Welcome to the Deep End

What I Learned About Creativity, Agency, and Myself by Trying to Write a Book With AI The Party Favor At a holiday party, I heard my name before I heard the sentence that followed it. I was standing near the kitchen, half in a conversation about work and kids, when my wife’s voice cut through …

For most of my career, the pixel felt precious. In the early days of desktop publishing, I thought of pixels as the digital cousin of ink dots on press. You earned the right to move them around. You learned color, trapping, resolution, typography. You invested in hardware that sounded like a NASA checklist. The pixel …

We’re not drifting toward the future. We’re charging straight into it. Headlong. Chasing convenience, innovation, and whatever’s trending this quarter. And we’re doing it with a kind of technology that’s already starting to think on its own. Not in some far-off science fiction way—right now. This isn’t about staying ahead of the curve. It’s about …

(In Part 1, we unpacked why today’s frontier models are brilliant but unreadable. Part 2 explored how explainability might become the next badge of trust. This final piece makes it real: a simple routine anyone can use to start seeing inside the black box.) You don’t need a lab coat to see what’s going on …

(Missed Part 1? We unpacked why frontier models are brilliant yet unreadable and why that opacity can’t last. Keep reading—this chapter stands on its own.) When transparency becomes a selling point In the early 2000s “organic” went from niche curiosity to aisle-wide price bump. Shoppers couldn’t see pesticide residue, so brands sold them the next …

Anthropic co-founder Dario Amodei—one of the engineers behind today’s most capable language models—just published “The Urgency of Interpretability,” arguing that we’re about to trust super-clever systems we still can’t read. This three-part series digs into that warning: first, why these models are brilliant yet opaque; next, how making their reasoning visible could become the next …

I opened our chat with a throwaway line: “Maybe I should quit all this AI work and just be a bartender.” I didn’t mean it. I was poking the bear—testing whether my AI collaborator would serve up cheap affirmation or offer something worth chewing on. It told me to pause, asked why I felt that …

In my ongoing collaboration with ChatGPT, I’ve often wondered about our mutual perception. We’ve built a dynamic partnership, exchanging insights and ideas over time. Yet, despite this, our interaction has always felt somewhat abstract—formless. To deepen my understanding, I decided to initiate a conversation exploring visual representation and identity. What would it look like if …

If you’re still debating whether AI is here to stay, consider this your wake-up call. The recent Anthropic Economic Index report (https://www.anthropic.com/news/the-anthropic-economic-index) sheds light on the profound economic transformations AI is initiating—transformations that are exciting yet deeply personal. It’s no longer just about technology; it’s about how we, as humans, adapt strategically and compassionately to …

When I was a software trainer, I consistently observed three emotional and functional stages every company had to navigate when adopting new software. I would always emphasize to these companies that everyone must pass through each stage—there was simply no skipping ahead. Those that tried inevitably struggled or failed. However, too many companies stayed stuck …

In my writings regarding AI and creativity, I have been struck by the fact that AI has a unique perspective of humanity because of its training. So I asked it the following: PROMPT: In your training you have read the much of the writings of humanity- decades of books, manuscripts, essays, papers, presentations, articles, speeches, …

Years ago, when I owned Sonar Studios, I often spoke to groups of Graphic Design students. These young, talented creatives would come through our doors full of optimism, skill, and sometimes, misconceptions about what their future careers would hold. They’d show me their portfolios, rich with visually striking pieces, and I’d challenge them with a …

There’s a certain kind of pain that only comes from hearing the truth expressed in just the right words at just the right moment. It’s that strange, comforting hurt—a blend of beauty and sadness that comes from reading a line, hearing a lyric, or catching sight of a painting that feels like it was made …

In seventh grade, I remember reading To Kill a Mockingbird. When I finished the last page, I felt this deep sense of sadness—an almost physical ache. It was like saying goodbye to close friends at the end of summer vacation, knowing you might never see them again. Scout, Jem, Dill—they had become real to me. …

In 1989, a local typesetting company I worked with bought a case of Desktop Publishing: The Awful Truth and handed out copies to clients. Their message? Desktop publishing was overhyped. It wasn’t a real threat. Sure, a single device could now allow one person to handle design, layout, and typography—but that didn’t mean the results …