Why I Traded My Lipstick and Pinstripe Suit to Live on an Island

Kate Byars | August 11, 2016

In 2004 I retired my lipstick and executive career to live on an island. I was thirty-four years old. I had been working since the age of eleven and quite frankly, I was tired. I was also curious. Curious about all the people who made their living leading kayak tours and whitewater adventures whilst I swam from corporate meeting to corporate meeting in a pinstripe suit. Curious about the wealthy folks who flew around in private jets from one vacation home to the next, while I racked up frequent flier miles pushing my TravelPro Platinum Rolling Garment Bag all over Asia and Europe. And curious to know if a simpler life, one that had nothing to do with the American Dream, would be more satisfying than the life I was living.

It’s never too late to be who you might have been.

I sold my 3,000 square foot home. I put my furniture up for sale on eBay. I gave away my classic, black Chanel winter coat and all the rest of my belongings. Except for a leather club chair I purchased when I was first promoted to Vice President of International Marketing at the tender age of thirty. I liked that chair. It was worn in all the right places. It smelled of high-end leather. It was a trophy for a big achievement at a young age. I wasn’t completely ready to let go. The club chair went into storage along with personal effects and mementos.

I bought seven mix-and-match, two-piece bathing suits from J.Crew. I was determined that my biggest decision each day would be what color bikini to wear.

I had recently learned to scuba dive and a few friends urged me to become a dive instructor. In the frigid 40-degree waters of a Texas lake, I earned my dive instructor credentials a few months before I departed for the Caribbean. I had possibly 100 dives. I had no idea what I was doing.

In March 2004 I spent my first night on Tortola, BVIs sleeping in a tiny bunk aboard a wooden yacht; a temporary space that the local dive shop lent me until I could find a roommate. The next day I would help tourists load kayaks onto their boats and lead dive tours underwater. I was now living, and working, in the British Virgin Islands. I barely slept that first night.

What I realize now, and didn’t realize then, is that I was choosing a path that few feared to tread.

There are lots of people who become dive instructors and work in the dive industry; and there are lots of folks who live on beautiful islands. However, leaving behind a hard-earned world of comfort and a skyrocketing career was absolutely abnormal.

Back home in Dallas I had a personal driver who picked me up for each business trip and drove me to the airport. I had a housekeeper, who took care of my home, especially when I was away. The yard guy kept my landscape looking great and the poop patrol scooped up my pooch’s nuggets. I even had a personal shopper at Nordstorm’s and another one at Neiman Marcus. For a simple girl raised with Midwestern values in a normal, upper-middle class home, this was impressive stuff. I was incredibly fortunate.

So why did I quit? And what was I looking for? Was I burnt out; disillusioned; depressed? I don’t think so. What I do know is that I felt pretty damn fine striding down the dock in my brand new Reef flip flops; getting my tan on 1,000 miles from home.

What I didn’t know is that my life in the islands would not simply be an escape from reality. Instead, I would face challenges and fears that rocked my very sense of self and forever change my life.

As the dawn broke on that first morning in the British Virgin Islands, I could only smile in anticipation at the journey I was about to take. A new world of possibilities lie in front of me and while there was no way for me to fully appreciate the changes that were about to occur, I was certainly excited and knew I was in the exact right place I needed to be…[to be continued].

Part II of the story: What Island Life Was Really Like

Part III of the story: How I Went from Corporate VP to Island Girl to Cave Diver


I believe we all have a bit of trailblazer inside us, don’t you?  I welcome you to subscribe to my Sunday morning email. Each week I share personal stories of blazing trails in business and in life.

It’s my passion to create change. I’ve always found that disrupting the status quo leads to an amazing life where nothing is impossible.

 If this article resonates with you, please share! Maybe we can all be inspired and learn from each other.
Share This