7 Books That Will Change Your Personal Trajectory over the next 20 Years

Some people read for pleasure, others read to build skills and to gain a competitive advantage. If you’re a regular reader of Influencive, then I’d wager you tend towards the former. Either way, it’s better than the embarrassingly large segment of the population that doesn’t read at all.

I read to learn from the mistakes of others, train myself to think with a long-term perspective, and because I value having my assumptions challenged. Over a few weeks, this won’t do much. But, over the course of a few decades, this marginal edge will separate me from the pack.

Regularly reading challenging material is a formula for success, whether you aspire to be a best-selling author, C-suite executive, or a game-changing entrepreneur. With that in mind, I’ve collected a list of books that will take some serious work, challenge you intellectually, and distinguish you from your peers.

Antifragile: Things That Gain from Disorder

In the battle arenas of intellectuals, Nassim Taleb brings a knife to a fistfight. Pulling no punches, Taleb is ready and willing to challenge the beliefs that you hold dear. His years working on trading desks before transitioning into academia have equipped him with a deep well of life experiences to validate his ideas.

Taleb’s core thesis is that the English language lacks a word to represent the opposite of fragility. Words like robust and sturdy imply an entity’s ability to withstand stress but fail to suggest that any benefit is gained. That is the key.

Do you benefit from the variability of life? Does strengthen you or tear you apart?

Taleb educates on structuring asymmetric risk that will lower your downside and increase your upside.


Big Ideas: the Lindy Effect, Antifragile vs. Robust systems, barbell investing strategies, the value of optionality, and much more.


The Inevitable: Understanding the 12 Technological Forces That Will Shape Our Future

Kevin Kelly was the founding editor of Wired Magazine and serves as one of the world’s leading luminaries on futurism and technology.

In researching for this book, Kelly traveled around the globe exploring research labs and peeking behind curtains. Through this experience, he wrote a thesis for the unstoppable technological trends that he anticipates shaping the next two or three decades of human life.

The Inevitable is generally an optimistic read as Kelly unpacks tech buzzwords and phrases, like artificial intelligence, Internet of Things, and the gig economy, and explains the underlying forces at play.


Big Ideas: Access vs. Ownership, Remixing, and the Cognifying of our surroundings.

The Alchemist

This international bestseller by Paulo Coelho is a favorite of Julia Roberts and Will Smith for good reason.

While we’ve all watched a few motivational videos or speeches on YouTube, The Alchemist plumbs deeper into your heart to deliver inspiration and personal agency to conquer any goal or climb any mountain. Coelho’s brilliantly simple and vivid writing tells the tale of a young dreamer who eventually realizes his potential and changes the lives of others.

You could also read The Little Prince by Antoine de Saint-Exupéry for a similar effect. Both deliver timeless inspiration in a style specific to great fiction.


Big Ideas:  Curiosity is magic and there is tremendous potential locked away within you.


The Life-Changing Magic of Tidying Up

To be great at anything, you have to be obsessed. Marie Kondo is obsessed with tidiness, organization, and cleanliness. From this obsession, a lot can be learned.

Kondo’s main thesis is that we own far too many things and that many of these items should be thrown away. She chronicles an in-depth process of going through all your possessions and determining what to remove.

Her personal clients often throw away 20-40 bags of stuff!

The Minimalism movement is already leading the charge on getting rid of the things you own, but Kondo goes a level deeper in exploring why people hoard items and struggle to let go. Baked within a book about tidying are key insights about personal psychology.


Big Ideas: Throw away most of your stuff, only keep the items you love, and aim for radical transformation.


Powerhouse: The Untold Story of Hollywood’s Creative Artists Agency

Author James Andrew Miller is the master of oral history. Much like his earlier book on Saturday Night Live and ESPN, Miller interviewed hundred of people in the process of producing this 700-page tome.

The book follows the rise of Ron Meyer and Michael Ovitz, who built the most powerful agency in Hollywood. Over multiple decades, CAA managed everyone from Sylvester Stallone and Tom Cruise, to Cher and Peyton Manning. By weaving together the personal accounts of hundreds of characters, Miller paints a complex picture about the realities of making it to the top.

The book also ends with one founder crashing and burning, while the other glides peacefully into retirement. After reading this, you will never look at popular culture the same way.

Big Ideas: Power often corrupts ego, relationships are everything, and culture is hackable.


Influence: The Psychology of Persuasion

My psychology classes in college put me to sleep. This book woke me up.

Robert Cialdini masterfully outlines the cognitive biases we humans suffer from that are consistently exploited by salesmen, family, and bullies. Much like Dale Carnegie’s How to Win Friends and Influence People, the truths hidden in could be used for good or evil.

Exploiting the six universal principles will transform your relationships and your business results.


Big Ideas: Bowing to Authority, Obligation of Reciprocity, and the Power of Social Proof.


The best part about reading these books is that, after completion, you’ll be able to see the world in a new light and share invaluable wisdom with the people close to you. They are gifts that keep on giving.

Have any books completely changed your life? Message me. I’d love to learn more.

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