James and Hugh Hefner at the Playboy Mansion

I met Hugh Hefner in 2007 in the library of his infamous Playboy Mansion in Los Angeles.

I was interviewing him for the UK magazine, Loaded, and got to spend 90 minutes with him.  Just me and Hef.

He, of course, was dressed in his famous silk pajamas.

When I asked him how many pairs he had, he told me: “I probably have about 100 pairs of pajamas in about 20 different colors. They are silk. I wear black during the day and multi-colored at night. I like purple.”

What a character!

While most people associate Hef only with his pajamas and harem of women (although he is currently married!), I was able to glean some important life lessons from the man who built a global brand and empire.

Those lessons have stuck with me today.

Here’s what Hef told me and what I learned:

Although you are born into a life, you MUST make it your own. In order to live out your dreams, and follow your passions (while becoming successful), you need to create your own path.

Hefner has certainly done so in a more public way than any of us have, but this can absolutely apply to anyone. Hefner created the life that he wanted to live out, and he is in almost absolute control of everything that happens to him (health and aging aside).

Because he re-invented himself as the person he wanted to be, and lives the life he wants to live, it’s not very hard for him to get things done. In fact when I asked him what his best pickup line was, he said, “‘Hi. My name is Hugh Hefner.’”  And that is not hard to believe.

If you see something that you want to change in your life, or in our world, change it. For example, when Hefner saw where the 1950s were going, he wanted to help turn them around.

He told me: “It’s like you are invited to the party and you get there on Sunday and the party is over and there’s nothing left but the dirty dishes. That’s the way I felt when I was growing up. So I think to some extent I expected after World War II, something equivalent to the roaring 20s, the celebration or party after World War I. When it didn’t happen that way, when the 1950s turned out to be a very conservative, repressive time and down instead of up, I knew we were in trouble. That was part of the inspiration for starting Playboy.”

Lead your life in the direction you want it to go, and don’t feel like you have to conform to every social norm.

If anyone has made the most of their life, it’s Hefner.  Since you only have one life, you have to live it to the fullest, and make it a daily celebration.

He told me: “The reality is there is more to life than drinking a beer with your buds and sitting in front of TV and watching a sports show.”

This “celebration” will take different forms for different people, so do whatever it is you need to do to take ownership of your life. We are only here for a limited amount of time, so you need to take advantage of it.

Hefner said, “I really think you only get one shot at it here and the magic of being alive is so precious that one should really think about it as a celebration and make the most of it. And that’s what I’ve done.”

Yes he has.

Be aware of your surroundings.

This applies to both interpersonal relationships, and overall success. When I asked him how an average guy should approach a beautiful woman, he answered: “The key to meeting a girl and the key to a relationship is communication. Communication is paying attention to the nuances and obviously listening to what’s going on.”

So whether you are talking to someone you are romantically interested in, or making a business deal, paying attention to your surroundings, picking up on signals that might not be as obvious are key. Use your brain.

Hefner also said: “The major sex organ is the brain. The wooing is in the communication.”

This applies to both picking up the opposite sex and a business deal. Use your brain, read the signs, and communicate appropriately.

When you work hard to create a life that you enjoy living, never lose your enthusiasm for it.

Beyond the fantasies of Hugh Hefner’s lifestyle, he also lives a truly happy life.

He said, “I don’t think I have ever lost the almost innocent enthusiasm for the life itself. In other words, I remain very close to the boy I was when I was young. And hold on to that. I was the kid who dreamed the impossible dream. And that keeps everything alive for me. I am an intensely romantic person. And I see my life with a remarkable clarity and introspection in terms of the good fortune of it all. I know that I am from my perspective the luckiest cat on this planet.”

Recognizing that you have a good life will also help keep you as grounded and humble as Hugh Hefner.

Hugh Hefner is a truly dynamic guy.

It was a pleasure to be invited into his home to interview him, and I was excited to able to take away some solid life lessons that I was able to share with you.

As we all travel through life, you must take control of your future like Hefner has done, to make your life the stuff of dreams.

As he said to me: “My life has been a quest for a world where the words to the songs are true. It’s an impossible quest. But well worth the trip.”

Although his legacy will probably go down in the books as the master of wearing a robe to work, Hefner really should be remembered for a few more important things. For one thing, his humility. He is truly one of the most down-to-earth, inviting guys I’ve met.

I felt like an honored guest at the Playboy Mansion, and not all powerful and successful people can make you feel that way. He should also be remembered for his youthful outlook on life.

Although he is pushing 90, I have never seen a man who is so full of excitement for the future, and the memories he has built for himself (and also for our benefit).

He reinvented himself, and he encourages that as a plan of action for anyone who wants to pursue their dreams.

Hefner has some pretty amazing things to teach us, so I’m just glad I was able to shake him down for the most important ones.

Thanks, Hef.

James

P.S. Reply to this email and let me know which of Hef’s advice resonated with you the most and what you’re going to do about it. I read every reply (yes, really).