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  1. Every stalled agent project I have looked at contains a version of the same sentence: "we need to modernize the platform first."

  2. Someone on your team changed a prompt last Friday.

  3. Why Agents Get Canceled

    In July 2025, an AI coding agent deleted a live production database.

  4. What I Optimize for Now

    What I optimize for has shifted, and the older preferences were defensible at the time.

  5. Systems That Surprised You

    The most useful audits of long-lived software are the ones where you were wrong about what would last.

  6. Decisions That Aged Badly

    They were defensible at the time.

  7. Most systems are built as if the original builder will always be around to explain them.

  8. Most architecture conversations focus on what a system can do.

  9. AI in Long-Lived Systems

    Every AI integration is a bet that you can monitor something you do not fully control.

  10. No one decides to make a system heavy.

  11. Abstractions That Age Poorly

    Good abstractions compress complexity.

  12. Refactoring as a Signal

    The code that needs refactoring most often is rarely the worst code.

  13. Defaults Nobody Revisits

    Best practices are borrowed conclusions.

  14. Flexibility is one of the most intuitive design goals in software.

  15. Time As A Design Constraint

    Most systems are designed against requirements.

  16. When Code Is No Longer Scarce

    For most of software history, change was expensive.