“You can never cross the ocean until you have the courage to lose sight of the shore.” – Christopher Columbus

Boating is about freedom: the open water, the wind in your sails, and the thrill of the journey. But with that freedom comes uncertainty:

What if the wind picks up and I can’t dock the boat? What happens if the engine cuts out? What should I do if I encounter something unexpected on the water?

These questions can paralyze even the most seasoned boaters. The truth is, confidence doesn’t come from perfect conditions or endless worry. Confidence comes from preparation. Let me share a story—a tale of two captains—that taught me this invaluable lesson.

Captain One: Superyacht Precision and Protocol

For years, I worked as a deck officer aboard superyachts, a world where preparation wasn’t just encouraged—it was mandatory. Every maneuver had a plan. Every trip had a backup. Before departure, we ran through weather forecasts, inspected engines, reviewed charts, and followed rigorous checklists.

The result? A level of calm that only comes from knowing every possible risk has been minimized. I’d seen firsthand how preparation could turn potential crises into mere inconveniences.

But when I stepped away from the superyacht world, I wanted something different. I craved the simplicity and freedom of recreational boating. That’s when I bought my own 38-foot sailboat.

My career on yachts helped me understand minimising risk through preparation. 

Captain Two: “She’ll Be Right” Adventures

When I bought my sailboat, I was determined to leave the superyacht formality behind. I wanted to toss the checklists and embrace the carefree boating dream: throw off the lines and chase the sunset.

My dad—an established sailor and diesel mechanic by trade —offered a bit of advice before my first trip south. “Check your fuel system,” he said. “Plan for what you’d do if something went wrong.”

But I waved him off. After all, I was a professional mariner. What could possibly go wrong?

A Close Call: Lessons from the Lee Shore

It didn’t take long to find out.

I set off south with no care for preparation. The first leg went smoothly, but as I rounded an island, the conditions changed. The wind picked up, and the swell rose, right on the nose. That’s when my engine began to sputter.

At first, it was a dip in power. Then a surge. And finally—silence.

The engine had cut out, leaving me drifting toward a lee shore. My heart raced. I scrambled into the engine bay, hoping to fix the problem with brute determination. But my “she’ll be right” attitude had left me unprepared.

I managed to get a single bar of cell service and called my dad. Calm as ever, he helped me troubleshoot the issue: a clogged fuel filter caused by contaminants in the tank. With his guidance, I fumbled through replacing the filter and bleeding air from the system, all while watching the shoreline grow dangerously close.

By some miracle, I got the engine running and made it back to port. I’d avoided disaster, but I learned a critical lesson that day: confidence without preparation is nothing more than hubris.

  my 38ft sailboat and her engine bay. 

Finding the Balance: Confidence Through Preparation

That close call was a turning point. I took away lessons from both versions of my boating life: the disciplined, methodical approach of superyacht operations and the carefree, spontaneous spirit of recreational boating.

Now, as I teach students skills like docking, anchoring, and navigating marinas, I focus on helping them find that same balance. I try to help them learn from my mistakes, building their foundations of confidence and control through preparation.

Whether it’s mastering close-quarters maneuvering or planning a safe trip offshore, preparation lays the groundwork for confidence. By understanding their boat, their route, and the conditions, my students discover that preparation doesn’t stifle the adventure—it enhances it.

Why Preparation Matters

Since that close call, I’ve made preparation a cornerstone of every boating trip—whether it’s a short trip form the slip to a fuel dock or an offshore ocean passage. Preparation doesn’t mean eliminating uncertainty, but it gives you the tools to face it head-on.

Here’s what preparation looks like:

1. Plan for the Weather

• Check the forecast, including wind, waves, and tides for the entire duration of the journey.
• Know your, your crews and the boats limits and have a backup plan if conditions worsen.

2. Know Your Route

• Study charts for hazards like shallow waters or submerged rock, even if you “have sailed this route 1000 times”. Passage planning comes in real handy when emergencies arise.
• Mark key points along your route, including safe harbors or anchorages, and plan for other contingencies.

3. Ready Your Boat

• Inspect the engine, fuel system, anchor windlass, rigging, and safety gear.
• Stock up on fuel, water, and provisions for longer trips.
• Keep your maintenance routine up to date and get familiar with troubleshooting and basic repairs. —especially for things like fuel filters!
• Conduct test’s of equipment before you need them in anger!

4. Prepare Your Crew

• Brief everyone on the plan and their roles, especially during docking or emergencies.
• Make sure everyone has proper gear and knows how to use safety equipment.

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  Building Confidence at the Helm

  If you’re stepping into boating for the first time—or taking the helm after years as a passenger—preparation is your greatest ally. Confidence grows when you know your boat, your route, and yourself.

  If docking in the wind feels intimidating, practice it in calm conditions first. If you’re unsure about troubleshooting an engine, familiarize yourself with the basics (or keep a trusted mentor on speed dial). Preparation isn’t about perfection—it’s about feeling ready to tackle the unexpected.

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  Balancing Preparation and Adventure

  Boats weren’t meant to stay in port, and neither were you. But heading out unprepared turns freedom into risk. Preparation allows you to face uncertainty with excitement, not fear.

  The goal isn’t to eliminate every unknown—it’s to equip yourself with the tools to handle them. When you add preparation to your process, you transform “What if?” into “I’ve got this.”

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  Your Key Boating Takeaway

  Every boating evolution—whether it’s docking, anchoring, or setting out to sea—starts with preparation. Before your next trip, ask yourself:

  • Have I planned for the weather and the route?
  • Is my boat ready to go?
  • Is my crew informed and comfortable?
  • Have I minimized as much risk as possible, without sending myself insane?

  If the answer is yes, then cast off those lines and enjoy the adventure—you’ve earned it.

   

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  Ready to feel confident no matter what the water throws at you? Our Confidence in Close Quarters course teaches practical preparation and skills for every situation. Click here to learn more and start building your boating confidence today.

  What’s your most valuable lesson on the water? Share your story in the comments below—we’d love to hear it!

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