Books To Change Trajectories

What to Read When Figuring Out What's Next

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Disclaimer: The views and opinions expressed in this blog are entirely my own and do not necessarily reflect the views of my current or any previous employer. This blog may also contain links to other websites or resources. I am not responsible for the content on those external sites or any changes that may occur after the publication of my posts.

End Disclaimer

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I’ve had some people ask me, who are at various stages- high school, college, starting out, in a rut, looking for something better…

What do I do if I don’t know what to do next?

I didn’t know my ass from my elbow in college, let alone what I wanted to do with my life.

If you’re lucky enough to have a passion for a particular thing early in life, great.

I think most people don’t.

You have to do the work to put yourself in a position to be ready for when a confluence of luck takes place.

Learn about a lot of things so that this idea of passion converges with an interesting and repeatedly intellectually rewarding way to make a living.

Anything you get good at can become a passion.

It’s rewarding and feels good to be good at something.

If you can choose a career where your theoretical financial upside is uncapped, even better.

If you’re young and stuck, read, read, read.

The compounding effect over time is amazing.

“Books are a uniquely portable magic.” -Stephen King

Reading a lot and reading broadly is, in my opinion, the single easiest way to improve oneself.

Give any of the books below a shot.

Better yet- create a “Book Stew”- read a bunch of these together at the same time.

Read promiscuously.

The sum of the parts of disparate and seemingly unrelated books create a unique aggregate, ideas coalescing into a mesh of the component pieces.

This is a list, in no particular order, of books to change your trajectory.

Hilariously non-exhaustive, and biased by the books I have read and remember reading.

Here are a lucky number 21 books that come to mind.

These are some of my books.

That’s part of it, of course.

You have to find your books.

The ones that do it for you.

Each of these books helped change my trajectory, course correct, overcome inertia, or see things in a new and novel way.

Now go read.

Put down that dumbass phone.

I can’t do that part for you

I’m excited for you.

Don’t slow down.

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Meditations, Marcus Aurelius - thoughts on how to live your life, from a long time ago. Marcus Aurelius was Roman Emperor from 161 to 180 CE and is considered the last of the "Five Good Emperors." These writings were a series of notes written to himself during his military campaigns and never meant to be made public. Thoughts on universal human ideas -anxiety, mortality, disappointment, and the search for meaning.

The Success Equation, Michael Mauboussin - think your success is due to your exceptional skill? Think again- how to untangle luck and skill in life and business, from my friend Michael Mauboussin. The older I get the more important and impactful this book is for me.

The Obstacle is the Way, Ryan Holiday - embracing rather than avoiding challenges transforms obstacles into opportunities for growth, innovation, and advantage. The book's title comes from Marcus Aurelius' quote that: "The impediment to action advances action. What stands in the way becomes the way."

When Breath Becomes Air, Paul Kalanithi - Absolutely beautiful. A neurosurgeon confronts his mortality and reflects on what makes life worth living.

The Algebra of Wealth, Scott Galloway - A terrific primer on how to approach becoming financially successful, and how to start early.

You Can Be a Stock Market Genius, Joel Greenblatt - look past the title, awesome book. My old head of trading boss and mentor handed out a copy of this book to every single person on our trading floor. Explains a number of trading/hedge fund strategies.

Mindset, Carol Dweck - How adopting a growth vs. fixed mindset transforms learning and achievement. The difference between (fixed) “I’m just bad at algebra. My brain doesn’t work that way” vs. (growth) “ I’ll figure this out. I just need more practice with this concept.”

Build, Tony Fadell - practical advice on product development, leadership, and career growth. From one of the creators of the iPod and iPhone at Apple and later the creator and founder of Nest Thermostat, acquired by Google for $3.2 billion in 2014.

Zero to One: Notes on Startups, Or How to Build the Future, Peter Thiel, Blake Masters- true innovation comes from creating something entirely new rather than iterating on existing ideas. This book came out of Thiel’s course at Stanford called CS 183: Startup with one of his students, Masters, taking notes and posting to his blog, which became very popular in the tech community and eventually turned into this book.

Influence, Robert Cialdini - how to get people to do what you want. Lots of interesting examples like this one - research shows that simply adding the phrase "but you are free to refuse" or similar language that explicitly acknowledges the other person's freedom of choice dramatically increases compliance with requests.

Die with Zero, Bill Perkins - spend your money and time on meaningful experiences throughout life rather than accumulating wealth until death. Maybe spend money on that trip now while you can still walk up the steps of Chichen Itza with your kids.

Atlas Shrugged, Ayn Rand - The only fiction book on this list. A dystopian United States where creative industrialists withdraw from society in protest against increasing government control. People rag on Rand for her oversimplifications and broad brushstrokes, but maybe that’s exactly what I needed when I first read this book in my early twenties. This book had a big effect on me. Don’t apologize for wanting what you get, and getting what you want.

Antifragile, Nassim Taleb - why certain systems don't merely withstand stress and disorder but actually benefit from it - yes, but for me this book is about thinking about optionality in life, creating uncapped upside and capping your downside.

Deep Survival, Laurence Gonzales - explores why some people survive extreme situations while others perish.

Atomic Habits , James Clear - Building systems for sustainable self-improvement. Introduces the "Four Laws of Behavior Change" as a framework for creating good habits and breaking bad one - Make it obvious(cue), Make it attractive(craving), Make it easy(response), Make it satisfying(reward).

The Almanack of Naval Ravikant, Eric Jorgenson - Collected wisdom on wealth, happiness, and personal philosophy. Again - high ratio of interesting information per page, including Naval's concept of "leverage"- some of the most powerful forms of leverage are permissionless (code and media) rather than permissioned (labor and capital). Writing code or creating content can influence millions with minimal marginal cost, while traditional leverage requires others' approval and has limited scalability.

Against the Gods: The Remarkable Story of Risk, Peter Bernstein - The history of risk. From when, in ancient times, priests and oracles would cast astragali (knucklebones of sheep) or similar objects as a way to divine the future, to the impact of the discovery of the bell curve and normal distribution in the 17th-18th centuries, to the importance of evolution of probability through the Pascal-Fermat correspondence. So much good stuff here.

Latticework: The New Investing, Robert Hagstrom - How to use and apply cross-disciplinary thinking in investing and beyond- e.g. “adaptation” from Darwin’s theory of evolution and Munger’s use of “availability bias” from cognitive psychology.

The 4-Hour Workweek, Tim Ferriss - One of my closest friends gave me this book almost 20 years ago, as part of his groomsmen gifts during his wedding weekend. “You need to read this”, he said to me. This was somewhat revelatory for me in how to think. Yes, this is the first of 3 Tim Ferris books on this list. These books have all helped me a lot. Great to read together.

Tribe of Mentors, Tim Ferriss - Short life advice from over 100 world-class performers, providing diverse perspectives on success.

Tools of the Titans, Tim Ferriss - distills the habits, tactics, and routines of world-class performers across diverse fields.