For as long as I can remember, I wanted to learn to surf. Maybe it was growing up in cold, snowy upstate New York where I first fantasized about living closer to the beach, surfing big waves and sunning myself on the warm sand rather than on our blacktop driveway while doused in baby oil, laying out on a cheap chaise. We were just happy to pretend we were somewhere exotic. We made the best of the weather and my dreams of surfing were just that: dreams. Forget the fact that the ocean terrified me, this was something I discovered (and overcame) during my time on Maui.
I learned the meaning of surfing the waves of life however, at a young age. My dad sold jeans throughout most of my childhood. He traveled with racks of clothes in his car trunk to show to buyers at local stores. But mostly, he worked from home and our basement doubled as his sample storage room as well as his office and our playroom. We loved having my dad around, and my stay-at-home mom did the books for his business. As I got a little older, I understood this meant that she was the family money manager. I was also led to understand that life was like the ocean with rolling waves that weren’t always predictable.
I was given a firsthand experience in learning to ride the waves of uncertainty at 14 when our planned vacation to Puerto Rico was abruptly canceled. My dad’s biggest account had just filed for bankruptcy and wouldn’t be paying their bills which meant the family income (and vacation budget) took a huge hit. Flights were canceled, my parents apologized and said we’d learn to surf some other time.
I eventually got over it, but I never forgot the sting of being let down when things didn’t go as planned. Ironically, these experiences didn’t steer me to seeking out a life of stability in the income department. Like my dad, I wanted the freedom to set my own hours and an unlimited opportunity to generate revenue. When I moved to Los Angeles at 28, I soon realized that the ceiling for my chosen editorial career was maxing out at 60K. Instead of just settling for that, I started pitching magazines for freelance writing jobs on the side. I worked on these assignments at night, and soon had generated enough extra income to feel confident enough to quit my day job at age 30. Within a few months, I had far surpassed my monthly income expectations and goals and never looked back. Working for myself, on a project-to-project basis, and later, running a commission-based luxury travel business, is what has truly taught me the meaning of learning to ride the waves.
As a business owner, you never know what each day will bring. That said, the thrill of being an entrepreneur with endless potential to earn money doing what I love has always allowed me to “surf” the waves.
Riding these waves has deepened my resolve to live my life differently while learning to process grief and manage stress and not let the waves of life crush me. When I opted to relocate to Maui for a while, it was finally an opportunity to literally learn to surf ocean waves instead of fearing them. It was time to put those childhood dreams into action.
When I found myself dating a surfer on Maui, I thought I’d hit the jackpot. This guy totally wanted to teach me how to surf and stand-up paddleboard. On our first date, despite my fears, we discussed him getting me out on the water. Our next date actually took place in rocky waters on a very windy day (not the type of conditions conducive for a beginner). He told me to lie down on the board when waters got rough promising he’d get us safely to shore. And, he did. But what I realized months later, after ending my engagement, is that I want someone to ride the waves of the ocean and life with me. I want to be with the guy I will learn from, not the one who is just going to tell me to lie down on my board and let him handle things. He ignored my sheer fear of the ocean and failed to show me how to properly use the paddle.
If nothing else, this failed attempt at learning to “surf” on a day with sub-optimal conditions further spurred my desire to master my fear of the ocean. It also motivated me to achieve my bucket-list goal of catching waves while standing up on a surfboard. Fast forward to the end of that year: I’d taken several surf lessons and had the thrill of standing up on a longboard an incredibly patient teacher. I found the entire process to be fun and cathartic and healing. It was a simple yet powerful metaphor for all I’ve experienced in life that has forced me to ride the waves over and over and over.
A friend who grew up on Maui told me that one of the things they teach kids there is never to turn your back to the waves. Face the waves, no matter how big, dive in and go under the water if you must. But, never turn your back and pretend the wave doesn’t exist. That will never end well. When things in life get rocky, as they will always do, the choice is always mine to roll with the waves, face them and surf through the process rather than run away from it or freak out over something I cannot control. This strategy serves me well, and it’s why nearly everyone on Maui knows how to swim and surf. It is part of the culture to swim and play in the ocean and that means learning to surf, literally. You can’t control the waves but you CAN learn to surf.