- Thinking in Systems: A Primer by Donella Meadows. For me, systems thinking has been the most effective universal tool for reasoning through complex problems, and this book is a readable, powerful introduction.
- Don’t Think of An Elephant! Know Your Values and Frame the Debate by George Lakoff. While written from a political perspective that some might find challenging, this book completely changed how I think about presenting ideas. You may be tempted to instead read his more academic writing, but I’d recommend reading this first as it’s much briefer and more readable.
- Peopleware: Productive Projects and Teams by DeMarco and Lister. The book that has given generations of developers permissions to speak on the challenges of space planning and open offices. Particularly powerful in grounding the discussion in data.
- Slack: Getting Past Burnout, Busywork, and the Myth of Total Efficiency by Tom DeMarco. Documents a compelling case for middle managers as the critical layer where organizational memory rests and learning occurs. A meditation on the gap between efficiency and effectiveness.
- The Mythical Man-Month by Frederick Brooks. The first professional book I ever read, opening my eyes to the wealth of software engineering literature waiting out there.
- Good Strategy Bad Strategy: The Difference and Why it Matters by Richard Rumelt. This book gave me permission to acknowledge that many strategies I’ve seen professionally are not very good, and a structured approach to writing good strategies.
- The Goal: A Process of Ongoing Improvement by Eliyahu Goldratt. Explores how constraint-theory can be used to optimize process.
- The Five Dysfunctions of a Team by Patrick Lencioni.
- The Three Signs of a Miserable Job by Patrick Lencioni. Another Lencioni book, this one explaining a three-point model for what makes jobs rewarding.
- Finite and Infinite Games by James Carse. Success in most life situations is about letting everyone continue to play, not about zero-sum outcomes. This seems pretty obvious, but for me it helped reset my sense of why I work.
- INSPIRED: How to Create Tech Products Customers Love by Marty Cagan. A thoughtful approach to product management.
- The Innovator’s Dilemma: When New Technologies Cause Great Firms to Fail by Clayton Christensen. A look at how being hyper-rational in the short-run has lead many great companies to failure. These days I think about this constantly when doing strategic planning.
- The E-Myth Revisited: Why Most Small Businesses Don’t Work and What to Do About It by Michael Gerber. The idea that leadership is usually working “on” the business, not “in” the business. Work in the business to learn how it works, but then document the system and hand it off.
- Fierce Conversations: Achieving Success at Work and in Life One Conversation at a Time by Susan Scott. How to say what you need to say, particularly powerful in giving structure to get past conflict aversion.
- Becoming a Technical Leader: An Organic Problem-Solving Approach by Gerald Weinberg. Permission to be a leader that builds on your strengths, not whatever model that folks think you should fit into.
- Designing with the Mind in Mind by Jeff Johnson. An introduction to usability and design, grounding both in how the brain works.
- The Leadership Pipeline: How to Build the Leadership Powered Company by Charan, Drotter and Noel. This book opened my eyes to just how thoughtful many companies are in intentionally growing new leadership.
Top posts for a time, the Reddit Digg comics immortalizes the migration from, and downfall of Digg. Since its first post of part 1 in 2009, the comics went on to be some of the most famous posts for years. They have now gone into distant memory, with part 2/3 being deleted and unavailable in the archives. Posts for Part 1 and Part 3 as well as the actual comics of Part 1, Part 2, and Part 3 can still be seen in the deep places of the web. The great war will inevitably be forgotten, but not today.
And the “how I made 2 million dollars on the stock market” is a much easier book that I read at the same time – it also explains some basic strategies. Could be read together. The reminiscences, however, are an absolute classic. The guy killed himself, by the way.