Happiest I've Ever Been
Ben Wallace's essay about coaching youth basketball and finding that happiness comes from physical presence, meaningful relationships, and agency -- not from rectangles on screens.
Key Quotes
"I fucking loved being a coach. And, I don't want to brag, but I was really good at it."
"I love being in the real world. If I taught those kids on Zoom... it wouldn't have been the same."
"For years, you've sat in front of a rectangle, moving tinier rectangles, only to learn that AI can now move those rectangles 10x better. As someone outside the equity class, you begin to wonder what your role is in this new paradigm. And whether rectangles were ever your ticket to happiness in the first place."
Key Themes
The "rectangles" framing is devastatingly precise. The entire tech industry -- from frontend to backend, from design to DevOps -- is fundamentally about arranging rectangles on screens. And now AI can arrange them faster. If your identity and happiness were built on being good at rectangles, what happens when the rectangles don't need you?
Wallace's answer: the rectangles were never the point. He was happiest coaching kids in a gym, not shipping code. Physical, tangible, relational work. The four ingredients he identifies -- meaningful work with people, physical presence, genuine agency, alignment with passion -- are conspicuously absent from most tech jobs.
Critical Analysis
This is the emotional companion piece to the structural arguments about AI displacing knowledge workers. Where economic analyses talk about labor markets and retraining, Wallace talks about what it feels like to realize your entire career might have been a detour from what actually makes you happy.
The essay is strongest when it's personal and specific. The middle school basketball team, the undefeated streak, the confidence that radiated into other areas of life. It's weakest when it reaches for broader claims about "many people in tech."
Connects to The Mundanity of Excellence -- coaching excellence, like swimming excellence, is about qualitatively different approaches, not just showing up. Wallace was good at coaching because he was naturally attuned to kids, not because he worked harder than other coaches.
Also connects to Things You're Allowed to Do -- Wallace's essay is implicitly about giving yourself permission to want something other than a tech career.
Sources: Happiest I've Ever Been Last updated: 2026-05-14