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Dennis Kennedy. Lawyer, author, blogger, speaker and podcaster Dennis Kennedy offers insights on the application of technology in the practice of...

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Denniskennedy.com news digest

  • 11 days

    The Inquest: Trading the AI Idol for Human Investigation

    In 1980, I wrote a senior thesis paper called “Imagination: A Romantic Ideal.” My investigation then was a critique of the German and English Romantics who, in their zeal to undo the “damage” of Enlightenment Reason, merely erected a new idol: The Imagination...

  • 20 days

    Retiring the Scoreboard: Why I’m Done Counting Books

    Retiring the Scoreboard: Why I’m Done Counting Books
    For many years, I ran a 52 Books in 52 Weeks challenge on my blog, usually as my first blog post of the year, which I updated each month. It was an annual public commitment, a visible signal of intellectual seriousness, and a helpful forcing function...

  • 22 days

    Why I’m Making Personal Strategy Compass Free (And What That Has to Do With Obli...

    I launched Personal Strategy Compass as a premium newsletter a year ago. The decision made sense on paper: quality content, established expertise, proven frameworks. But something never quite felt settled.
    Not wrong, exactly. Just… misaligned.
    Then I drew an Oblique Strategies card during my own quarterly planning: “Honor thy error as a hidden intention.”...

  • 1 month

    The Great Career Security Fallacy

    Why Your 2026 Career Security Depends on Your December Energy Audit
    As the legal market approaches the end of 2025, a pervasive, quiet anxiety has taken hold. Between the “spreadsheet economics” of law firm layoffs and the looming shadow of 2026, many senior professionals are responding with a predictable, yet dangerous...

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