Every year, the cycle begins again.

We promise ourselves that this will be the season we finally nail our starts, trim perfectly in light air, or stop letting that one rival boat sneak ahead on the final leg. We set resolutions, intentions, plans, and goals—sometimes all four at once.

But what’s the difference? And why do so many of these good intentions end up like an untrimmed spinnaker—full of promise, but collapsing at the first puff?

It turns out, how we think about progress matters as much as how we pursue it. That’s true in sailing, and in life.

The Four Tools of Change

If sailing teaches us anything, it’s that no single tool solves every problem. A winch is not a cleat, and a compass is not a chart. The same holds true for how we frame improvement: resolutions, goals, plans, and intentions each serve a unique purpose.

• A Resolution is a decision to act. It’s Henrietta the Chicken’s moment of resolve: “I’m going to cross that road.”
  
• A Goal defines the destination. It’s “the other side”—a tangible outcome you can aim for.
  
• A Plan maps the route—the tacks, gybes, and laylines that connect intention to execution.
  
• An Intention is the compass bearing—the why that keeps you on course when the wind shifts.
  

When we mix these up, we get lost. When we use them together, we move with purpose.

Stoicism at Sea

Sailboat racing, like Stoicism, teaches us to control what we can and accept what we can’t.

We can’t command the wind, but we can trim the sails. We can’t dictate the current, but we can choose our heading.

Epictetus might have made a fine tactician; Marcus Aurelius would have written beautiful post-race debriefs. Stoicism’s essence—focus on the process, not the outcome—is the same mindset that wins regattas and builds better sailors.

Goals and results matter, but they are byproducts of good process. The true sailor’s peace comes not from trophies, but from mastering the art of decision-making in motion—being calm in chaos, deliberate in uncertainty, and curious always.

Learning Theory in Action

At North U, we don’t just teach you how to sail—we teach you why things work.

That’s the foundation of real, sustainable learning.

Learning theory tells us that deep understanding—the kind that lasts—comes from reflection and feedback, not repetition alone. That’s why we coach sailors to debrief every race, to ask “what happened, why, and how can I adjust?”

It’s not about memorizing tactics; it’s about developing the mental flexibility to adapt when everything changes (because it always does).

Turning Intention into Action

Let’s take a page from Henrietta’s logbook.

• Resolution: “I will improve my upwind speed.”
  
• Goal: “Hold height and pace with the top three boats by midseason.”
  
• Plan: “Sail twice a week, focus each session on one trim variable, record speed vs. angle data.”
  
• Intention: “I intend to be curious, not judgmental—to learn, not to prove.”
  

When these four align, learning becomes less about perfection and more about progress.

You stop fearing mistakes, because each one is simply another data point on your course.

The North U Perspective

At North U, we’ve been helping sailors set better goals and reach them for over forty years—not by promising instant results, but by teaching enduring principles.

We invite you to start this season with a clear head, a steady hand, and a stoic heart.

Bring your curiosity, your humility, and your willingness to learn. Leave the ego on the dock.

Remember:

• Resolutions commit you.
  
• Goals direct you.
  
• Plans guide you.
  
• Intentions define you.
  

The wind will shift. The mark will move. The only constant is your mindset.

So, trim in, stay curious, and sail with intention.

Because the other side of the road—or the racecourse—isn’t where the lesson ends.

It’s where it begins.

About The Author

Kristen Berry is a dedicated sailing educator and US Sailing-certified instructor with a passion for helping sailors of all levels achieve their goals. As the owner of Gale Force Sailing in Annapolis, MD, Kristen provides personalized training and expert coaching, blending hands-on experience with an approachable teaching style. His extensive background includes working with the U.S. Naval Academy’s Basic Sail Training program and serving as an advisory board member for New York’s Hudson River Community Sailing organization.