If May taught me anything, it’s that most strategies are just vibes with a spreadsheet. The real work? It’s in building systems that don’t collapse the moment a VP gets bored. Strategy without focus is theater. Engineering without systems is chaos. Leadership without sanity? That’s called a startup. Here’s what I read to make sense of it all.
Strategy & Organizational Clarity
Good Strategy/Bad Strategy by Richard Rumelt
This is a brutal takedown of corporate nonsense masquerading as strategy. Rumelt points out that most “strategic plans” are just goals with no diagnosis or coherent action. His framework is sharp: a real strategy identifies a challenge, offers a guiding policy, and lays out coordinated actions. Everything else is PowerPoint theater. It’s not sexy, but it’s a sanity check every leadership team needs.
Rework by Jason Fried & David Heinemeier Hansson
This one reads like a series of slaps to the face. The authors reject everything from meetings to growth-for-the-sake-of-growth. It’s opinionated, blunt, and sometimes smug, but refreshingly clear. Some of the most shocking advice? Fire your workaholics. Ignore your competitors. Don’t write a business plan. Planning is guessing. Meetings are toxic. And staying small is not a stepping stone - it's a strategy. Key takeaway: most companies overcomplicate everything and hide behind process. Do less, faster. Make things people actually want. Ignore the business school playbook.
No Rules Rules by Reed Hastings & Erin Meyer
Netflix’s cultural strategy is bold: eliminate rules, increase context, and trust people. It sounds great in theory, until you realize how much of it relies on extreme talent density and brutally candid feedback. Still, there’s gold here. Giving people freedom and accountability works, if you're willing to fire quickly, pay top-of-market, and tolerate a fair bit of mess while the system stabilizes.
Interestingly, this echoes much of the ethos behind Rework. Both books strip away bureaucracy and challenge the sacred cows of traditional management: meetings, policies, over-engineered processes, and replace them with an unapologetically lean, trust-first approach. Where Rework tells you to stop planning and start building, No Rules Rules tells you to stop managing and start trusting. Both assume a baseline of high quality people, and both are allergic to the idea that more rules lead to better outcomes. If anything, they argue that rules often get in the way of real work.
Behavior & Influence
Nudge: The Final Edition by Richard H. Thaler & Cass R. Sunstein
The core idea is deceptively simple: small changes in how choices are presented can dramatically shape outcomes. Defaults matter. Friction matters. People are lazy and irrational in predictably human ways. If you design anything - products, policies, onboarding flows - this book will make you paranoid about every button, checkbox, and menu item. Good. You should be.
Software & Systems Engineering
The Mythical Man-Month by Frederick P. Brooks Jr.
Written in the 70s, still painfully relevant. Brooks’ law - that adding manpower to a late software project makes it later - should be engraved on every manager’s desk. The essays cover everything from communication overhead to conceptual integrity - the idea that a system should feel like it was designed by one mind, not stitched together by a committee of well-meaning chaos agents. Without it, your architecture turns into a pile of 'clever' hacks and contradictory patterns. There’s wisdom in every chapter, and more than a few haunting truths about how little the industry has learned.
This book actually inspired me to write about a simple framework that can be used to run your engineering team:
Software Engineering at Google by Winters, Manshreck, Wright
A practical, deep look at how Google builds software at scale. Not just code, but culture. Topics like code review, testing infrastructure, and team structure are unpacked with engineering maturity you don’t see often. The book’s biggest strength is its honesty: scaling quality requires process and discipline, not just smart people. I think this book is a powerful antidote to the "AI will replace engineers" doom prophecies. Even though that wasn't a problem that existed when it was written, the book shows why even if AI writes every line of code tomorrow, software engineers aren't going anywhere.
Designing Data-Intensive Applications by Martin Kleppmann
Dense, technical, essential. If you work anywhere near distributed systems, this is your handbook. Kleppmann breaks down topics like replication, consistency, and fault tolerance with clarity and depth. This isn’t light reading, but it’s a must for anyone pretending to care about data reliability. Kleppmann doesn’t just explain trade-offs; he puts you in the middle of them, where every decision has consequences and latency comes with a moral cost.
Closing Thoughts
May was about clearing mental fog and operational clutter. The best strategy is boring. The best systems are invisible. And the best organizations are designed, not wished into existence.
If your strategy sounds good but changes nothing, it’s theater. If your team is scaling but your systems aren’t, it’s debt. And if you’re still winging your engineering processes… Godspeed.
Because at some point, the chaos stops looking like innovation—and starts looking like incompetence.
Let me know what books helped you make sense of the madness lately. Always looking for the next useful idea.
Bonus points if it’s older than I am.
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These recaps are awesome! Thank you for doing them.
I’d like to hear more about “fire your workaholics”, for obvious reasons haha
I love this, man. Your point about chaos masquerading as innovation is spot on. Too many teams confuse motion with momentum. But I think the thread running through these books is less about systems or strategy and more about courage. Courage to say no to bloated processes, to trust your people over policies, to design for trade-offs rather than perfection. I’ve been rereading Antifragile by Nassim Taleb lately, and it complements your list beautifully: systems that thrive aren’t just robust, they’re antifragile... gaining from disorder. We can design organizations to embrace uncertainty, like Kleppmann’s data systems embrace latency. But how do we cultivate the discipline to build invisible systems without losing the spark of creativity? And how do you pick which books to read every month? What's your selection process like?