Why I Shaved My Head on a Billionaire’s Private Island

When I got back to California, everyone asked if I was sick or had lost a bet, but no one guessed the real reason I shaved my head… 

When Marshall Sylver (pictured here with me) invited me to attend his $50,000 high-level mastermind on Necker Island, Sir Richard Branson’s private island in the Caribbean, I initially thought that there was no way I could go because I was in a state of financial crisis.

In just 4 years, I had turned $10,000 of my own money into $6,000,000 in real estate and was on track to retire by the time I was 31.  But then the market crashed, and I lost everything. 

I had no money and no credit, but I did have a strong intuitive hit that I was supposed to be part of that mastermind.  

So I told my inner critic to take a coffee break and decided to write down at least ten ways that I might be able to manifest the money to go… no matter how crazy.  Then I pursued the ideas that seemed the most likely to work and a combination of them actually got me to Necker Island.

I decided to shave my head while I was there as a ritual to let go of the past and rebirth myself into the next chapter of my life.

What better place than on a billionaire’s private island?

Just as the last lock of my hair fell away, it started raining, which felt to me like a baptism from the Universe.

Shaving my head felt AMAZING!  The sensation of the warm Caribbean breeze on my bare scalp was absolutely delicious.

Then I took my hair down to the beach and threw it in the ocean to represent letting go of the trauma from losing everything in the real estate crash.

I’ll always be deeply grateful for that opportunity because it was the beginning of turning everything around.  

I got the tools, connections, and divine downloads I needed to birth the next level of my work into the world, and in the 12 years since then, I’ve gone on to make millions of dollars doing what I love, while supporting other entrepreneurs to create more ease, peace, and freedom around finances.

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Penelope Jane Smith is the premier financial freedom coach for women entrepreneurs and the go-to expert for some of the biggest names in the conscious business industry. More about Penelope. 


  1. Stephen Dinan on July 14, 2020 at 7:57 pm

    I love the boldness in the post, the willingness to truly go for the destiny path. Penelope is a total inspiration when it comes to dreaming big and going for it. She dares us all to baptize ourselves in our highest possibility.

  2. TailWaggingWellness on August 12, 2022 at 4:14 pm

    I just love your integrity, trust in yourself and boldness, Penelope! Nancy

  3. Kicki on August 15, 2022 at 3:07 am

    Beautiful way of letting go. It’s never too late to start over 🙌

  4. Lola on September 2, 2023 at 11:53 pm

    This is clearly bollocks, everyone knows marshall sylver is a criminal preying on vunerable people, he has been tried in court for fraud! Haha this is obviously a copy cat woman trying to defraud more people to make herself rich. You don’t actually explain *how* you made the money. Because you didn’t.. please don’t fall for this folks.

  5. Max on November 7, 2023 at 6:22 pm

    This website is poorly made. Doubt a business of a millionaire, would have such budget poor performance on their website.

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