Proof of Concept

In American football, quarterbacks are taught a technique called Climbing the Pocket. I’ll quickly provide an overview of this concept to ensure non-football watchers resonate with this. In football, the quarterback relies on five very large men on the offensive line to create a pocket to ensure he has enough time to throw the ball to a receiver. On the other side, the defense has five (also very large) men breaking through the pocket to take down the quarterback; called a sack.

When people say taste and judgment are the differentiators in this AI era of design, nobody really tells you how to develop them. Training your design senses is rigorous work, no different from training as a boxer or musician. The foundations are harder to establish now. Giving a designer an agentic toolset without those foundations is like giving a pianist-in-training a DJ set instead of a piano. The answer seems obvious: be highly generative and make a lot of work.

I’m not a person to make a declarative statement or hot take on the spectrum of options. That’s why my life principle is, “Have your cake and eat it.” I do this with life, especially food: the Arnold Palmer, Cronut, and Ramen Burger are abundantly clear examples of this principle in action. This also applies to technology, software design, and company building. Recently, Peter Yang posted online regarding an interesting tension about agents on the cloud or run locally.

During my previous trip from San Francisco to Sydney, I watched one of my favorite films: Enter the Dragon. This film is martial art's legend Bruce Lee’s most iconic film: part martial arts showcase, spy thriller, and the expressions of his speed, charisma, and philosophy on screen. With 15 hours in the air, one film turned into a Bruce Lee marathon. Yes, I even watched the awkward posthumous Game of Death, an unfinished film assembled after his death.

When it comes to Design’s role in the AI era, the headlines are dominated by taste and judgment. Though the importance is true, the discourse rarely says where they come from or how to apply it. However, there is one attribute that withstands the test of paradigm shifts and transformation: mastering the materials. In its rawest form, design is taking material and applying a method to it, resulting in a new artifact or object never seen in this world.

Public speaking is one of two categories: cringe or craft. I believe when speaking is the latter with the right intention, the message transcends generations and can spark a person in the audience onto an entirely new trajectory.

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.