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 that has governed my work ever
Continue Reading The Inquest: Trading the AI Idol for Human Investigation
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 finished the books. I kept
Continue Reading Retiring the Scoreboard: Why I’m Done Counting Books
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 you’re unfamiliar with Oblique Strategies, it’s a deck
Continue Reading Why I’m Making Personal Strategy Compass Free (And What That Has to Do With Oblique Strategies)
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 harder.They are staying later, billing more,
Continue Reading The Great Career Security Fallacy
This work is licensed under a Creative Commons Attribution 4.0 International License (CC BY 4.0). Part of my #blogfirst Project.Adapted from a keynote address given to the National Association of Women Judges in October 2025
At a Glance
Continue Reading The Holmesian Leap: Solving the “Wicked Problem” of Access to Justice with AI
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 quiet, unnerving silence? I call
Continue Reading Personal Strategy Compass Newsletter #11: The Strategic Probe
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, perhaps counterintuitive, solution for you: the
Continue Reading The Power of the Strategic No
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 KennedyAugust 19, 2025Kennedy Idea Propulsion Laboratory Working Paper No. 2025-01
License: This work is licensed under the Creative Commons Attribution-ShareAlike 4.0 International License (CC BY-SA 4.0). Other licensing inquiries
Continue Reading The Operational Protocol Method: Systematic LLM Specialization Through Collaborative Persona Engineering and Agent Coordination
After a truly rewarding run, I am concluding my service as the Director of the Center for Law, Technology & Innovation at Michigan State University College of Law.It has been an immense privilege to work with so many brilliant students, dedicated faculty, and professional colleagues. I am incredibly proud of what we built together, especially our foundational “AI and the
Continue Reading My Next Chapter
We often talk about starting new projects, brainstorming innovative ideas, and maximizing our billable hours. But what about the silent drain on our productivity? I’m talking about the multitude of unfinished tasks, lingering commitments, and half-completed initiatives that clutter our minds and sap our energy.
In the latest issue of my newsletter, Personal Strategy Compass, I focus on
Continue Reading The Invisible Productivity Drain: Why “Finishing” Should Be Your New Focus
The Starting Gun for Legal AI Has Fired. Who in Our Profession is on the Starting Line?
The legal profession’s “wait and see” approach to artificial intelligence is now officially obsolete.
This isn’t hyperbole. This is a direct consequence of the White House’s new “Winning the Race: America’s AI Action Plan.” After spending the last few days studying the plan
Continue Reading Is the Legal Profession Ready to Win the AI Race? America’s AI Action Plan Has Fired the Starting Gun
If you are a high-achieving professional, you live with a fundamental tension. You know that deep, strategic thinking is the engine of your success, yet your calendar is a fortress that rarely permits the quiet time required for it. Important decisions loom, but the sheer complexity of your options leads to the all-too-familiar state of to busy to find the
Continue Reading Bypass Analysis Paralysis with the 20-Minute Lightning Round
It’s mid-June, and for many legal professionals, there’s a subtle but powerful shift in the air. We’re at the halfway point of the year. The initial burst of January motivation has long since faded, and we’re deep enough into the year to see whether our original plans are holding up against reality. Too often, we just keep pushing ahead, hoping
Continue Reading The Most Important Meeting You’ll Take All Year: Your Halftime Personal Quarterly Offsite
I’ve been working on organizing and optimizing my AI prompts and prompting methodologies. I noticed that I have two major categories of approaches.
The first I call “complex, structured prompting.”
Google Gemini describes that, and I think accurately, as “a systematic, engineered way to interact with AI. It’s about building a personalized ‘cognitive operating system’, which aims to augment your thinking, streamline
Continue Reading HyperCard: Illustrating My AI Prompting Approach
You’ve blocked out your Personal Quarterly Offsite (PQO). Great start. But let’s be honest: carving out those few hours for strategic thinking is only half the battle, especially for busy legal professionals.
The real challenge? First, protecting that sacred PQO time from the inevitable barrage of external and internal distractions. Second, ensuring the brilliant insights you gain don’t just evaporate
Continue Reading Fortifying Your Strategic Time – Personal Strategy Compass #6
Issue 5 of my Personal Strategy Compass Substack email newsletter (premium) has been published and sent. It has some new insights and some practical materials to help you move forward with my favorite personal productivity tool – Personal Quarterly Offsites. And I’ve made part of it available for free.
Over the years I’ve borrowed good ideas from everywhere—design thinking, Open
Continue Reading Declaring Your Major: One Decision That Can Turbo‑Charge Your Next Quarter