Chasing the Dreamboat: How Chief Officer Wesley Walton broke into the yachting industry

From pinching pennies to stow-away stealth, breaking into yachting can be a risk-it-all endeavor.

Thinking about entering the yachting industry? It is definitely a topic of conversation to spark interest at any dinner party. Here is the story of how I ended up choosing a life on the open seas, serving the rich and famous. 

Born and raised in Johannesburg, South Africa, I moved to the Eastern Cape to complete my bachelor’s degree in economics and environmental science. My plan was always a career in renewable energy, but life had other plans for me. 

I decided to take a gap year before settling down into a corporate job and putting all my energy into climbing the ladder, so I started playing with some ideas: ski instructor, lifeguard at Disney World, country club valet, etc. A friend mentioned the yachting industry, which, believe it or not, was still relatively unheard of among South Africans back then.

I did some digging into it and was captivated — I mean, who wouldn’t want to get paid to travel to exotic locations all over the world on beautiful, multimillion-dollar yachts? I thought this was something I could definitely get on board with. Before I knew it, I had thrown my life savings from coaching rugby and waterpolo into entry-level courses and a one-way plane ticket. 

First stop: Cape Town, to complete my STCW and other prerequisites. I’m sure all yacht crew have great memories of those intense days of learning to survive at sea and fight fires. It’s your first introduction to the like-minded friends you will share the industry with. I still have close relationships with a few of the people I did my very first STCW with. 

Once I had paid for my yachting courses and my overseas flight, I very clearly remember scrapping together all that I had left, not much more than $1,000. It was still a substantial amount, I thought — until I got to Florida. Here’s a rundown of Day One: taxi, $34; one week’s rent, $250; printing CVs and business cards, $50; cellphone SIM card, $50. 

I realized I had not much longer than 10 days to turn this dream into reality before going broke. I walked over 20km a day to meet crew agents, bought all my meals and toiletries at the Dollar Tree, and went to every Triton networking event — not only to gather information and meet people in the industry, but also to get a free meal. Times were tough and I had to go out of my comfort zone to make ends meet. 

After the first week, I knew I could no longer wait around hoping my phone would ring for a job. I had to take action and risk it all, or I would be back on a plane to South Africa before I knew it. So on the Monday of my second week, after the next $250 was spent on accommodations, I managed to talk a mate into letting me sneak into the trunk of his car as he went to work in one of the shipyards, so I could avoid being turned away at the security gates. Once through the gates, I was determined to talk to every yacht in the yard and hand out my business cards, which I had hidden in a sleeve of tissues in my backpack in case a security guard stopped me — I had to give them every reason to believe I belonged there. Nevertheless, after being rejected more times than anyone would believe possible, I retreated to face the reality of my bleak situation.  

While grocery shopping at the Dollar Tree once again, my phone rang. I was so excited I dropped the phone in the middle of the shop. I knew the only people who would have this number were the agents and yachts I had given my business card to. A yacht that needed some help prepping for their season had called to offer me a few days of work. I couldn’t believe my luck! This meant I could survive possibly another week and keep looking for something more permanent. 

I got to the yacht very early and anxiously waited for someone to welcome me on board. The moment finally had come when I had to prove myself, to make sure all the money and sacrifice were worth it. Once welcomed on board and given a couple of tasks, the chief officer told me, “We have cameras all over the boat, so we always know when you are not working.” I saw those cameras all over the boat, and I made sure I never put down my tools until I was told to!

Looking back, I am pretty sure this was just the chief officer messing with me. However, the hard work I put in led from a few days of work to a week, and finally, to a permanent position on that yacht. Before I knew it, I was whisked away to the Bahamas and across the Atlantic for my first Mediterranean season. 

Everything fell into place after taking that big risk. The intended gap year has turned into a 10-year career, and I don’t plan on becoming land-based anytime soon. If I could give one piece of advice to anyone just starting out, it would be this: “You have to make it work for yourself; you cannot sit around waiting and hoping it will just happen for you.” 

Chief Officer Wesley Walton has been in yachting for 10 year. He recently earned his 3,000GT Captain’s License.

Click here for more information on mastering your CV and here to learn about negotiating your pay. Read about RYA’s crash courses here and learn about creating relationships with crew agents here.


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