Redefining Manhood: The Best Books on Masculinity for Men of All Ages

The world of men is in disarray–it doesn’t take a genius to see it.

Wives are sleeping alone at night. Children are growing up without fathers. Family, as we have known it for so long, is falling apart.

And for what reason? Men don’t know how to be men anymore. They don’t know their place and seem lost in their importance.

Afraid of crossing society’s ever-evolving code of rules detailing the proper conduct of men, we have slunk back into the shadows and relinquished the reins of our lives to anyone that cares to take them.

We’re afraid of pissing anyone off, so we sit back and watch everything- our lives, meaning, and identities- be stripped away from us, rearranged, reassembled, and handed back to us.

But what are we to do? Isn’t it how it’s meant to be? Did we not overstep our bounds in the past? Isn’t a bit of admonishment merited?


What began as a legitimate and necessary questioning of gender roles has swung to the extreme, evolving into a direct and brutal degradation of one of the two genders that keep this world spinning.

“Do we even need men?” they ask. “Wouldn’t the world be a better place without men?”

Afraid of coming off as aggressive and thus digging ourselves deeper into the hole we’ve dug for centuries, men tend to tiptoe around these questions and leave them unanswered.

Over my ten-plus years as a men’s coach, I’ve seen the topic of masculinity as one of the most important and neglected topics in everyday conversation.

Modern men turn a blind eye to these crucial topics without fully realizing the damage they are doing to themselves. The truth is these need to be things that every man grapples with–questions that every man answers for themselves.

What is masculinity? What does it mean to be a man? Where is the line between aggressiveness and assertiveness? What does it mean to be confident, and what does it mean to be arrogant?

The following ten books, penned by ten brilliant men, seek to answer these questions and provide insight into what it means to be a man.

1. The Way of the Superior Man

Perhaps the best book in answering the big question–what does it mean to be a man–is David Deida’s The Way of the Superior Man.

This book could be life-changing if you struggle with relationships, motivation, or even just understanding what it means to be a man in the modern world.

Deida dives into what it means to be a man spiritually, exploring what masculinity means in real life and giving the perfect definition of a man.

A superior man, David claims, generates energy from the Masculine and infuses his whole being with–his career, relationships, and purpose.

He analyzes gender relationships and discusses how men should relate to women, emphasizing the importance of recognizing and intentionally enjoying the differences between you and the woman you’re in a relationship with. This book is a must-read if you’re looking for top-notch advice to be a great lover.

The Way of the Superior Man is a well-rounded study of what it means to be a man in every sense of the word. Deida emphasizes a man’s purpose, insisting that it is the most valuable thing in his life (even above his woman). A woman only wants to find a man whose purpose is the most important thing to him.

2. Think and Grow Rich

With a quick skim of Think and Grow Rich, you may think it to be a business book providing a few practical lessons for your road to financial success. A deeper look will reveal that this masterpiece is so much more than that.

Napoleon Hill’s masterpiece is a guide for life. While it offers invaluable business advice, Think and Grow Rich is about planting and nourishing a healthy mindset that will lead to abundance and wealth in every area of life.

If you take this book as a guide in business, your business will be successful. If you take it as a guide for life, your life will be successful. The book was written in 1937 and has been a game-changer for so many for over eighty years. Hill spent decades of his life studying the icons of business and success (Ford, Carnegie, etc.) and getting into their minds.

He speaks to the importance of laying behind the poverty mindset that binds so many and embracing an abundance mindset in every area of life, as well as the importance of a mentor and the enlistment of partners.

Don’t go at it alone. 

3. The Way of Men

It’s easy to see modern men and our distant ancestors as entirely different breeds of men. This, however, is not the case. The blood that runs through your veins is the same blood that ran through the veins of our forefathers–the ones who killed mammoths with their bare hands and ran for hours on their bare feet.

Jack Donavan’s The Way of Men is the place to start if you’re looking for a well-rounded, no-B.S. description of what a man is.

He meets the topic of masculinity head-on, explaining what it means to be a man in terms of our evolutionary biology and history. He explains the importance of certain tribal customs of the past and how men are today versus how we should be.

While it is third on the list, The Way of Men is in no way less superior than The Way of the Superior Man. This book is a crucial stepping stone in your journey to becoming a new man.

4. Iron John

As the world changes, people do too. Being a man one thousand years ago is nothing like being a man in the modern world. This is a truth and a necessary truth.

But have we lost something? Are all of our changes for the better, or did we leave something behind that would have been better to bring along? What are we missing that men had so many years ago? Can we get it back?

In Iron John, Robert Bly takes readers back to the source of their masculinity and tries to find a healthy middle-way between the rock-hurling caveman of the past and the spectacled office worker of today.

It is a short story written as a symbolic coming of age of a young man and takes readers through the different stages of becoming a man. It mourns the slow slipping of the father role from our society and the lack of a masculine rite of passage into manhood.

If you appreciate a book bursting with symbolism and allusions to the higher authority of history, Iron John is the book for you.

5. The Mask of Masculinity

In our attempts to fit into our unpredictable, ever-changing world, men learn to do all sorts of masks. We find ways to act and look that help us define who we want to be.

We know the world likes a powerful man, so we pursue wealth and put on the Material Mask. We learn to fear genuine emotion and thus don the mask of the Joker or the Stoic–untouched by life’s true joy and pain. We’re insecure and afraid of our importance or lack thereof, so we put on the mask of the Aggressor–we become the man who cannot back down from a fight, eager to prove his worth.

In The Mask of Masculinity, Lewis Howes breaks down and seeks to deconstruct the many masks of masculinity.

He claims that to live your most fulfilling life and truly step into your full potential as a man on this earth; you must learn to identify the masks you wear so you can take them off and face the world as you are.

The Mask of Masculinity is one of the top books for understanding how to live life honestly and embrace healthy masculinity.

6. Way of the Peaceful Warrior

The world is trying to do away with everything that makes men masculine. They don’t want men to be strong. They don’t want men to protect them. They don’t want men to lead in any way.

They’re trying to take every ounce of masculine energy in our bodies, twist it into a new and unrecognizable shape, and put it to use in the ways they see fit. They’ve seen the damage men can do and are ready to see it end. What they don’t realize is that they need men. The world needs men.

Men are warriors. Rather than taking away their swords altogether, we need to teach them how and when to use them.

In The Way of the Peaceful Warrior, Dan Millman tells a great coming-of-age story of a young man trying to find his place in the world–learning how to use his sword. He is an Olympic gymnast who finds a mythical mentor named Socrates, who helps him direct his life.

This book will help you delve into the meaning of your life, what you’re doing here, and what your life’s purpose may be. It is equal parts practical and spiritual, so it does have something for everyone.

7. Wisdom of Insecurities

In Wisdom of Insecurities, Alan Watts dives into the philosophy of life, security, and happiness. He analyzes humanity’s constant need for reassurance and continuous push for pleasure and what we do about it versus what we should do about it.

It’s tough to give a perfectly accurate summary of this book as Watts’s analysis is so meticulous and so detailed, but the three main topics discussed can be summarized as follows:

  1. Without religion to reassure us, life becomes painfully uncertain
  2. Consumerism is accompanied by the empty promise of happiness
  3. Pleasure and pain are two inseparable friends: none ever comes without a bit (or a lot) of the other

He is a philosopher at heart, so if you read this book, I suggest reading it well and keying into each word he writes.

He tells us that if we can explore what makes us feel insecure, we can understand it, accept it, work through it, and become more confident.

8. No More Mr. Nice Guy

We hear it every day: “Nice guys finish last.” But what does it mean?

Why do nice guys finish last? What does it mean to finish last? What is a nice guy?

In No More Mr. Nice Guy, Robert Glover dives into the nice-guy syndrome. The book was written in 2000, but it seems its words get more and more relevant daily.

He talks about people-pleasing habits and how to overcome them–how to stop being a spineless pushover and get what you want. So many men nowadays back down from difficulty in life because they’re “easy-going guys.” Every human being who has accomplished anything of note (even just a successful relationship) has stepped on a few toes.

If you want to be someone that anyone in the world will remember, you have to put the nice guy to bed and learn what it means to be assertive.

Glover’s No More Mr. Nice Guy could be a fantastic place to start if you’re looking for a guide on how to do just this.

9. The Truth

Let me guess. You’re thinking, Wait, Neil Strauss! I’ve seen that guy’s name somewhere.

Yep, he wrote The Game… the book that everyone hates–the book that kickstarted the pickup industry and continues to inspire young men to treat relationships as a game.

So, why is this book here? Because in Strauss’s unique dive into sexuality, he learned some valuable things.

While you don’t have to support or run your life by the ideas put forward in this book, it is fascinating.

Strauss discusses his personal life and his difficulty with monogamous relationships, dabbling in polyamory, and finally, finding some form of real love.

This book is for you if you’re ready for your mind to be stirred by new (and uncomfortable) ideas.

10. To be a Man

Understanding how your brain works is one of the best ways to understand your identity as a man and to study your masculinity.

In To be a Man, Robert Masters breaks down the psychology of masculinity. This is a great place to start if you’ve ever wanted to understand what it means to be a man, how to be more masculine (in the right ways), and how to understand your primal urges and what they mean.

Masters uses his deep knowledge of gender dynamics and his complex understanding of the human psyche to provide valuable insight into relationships–emphasizing the value of a healthy dating life and male friendship.

The book explains many of the core principles of masculinity, diving into concepts like anger, men’s primal side, and sexuality.


The world has become confusing for men from all walks of life. Pick up the most modern self-help books for men, and they’ll say something about kissing your masculine energy goodbye and embracing your feminine side.

While there is undoubtedly some value in this idea and men should be creatures possessing a delicate balance of raw power and emotional tenderness, telling men to lay down masculinity altogether is ludicrous.

We need men who know how to be men. We need men who understand the important pieces of being a man, know that their emotions are just a part of their masculinity, and understand that strength and leadership are equally important.

Books are the right place to start if you are on a journey to understand what it means to be a man. Whether you need the no B.S. definitions of The Way of the Superior Man and The Way of Men, the more philosophical approach of To be a Man or Wisdom of Insecurities, or even the comedic prose of Neil Strauss’s The Truth, good books like these have the potential to change your life.

If you are looking for guidance on your journey to rediscover and embrace your masculinity, here at knowledge for men, we want to help. Over the past few years, we’ve seen men transform their lives with our programs.

We have the best-trained coaches in the industry with decades of experience, and they’re eager to help you turn your life around. Here at Knowledge for Men, our goal is to help as many men as we can rediscover their healthy masculine side and set out to turn the world upside-down.

Reading these ten books about manhood and masculinity above can give you valuable insight and get you started on your journey, but knowing and understanding are different than changing. You have to do more than reading.

Changing your life is about acting intentionally–finding the things you want and not letting anything get in the way of you getting them. We help you do that here!

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