PHILOSOPHY → PRODUCT STRATEGY

Kept showing up in roadmap debates. The way I'd hold two contradictory priorities without rushing to resolve them. Finally traced it: ambiguity tolerance.

Thought it was just vocabulary — sounding smart in meetings. No, it's the whole frame. Philosophy trains you to sit with "we don't know yet" without panicking. Product needs that.

Also: asking "what do you mean by X" before solving for X. annoys people sometimes

cf. Wittgenstein on language games → see: stakeholder alignment

re-read this after the OKR disaster of Q3. held up.

pattern recognition protocol initiated

FIRST PRINCIPLES → DEBUGGING

Works on code. Works on arguments. Works on relationships.

The move is the same: stop. what are we actually assuming here. Nine times out of ten, the bug is in the assumption layer, not the logic layer.

Thought this was just "being analytical" — no, it's a specific skill. Learned it from physics, reinforced by bad code reviews, now can't turn it off.

see also: Feynman on cargo cult science

applies to self-debugging too. uncomfortable but useful.

STRATEGY GAMES → ORGANIZATIONAL DYNAMICS

Twilight Imperium taught me more about alliance formation than any management book. Not sure if this is profound or just fun to say

Real insight: resource scarcity changes behavior. In games, you see it in 4 hours. In orgs, same dynamics, slower clock.

Also: people reveal their actual decision-making style when there's no "right answer" — spreadsheets can't capture this spreadsheets actively hide this

run a game night before hiring for leadership? half-joking.

TRAVEL RISK → DECISION FRAMEWORKS

Kawah Ijen at 2am. Active volcano. Acid lake. Blue fire.

Calculated risk vs. recklessness: there's a guide, there's a path, there's a gas mask, there's a turn-back point. The risk is real but bounded.

Realized later: this is exactly how I think about product bets. What's the worst case realistic downside? What's the escape hatch? What would make us turn back?

Does this apply to career decisions too

related: survivorship bias in travel stories

QUIZZING (age 12) → CONNECTING DISPARATE FACTS

This is where it started. Not the competition — the rabbit holes.

"What year was X invented" → but why then? → what else was happening? → oh interesting → 3 hours gone.

The skill: holding random facts loosely until they suddenly connect. Can't force it. Can only feed it.

still happens. lost yesterday to a Wikipedia spiral about █████████

cooking intuition → system design

jazz improvisation

why maps fascinate

translation as worldview

tinkering with Jekyll

Current question: what do lending systems and writing have in common?

Both are about trust calibration. Both require reading signals that aren't explicit. Both fail when you optimize for the wrong proxy metric.

Still pulling on this thread