The Grow Dangerously Book List: Essential Reading for Bold Living

Introduction

“A reader lives a thousand lives before he dies . . . The man who never reads lives only one.” — George R.R. Martin

I’d take that quote further and posit that the man who reads will truly live. Not just the worlds inside the pages he turns, but the real-life experiences they inspire.

Why?

Because the books we’re about to introduce are guaranteed to inspire action, boldness, and living on one’s terms.

The right book at the right time can change everything.

We’ll arm you with:

• philosophy

• wealth knowledge

• travel inspiration

• health insights

• self-improvement tools

…and much more.

At Grow Dangerously, we believe that growth isn’t meant to be safe—it’s meant to be a bit uncomfortable, help you break free, and teach the art of living.

These books are handpicked to do just that, from building resilience (Meditations), to growing into the man you are (Iron John), to chasing adventure (The Motorcycle Diaries).

Let’s dive in.

[This guide is one of our 10 deep dives in the Grow Dangerously library.]

Disclosure: This post contains affiliate links. If you purchase through these links, I may earn a small commission at no additional cost to you. Thanks for supporting Grow Dangerously.

The Classics: Timeless Wisdom

Hand-picked classics for the best ways of thinking throughout history.

Meditations by Marcus Aurelius

You can’t talk about “timeless classics” without bringing up Meditations.

One of history’s greatest leaders and thinkers, Marcus Aurelius left us with this absolute gift. Peering into his mind via daily dairy entries, we get to see the inner workings of a great mind.

While I like to feel sophisticated reading the original text translated from Greek, it’s a bit dense. The book can be dense and a bit confusing at times due to the language, so I recommend starting with the modern-language version.

As a Man Thinketh by James Allen

An absolute game-changer of a book, James Allen writes the foundation of the ways our thoughts impact our lives.

This concept is seen throughout the self-help world today.

It’s a simple, quick read… but one you’ll likely be going back to multiple times. Absolutely one of the books every man must read.

The Art of War by Sun Tzu

An icon. The title alone is enough to pique my interest. Sun Tzu’s lessons in strategy and discipline are applicable far beyond the battlefield.

Another short one that likely requires multiple passes, this book is an essential read.

Tao Te Ching by Lao Tzu

Complementing Stoicism, this is a classic on Taoism—another powerful ancient philosophy.

Timeless wisdom on balance, simplicity, and the flow of life. Taoist thinking is very interesting, even setting the foundation for modern thought on men’s sexual discipline.

Men’s Work: Masculinity and Becoming Grounded

Books to help men reclaim strength, purpose, and authenticity.

Iron John by Robert Bly

I can’t think of a book that was more needed when it came out. As James Hollis puts it:

“That [Iron John] would become the number one seller on the New York Times book list is astonishing, especially since it is not easy to read and employs concepts that are not common currency.

But the very fact that its ancient motifs found such a ready response suggests it is a good paradigm for modem men's relationship to the primal masculine.”

No More Mr. Nice Guy by Dr. Robert Glover

A book every man should read if they find themselves:

• avoiding risk

• people pleasing

• being passive

• seeking approval from women and other men.

This one was transformative for me. It allowed me to embrace my flaws, accept myself, and level up in so many ways. Glover has changed countless lives with this book.

Dating Essentials for Men by Dr. Robert Glover

Despite its title, I don’t consider this a dating book. This book is very different from the “pick-up, get more girls” approach of many men’s dating books.

Rather, it’s a continuation of No More Mr. Nice Guy—helping men face their fears, become more social, and get out of their comfort zones.

This one revolutionized the way I live—talking to strangers in public, trying new skills, and living passionately are all norms in my life now, thanks to the book.

Battle Cry by Jason Wilson

A powerful exploration of emotional health and strength in men’s lives, this book challenges the way we think about masculinity.

A martial arts coach, boys’ mentor, and generally badass motherfucker, Wilson suggests a different approach to being a man.

He calls this comprehensive masculinity—embodying all parts of the human spectrum. Powerful, assertive, and strong—but also forgiving, compassionate, and loving.

One of the books every man should read. This one had me in tears a few times.

Healing Work: Confronting Inner Struggles

Books to help you process trauma, confront shadows, and find true healing.

Under Saturn’s Shadow by James Hollis

I’m currently reading this book, and I can’t put it down. Hollis gives a masterclass on Jungian concepts such as the mother complex, the father wound, and the shadow.

He paints a vivid picture of how so many men are controlled by these things, without being aware of it.

This is a must-read.

The Body Keeps the Score by Bessel van der Kolk

Heavy, dense… but worth it. This book transformed my understanding of trauma, its effects, and ways to heal.

It also upended my former beliefs about the body-mind separation.

After reading this, you’ll be convinced that the body and mind are much more related than you thought. You’ll be armed with tools to understand your trauma and ways to heal it.

In the Realm of Hungry Ghosts: Close Encounters With Addiction by Gabor Maté

Had to have a Gabor Maté book on the list. He’s got tons of books, so I included the one people generally recommend to start with.

Maté is a highly respected expert in trauma, mental health, and addiction. You’ll definitely find gems in all of his books and podcast appearances.

Adventure: Fuel for a Bold Life

Books that inspire exploration and stepping outside your comfort zone.

The Motorcycle Diaries by Ernesto Che Guevara

The inspiration behind the name of our series, this one inspired my chronicling motorcycle journeys in LatAm and their accompanying philosophies.

This is a story of youthful discovery and awakening.

Greenlights by Matthew McConaughey

A memoir of adventure, resilience, and chasing opportunity. From motorcycle routes through Europe, cross-country RVing in the US, to Amazon river floating, McConaughey gives us tons of inspiration.

Packed with gems about life, love, pursuing dreams, and travel, this is a badass book.

Not everyone is a fan of McConaughey, and I get that. I wasn’t a fan until I gave this book a chance. After reading, I admire and respect the guy.

The Great Railway Bazaar by Paul Theroux

Ever thought about sending it and going on a four-month journey through Europe and Asia by train? Ya should…

Theroux chronicles just that, and more. If nothing else, this book helps us to break the limits we place on ourselves, allowing us to live more boldly.

Vagabonding by Rolf Potts

A practical guide and more to embracing long-term travel. This is one of those books every man should read if they’re hungry for adventure.

You want to leave town, only to return a changed man? Crack this book open…

Health Essentials: Mind and Body Optimization

Books that explore the power of breathing, dopamine, and overall well-being.

Breath by James Nestor

A concept so simple couldn’t be this powerful, could it? I credit James Nestor with a tenfold increase in my health, energy, and sleep quality.

A lifelong mouth-breather and snorer, this one rocked my world.

The Molecule of More by Daniel Z. Lieberman and Michael E. Long

It is paramount to at least have a basic understanding of dopamine. Why? It affects nearly everything.

Understanding dopamine’s impact on motivation, love, and addiction will put you ahead of the pack.

Why We Sleep by Matthew Walker

Greatest performance-enhancing drug—across mood, energy, clarity, health, and emotional regulation—sleep.

For those not tapped in, this book unlocks the power of sleep for mental and physical health.

The Oxygen Advantage by Patrick McKeown

Complementing Nestor’s Breathe, this book dives further into the far-reaching impacts of breath.

McKeown provides practical tools to skyrocket our health, energy, moods, thinking, and physical performance.

Wealth Generation: Building Financial Freedom

Books that teach you how to create abundance and live on your terms.

Secrets of the Millionaire Mind by T. Harv Eker

An iconic ‘money mindset’ book, this one helps us unpack our beliefs around money. These beliefs alone are enough to decide our financial fate, so be sure to dig deeply when reading.

I personally tapped into much greater earning potential with this one, and it set me on the right path to generating wealth.

Work Optional by Tanja Hester

Such a FIRE book (Financial Independence, Retire Early). This one drops game on the steps and tools to break free from the system.

With advice as hands-on as formulas to calculate how much you need to save to retire early, Hester helps us design a life free from corporate 9-5s.

Rich Dad Poor Dad by Robert Kiyosaki

This book is on every money-related book list. In line with the Millionaire Mind concept, it seeks to teach how the wealthy think about life and money.

A classic on building assets and financial literacy. A book every man should read if they want to be financially savvy, let alone free.

Getting To It

Did we miss an iconic book? Have you read a life-changing book that we don’t know about? Share it with us on Instagram, we may add it to the list.

It’s simple—open up a book, gain insight, grow.

This list contains inspirational journeys that make you want to get out there and see the world. It’s got books to unchain you mentally so you can make the move. And it’s even got practical financial tools to help you make it happen.

I recommend bookmarking this page so you can revisit it in the future.

Did we miss an iconic book? Have you read a life-changing book that we don’t know about? Share it with us, we may add it to the list.

Subscribe for more growth resources, and here’s to your continued growth and travels.