Proof of Concept

When you look at the future geology of design leadership, there are two forces of nature hitting the industry: multi-modal and multi-generational. The first is the AI and agentic era of software we find ourselves in. Software and business models are being re-written as we speak to be AI-native. The second is there is a generational shift in the pipeline of professional designers. One group is emerging in their career and the other are at the end of theirs; retiring or fading into obscurity.

The work schedule used to bully me endlessly. Every day I’d wake up already overwhelmed, thinking about what was waiting in the inbox. Digital work is infinite in its scrolling, its notifications, its channels all screaming for attention. Before you can do anything productive, you’re behind on the 72-message Slack threads where everyone and everything is vying for a piece of you.

Proof of Concept hit 300 issues; a milestone I never set out when starting in 2020. I started Proof of Concept as part of the On Deck Writing Fellowship in 2020. At that time, I was the flaky writer who said they wanted to publish more, and did about once a year. In one of the fireside chats I remember Polina Marinova saying a phrase I’ll never forget, “Consistency builds trust.” I needed to build trust, not with an audience, but myself to write.

I’ve written about mobile setups, my travel work setup, and other posts about working on the go. As I embark on a trip around the world (literally from Sydney, Singapore, Amsterdam, and back to California), I figured it’s time to write about creative work while traveling again. Traveling forces you to re-wire what you’re thinking about. You’re away from home, loved ones, and common routines. Travel also changes your relationship to constraints.

One of the many fond memories I had growing up was earning the five stars from Pizza Hut’s Book It program to get my Pepperoni Personal Pan Pizza. As we waited for our food, my mother would gift my brother and I a few quarters to play an arcade game of our choice. Among the rotation of The Simpsons Arcade Game and Altered Beast, there was also Street Fighter II. Down, down-forward, forward, punch. I didn’t know what those inputs meant the first time I saw a fireball come out of Ryu’s hands.

I’ve been using agents a lot this year, and it’s incredible how powerful they’ve become. It started last winter break when everyone was using Claude Code. All of the sudden, I’m using Claude Code, Codex, Gemini, Cursor, Replit, Rovo Dev, and of course, OpenClaw. My focused habits went from one screen and one window to look at to a dozen Terminal windows managing my agents like I was playing StarCraft II. Here’s the truth. It’s a lot of fun.

Draftsmanship originates from the word draught, meaning “to draw or pull.” It’s an attribute defined as the art, skill, or technique of producing drawings, plans, or sketches, particularly emphasizing high-quality, precise, and accurate representation. For design and engineering, it’s a foundational skill that is taught. However, with the speed of production increasing with AI, the declaration of design as the first casualty is making the rounds of discourse. It couldn’t be more wrong.

Whether it’s building them, leading teams that owned them, I’ve spent most my career inside a design system. As a designer, I was one systems designer who broke things in favor of evolution. My intention was not malicious rather to future proof the system. Design Systems in the Blitzscaling era of the 2010s were built for a different purpose than what’s needed for the AI Scale era we’re living in the 2020s. We’re moving from Design Systems to Inference Systems.

The leadership role has changed drastically in the past three years. We’ve moved from the blitz scaling era to the scale era of AI. Though managing towards outcomes is still the focus, the way we do it has changed. As organizations figure out how to go from AI-novice to AI-native, it’s important to find new ways of working across various companies and crafts. This results in leaders needing to conduct their own personal discovery.

In The Avengers #54, a mysterious villain called the Crimson Cowl is orchestrating attacks against the team. It’s not until the last page that the cowl drops and we see what’s underneath: a robot. The next issue reveals him fully—Ultron-5, a living automation built by Hank Pym using his own brain patterns. By the time anyone sees Ultron, he’s already on version five.