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

For years, I’ve explored productivity techniques, technology tools, and strategies. I now have found and developed one practice that has had the most profound impact – the Personal Quarterly Offsite (PQO).

Frankly, I believe the PQO is the most important work I do. It’s not just about setting goals; it’s about intentionally designing a life you want to live. It’s…
Continue Reading Unlocking Your Potential: Why the Personal Quarterly Offsite is My Most Important Work (and How It Can Transform Yours)

Well, here we are again. Another February 15th and another blawgiversary for DennisKennedy.Blog. It’s hard to believe it’s been twenty-two years. since I wrote that first bold and triumphant announcement, echoing Babylon 5: “And so it begins . . .” I genuinely thought I was late to the blogging party back in 2003. Turns out, I was just early for…
Continue Reading Celebrating the 22nd Birthday of DennisKennedy.Blog

The latest issue of the Personal Strategy Compass newsletter (premium subscription only) is out, and it’s all about getting back on track with your quarterly goals – even if you’re feeling a little behind. We’re diving into the “grace period” PQO, a shorter, more forgiving approach to getting back on track after your Personal Quarterly Offsite, perfect for those mid-quarter…
Continue Reading Personal Strategy Compass Newsletter – Issue #3: The Grace Period PQO

I’ve long advocated for Personal Quarterly Offsites (PQOs) as a powerful personal tool for legal professionals. Taking a half-day each quarter to step back, reflect, and plan can drastically improve focus, productivity, and long-term strategic alignment.

Let’s be honest: most “personal productivity” advice is, well, let’s just say overhyped. PQOs actually work because they are personal and structured. Your personal…
Continue Reading Free Personal Quarterly Offsite Handout – And a Better Way to Do PQOs in the Age of AI

“I don’t have time for personal strategy planning. I’m so busy that I don’t have time to anything but work.” Sound familiar? In this month’s issue of my Personal Strategy Compass newsletter (paid subscription only), I’m tackling the #1 objection I hear about Personal Quarterly Offsites (PQOs). I’ve developed a stripped-down approach called the Minimum Viable PQO (“MVPQO) that takes…
Continue Reading Minimum Viable Personal Quarterly Offsites – My New Newsletter Issue

As an avid reader, for many years I have set the goal of reading 52 books in 52 weeks. It’s ambitious, but reading is a hobby and this exercise helps me keep track of what I’ve read. In 2024, I read 72 books, exceeding my goal by quite a bit. Or, more accurately, I listed 72 books that I read.
Continue Reading 52 Books in 52 Weeks – 2025

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 was interesting.

This is the…
Continue Reading AI’s Role in Legal Practice: High-End and Middle Ground

I’m excited to announce the launch of Personal Strategy Compass, my new premium newsletter focused on helping professionals implement Personal Quarterly Offsites (PQOs) in their lives and careers. Subscribe here.

Does this seem all too familiar?

Late on Sunday night, sleep eludes you. Your law practice is successful by any objective measure, but something isn’t right. Maybe you’re…
Continue Reading Introducing Personal Strategy Compass: A Masterclass Newsletter for Strategic Life Planning with Personal Quarterly Offsites

I see the future of legal education transforming before our eyes, and I’m excited to share that I’m contributing in my own small way to that transformation. My Fall 2024 syllabus for “Artificial Intelligence and the Law” at Michigan State University College of Law is now available on the Syllabi Commons, thanks to John Mayer at CALI. Think of…
Continue Reading Syllabus for My AI and the Law Course Now Available on the Syllabi Commons

If innovation is on your law department’s agenda for 2024, this message is for you. As 2024 draws to a close, I’ve found myself reflecting on how far the world of law department innovation has come—and how much work remains. There’s one small problem: I have only one or two open slots left for 2024 keynote presentations in December.

My…
Continue Reading Don’t Miss Out: Final Law Department Innovation Keynotes with 2024 Pricing

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 legal technology. There are too…
Continue Reading Lessons from My Career in Legal Tech – 2024 Edition

About a year-and-a-half ago, Tom Mighell and I decided to start an interview series on our podcast, The Kennedy-Mighell Report. We called it “Fresh Voices on Legal Tech” because we wanted to highlight both a new generation of legal tech and new perspectives and approaches on legal tech. We thought “fresh voices” covered what we wanted to accomplish and…
Continue Reading The Fresh Voices on Legal Tech Podcast Interview Series