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
Is your leadership team asking for more innovation from your law department? Is delivering innovation results on your department or personal annual objective list?
C-suites are demanding that their general counsels and law departments accelerate their efforts to keep pace with innovation goals across the organization. They want their law departments to be as
