← Back to the entrance

This is a useful lie: a temporary path through a growing corpus. The essays remain where they were written. The path may move.

  1. Essay

    I Am Jack’s New Toy

    Every generation of enterprise software invents a tool to liberate people from the previous system, then builds a new institution around using it.

    Why now: Begin with the recurring institutional habit of turning a liberating tool into another administrative surface.

  2. Essay

    I Am Jack's Anti-Jack

    When organizations reward completed work without measuring whether anything improved, they become excellent at maintaining yesterday.

    Why now: Completion is not meaning. This establishes the difference before the machinery gets larger.

  3. Essay

    I Am Jack’s Top Priority

    A project that is never required to finish can never be allowed to fail, which is how a top priority becomes permanent background radiation.

    Why now: Priority becomes deferral when something can remain important forever without being required to finish.

  4. Essay

    I Am Jack's Shit

    A replacement product can discard the visible mess of a legacy system while also stranding the implementations and knowledge embedded inside it. The result is not modernization but forced reinvention, redistributed across users, partner teams, and the people rebuilding what already worked.

    Why now: Modernization meets memory, migration, and the cost of pretending prior knowledge is disposable.

  5. Essay

    I Am Jack’s High Cost of Delivering Measurable Value

    AI can make valuable work faster, safer, and easier to measure. In a dysfunctional organization, that evidence does not necessarily earn support. It can expose the architecture, process, and authority that made the work expensive in the first place.

    Why now: AI makes useful work cheaper to produce and, inconveniently, easier to use as evidence against the process surrounding it.

  6. Essay

    I Am Jack's Backlog Item

    A backlog item is supposed to reduce uncertainty enough for work to begin. When every unanswered possibility becomes a reason to keep clarifying, refinement preserves ambiguity and clarity becomes delay.

    Why now: The system attempts to create clarity and discovers an efficient method for postponing action.

  7. Essay

    I Am Jack’s Undigested Achievement

    A finished, tested, documented piece of work can remain institutionally unreal until every dependent approval, environment, and status field has processed it. The organization does not lack nourishment. It lacks the ability to absorb what was already delivered.

    Why now: The work can be finished while the organization remains unable to absorb it.

  8. Essay

    I Am Jack’s Human in the Loop

    Human oversight should challenge assumptions, resolve ambiguity, and authorize consequential transitions. When the human becomes a permanent serialization point, safety becomes delay—and AI may be most useful not only when humans preserve context for machines, but when machines preserve context for humans.

    Why now: The gate is finally put on the table: humans belong at consequential decision boundaries, not as permanent serialization points.

  9. Essay

    I Am Jack’s Body Double

    Organizations sometimes assign the same experimental work twice, but not with equal ownership. One person receives the spotlight and the authority to narrate; the other absorbs implementation risk and remains available as proof, fallback, and insurance.

    Why now: The technical system resolves into a power system: ownership, visibility, contingency, and who gets to narrate the work.

  10. Technical appendix

    The Anti-Fowler Principle

    Every useful architectural idea eventually becomes a rule applied by people who remember the noun and forget the conditions.

    Why now: Optional deep chamber, but still part of this path: architecture becomes doctrine when the nouns survive and the conditions disappear.