What Hugh Hefner Taught Me About Life, Success, and Happiness

Few men had more of an impact on the social landscape of the 21st century than Hugh Hefner. The Playboy bunny logo is one of the most recognized logos in the world behind Apple and Nike.

He was loved by many and reviled by many more, but whether you view him as a champion of sexual liberation and civil rights or a chauvinist who proudly objectified women… You can’t deny that the man knew what he was doing.

Hugh not only broke into one of the most difficult industries in the world, but he did so by revolutionizing the conversation that our society was having about one of the most taboo and staunchly guarded topics… Sex.

With his recent passing, I began looking into Hugh’s life more and more to truly understand the man behind the playmates.

And I was surprised at what I found.

While you might not agree with his legacy, there was far more to Mr. Hefner than the robe, tobacco pipe, and scantily clad women.

He was an articulate, well-rounded social activist, and a key influencer of the entire 20th century.

Whether you love him, hate him, or just don’t care, there is still something that everyone can learn from the life and legacy of Hugh Hefner.

Here are the 7 lessons that Hugh taught me about life, success, and happiness.

1. Find Your “Blue Ocean”

When Hugh Hefner decided to start Playboy Magazine (originally named “Stag Party”), he was up against fierce competition in one of the most unforgiving industries.

If he wanted to make his idea work, then he would be forced to compete against big names like Esquire and GQ and he would be doing it with less than a tenth of their resources.

But this didn’t bother Hefner for one simple reason…

As far as he was concerned he didn’t have any competition.

At least not really…

In marketing and advertising, any industry that is already saturated with competition and a clearly defined offer is known as a “Red Ocean.”

Hugh created a “Blue Ocean” by creating and publishing a magazine that, up until that point, had never existed.

He wasn’t creating just another men’s magazine or just another nudie mag. He was providing the industry with something it had never seen before.

He was providing men all over the country with a magazine that elegantly satisfied their interest in politics, philosophy, life advice while also discussing (and making acceptable) one of their biggest interests of all time… Sex.

GQ and Esquire were great for men who wanted canned advice and politically correct analyses of social issues.

Porno mags were great for men who just wanted to enjoy some visually titillating “literature”.

But Hugh knew that neither of these extremes really spoke to the heart of men.

He knew that men wanted it all.

They wanted intelligent discourse about modern politics, applicable advice for overcoming their biggest challenges, and a thought-provoking and visually appealing conversation about sex.

And so he gave it to them.

His strategy worked in 1955 and it works today.

When I founded Knowledge for Men, I did it because none of the other brands that I saw were having a real conversation with men about the things that are most important.

I knew that men wanted to learn and talk about things like relationships, sex, masculinity, health, wealth, and personal growth and that they wanted to do so in an uplifting environment where they could learn from the best.

I found my “Blue Ocean”.

But what’s yours?

2. Outwork Your Competition

I have no plans to retire. It’s the perfect combination of work and play that keep you young. If I quit work it would be the beginning of the end for me

While you might know Hefner as the mysterious and woman-crazy partier that was portrayed in the media, behind all of the exotic playmates, wild parties, and luxurious living was a man with an insatiable work ethic.

Before we had Gary Vaynerchuk, Grant Cardone, and Andy Frisella, we had the original hustler and game changer, Mr. Hugh Hefner.

Not only did Hugh regularly work long and difficult days, sleeping at the office, alienating the people closest to him, and resorting to prescription drugs in order to function… He did so with a smile on his face.

Hugh would, quite literally, sleep at his office for months on end, passionately pouring himself into his work with little regard for his health or his family.

While his level of commitment might be classified as clinically insane by some, many others realize that it is just the price you have to pay to become iconic.

I personally found Hugh’s work ethic a bit too extreme for me.

I want to build a business I enjoy so I can have time out with my friends, have an abundant dating life, and still have time to take care of my body.

However, I also realize that, in order to build a 9-figure empire and completely revolutionize the world in under half a decade… This kind of workaholism is the only option. And hey he lived a long life!

3. Be Willing to Side with the Minority 

I fought racism, then sexism, now I’m fighting ageism. One defines oneself in one’s own terms, if you let society and your peers determine who you are, you’re less for it

Most of you probably know that Hugh Hefner was the leader of the 60’s sexual revolution.

But many people don’t realize that Hugh was just as passionate (if not more so) about the civil right’s movement of the early 60’s.

Hugh had never been a racist, and even when it was commonplace to look down on another man for the color of his skin, Hugh took no part in it.

In fact, he was one of the leading proponents of the Civil Rights movement and he took every opportunity that he could find to help support it.

When he opened up the Playboy Penthouse and later the Playboy Night Clubs, he invited renowned black musicians like Miles Davis and John Coltrane to play at his venues.

He regularly published interviews with prolific black thinkers and influencers including Malcolm X and Martin Luther King Jr. when no other magazine would dare do it.

And he was the first person to ever publish a magazine edition with a non-white centerfold.

Although you and I celebrate his actions in 2017, the general sentiment towards Hugh’s stance on Civil Rights was not so positive in the 1960’s.

He received countless letters from previous subscribers who condemned Hugh and his beliefs, he was regularly threatened with violence, and on occasion, he was even the target of political slander due to his stance on Civil and Human Rights.

But Hugh never budged.

He stayed true to his character and continued supporting the Civil Rights movement through the ups and downs and today, is generally regarded as a hero of the era.

4. Don’t Worry About the Opinions of Others

Life is too short to live someone else’s dream

One of the things that I respected most about Hugh Hefner was that millions of people loved him, millions more hated him, but no matter what people thought… he didn’t give a damn.

He built his company for himself.

He built a life that he was proud of.

He lived life the way that he wanted to and didn’t apologize for a second.

If you loved him, great.

If you hated him, he didn’t care.

He was his own man and he didn’t care about the opinions and thoughts of people who didn’t truly matter.

In your own life, you need to ask yourself, Am I living for society, my friends, and my family? Or am I living for myself?

This isn’t a selfish question either.

Hugh had plenty of opportunities to bend a knee and allow society to tell him what to do, but he refused.

He lived life his own way and according to his own code, and because of this, he revolutionized an entire generation and created a business that surpassed his wildest dreams.

If you aren’t living your own dream and purpose, then you are living to build the dreams of someone else.

I challenge you to take a hard honest look at your own life.

What would you do if you truly didn’t care about the opinions of other people?

What would you do if you were free of the scrutiny and judgment of your friends and family?

What cause would you stand for? What impact would you have? What would you give the world that it’s never seen before?

When you are living your life to please others, you start to play life small, you stay safe and hidden among the crowds of men leading lives of quiet desperation.

But when you are willing to take a gamble on yourself, when you are willing to step up and pursue your dreams, your goals, and your aspirations, you can create something truly exceptional.

I don’t just say this because it’s how Hugh lived either.

I say it because I am living it.

When I started Knowledge for Men, my friends and family told me that I was crazy, that I should play it safe, that I should get a “real” job.

When I started to see a certain level of success, my friends and family started telling me that what I was doing was wrong, that my opinions, my beliefs, and the material that I shared with my audience was actually detrimental to their success and well being (simply because the material in question made my friends and family uncomfortable.)

But through it all, I marched to the beat of my own drummer.

I kept pushing forward because I believed in my mission and my purpose.

And I couldn’t be more grateful for it.

Not only have I been able to build the life and business of my dreams because I ignored the opinions of people who didn’t have the results that I wanted, but I have been able to help and serve hundreds of thousands of men all over the world.

If I had played it safe and done what everyone else wanted me to, you wouldn’t be reading this right now and the lives that the Knowledge for Men brand has shaped and changed would be wildly different from what they are today.

So take a chance on yourself.

Trust yourself.

And ignore the haters.

Your life and our world will be better for it.

5. Don’t Be Afraid to Take Big Risks 

Playboy Club

At several points throughout his life, Hugh bet everything he had (literally) on himself. He knew that failure would destroy him and his company, but he believed in himself and his team so strongly that he was willing to make that gamble and pursue his dreams.

Nowhere is his appetite for risk better illustrated than his Playboy nightclubs.

In the early 1960’s, Hugh and his team decided that they wanted to expand their operation and open up a nightclub in one of the most expensive and challenging locations in the world…

New York City.

Hugh knew that a nightclub in New York could launch the Playboy empire to heights that they had only imagined up until this point.

Against the wishes of his partners, Hugh decided to invest more than $7,000,000 in the project (a lot more money today), which surpassed their original budget by millions and put the company in the red.

But Hugh believed in the vision and the company and he wasn’t going to sit idly by with an opportunity of this magnitude.

For months, Hugh and his team worked tirelessly, promoting, renovating, and negotiating deals until finally, the club opened.

And it paid off in ways that Playboy’s founder had only dreamed of.

The revenue was staggering and within the first month, Playboy had recouped their entire investment and put the company back on the rise.

His project was a huge success that would launch Hugh and his company to new heights and unprecedented levels of revenue for decades.

But none of it could have happened if Hugh had not been willing to take risks, if he hadn’t been willing to believe in himself, and if he hadn’t been willing to go after his dreams.

So what about you?

What risk are you waiting to take? What dream have you been dying to pursue? What is that thing that would 10X the quality of your life if you could just bring yourself to take action?

Write it down right now.

Then go and do it.

Life is too short to sit on the sidelines and watch other people succeed and live out their lives.

You must take risks, step into the unknown, and trust that you will either find a way or make one.

6. Do it for the “Why” 

Sexual Liberation

I would like to think that I will be remembered as someone who had some positive impact on the sociosexual values of his time. And I think I’m secure and happy in that.

Hugh didn’t start Playboy magazine for the money.

He didn’t start it for the fame.

He didn’t even start it for the beautiful women who so frequently graced his side.

He did it because he believed in the mission.

He did it because he had a strong burning “Why”.

He had a desire to change the conversation that our society was having about women and sex. He had a desire to serve and liberate the repressed minorities. And he had a desire to make his own dent in the universe.

If he’d pursued Playboy only for the money, he would have failed as soon as he hit his first road block (and if you know anything about his story, you know that there were many road blocks).

Instead, he created one of the most impactful and iconic brands of the 20th century and he forever changed the way that our society views women, sex, and life.

What about you?

Why are you doing the things that you do?

Is it for the money? Is it because you want to be famous? Is it because it’s the safe thing to do and your parents would be upset if you went in a different direction?

If so… It’s time to wake the hell up.

If you are not living your life fully and pursuing something that lights you on fire and makes you feel so passionate that you barely want to sleep at night… Then you are wasting the most precious gift that you have ever been given… your life.

Find something that you love, find something that you are passionate about, find something that you believe in so strongly you would be willing to die for it, and then give your heart and soul to that thing.

Let it consume you and move you forward.

If you do, you will be able to look back on your life as Hugh did and honestly say “You know, I think I’m the luckiest cat that ever lived“.

7. Remember that Your Time is Short 

Hugh Hefner Playboy Bunnies

I urge one and all to live this life as if there is no reward in the afterlife and to do it in a moral way that makes it better for you and for those around you, and that leaves this world a little better place than when you found it.


Life is short.

You don’t know how long you have left on this planet, you don’t know when you will draw your last breath, and you don’t know when you will wake up one day only to find that you don’t get one more day to pursue your dreams and goals.

We don’t know how much time we have to live our lives which makes every second that we do have that much more precious.

So why would you waste it?

Why would you live one second of your life in pursuit of someone else’s dreams?

Why would you play it small and not go for your goals?

So why not live a life that you can look back on with a smile instead of regret? Why not live a life that is so full and rich and joyful that you wouldn’t trade it for the world?

The only thing that is stopping you is yourself.

Remember just how fragile your existence is and how quickly your life can end.

When you remember this hallowing truth, your perspective will shift and your life will never be the same.

You are going to die…

It’s time to act like it.


Whether you love him or hate him, Hugh Hefner built a life and a legacy that will be remembered for decades.

He took the world by storm, turned social norms on their head, and stood up for what he believed in.

He created a business that changed the world and liberated an oppressed society.

And he had a helluva time doing it.

You might not agree with everything that the man stood for, but everyone has something to learn from Hugh’s life and success.

What are your thoughts on Hugh Hefner? What life lessons did you learn from the man behind the Playmates? Share this post on your favorite social media channel and let me know!


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