11 Playboy Traits All Legendary Bon Vivants Share

What is a playboy?

A playboy lives the lifestyle of a bon vivant – a man of leisure who appreciates the finer pleasures of the world.

Even though he is the kind of man many want to be, only few know what it takes to live the lifestyle.

What do they all have in common?

I analyzed the lives of these legends:

And I found 11 playboy traits they all share.

Table of Contents

1. They Think Big

Legendary playboys are visionaries.

They see the world as a playground of infinite possibilities and aren’t afraid to dream big.

Their goals are audacious, and they pursue them with relentless passion.

Whether it’s building an empire or planning an exotic adventure, they never settle for mediocrity.

Thinking big drives their ambition and fuels their achievements, setting them apart from the crowd.

They understand that if you think small, your life will also be small.

Your only real limit is the scope of your thinking.

Playboys live larger than most because they think bigger than most.

They think of life outside of “wagie world“.

2. They Are Nonchalant

A defining trait of a legendary playboy is his effortless grace under pressure.

He remains calm and composed, no matter the situation.

This nonchalance adds to his charm, making him appear confident and unbothered.

He doesn’t sweat the small stuff and handles challenges with a cool demeanor, which only enhances his allure.

A playboy carries himself with “amused mastery“.

He has seen it all and done it all.

Nothing phases him.

3. They Don’t Accept “Average”

Mediocrity is the enemy of the bon vivant.

He rejects the mundane and strives for excellence in all areas of life.

From the clothes he wears to the conversations he engages in, everything is curated to be exceptional.

This refusal to accept average drives him to constantly seek out and create extraordinary experiences.

A playboy’s overwhelming desire to experience life makes it impossible for him to accept average.

Average = low entropy.

His abilities and perspective allow him to command the higher branches.

4. They Have Unfair Positioning

Legendary bon vivants often find themselves in advantageous positions that others might consider “unfair.”

This could be due to their:

Unique skills
Charismatic personalities
Or their knack for being in the right place at the right time.

They leverage these positions to their benefit, ensuring they always have an edge over the competition.

Playboys attract more with less.

They understand that superior positioning allows the best opportunities to come to them.

Instead of wasting their energy chasing things, they invest in a powerful and attractive setup.

This has everyone they want to meet wanting to come to them and paying for the privilege of doing it.

James Goldstein has the “Sheats-Goldstein Residence”
Ari Onassis had his yacht “The Christina O”
Hugh Hefner had his Playboy Mansion
Dan Bilzerian has his Bel-Air mansion
Richard Branson has Necker island

5. They Have A Strong Purpose + Vision

Purpose and vision are the cornerstones of their success.

They have a clear understanding of what they want to achieve and a well-defined path to get there.

This strong sense of purpose drives their actions and decisions, providing them with the motivation to pursue their dreams relentlessly.

Their vision is their guiding star, helping them navigate through life’s challenges with determination.

After all, a playboy life is not handed to you.

It is constructed out of your own vision for yourself.

However, if there is no conviction / purpose behind it, you get sucked back into the matrix.

6. They Are 100% In Love With Themselves

Self-love is the engine that runs everything.

When you love yourself unconditionally, you only surround yourself with what you love.

This complete acceptance and love for themselves boost their confidence and charisma.

It enables them to interact with others from a place of abundance rather than neediness, making them more attractive and magnetic.

7. They Live Eclectic Lives With Multiple Interests

Have you ever met a boring playboy?

Nope.

They go deep on the themes that interest them.

A true bon vivant is never one-dimensional.

They cultivate a wide array of interests and hobbies, from art and music to sports and travel.

This eclectic lifestyle and overflowing passion not only enriches their own lives but also makes them more interesting and engaging to others.

Their varied interests provide them with endless stories to tell and experiences to share.

(And as a side effect, causes them to develop extreme amounts of swag).

8. They Have Time + Location + Financial Freedom

Freedom is a hallmark of their lifestyle.

Every single legendary playboy owns cash flowing assets.

This is what allows them to have time + location + financial freedom.

(The key ingredient that gives them the ability to sculpt the exact life of their dreams).

They have designed their lives in such a way that they are not bound by constraints.

This freedom allows them to:

Pursue their passions
Travel the world
And indulge in their interests without limitations.

It’s this sense of liberation that makes their lives so enviable.

9. There Is No Separation Between Work And Play

For legendary bon vivants, work and play are seamlessly intertwined.

They have managed to turn their passions into their profession, blurring the lines between what they do for a living and what they do for fun.

This integration means they are always engaged in activities they love, making their lives feel like a continuous adventure.

A playboy uses his business in perfect harmony with his life.

A business should only be used as a vehicle to optimize your lifestyle.

If your business is not giving you access to greater opportunities, you’re working in the wrong one.

10. They Created + Designed Their Own Character + Lifestyle

Legendary playboys don’t accept the script + identity that was handed to them.

They designed their own character and lifestyle, aligning their actions with their values and aspirations.

This intentional creation of self and surroundings ensures that they are always living authentically and on their own terms.

Their lifestyle is a reflection of their personal brand, meticulously crafted to express their unique identity.

They understand that personal narrative + self-image is the controller of destiny.

This is what allows them to do what others can’t.

They are the architects of their own destiny.

11. They Give Themselves Permission To Enjoy Life And Have Fun

Perhaps the most important trait is their ability to give themselves permission to enjoy life.

They understand that life is meant to be lived fully and joyously.

They prioritize fun and pleasure, seeking out experiences that bring them happiness and satisfaction.

This proactive approach to enjoyment is what makes their lives so vibrant and fulfilling.

Being a playboy is ultimately about having fun.

They go into every situation with a frame of self-amusement.

They see the world like a kid in a candy shop.

Conclusion

In essence, legendary bon vivants are masters of living well.

They combine ambition with ease, purpose with passion, and freedom with responsibility.

Playboys share these 11 traits which allow them to live life to the fullest:

By embodying these traits, they create lives that are not only successful but also deeply satisfying and richly textured.

P.S. Want to learn more about getting better game? Read “ON! For Him“.