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Becoming a Scuba Diving Instructor in the Caribbean in a Career Change

Mark scuba diving in Turks and Caicos.
Mark scuba diving in Turks and Caicos.

TT: Ever wonder how to become a dive instructor abroad? Check out this epic interview with Mark Gregory, a man who completely switched careers in order to teach scuba in the Caribbean! Mark, tell us about your background.

Mark: I am from a typical immigrant family with origins in Ireland and Germany. I’m second generation — my grandparents were from the home-land. We were a working class family where both my parents worked just to get by and provide for the three boys; they traveled maybe once a year and I think my father left the country once while he was alive (Bermuda I believe, very close by).

We lived in East Rockaway, Long Island, New York in a very small town of similar demographics. I was the middle child who was the typical black sheep…

Mark's view from a boat in Thailand headed to James Bond Island.
Mark’s view from a boat in Thailand headed to James Bond Island.

We were encouraged — if not expected — to work from the day we could get a job. We were all paperboys at first then we all ended up working in restaurants as we could get free food there. Mom did what she could and believed in the 6pm family dinner, but her creations were far from gourmet. I was very jealous of my Italian friend’s meals, especially on Sunday.

I started in the restaurant business at age 14 and worked at no fewer than two jobs until I was 26 years old. After being the first person in my family to graduate college, I got a suit and tie job in Advertising. I could talk about the many jobs I had, but that’s not the point of this.

At 26, I decided to quit being a cook on the weekend and at night to follow my career. I ended up by no real design in media (TV and Radio) where I heard they paid well. I bought TV commercials for brands like P&G and General Motors. It was an 80 hour work week where I got paid for 40… probably not legal in retrospect.

At the Giza, Egypt pyramids: one of Mark's lifelong dreams.
At the Giza, Egypt pyramids: one of Mark’s lifelong dreams.

Two years later at 28 I got a sales job at the Food Network (selling commercial units to buyers like myself, in essence flipping to the other side of the desk). I somehow fell in love with food, and my 12 years in a kitchen helped me talk about the shows with ease. Oh, and salespeople worked 35-40 hours a week and always seemed to be coming back from some exotic vacation all tan and wearing expensive suits…. So for the first time in my life I had only ONE job that could pay my bills with some left over.

I also got scuba certified a year earlier and started to explore diving in NY and reading all the trade magazines about exotic travel and dive vacations.

I worked in media sales for 22 years, and worked at various networks (Vh1, The CW, Food Network). I was a natural in sales and enjoyed presenting and cutting large deals. My personality and skills were perfectly suited to the job (which I didn’t know until I was doing it). I like presenting, was always better at math than anything else, and I am very competitive (middle child) so having a goal every year was a great incentive for me; also the more you sold, the more money you made, and that was something I was tired of worrying about all the time.

Mark scuba diving right next to a shark!
Mark scuba diving right next to a shark!

I was very successful and thrived in selling, and enjoyed it more than I could have imagined. Most of my career was at Food Network. Everyone thought a network all about cooking was never going to work, and was a bad idea…. I was just following my passion and could get back into food without standing behind a stove in the summertime.

I had always planned to retire early, as no one in TV was ever over 50 years old and they sort of pushed the sales people out at a relatively young age. So once I started making money, I started saving it.

Due to the new lifestyle selling provided, I could actually go on three to four vacations a year! We had a cyclical business: very busy, then a few down weeks. So I now had the means and the time to go away…

Mark at the ancient temples of Angkor Wat, Cambodia.
Mark at the ancient temples of Angkor Wat, Cambodia.

As I was a scuba diver, I started going to dive destinations by myself or with a girlfriend I could drag along. I started in Key Largo, then went to Belize, inspired by Jimmy Buffet’s book “A Pirate Looks at 50” (He detailed all these cool places he wanted to get to before he was too old to enjoy them).

I have been lucky enough to have seen some of the planet’s best places to dive: Galapagos, Maldives, Egypt, Fiji, Thailand and most of the Caribbean…

So, fast forward to today. I turn 50 this year, and moved to St. Maarten 7 months ago. I am a Dive Instructor (I worked my way up the educational ladder in diving) and work for a somewhat busy dive shop here on the Dutch side. I have been talking about moving to someplace I loved on vacation for like 10 years, and my friends were sick of all the talk. It is now a reality.

After leaving my job due to boredom and the lack of any sort of satisfaction aside from a good salary, I started to seriously apply my energy to moving away. I was actually about to rent my house and just drive to Islamorada, FL as they have good diving and affordable living, along with many dive shops, so I figured I could wing it and find work as I would be there in person. It wasn’t my dream location, but it was a start — a step towards breaking the “I’ll always be a New Yorker” mantra.

I was clearing my life of all my possessions (I am actually the opposite of a hoarder — I am a chucker and I throw everything out so I have the little I need to make me happy). All I need in essence is an acoustic guitar, my Mac, my cameras, my mountain bike, my dive gear, books and a comfy bed. So as I was preparing to just cut loose and go south, my dive shop on Long Island got a call from the folks in St. Maarten asking if they knew a talented Dive Instructor who wanted to live in the Caribbean, and my buddy handed me the phone. That’s how I got here specifically.

How to travel the world by becoming a scuba diving teacher, explained by a dive instructor in the Caribbean who changed careers from something totally different.
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TT: Hah! That’s amazing! What a story. Now, tell us more about other travels that had a big impact.

M: One of the trips I took that really got me thinking leaving my regular life was truly possible was Thailand. I got laid off suddenly as this start-up company I was working in downsized overnight. I found myself staring at an empty November and December with some money in my pocket and odds-are another crummy New York winter.

So, I asked my friends, “Where should I go? I have no limitations!” (I was not stuck to the one week off and back to work chains most Americans have to deal with). Thailand came up in a few conversations, and I researched the diving, and December was the best time to go! I am a planner and an avid researcher, so I met a few friends who had been there, and bought the Lonely Planet book, and poured through it with highlighter in hand and those colored page marker “stickies.”

It was the first time I ever backpacked. All I needed in one bag! It was terrifying for me… I am a big “just in case” packer. No room for that in backpacking, through. Best advice I got, “If you need it, buy it there. Everything is a dollar!” It really got me out of my comfort zone and opened my eyes. I don’t need all this stuff — I need flip flops, a hat, tees, sunscreen, a camera, and some money for food. Incidentally, in Thailand that means about $20 a day if you eat like me.

The reason Thailand is so popular is the ease with which you can travel, and of course the shocking fact to most people that you can live and have a great time without spending much money at all. Oh yes — and it’s exotic and a great place to dive, sight-see, eat and experience.

By my third week (I booked almost the whole month away, a first for me, December 5th to the 26th) there I was loving life, making friends and comfortably living a much more laid back life. I was diving, reading, exploring, mopeding, and relaxing at night at a bar with new friends and having a few drinks. No one was carrying their phones around and staring at them. I even got offered a job at the Dive shop in Ko Lanta I was diving with, and it shocked me that I could do this. If only I could let go of New York and my stuff, I would be free. It set the hook in me that it was a real possibility, and my choice to make.

Eating Thai soup on a 90-degree day.
Eating Thai soup on a 90-degree day.

TT: So true. How do you find your travel opportunities?

M: I used to pour through magazines like T&L, Traveler, Scuba Diving and Food magazines, etc. but most have faded away, especially in travel. I also am a Bourdain fan, and loved his show and approach to travel. I find a place I am interested in and start with Google and some of my dive sites, ask friends or look through old mags or YouTube videos. YouTube is great for specific cities and blogger inside info, and more realistic, down-to-earth reviews.

I have many friends who love to travel, so I have an enormous amount of information all around me (FB helps with the long distance ones). If you love to travel, you usually meet others like you and stay friends for life. Three of my friends quit their jobs to travel the globe. They even wrote a book about it called The Lost Girls. [Note: Affiliate links in this article provide a small commission from any purchases, at no extra cost to you.]

Luckily, my best friend John had the travel bug too, and would occasionally call me up and say something like, “Read about Prague. Wanna check it out?” I said yes to almost every call (Mexico City, Paris, Prague, Barcelona).

Food was a key factor in finding destinations. Being in the food world and being a “food enthusiast” — not a “foodie” — helped me find spots. Experiencing a destination’s culture and food was key to most of my travel. It’s one of the main reasons to go for me. I used to hear stories of tourists in Paris eating at McDonalds and wanted to slap them. A ham and cheese sandwich bought on the street in Paris is better than anything you could get in most American cities for lunch. Don’t get me started on croissants and breakfast. Ahh (one of many good onomatopoeia examples…), the French!

Another key factor in travel for me was history: seeking more information or experiences about history will get you motivated to go to Egypt, Mexico, Central America, or just about anywhere in the world with an open-eyed sense of curiosity, and the desire to see it with your own eyes.

Mark in the Food Network kitchens.
Mark in the Food Network kitchens.

TT: Yes! How did you find the money to fund your travel?

M: I am a big saver and a planner, so I would wait for a good commission check and put it away. I also learned early to join every rewards program I could, and start banking points. If you ever travel for work, this is a great benefit. All your travel points are on your personal account!

I am a lover of American Express and found they always took great care of me with both protection and transferrable points for airfares and hotels. I literally only have ONE credit card, and it’s an Amex, I put everything I can on it and carry it in my pocket (when living in New York it was accepted everywhere). They also give you amazing summaries at the end of the year. OK, now I sound like a commercial. Hah! Join them all early and learn the benefits thresholds and flexibilities.

A life-altering meal Mark ate in Mexico City, at a restaurant where he couldn't even communicate with the waiters.
A life-altering meal Mark ate in Mexico City, at a restaurant where he couldn’t even communicate with the waiters.

TT: Smart. Tell us one moment from your travels that was particularly powerful.

M: I went to Fiji with a group of friends I had met diving in Dominica (a very small island in the Caribbean) and we went for a very specific dive in Bequa Lagoon with sharks.

They take you to 77 feet and feed the sharks out of a garbage can full of whole fish. It was terrifying, exhilarating and awesome all at the same time! We had all different kinds of sharks — about 25 sharks in all — swimming around us and over us. It was my first time seeing Bull sharks and Lemon sharks, and they were huge, 8-10 feet in length, and coming very close to us.

As I was taking photos, I had asked to get away from the chaos of the main feeding area so I could get better pictures…. not recommended, but they obliged me with an escort of sorts on the second dive. I had my own guide “to watch my back.” I got some pretty amazing pictures, and had a close encounter with a huge Bull Shark who came in close to smell my camera and see if it was on the menu… (large strobe lights attract sharks due to the frequency of the sound they make when they reset).

I learned a great deal about sharks that day and realized 95% of what I knew before was completely inaccurate. Sharks are cautious and calculated eaters 99.9% of the time, and not these killing machines they are portrayed to be. They are fascinating, mythical and a marvel to see in the wild.

Super up close with a Bull Shark in Fiji!
Super up close with a Bull Shark in Fiji!

TT: I bet! How have your travels impacted you in your current career, and how have your travels impacted you as a person?

M: I think having the experiences gives you relevant stories to use for examples and lessons; they lend you both the credibility and anecdotes to talk about the topic at hand. For me, my experience gives me confidence and humility, as I know there is always more to learn. Someone who is “ever the student” makes a good teacher.

As a person, I see the difference between people who understand the world, and see it in a different way from those who don’t. Travel opens your eyes; travelers “get it.” It changes you in an impactful and unique way. You become even more open-minded and more curious. It fills a void for me. The more you see of the world, the more you want to see. The world gets larger, not smaller. Experiences enrich the soul.

Mark diving off North Carolina. What a shot!
Mark diving off North Carolina. What a shot!

TT: Beautifully put. What advice do you have for teachers who are dreaming of travel, or travelers dreaming of teaching?

M: Find inspiration anywhere: books, videos, blogs, clubs… follow a passion you already have like skiing, biking, or hiking, and see if you can teach that and where…. There is so much information out there at the click of a mouse, so start digging. Start basic and hone in. I love to start by staring at a map and seeing what interests me. If money is a challenge, start in Asia, because once you get there it’s easy to get by. Just Go!

TT: Thanks so much, Mark! Readers, what questions of comments do you have for this remarkable dive instructor?


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Monday 12th of June 2017

Woow, this looks really amazing, This is really on my have to do list before i get into my 40's

Keep posting, Kind regards Stefanie

Mark Gregory

Saturday 27th of May 2017

Thanks, Lillie, for letting me tell my story. I hope your readers find it fun and interesting. It was a pleasure to write... to pause and reflect on my life.

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