Trails

Curated collections of excerpts and highlights

The KnowledgeLeonardo da VinciZero to OneiWozElon Musk

Rebel Circuits

Rule-breaking as path to understanding.

Conventional wisdom First-principles thinking Hacker definition Hacker motivation Pirate spirit
SuperforecastingSeeing Like a StateTuring's CathedralCoders at WorkCreativity, Inc.

Expert Intuition

Expertise defies formalization; conscious effort defeats itself.

Intuition Meditation Mētis knowledge Overthinking Tacit knowledge
BehaveThe Inner Game of TennisThe InformationThe Rational OptimistAlan Turing

Copy Machine

Imitation powers both learning and conformity.

Cultural transmission Group uniformity Imitation Imitation Game Imitation learning
The Elephant in the BrainBehave21 Lessons for the 21st CenturyTitanSteve Jobs

Useful Lies

Self-deception as strategy: the best liars believe themselves.

Blue lies Evolutionary psychology Hidden motives Post-truth species Self-deception
The KnowledgeThe Rational OptimistGuns, Germs, and SteelThe Dream MachineThe Origin of Wealth

Collective Brain

Why isolated groups lose knowledge and capabilities.

Bus factor Collective knowledge Critical mass Isolation effects Knowledge transmission
Steve JobsLeonardo da VinciAlan TuringTitanElon Musk

Father Wound

Absent fathers forged titan ambition through unmet longing.

Abandonment issues Childhood trauma Entrepreneurial ambition Father-son relationship Psychological impact
Guns, Germs, and SteelBehaveThe Elephant in the BrainThe Dictator's HandbookTitan

Winner's Lock

Winners eliminate competition; victory becomes permanent control.

Coalition dynamics Coalitions Dominance hierarchy Success feedback loop Vertical integration
At HomeGuns, Germs, and SteelEconomics in One LessonThe Origin of WealthZero to One

Commodity Clock

Every treasure becomes tomorrow's ordinary commodity.

Creative destruction Invention diffusion Red Queen races Technological waves Temporary advantage
The Mom TestDeveloper HegemonyFreakonomicsThinking in SystemsWhy Greatness Cannot Be Planned

Proxy Trap

Metrics become mirages when optimized directly.

Deception Incentives Measuring progress Objective function Perverse instantiation
SuperforecastingThe Book of WhyHackers & PaintersOut of the CrisisThe PayPal Wars

False Positives

Rare signals drown in false positives.

Base rate Fraud control Nuclear early warning Outside view
The Elephant in the BrainBehaveCollapseThe Mom TestHackers & Painters

Polite Conspiracy

Silent agreements to avoid uncomfortable truths.

Hidden motives Psychological denial Rational individual Self-deception Unsayable truths
The Dictator's HandbookSteve JobsHatching TwitterThe PayPal WarsFounders at Work

Ejection Seat

Founders ousted through political power dynamics.

Board meeting Corporate politics Executive conflict Founder danger
The Design of Everyday ThingsAbout FaceThe Inner Game of TennisSuperforecastingBoyd

Intuitive Flow

Mastery means bypassing conscious thought entirely.

Expert intuition Mētis knowledge OODA Loop Pattern recognition Peak performance
Leonardo da VinciConspiracyBoydThe Inmates Are Running the AsylumThe Inner Game of Tennis

Necessary Drag

Removing friction sometimes creates chaos.

Clausewitz friction Cognitive friction Convenience Policy resistance Satisficing
The Dictator's HandbookThe Ascent of MoneyManufacturing ConsentDeveloper HegemonyWhy Nations Fail

Winning Coalition

Organizations minimize coalitions needed to maintain control.

Concentrated power Power dynamics SNAFU Principle Selectorate theory Separation of powers
The Master SwitchGuns, Germs, and SteelThe Making of the Atomic BombWhat Technology WantsAbundance

Multiple Discovery

Ripe ideas emerge independently across the world.

Adjacent possible Cumulative development Invention inevitability Simultaneous discovery
How to Read a BookSuperforecastingSeeing Like a StateCollapseGuns, Germs, and Steel

Hidden Structure

Copying forms without understanding structure guarantees failure.

Blueprint copying Idea diffusion Rules vs. habit Tacit knowledge
BehaveThe Elephant in the BrainThe Rational OptimistThe Dawn of Everything21 Lessons for the 21st Century

Costly Signals

Actions must be expensive to be believed.

Conspicuous displays Easter Island Escalation concept Handicap principle Potlatch festivals
Chaos MonkeysPhilosophy in the FleshTitanDebtThinking in Systems

Deferred Debts

Gifts, moral debts, and technical debt share logic.

Exponential growth Gift exchange Moral Accounting Technical debt
Bullshit JobsFour Thousand WeeksLeonardo da VinciThe Dream MachineMasters of Doom

Joy Dividend

Joy became more productive than efficiency optimization.

Busyness prestige Creative work efficiency Joy in work Playfulness Serendipity
SuperforecastingHow to Read a BookBecoming a Technical LeaderThe Inner Game of TennisThinking in Systems

Mastery Ravine

Getting worse precedes getting better in skill.

Conceptual breakthrough Error embracing Mental grooves learning plateau
The Inmates Are Running the AsylumSkunk WorksWhere Wizards Stay Up LateThe Soul of a New MachineFounders at Work

Trust Networks

Large coordination emerges from small-scale trust.

Inter-agency coordination Managerial candor Pixar Braintrust Team building
The Worldly PhilosophersAn Elegant PuzzleThe Master SwitchSeeing Like a StateCoders at Work

Legibility Tax

Standardization enables scale but destroys local knowledge.

Central planning Decentralization Large-scale changes bureaucratic capitalism
Thinking in SystemsPhilosophy in the FleshPrisoners of GeographyThe InformationAmusing Ourselves to Death

Shaping Structure

Method of creation shapes what is created.

Conway's Law Embodied mind Geopolitics Physical constraints
The Ascent of MoneyThe Worldly PhilosophersWhy Nations FailThe Master SwitchTitan

Kronos Cycle

Open systems consolidate into monopoly, then repeat.

Creative destruction Disruptive technology Monopoly capitalism Schumpeter
Out of the CrisisThe PerfectionistsAlan TuringTo Engineer Is HumanIntuition Pumps And Other Tools for Thinking

Testable Thinking

Transforming vague concepts into testable frameworks.

Clarification chain Fermi estimation Intuition pumps Tolerance concept
The Cuckoo's EggThe GoalThe Effective EngineerThe Art of Doing Science and EngineeringHow to Measure Anything

Hidden Meters

Building observability changes what you see.

Hawthorne effect Observer bias Statecraft optics System monitoring Work-in-process
The Rational OptimistLeonardo da VinciHow Asia WorksThe Hardware HackerThe Innovators

Ideas Mate

Weak IP accelerates innovation through collaborative copying.

Hacker culture Innovation spillover Japanese copying Open source Renaissance workshops
The Design of Everyday ThingsHow to Read a BookSeeing Like a StateThe KnowledgeSuperforecasting

Illegibility Premium

Practical knowledge defeats rationalized systems.

Craftsmanship Industrial policy Intuition Pattern recognition Procedural knowledge
Turing's CathedralThe Soul of a New MachineThe GoalThe Dream MachineThe Idea Factory

Unreliable Parts

Mega-projects orchestrate unreliable elements into coherent wholes.

Computer reliability Design redundancy Failure analysis Multidisciplinary expertise
BoydThe Guns of AugustThinking in SystemsThe Origin of WealthCountdown to Zero Day

Tempo Gradient

Decision-making speed determines conflict outcomes.

Cyberstrike advantages Fast takeoff OODA Loop Time delays
Chaos MonkeysHatching TwitterNo FilterFounders at WorkCreativity, Inc.

Desperate Pivots

Desperation, not genius, drove transformative pivots.

Hindsight bias Odeo reinvention Pixar Image Computer Startup pivot
Seeing Like a State1493Thinking in SystemsWhat Technology WantsSteve Jobs

Simplification Trap

Simplification enables breakthroughs or destroys value.

Resilience trade-offs System resilience Uniformity and creativity Utilitarian simplification
Zero to OneConspiracyThe Ascent of MoneyFreakonomicsFounders at Work

Information Edge

Knowing what others don't creates competitive advantage.

Competitive advantage Contrarian thinking Information asymmetry Intelligence network
The Rational OptimistGuns, Germs, and SteelDebtLongitudeThe Perfectionists

Measuring Trust

Precise measurement creates infrastructure for distant trust.

Invention of writing Longitude measurement Mass production Medieval trade Standardization
The BoxThinking in SystemsThe End of the World is Just the BeginningCreativity, Inc.How the World Really Works

Steel Box

Container shipping remade global supply chains.

Containerization Just-in-time manufacturing Labor displacement Leverage points Unintended consequences
Intuition Pumps And Other Tools for ThinkingThe Inner Game of Tennis21 Lessons for the 21st CenturyThe Art Of LovingThinking in Systems

Self-Surrender

Ego-dissolution enables both transcendence and manipulation.

Alcoholics Anonymous Flow state Imitation Letting go System mastery
The Art of Doing Science and EngineeringAlan TuringThe Dream MachineSkunk WorksThe Soul of a New Machine

Tinkering Sanctuary

Protected spaces insulated from interference enable breakthroughs.

Hands-On Imperative Opportunistic exploration Project isolation Protecting new ideas
Four Thousand WeeksLeonardo da VinciThe PerfectionistsHackers & PaintersFounders at Work

Perfectionist's Trap

Pursuit of perfection prevents completion.

Overengineering Shipping products Unfinished works Worse is Better
Enlightenment NowThe InformationWhat Technology WantsThe Origin of WealthBoyd

Entropy Tax

Import order constantly or dissolve into disorder.

Material decay Open systems Second Law Self-organization System resilience
StructuresTo Engineer Is HumanWhat Technology WantsThe PerfectionistsThe Origin of Wealth

Invisible Crack

Microscopic defects propagate silently until catastrophic failure.

Brittle fracture Conformity Metal fatigue Self-deception gradual change
The GoalThinking in SystemsStructuresWhere Wizards Stay Up LateAn Elegant Puzzle

Pacemaker Principle

Constraints in one part dictate the whole.

Price inelasticity Strait of Hormuz Throughput limitation Weakest link
Philosophy in the FleshIntuition Pumps And Other Tools for ThinkingHow to Measure Anything21 Lessons for the 21st CenturyThe Design of Everyday Things

Mental Maps

Simplified models systematically fail in complex reality.

Chaos theory Folk psychology Heuristics Mental models State legibility