All essays.
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No. 81 June 11, 2026 Data Metabolism
90% of Information Systems is Physical, the Other Half is Psychological
Why do we keep coding and encoding the same things?
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No. 80 May 26, 2026
Information Entropy Diagnostic
The Context Entropy Scan — Incontextable Incontextable — diagnostic instrument The Context Entropy Scan For each signal, mark how frequently your team or…
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No. 79 May 24, 2026 Data Metabolism
Discomfort In Numbers
Framing matters. Presenting data well is a valuable skill.
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No. 78 May 20, 2026 Data Metabolism
Reversing the Division of Cognition
Reversing the Division of Cognition In order to streamline our organizations, we have inadvertently made ourselves less intelligent.
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No. 77 May 13, 2026 Knowledge Turns
Maintaining Coherence: Invisible yet Indispensable
As information accumulates inside an organization, something less visible begins to grow alongside it.
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No. 76 May 9, 2026 Information Half-Life
Documentation is Not Context
When organizations lose clarity, the instinct is to document.
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No. 75 May 1, 2026 Knowledge Turns
Return on Context: The Hidden Constraint in Modern Organizations
Data and storage are inexpensive, but maintaining context across an organization is the real challenge that organizations face.
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No. 68 April 25, 2026
The Big Threat that Zero Trust Never Sees
The Unquestioned Assumptions and Questionable Data Guiding Organizational Decisions Trust with a circle and an X through itThe real danger isn’t access to…
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No. 69 April 25, 2026
Adding More Information Tools Is the Right Answer to the Wrong Problem
The problem isn’t that people lack information.
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No. 02 April 21, 2026
What Everyone Has Wrong About Project Management and Budgeting
Variability is Information When a project falls behind schedule the response is almost always some version of better planning next time.
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No. 03 April 15, 2026 Data Metabolism
Organizational GLP-1
Metabolizing Data Ingestion GLP-1 wasn't developed for obesity.
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No. 04 April 7, 2026
What’s Not Included in Any Software Package
Four organizations and one practice that figured this out — and what they built instead.Amazon didn’t solve its meeting problem by buying better meeting…
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No. 05 April 2, 2026
The Curse of Proxy Linearity
Knowledge doesn’t flow through predefined channelsOrganizations don’t actually know how knowledge moves through them.They know how information is supposed to…
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No. 06 March 31, 2026
The Linear Lie
Knowledge doesn’t move in straight lines.
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No. 07 March 22, 2026
Knowledge Turns: The Metric We Never Built for Knowledge Work
The Organizational Entropy Problem Nobody Is MeasuringIn the 1990s I worked alongside people who were trying to do something genuinely difficult — measure…
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No. 08 March 17, 2026
AI Changes Everything But Not How You Think
Human Cognition Is Still the ConstraintIn seventh grade I went on a field trip to the General Motors assembly plant in Framingham, Massachusetts.
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No. 09 March 11, 2026
Move Fast and Who Knows What Breaks
Internet Speed gave us a decade to notice what was breaking.
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No. 10 March 10, 2026
The End of the Meaningless Acronym
CRM. ERP.
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No. 11 March 9, 2026
The Risk That Doesn’t Have a Date
Your organization has a CISO. It doesn't have a KIO.
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No. 12 March 4, 2026
The CHEF Model: How Business Information Systems Hide What Matters
The Unintended Consequences of Embedding Best Practices Organizations built systems to capture what they know.
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No. 13 March 2, 2026
Friction is a Valuable Filter
Efficiency's Blind SpotEvery productivity platform, every workflow automation, every scheduling tool, every AI assistant is built on the same premise: friction…
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No. 14 February 26, 2026
The Cost of Frictionlessness
Why the path of least resistance often leads to the industry floorIn the Algorithmic Age, friction is treated as a defect.Interfaces are redesigned to remove…
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No. 63 February 26, 2026
The Black Swan Hiding in Your Information Management Stack
How unquestioned assumptions quietly compound systemic risk Most organizations think their biggest risks are visible.
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No. 15 February 24, 2026
The Renting Trap
Why Your AI Strategy Is Making You IdenticalThe difference between a utility and a competitive advantage.In my last post, I discussed Strategic Convergence…
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No. 16 February 23, 2026
The Algorithm Doesn’t Know What Time It Is
Preserving Interpretive Capacity in the Age of Infinite OutputThere is a particular kind of confidence that comes from having access to a lot of processed…
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No. 17 February 19, 2026
The Algorithmic Age — And the Threat to Strategic Differentiation
Preserving Competitive Distinction in a High Velocity WorldWe are entering a new operating environment.Not just the Information Age.Not simply the AI Age.We…
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No. 18 February 16, 2026
Roger Smith’s Ghost and the “Orphans of Automation"
From Robot Arms to Large Language Models: The Danger of Scaling Incoherence to the Nth PowerIn the 1980s, GM Chairman Roger Smith had a vision.
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No. 72 February 11, 2026
Dissing the Default
Defaults are decisions you didn’t make Years ago Joel Orr told me something I didn’t fully understand at the time: Structure is destiny.
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No. 71 February 10, 2026 Information Half-Life
The Vulnerability Every Scanner Misses
Information decay is a threat no software can detectYour dashboard is green.
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No. 73 February 1, 2026
Why Cloud Computing Is No Longer Enough
The information landscape has shifted—and most organizations are still operating in the last era.
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No. 64 January 27, 2026 Total Cognitive Load
Context Loss Prevention
Losing data is problematic, but losing understanding is catastrophic
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No. 56 January 25, 2026 Data Metabolism
The Big Lie of Big Data: That the Business Still Makes Sense
Why lack of coherence is more dangerous than missing data For decades, people inside organizations have complained about the same thing: “The systems don’t…
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No. 70 January 22, 2026
The Slow Information Movement
Why clarity beats velocity in the age of infinite output We don’t have an information problem.
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No. 61 January 21, 2026 Total Cognitive Load
Next-Generation Content Filtering
Combatting Terabytes of Empty Content When most people hear “content filtering,” they think about moderation.
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No. 74 January 20, 2026
More Faster / Less Better
There are two philosophies competing inside the workplace.
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No. 55 January 15, 2026
Why Shared Intelligence (SI) is More Important Than AI
Artificial intelligence may dominate the conversation, the idea of building Shared Intelligence across the organization is the core capability that will make the biggest difference in the long run.
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No. 60 January 12, 2026 Information Half-Life
The Hidden Weakness in Your Technology Stack
Why your biggest technology risk isn’t a vulnerability—and can’t be patched Most organizations think they understand their technology risk.
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No. 59 January 9, 2026 Knowledge Turns
Shared Intelligence is Not a SharePoint Site
We have been sold a lie: that if we just "capture" enough information, we will magically become smarter.
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No. 57 January 8, 2026 Data Metabolism
When There Is No Safe Place for Doubt
Why systems reward certainty — and punish thinking
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No. 65 January 6, 2026 Total Cognitive Load
The Layer of Nonsense in Modern IT
Why More Tools Don’t Lead to Better Understanding Modern IT didn’t become complex overnight.
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No. 62 January 5, 2026 Data Metabolism
The Context Files — Episode 2
The Boeing 737 MAX: When Safety Became a Data Problem Episode 1: The Challenger Disaster demonstrated how critical context was known, discussed, and even…
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No. 58 January 1, 2026 Data Metabolism
Why This Matters Now
Exposing the Hidden Risk of Default Settings Automating Decisions Faster Than We Are Understanding Them Tools like SharePoint, Teams, and now AI copilots…
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No. 21 December 31, 2025
The Two Fatal Flaws of the Data Age (Part 2)
Why AI Doesn’t Fix the Problem (It Exposes It)First, we believe data produces knowledge.Second, we believe data explains people.Thanks for reading…
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No. 22 December 30, 2025
The Two Fatal Flaws of the Data Age – and It's Not What You Think (Part 1)
It's What's Not in the Data that MattersWhen people criticize the Data Age, they usually reach for the obvious villains.Too much data.Bad dashboards.Biased…
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No. 23 December 29, 2025
Your Amazon Order History Isn’t Knowledge About You
Why past purchases don’t explain future behaviorYour Amazon order history feels like pure fact.You bought these items.Thanks for reading IN-CONTEXT-ABLE!
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No. 24 December 24, 2025
Why the Cluetrain Manifesto Was Right — And Why It Still Hurts
How We Spent 25 Years Avoiding Cluetrain’s Real WarningIn 1999, four people wrote a strange little book that sounded less like management theory and more like…
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No. 25 December 22, 2025
Why You Should Never Trust a Dashboard
Dashboards are seductive.They glow.They animate.They reassure.They make complexity look tidy and controllable—like the world is finally behaving itself.Thanks…
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No. 26 December 18, 2025
The Single Source of Truth Fallacy
Why False Certainty Is the Most Dangerous Property of InformationOrganizations say they want clarity.And they’re right.
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No. 27 December 15, 2025 Data Metabolism
The Context Files — Episode 1
When Meaning Broke: The Challenger Disaster and the Anatomy of Information Failure On January 28, 1986, the Space Shuttle Challenger disintegrated 73 seconds…
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No. 28 December 15, 2025
Why Efficiency Thinking Is the Last Great Industrial Myth
What happens when optimization scales faster than meaningEfficiency is one of the most successful ideas ever invented.It transformed agriculture.It powered the…
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No. 29 December 14, 2025
The Hidden Cognitive Complexity Tax
Why “Everything Works — Mostly” Is Wearing Organizations DownHere’s the most accurate description of life inside most organizations:Everything…
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No. 30 December 14, 2025
The Infrastructure Layer AI Cannot See
Why every organization will need a Context Management System — whether they plan to or notAI is being framed as a tool revolution.That framing is wrong.Thanks…
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No. 31 December 13, 2025
Why Your AI Stack Is Fragmenting Reality
The Hidden Crisis No One Wants to Name — Yet Everyone Is ExperiencingThere’s a strange tension building inside organizations right now.On one hand, AI tools…
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No. 32 December 12, 2025
The Context Big Bang
How information began scaling faster than meaning — and why every organization is still dealing with the fallout.There’s a moment in organizational history we…
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No. 33 December 11, 2025
What CAD/CAM Taught Us About the AI Revolution (And Why We Forgot)
The 45-Year-Old Lesson About Technological Breakthroughs That Everyone’s IgnoringThere’s a question the AI world should be asking far more seriously:If the…
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No. 34 December 9, 2025
The Context Age Is Here
And no amount of better software can fix the meaning problem.
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No. 35 December 7, 2025
The Philosophical Roots of InContextable
How a lifetime of watching information misbehave revealed the real reason work keeps breaking.RootsPeople sometimes ask where InContextable came from.
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No. 36 December 7, 2025
The Context Entropy Scan
(If the work feels messy, it’s because meaning is leaking somewhere)Entropy isn’t just for physics.It shows up in organizations every day —as the slow, steady…
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No. 37 December 7, 2025
The Context-First Meeting
(Fix the context first, and everything else falls into place)Most meetings fail for a simple reason:People enter the same roomwith completely different…
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No. 38 December 7, 2025
The No-New-Tools Challenge
(Because clarity beats software 10 times out of 10)When teams feel friction, the first instinct is often:“We need a better tool for this.”A new platform.A new…
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No. 39 December 7, 2025
The Two Versions of Reality Test
(Because alignment on words isn’t alignment on meaning)Two people can agree on the same sentenceand still be imagining entirely different realities.This is how…
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No. 40 December 7, 2025
Write the Meaning First
(Your message shouldn’t require archaeological excavation)Most communication fails because the meaning is buried under updates, details, or requests.People end…
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No. 41 December 7, 2025
The Two-Layer Decision Template
(Decisions fail when the reasoning disappears)Most decisions look clear the day they’re made.But weeks later, no one remembers why they were made.And when the…
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No. 42 December 7, 2025
The Context Snapshot
(A lightweight ritual that prevents projects from drifting into the wilderness) Projects don’t go off the rails suddenly.They go off the rails quietly — one…
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No. 43 December 7, 2025
The Reverse Brief
(The cure for “That’s not what I meant”)You’ve probably had this experience:You explain something clearly.The other person nods.They seem to understand.Then…48…
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No. 44 December 7, 2025
The One-Sentence Context Check
(A tiny habit that prevents hours of rework)Most misunderstandings don’t come from bad communication.They come from missing intent.A message can be technically…
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No. 45 December 1, 2025
The Illusion of Coherence (and the Search for Better Explanations) Part II
How Naval Ravikant and David Deutsch Shaped the Birth of InContextAbleFor all the talk about dashboards, AI, “data-driven decision making,” and digital…
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No. 46 December 1, 2025
The Illusion of Coherence (and Why Big Companies No Longer Have It) Part I
Why Organizations Can’t Standardize on a Single RealityFor decades, we’ve told ourselves a comforting little bedtime story about leadership:“The CEO has a…
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No. 47 November 30, 2025
The Corporate Cognitive Capacity Crisis
Organizations aren’t running out of information.
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No. 48 November 30, 2025
The Information You Trust Most Is Probably the Least Useful
Organizations don’t treat all information equally.
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No. 49 November 30, 2025 Data Metabolism
The Collapse of the Hierarchy
The Big Idea: Traditional hierarchy works until the environment moves too fast for permission structures.
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No. 50 November 30, 2025
The Context Explosion
The Half-Life of Everything Is ShrinkingThe shift toward speed began as a competitive advantage.“Time to market” became the mantra.Thanks for reading…
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No. 51 November 26, 2025
The Context Map
A simple tool to finally see how work actually happens How to see how work really happens (so everything else becomes easier)Every organization struggles with…
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No. 52 November 24, 2025
The One-Page Context Map
A practical tool for understanding how work really gets done (before adding more tools, AI, or process)Most organizational problems look complicated because…
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No. 53 November 24, 2025
The Collapse of the Hierarchy
The Structure of Work Has Changed — The Mindset Hasn’t (Yet)Why the Org Chart Is Failing Faster Than Anyone Wants to AdmitModern organizations are haunted by a…
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No. 54 November 24, 2025
Welcome to In-context-able
Escaping the Noise: A New Way to See Work, Information, and AISomething clicked for me recently.For years I’ve been circling around a set of big ideas about…