Horizons

August 28, 2026
Wednesday I wrote that Thursday was a go for my first real hands-on sailing experience with Otter Sailing Adventures. https://www.ottersailingadventures.com

As I sit here on Edisto Island, I am writing an update and reflection from my journey yesterday…

Despite being nervous and not knowing what to expect, I spent the day aboard Traveller, Barry Gupton’s Catalina 275 Sport, learning how to actually sail instead of just reading and thinking about sailing. It was a memorable experience. I did it.

Around 9am, we started by preparing the boat. We swapped the self-tacking jib for the 150 genoa. I learned how to fold and stow a sail. We went through all the pre-reqs and safety checks, etc. He explained all the parts of the boat and gave a good understanding of what everything does and why they’re important.

By 9:45, we headed out down the creek, heading into St. Helena Sound and toward the Atlantic Ocean.

The wind was pretty light when we started. We motored out for a while and tried getting under sail, but there just wasn’t much wind to work with. As the morning went on and we got farther out, the wind started to pick up and Traveller finally came alive.

10:30-11:00am, that’s when the work really began.

Barry was great about explaining not only what we were doing, but why we were doing it. More importantly for me, he listened to my questions and gave me the opportunity to actually do the things he was teaching me instead of just watching him do them. He let me do the work.

I learned to raise and lower, furl and unfurl and reef the mainsail and headsail, jib and tack to port and starboard, bring the boat head-to-wind and put her in irons, use the Raymarine autopilot, and start paying attention to what the wind and water were telling me.

And then I got the tiller.

A lot.

I even got to experience some unpredictable gusts and learn how to handle them, which is where the reefing came into play. “Reef early, reef often”, he said. Which resonated with me given the videos I’ve watched from Be the Captain on YouTube. At one point Barry mentioned the wind was around 10–15 knots, which gave me the opportunity to actually learn why and how we reef both the mainsail and headsail when needed, not just read about it. It was such a learning experience.

Around 12:30pm, as the day went on and I became more comfortable, Barry let me do more and more myself. By the latter part of the trip, I was spending a lot of the time actually sailing Traveller.

Sailing is work.

I knew this going in, but I wasn’t sure what to expect. I’d never handled a sailboat, let alone even been on a sailboat before. I’d only seen them in videos and photos, read about them in books, worked through NauticEd training, and watched them from a short distance on the water.

Lines. Sails. Tacking. Reefing. Watching the wind. Watching the boat. Making adjustments. Thinking about what needs to happen next.

And I absolutely loved it.

Eventually everything was set, the wind was cooperating, and there wasn’t another task immediately waiting. I just sat at the tiller, looked out across the ocean, and enjoyed the fact that the boat was moving under sail because of all the work we’d done.

After all the reading, videos, questions, thinking about boats and wondering what actually sailing one would be like…

I was sailing.

That was the moment. It felt like freedom.

Despite all the research and learning I’d done prior to this, some of it was difficult to make sense of, it was somewhat confusing. Once I actually got on the boat, started doing the things, all of the terminology, training, videos and reading, finally clicked into place. That was when it all came together.

Huge thanks to Barry for his patience, knowledge, and willingness to let me learn by actually doing. I went into the day hoping to get my first real taste of sailing.
I came back wanting more.

One last thought. I owe a large portion of this to Sailor James & The Good Ship Triteia on YouTube. About a year ago, in August of 2025 (almost literally to the day), I watched one of Sailor James’ videos and shared my interest in the idea with my family. Sailing Alone 11,500 Nautical Miles Across the Entire Pacific Ocean on a $2400 Sailboat https://youtu.be/lBzwx7J8c48 . This video changed my view of how life should be experienced. Between that and all my reflections over the past year, if it had not been for him, I probably wouldn’t be here today. His support, engagement, encouragement, through his videos, live chats and streams, have helped support my direction, my compass, and the idea, to Choose Your Tide.

Fair winds.
— blueWater baboon

Had a really good conversation with Barry this morning and got an idea of what to expect.

We’ll be setting the sails and departing around 9:30 tomorrow morning for an all-day training session. 😁

Embracing the Journey: The Story of blueWater baboon

There comes a moment in life when you stop and ask: What am I actually doing all this for?

For years, I chased the classic script—climbing the ladder, collecting promotions, chasing the next milestone, the next achievement, the next thing that was supposed to finally make me feel “successful.” Like so many others, I followed the well-worn path society lays out: more titles, more stuff, more status, more productivity.

And for a while, it worked. Until it didn’t.

The more I accomplished, the louder the quiet voice inside became. Something was missing. I craved peace. Freedom. Purpose. A life that actually felt real.

The moments that made me feel most alive weren’t in boardrooms or during performance reviews. They were on quiet beaches at sunrise, salt air on my face, waves rolling in, my family beside me, staring at that endless horizon. In those moments, the ocean stopped being just a place—it became a reminder.

A reminder of freedom.

A reminder that life is so much bigger than our calendars and obligations.

A call to something deeper.

Where the Name Began

The name blueWater baboon originally comes from an old, haunting Dave Matthews rarity called Blue Water Baboon Farm. I was a devoted Dave Matthews Band fan for many years, and for reasons I couldn’t fully explain at the time, the song stayed with me through some of my hardest years.

One image in particular—“reach my hands to cup the sky … a bitter blue”—felt like reaching for help, answers, or escape from something tearing you apart.

That was what the song meant to me.

And although I couldn’t have explained it then, the words blueWater baboon became tied to that period of my life. They carried the weight of searching for something I couldn’t yet understand.

Years passed. My life changed. I changed.

Eventually, blueWater baboon began to mean something different.

The water itself hadn’t changed.

What it meant to me had.

The Dream That Became blueWater baboon

Eventually, that pull became impossible to ignore. I started dreaming of standing at the helm of a sailboat with nothing but wind, water, and sky around me. No notifications. No meetings. No expectations. Just presence, movement, and the simple joy of being exactly where I was.

The ocean wasn’t an escape. It was freedom.

Freedom to choose my own course.

Freedom to define success on my terms.

Freedom to rediscover what truly matters.

That dream evolved into blueWater baboon—not just a brand or a business, but a mindset. A way of life. A reminder that life is something we’re meant to participate in—to be part of the journey—not something to let pass us by. A quiet reminder that there’s another path available to all of us if we’re brave enough to take it.

A path that values experiences over status.

Meaning over recognition.

The journey over the destination.

And most importantly, a life that feels truly alive again.

The Meaning Behind the Compass & Baboon

The blueWater baboon carries two simple but powerful ideas that continue to guide everything I do: direction and freedom.

The Compass represents direction.

The Baboon captures a feeling of freedom.

Together, they remind us that while we can’t control the winds, the tides, or many of life’s circumstances, we can choose our heading—and we can choose how we move through the world.

The Compass: Choosing Your Heading

Stand at the edge of the ocean and look out. The horizon stretches forever. Possibility, adventure, uncertainty, and the unknown all live out there.

The ocean teaches humility fast. You don’t control the weather. You don’t control the currents. Life has a way of reminding you how small you are.

But here’s the beautiful part: you still get to choose your direction.

The compass doesn’t promise calm seas or easy passage. It simply points the way. It says, Even in uncertainty, you have power. You can decide what kind of life you want to live. You can choose to follow the path that feels true to you instead of drifting with the crowd.

The compass is a symbol of courage—the courage to step away from other people’s expectations and sail toward a life that feels authentic. Even when the destination isn’t fully visible. Especially when it isn’t.

The Baboon: Freedom in Simplicity

Baboons are not simple creatures. They live in sophisticated, hierarchical troops where social dynamics, alliances, and status play real roles in survival.

They navigate complex relationships, remember who’s who, and work hard to protect their place in the group.

And yet—that’s exactly what makes the baboon such a strong idea for me.

Unlike humans, baboons don’t chase symbolic status—the kind built on titles, followers, luxury possessions, or performative success. Their world is immediate and grounded. They focus on what truly sustains life: family, connection, community, exploration, play, and being fully present in their environment. They adapt, forage, travel, and live in the moment without the weight of abstract expectations or endless comparison.

In a world that constantly pressures us to become somebody—to build a personal brand, climb invisible ladders, and measure our worth by external validation—the baboon carries a feeling of permission. It reminds me that we don’t have to play every game society presents.

The baboon isn’t “nobody” because he’s insignificant.

He’s nobody because he doesn’t need to be somebody in the way we’ve been taught.

There is profound freedom in that realization.

Together: Direction and Freedom

The compass says: Choose your course.

The baboon says: Stay grounded in what matters while you travel it.

One gives direction. The other gives perspective.

One reminds us where we’re going. The other reminds us why.

Together, they form a gentle rebellion against the noise—the pressure to achieve more, buy more, produce more, and become more. They remind us that life isn’t a race to some imaginary finish line.

The goal isn’t to arrive.

The goal is to live.

To explore.

To learn.

To grow.

To connect.

To stand at the water’s edge and choose a heading that feels true to who you are.

The compass is the courage to move forward.

The baboon is the freedom to let go of everything that doesn’t matter.

Together, they’re a reminder that real freedom isn’t found at the destination.

Freedom is found in choosing your own tide—and enjoying every moment of the journey.

If any part of this resonates with you, you’re already on the path. Welcome aboard.

Let’s sail.

— blueWater baboon

People usually ask about the name first.
“Why blueWater baboon?”
It’s a fair question.
But the story was never really about a baboon.
It’s about a life I was trying to find.

And for the first time in a very long time…
there was something beyond the horizon.

And I am going.