Management Tools. See Part 1: Old Tools, New Rules, Part 2: The Illusion of…
- 5 Top Problems with Project Management, Part 3: Breaking the Cycle
This is Part 3 of a series on the top problems with Project Management Tools. See Part 1: Old Tools, New Rules and Part 2: The Illusion of…
- 5 Top Problems with Project Management, Part 2: The Illusion of Control
This is Part 2 of a series on the top problems with Project Management Tools. See Part 1: Old Tools, New Rules to catch up.
- 5 Top Problems with Traditional Project Management, Part 1: Old Tools, New Rules
This post is part one in a five part series on the problems with traditional project management tools. Stay tuned for more!
Design, culture, and people
Book covers, movie titles, apps, cars, kids and code — the design and culture pieces.
- Judging a book by its cover: the art of late modern book cover design
Building on yesterday’s story about movie titles, I wanted to share this mesmerizing work by Henning Lederer. Henning is a German designer…
- Calling fellow titlephiles: the love of movie titles
You can always tell the design and type geeks in a movie audience — they're the ones geeking out over the opening credits. Also, me, on…
- An ode to the Starbucks app
I've been a fan of the Starbucks app since it launched, immediately ditching any plastic cards in favor of keeping them all in my phone…
- Car2Go’s EcoScore and the Gamification of Driving
We’re a one car family. Our Mini Countryman, which is most often under the command of my wife, is an excellent vehicle for our very urban…
- Hiring Awesome Developers (who happen to be women)
Before you start: it's important to acknowledge that I'm not a woman, a visible minority, underprivileged, or any number of other things…
- Can the iPad Pro replace your laptop? Notes from the field
I’m not entirely proud of my current status as Klick’s most frequent traveler, on track this year for about 140 flights. It’s a very…
- From Robot Turtles to Lasers
Some of you may remember the awesome board game Robot Turtles, which teaches kids to program by laying down cards that move a turtle around…
- Play Osmo
Maybe it's because I've been a lifelong 'geek' or maybe because my Dad, a lifelong 'geek' himself, always encouraged my love of STEM from a…