The March issue of my Personal Strategy Compass newsletter is out.
This month’s piece explores something I’ve been noticing about strategic planning. The hardest part is usually not the work of planning itself. It’s the residue that planning drags along with it.
Ideas, priorities, and intentions tend to accumulate. We carry them forward month after
Let me explain why that is a principle, not a preference, and
The promise is leverage: brief, high-intent sessions. You bring the question, the tool brings the synthesis, and you leave with more than you arrived with. That is the value proposition.
Here is what often happens
We pay AI tools to do the hard work, like the synthesis, the heavy lifting, and the cognitive labor we do not have time for. What we often get instead is a tool that produces a decent first draft and then hands the real work back to us.
Not just the hard work. The administrative
We’ve spent the last couple of years treating generative AI like a vending machine. Select a task. Insert a prompt. Retrieve a product. And to be fair, in many legal and professional contexts that’s exactly the right frame: accuracy and precision matter and “creative” output in payroll or billing codes is usually just a polished
For more than two years, lawyers have been told that success with generative AI depended on writing better prompts and a search for the perfect “magic wand” prompting formula. That was the wrong lesson. The real change in 2026 is not found in the model itself, but in the professional posture required to use it.
I had a long session recently with a public genAI tool that taught me something more important than the topic I started with.
The lesson was not about whether the model was “smart enough.” It was about control. At a certain point, I realized I was no longer simply prompting an LLM. I was negotiating
DennisKennedy.Blog was born on February 15, 2003.
23 years. The tools change. The mission remains.
Still here. Still at it.
[Originally posted on DennisKennedy.Blog (https://www.denniskennedy.com/blog/)]
DennisKennedy.com is the home of the Kennedy Idea Propulsion Laboratory
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I ran an experiment at the beginning of February.
I closed my planning system and didn’t look at any of it for 48 hours. No peeking. No referencing. I just paid attention to what actually pulled at my thinking when nothing was prompting me.
Then, on Monday morning, before I opened anything, I wrote down
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.
