In the beginning...

When I meet new people outside the yachting community they are often unaware and surprised that this line of work even exists. The question I am most often asked is “How did you get that job?”

First off, let me say that while I love my job it isn’t always as glamorous as it appears from an outsider’s perspective. I could get into the details but that’s a post for another time.

So, how did I end up in this niche market? Let’s start at the beginning. I had the good fortune to grow up on Lake Gaston in rural North Carolina. My entire youth was spent in and around the water, driving boats and learning to sail. As a kid, I had more interest in going fast on the ski boat than the often slow sailing on the shifty winds of a lake. Even so, I gained a basic understanding of how to handle a sailboat and learned a bit from my father who loved to take our Hobie 16 out for afternoon cruises.

Here’s a video of my brother and I playing on the Hobie when we were younger. Definitely amateur hour - complete with woo girl screams from my brother and nice shot of him getting catapulted during a capsize. You have to start somewhere, right?

Fast forward to college. I attended the University of North Carolina - Wilmington. It is a great school in beautiful coastal NC. After I left for school, my parents decided to sell our lake house (very sad day...) and I inherited the Hobie from my father (very happy day!). I started sailing the boat on the ocean and in the Intracoastal Waterway near Wrightsville Beach, NC. Serious game changer! I had sailed larger boats on the ocean before but having my own boat and the freedom to explore was a new experience. I was hooked! I decided then that I had to find a way to get paid to sail.

So I started the job search for a sailing instructor gig. Lucky me, the sailing club on the upscale vacation community of Bald Head Island, NC was hiring. I managed to land the job through a good interview. It certainly wasn’t my sailing skills though because at this point I was hardly more than self-taught. Fake it til you make it, right?

New digs!

So now that I landed the job I had to get my credentials up. I attended a US Sailing Keelboat Instructors course, did well and learned a lot about teaching, and became certified. I started the new gig sailing Harbor 20 sloops in the challenging Cape Fear region of NC, where Bald Head Island is located. I have to say that there was a pretty steep learning curve. The boats were not designed for the conditions of Cape Fear and I was still untested. Often students would ask a question about a specific aspect of sailing, I would give a vague answer and then go home and google it. Through this process and my enthusiasm for the job I gained a lot of experience.

Later that season our sailing club manager, an old salt schooner captain from the Caribbean, managed to strike a deal to trade our unsuited Harbor 20s for a pair of J80 sloops. The J80 is a hot rod that feels like a proper keelboat but has the nimble handling of an dinghy. Oh what an upgrade! The J80 was an amazing teaching platform and a joy so sail.

The J80 in all its glory. Yes... I'm wearing a pirate hat, don't judge me.

From then on sailing was an addiction for me. It wasn't long before I was sailing bigger boats and joining as crew on ocean crossings. Stay tuned for the rest of the "How I got here" story and more sailing related posts. Meanwhile, here's a video of me as a cocky young sailing instructor preforming a perfectly executed Captain Ron docking maneuver under sail.