I have just posted a trio of new research white papers to SSRN. These represent the latest output from the Kennedy Idea Propulsion Laboratory and the culmination of my work over the last month to move AI beyond “utilitarian drift.” This is the cycle of incremental efficiency gains that ultimately generates no transformative insight.
Dennis Kennedy
Dennis Kennedy is a well-known lawyer, author, blogger, speaker and podcaster who is considered among the most influential authority on the application of technology in the practice of law. He is widely-praised for his ability to communicate complex technological and legal issues into language that non-experts can easily understand.
Human-in-the-Loop Is Systems Stewardship
An investigation into why serious AI work depends less on clever prompts and more on defending invariants, boundaries, and human judgment.
At the end of a long, technical AI session this week, something became clear to me: human-in-the-loop is being misunderstood in ways that matter.
The issue wasn’t whether the system could generate outputs quickly…
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.
Through a concrete analysis of Keats and Poe, I discovered a truth…
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. I…
Why I’m Making Personal Strategy Compass Free (And What That Has to Do With Oblique Strategies)

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.”
If…
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, reflex.
They are working…
The Holmesian Leap: Solving the “Wicked Problem” of Access to Justice with AI
- The Problem: The self-represented litigant (SRL) crisis is not a simple “information gap” but a “wicked
Personal Strategy Compass Newsletter #11: The Strategic Probe

For ambitious professionals, saying “no” is a celebrated strategic act. We use the “Strategic No” to reclaim our time, prune our commitments, and simplify our lives. It’s a powerful feeling of control and liberation.
But what about the day after?
What happens when the relief of a clear calendar fades and you’re left with a…
The Power of the Strategic No
Reclaim Your Focus with the Strategic No

Are you a high-achieving professional feeling the quiet hum of overwhelm? Do you suspect you’re ahead of your organization, sensing a career pivot on the horizon, but find yourself trapped by commitments that no longer ignite your passion? If so, you’re not alone. And I have a powerful…
The Operational Protocol Method: Systematic LLM Specialization Through Collaborative Persona Engineering and Agent Coordination

This paper has been published and and a PDF of it is available at https://papers.ssrn.com/sol3/papers.cfm?abstract_id=5397903
The Operational Protocol Method: Systematic LLM Specialization Through Collaborative Persona Engineering and Agent Coordination
By Dennis Kennedy
August 19, 2025
Kennedy Idea Propulsion Laboratory Working Paper No. 2025-01
License: This work is licensed under the Creative Commons Attribution-ShareAlike 4.0…