Meet O Mag Insider – Sarah Greaves-Gabbadon!

Age: 53

Occupation: Jet setting travel writer; on-camera host; black-belt shopper

What did you want to be when you were a little girl?

My parents tell me the first thing I said I wanted to be was a pilot; I guess travel has always been in my blood! But I remember wanting desperately to be to an actress –  which explains how much I love being on camera today!

What are some different jobs you’ve had in your life?

My first job ­– a summertime stint when I was in high school in Kingston, Jamaica – was as an inventory clerk in the Woolworths warehouse. It was dull and monotonous and nowhere near as glam as the department store jobs my friends had. But it taught me that I definitely didn’t want to be chained to a desk all day. In college I had part-time jobs in fast food and in a bookstore. Since graduating from university I’ve worked in the travel industry in various capacities, including in PR for a hotel company and airline and now as a travel writer, on-screen host, and Caribbean expert.

What do you work toward in your spare time?

Because I’m often asked to participate in and write about destination races, I try to stay in half-marathon shape year-round by running and working out several times a week. I’m also trying to read more books – but I can’t seem to tear myself away from scrolling through social media!

Are you a morning person or a night owl?

I’m definitely a lark! Because I live in Miami, it’s not unusual for me to wake up at 5am to hit the road before the sun gets too fierce. But once the sun goes down it’s all over for me! I’m in bed by 9pm.

What are you most proud of?

Like many gen-Xers, I was brought up to believe that after I earned my degree, my career would be a smooth upward trajectory to retirement. Ha! In my mid-30s I moved from Jamaica to the U.S., leaving behind a successful career in hotel PR. I arrived in Florida in 2003, got a job, bought a house, and then got laid off six months later! But I found another job and transitioned to travel writing and editing. In 2007, when the magazine I worked for folded, I created the JetSetSarah brand and a thriving business as a travel content creator for print, digital and video outlets, including Travel + Leisure, USA Today, Essence and AARP.  So I’m most proud of the way I’ve been able to reinvent myself and my career, to stay relevant and to keep hustling, even in my 50s.

What are you known for?

My eclectic style and love of color always gets me noticed – and I quite enjoy that! My friends know I can sniff out a “shopportunity” anywhere, and that I know no fatigue when I’m in a retail environment. I’m also known for having a bad memory. My friends are my external hard drive!

What inspires you?

The places I’m privileged to travel to and the people I meet when I get there affect me deeply. I’m also inspired by my parents and grandparents, who, as immigrants from the Caribbean to England, sacrificed so much so I could have the opportunities I enjoy today. I never forget where I came from, and I’m proud to carry my family’s “flag” wherever I go.

Tell me something about you that most people don’t know

Although I live in Miami and work in the Caribbean, I’d really prefer to live somewhere with seasons. Honestly, constant heat can be tiresome. And I’m really jealous of the sartorial opportunities (Jackets! Hats! Coats! Boots!) the seasons provide. I’d move to New York City in a heartbeat!

Why did you apply to be an O Mag Insider?

As a “Carivangelist,” I’m hoping that being an Insider will give me opportunities to spread the “gospel” of the Caribbean to more people, and to position myself as a Caribbean travel expert in the media. I’d love to have my own TV show to share my unique perspective on travel with the world. It’s been less than a month since I was selected, so I’m really looking forward to meeting and getting to know my fellow Insiders over the course of the year. And it goes without saying that I’d love to meet Oprah! I’d love to clue her into some Caribbean spots she might enjoy.

How do you live your best life?

I believe that it’s my responsibility to make myself happy, so I try to do that every day. I run and workout because, no matter how hard it is, it never fails to make me feel good afterward. I’m pursuing a career doing what I love, traveling the world. I protect my time and space and surround myself with good people, many of whom I’ve known since childhood. I nurture my relationships and try (with varying degrees of success!) not to take myself too seriously. And I never pass up buying a fabulous accessory!

What are you reading now?

I just finished Patsy by Nicole Dennis Benn. The title character’s circumstances and mine are completely different, but we’re both immigrants from Jamaica to the U.S. so I can really relate.

What’s a day in your life like?

It depends whether I’m traveling on assignment or at home. Between trips, most days start before dawn with a run or HIIT workout. Then I’ll spend most of the time at my desk, writing stories, managing my social media feeds, emailing editors, and chasing invoices. On Fridays I like to meet other local freelancers or PR people for lunch or drinks because creating a professional community is very important when you’re self-employed and work from home.

I travel about three times a month, mostly to the Caribbean. Travel days usually start with a pre-dawn workout and an early-morning flight. Once I touch down, I’m usually following an itinerary organized by the resort or destination that’s tailored to my story angles. In a single day I might interview a chef or artisan; tour a new hotel; explore the town; attend a tequila tasting; take a sunset cruise; and have dinner with the hotel manager, all while juggling emails from editors and sources. Trip days start very early (I like to run in my destination, too) and usually end late at night. They’re a lot of fun but also very tiring. And certainly not as relaxing as they might seem on my Instagram!

This is part of an ongoing series, introducing you to the dynamic individuals who make up O, The Oprah Magazine’s Brand Ambassadors known as the O Mag Insiders. For more information on the program or to apply, click HERE.

Read the last O Mag Insider feature HERE!

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