Espresso Shots 1-18-26

It's that time again for my weekly update, which includes a short collection of noteworthy finds, posts that inspire, as well as a few reflections from the past week or two. I'll aim to land these in your inbox by the weekend, in time to pair with your morning coffee (or your preferred cup of inspiration).

The Latest Drippings ☕️

• The Problem is Defining the Problem: The Unreasonable Effectiveness of Caring. I came across an article about Paul MacCready, 'You Are Solving The Wrong Problem', published in 2011, that discussed his creation of the first human-powered airplane. 'The startling realization that people were solving the wrong problem' when it came to human-powered flight. The problem was the process itself, and figured out 'how to build a plane that could be rebuilt in hours, not months'. Fast forward to 2026, and the fundamental issues faced by many who use AI/LLMs with quality remain. 'Agentic coding -- using LLMs to write code -- is certainly a way to write more code more quickly... You achieve what you want by being able to define what you want. Defining what you want is hard.' Something to think about.
• You Can't Debug a System by Blaming a Person — Humans in Systems. 'The difference is that you treat those actions as clues, simple data points and not verdicts.' I wrote a ton already on this in When It Falls Over, 'When you stop expecting smoothness, disruption stops feeling catastrophic. It becomes information. It's a recognition that shit happens.'
• Intellectual Rigidity Is Making You Boring as Fuck. Oh, I liked this article quite a bit where the author examines how the 'root of rigidity is often fear'. 'At a certain point, you're not having a conversation with someone's curiosity. You're watching someone protect a worldview they’ve built their entire identity around. That’s when a normal discussion starts feeling like a personal threat.'
• The Curiosity Tour. Speaking of curiosity, how about a curiosity tour? Ben Werdmuller (whom I follow regularly), points to a post that discusses the differences between looking for a cog job and the process for finding a linchpin job. 'The linchpins... invent, lead (regardless of title), connect others, make things happen, and create order out of chaos. They figure out what to do when there's no rulebook.' (Side note: Purchased Seth Godin's Linchpin)
• How to Reinvent Your Life. 'Complacency is a disease of affluence: if our lives were worse perhaps we’d be desperate enough to take chances, since we’d be less afraid of what we have to lose.' I have mentioned Scott's new book, 'Rules to Live By' before - just go read this. Too much goodness to describe here. ;)
• Our Algorithmic Grey-Beige World. Om Malik perfectly describes how everything feels the same these days and that the algorithm is making everything blah. 'Algorithmic reality doesn’t just commodify interaction. It standardizes imagination. The algorithms squeeze creativity out of millions by showing them exactly what “works.” We don’t get unique. We get infinite variations of the same.'
• Be Wary of Digital Deskilling. Over my time off during the holidays, I spent an inappropriate amount of time playing with Claude Code (don't get me started on the 'Ralph Loop Coding'). On one hand, I had some incredible breakthroughs and built some crazy stuff. Still, I walked away feeling that I didn't learn anything. Cal Newport has a really thoughtful post on the deskilling that touches on this.
• Meet the Man Hunting the Spies in Your Smartphone. This stuff often reads like a plot of a movie.
• My 2026 Goal Is to Be Bored More Often. I love being bored, as crazy as it sounds. I'm also a proud member of the 'choose boring technology'. 'When we’re bored, we think. We get ideas. We let our mind wander. We ask ourselves; what if? We remember. We imagine. We relive. We learn. We reprioritize. We plan. We decide.'
• 3 + 4. What happens when you switch to a three-day workweek? 'This really changes the dynamic of the week. It no longer feels like an extended weekend. What I mean is that usually we think about the working week as the default and the weekend as the exception. That’s been flipped on its head for me. The three days I spend working feel like the exception. Once again, this decision meant earning less money. But I’ve decided that I value time more than money.' Work to live, or live to work - an important question.
• Geezer Magazine: The Brilliant Brainchild of Insanity. I heard about Geezer Magazine a few months back from Greg Storey, and it was an instant subscribe. The first issue is brilliant and I can't wait to see what's next.
• National Clean Your Desk Day. Didn't know this was a thing, but boy, did I need a declutter this week. Timely.
• How TiVo Killed Live TV. A great retrospective on TiVo and how, ultimately, they became a victim of their own success. 'The company never managed to turn its game-changing concept into a big business or a truly lasting hit product. Meanwhile, the changes it helped bring about in our consumption habits eventually left TiVo behind. We all live in the world TiVo imagined — but we mostly do it without TiVo.'

Amor Fati ✌🏻