Two Lessons I Learned Surfing with Tito

Last spring, I spent a week surfing in Cabarete, a vibrant beach town on the north coast of the Dominican Republic. Though I love surfing, I’m not particularly good at it. So, I enlisted the help of a local surf instructor named Tito because I’m all about getting the right coaching to improve. (And maybe that’s a third lesson, but I digress.)

At the end of the week, I walked away with two lessons that go far beyond surfing.

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1. Sometimes You Need to Change the Board

On the third day, things started going wrong. Despite catching waves, I couldn’t stay on my feet for more than a few seconds. Every time I stood up, I’d immediately lose balance and wipe out. It was a stark contrast from how things had been going just the day before, and frustration started to set in.

After about 15 minutes of struggle, Tito suggested we head back to the shore to switch boards. I was confused. It was the same board I’d been riding for the past three day — or so I thought. But when we pulled the board out of the water, we discovered the problem: one of the fins was missing. The stabilizer that had kept the board balanced was gone, making it far less stable.

We grabbed a new board and headed back out. Suddenly, everything clicked again.

And that’s when it hit me: sometimes, when things feel off, you need to change the board. Whether in surfing or in life, adjusting your tools or approach can make all the difference when you’re searching for flow.

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2. Be Ready, Take a Deep Breath, and Don’t Look Behind You

By the end of the week, Tito told me I was ready to head “outside” the break — where the bigger waves were waiting. To say I was nervous would be an understatement.

“Do you trust me?” Tito asked.

“Ummm, sure,” I replied, less than confidently.

But off we went.

“Here’s what you need to do,” he explained. “Be ready, take a deep breath, and don’t look behind you.”

I followed his advice. When he said goI paddled hard and caught the biggest wave of my life (which, to be clear, wasn’t that big by most standards, but it was huge for me). Unfortunately, there’s no photographic evidence, so you’ll have to take my word for it.

Just before you catch a wave, there’s this moment where everything comes together — you feel it’s time. You take a deep breath, paddle hard, and commit. Once you’re on the wave, there’s no looking back. Focusing on what’s behind you will throw off your balance or, worse, cause a wipeout.

Life is no different. Opportunities roll in like waves, and when one comes your way, you’ve got to be ready. If you spend too much time looking back, you’ll miss what’s right in front of you. And when it’s time to take that leap, trust yourself, focus ahead, paddle hard and don’t look back.

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Those two lessons — sometimes you need to change the board, and when it’s time, don’t look back — have stuck with me long after I left the beach. Turns out, surfing teaches you a lot more than just how to ride waves.

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