32 books that shaped my career (and saved me from a $200,000 MBA)
A self-made syllabus for independent thinkers outside the Ivory Tower.
Reading presents a strange paradox.
People who don't read do not see the value in books, while the biggest readers never feel like they read enough.
I’m in the latter camp.
I’ve come to believe there are few problems that cannot be solved with a very large stack of books.
Years of heavy reading are what prepared me to live on three continents, work at Business Insider, publish two books of my own and start a business.
Books also helped me realize that most of what’s useful in work and in life doesn’t come from institutions.
It comes from ideas, usually old ones.
I’ve put together reading lists before, but the one I’m sharing today is built specifically as a kind of indie MBA. Not a credential, but a compass. Not academic, but useful.
As much as I love fiction, this list is mostly non-fiction.
These are books that sharpened my thinking and challenged my beliefs while providing concrete skills and systems.
Thirty-two books divided by six sections:
Mindset
Entrepreneurship & Strategy
Financial fluency & Investing
Leadership & Decision-Making
Big Ideas & Systems Thinking
Storytelling & Writing
Let’s get started.
Mindset & Growth
1. The War of Art by Steven Pressfield:
Becoming your own boss means fighting resistance every day. This is your field manual.
2. Essentialism by Greg McKeown
The art of doing less, better. A helpful guide for avoiding burnout and learning what to focus on.
3. Man’s Search for Meaning by Viktor Frankl
An important guide to finding purpose in adversity. Required reading for navigating the psychological side of independent thinking.
4. Zen and the Art of Motorcycle Maintenance by Robert Pirsig
A philosophical deep-dive into quality, craft, and meaning in work. One of my favorite examples of useful fiction.
5. The Almanack of Naval Ravikant edited by Eric Jorgenson
A decade’s worth of wisdom, mental models, wealth-building advice and life philosophy into one compact book.
6. The Psychology of Money by Morgan Housel
Success isn’t just about what you know — it’s how you behave. This book will challenge how you think about risk and reward.
Entrepreneurship & Strategy
7. Purple Cow by Seth Godin
You can’t succeed if no one notices you. Godin teaches how to stand out and win in the free market (without selling out).
8. Start With Why by Simon Sinek
People don’t buy what you do, they buy why you do it.
9. Made to Stick by Chip & Dan Heath
Whether it’s a pitch, a blog post, or a brand story, your ideas need to stick. Forgettable businesses, writing, and ideas do not last.
10. Hackers & Painters by Paul Graham
A startup philosophy bible disguised as an essay collection. Creative, technical, and subversive in ways that will challenge your current views on building a business.
11. How to Win Friends and Influence People by Dale Carnegie
One of the most important books I’ve ever read, and continue to re-read. So much of life and work hinges on being likable and persuasive.
12. The Defining Decade by Meg Jay
Your twenties matter more than any other decade in life. This book is instructive in thinking about how to use these years wisely in work and relationships.
Financial Fluency & Investing
13. Reminiscences of a Stock Operator by Edwin Lefèvre
A century-old classic that still reads like a masterclass on risk-tolerance, markets and human behavior.
14. The Big Short by Michael Lewis
Want to understand how people really behave in crisis? This is a story about human nature disguised as an insider’s account of the 2008 financial crisis.
15. Liar’s Poker by Michael Lewis
Wall Street used to be even more of a jungle than it is today. Great book to understand money, influence, and generating wealth in one of the wildest eras in financial history.
16. Narrative Economics by Robert Shiller
Numbers matter, but so do stories. This book explores how narratives move markets, for better or worse.
17. The Lords of Easy Money by Christopher Leonard
A readable crash course on the Federal Reserve, money printing, and why everything feels more expensive now.
18. The Smartest Guys in the Room by Bethany McLean & Peter Elkind
The Enron collapse wasn’t just fraud. It was hubris and misaligned incentives. An important book to understand one of the worst corporate failures of all time.
Leadership & Decision-Making
19. Extreme Ownership by Jocko Willink & Leif Babin
How to take responsibility for everything above and below you.
20. The Dichotomy of Leadership by Jocko Willink & Leif Babin
A follow-up that dives into the nuance of leadership. When to step in, when to step back and how to delegate.
21. Principles of Philosophy by René Descartes
Clarity of thought is one of the most important themes of this list, and it arguably starts with this 400-year-old book. It is old philosophy that offers a still-useful framework for breaking down complex problems to first principles.
Big Ideas & Systems Thinking
22. Boom and Bust: A History of Financial Bubbles
Every financial cycle feels new, but history rhymes. This one explains how bubbles form and pop.
23. The Righteous Mind by Jonathan Haidt
Why smart people disagree over big ideas and what morality has to do with business and leadership.
24. Lessons of History by Will and Ariel Durant
History is a story with the same themes and characters appearing over and over again. You can finish this book in a day and get an amazing overview.
25. The Road to Wigan Pier by George Orwell
A piercing look at the relationship between work and dignity. Relevant for anyone thinking about systems and structures in the working world.
26. Twilight of the Elites by Christopher Hayes
A thoughtful exploration of meritocracy and how legacy institutions have earned the mistrust of the American people.
27. Walden by Henry David Thoreau
A meditation on simplicity, minimalism, and independent thought. It’s about a man who left society to live in the woods, but the lessons are universal.
Storytelling & Communication
28. The Hero with a Thousand Faces by Joseph Campbell
A blueprint for the narrative arcs that shape culture, business, and leadership. Important for understanding the power of story.
29. Bird by Bird by Anne Lamott
For writers, founders, and creators, a charming and wise guide to the craft of storytelling.
30. On Writing by Stephen King
Equal parts memoir and manual, this book distills what it means to write clearly, honestly, and without pulling punches. How to say what you mean and mean what you say.
31. Nobody Wants to Read Your Sh*t by Steven Pressfield
A blunt and fast crash course in copywriting, story structure, and how to keep your audience top of mind.
32. The Elements of Style by Strunk & White
Short, sharp, eternal. I read this every year. Better writing affords better thinking, which opens the door to better work and business.
I plan to put together more book lists this year, built around different goals and themes.
If you have any suggestions, I’m all ears — reply directly to this email or leave a comment on the post.
Have a great afternoon!
Phil Rosen
Co-Founder & Editor-in-Chief of Opening Bell Daily
