Most legal AI talk is still focused on whether the engine starts, while the real danger is that no one knows who’s actually steering the car once it hits the highway. It turns out the human in the loop isn’t a safety feature if the human doesn’t know which loop they’re currently standing in.
We
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
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
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
I spent the month of November doing what I called an “AI Sprint,” in which I experimented with a lot of new approaches and tried generating new types of outputs. I haven’t shared much of that yet, but I thought this exploration of what “AI in the Middle” might mean in law and law practice
This past Sunday, I was deeply honored to receive the Lifetime Achievement award at the American Legal Technology Awards.
As I stood there, absorbing the magnitude of the moment, I couldn’t help but think about the vast network of innovators, mentors, and colleagues who have shaped not just my career, but the entire field of
Summer is a great time to spend some time on legal innovation efforts, especially in law departments. To help innovators in law who want to work on the innovation process in a thoughtful, structured, and disciplined manner, I’ve made available for free download a PDF version of my book, Successful Innovation Outcomes in Law: A
And this blog reaches age 21. I’m planning a light celebration with cake, but the blog is lobbying hard for drinks and a night out. That’s been an ongoing source of tension.
I was asked in maybe 2006 how long I expected to keep writing this blog. My answer was that I couldn’t really see
I had hundreds of reasons to leave Twitter/X in 2023. However, I found that more difficult to do than I would have expected. So, I lingered there in a kind of downward-drifting limbo.
I told many people over the last several months that the most difficult issue for me in leaving was saying goodbye to
Would you help me out with a LinkedIn poll I’m currently running?
I’ve been told by several people (yes, more than one) that I should share what I’ve been doing with ChatGPT for personal productivity, planning, and innovation, and give some practical tips on those approaches. I’ve been doing a ton of experiments and have
