Lake Michigan is amazingly beautiful in the summer.

It’s almost hard to believe that something this big isn’t the ocean, it’s roughly 80% the size of South Korea where I grew up. When I sit by the water, the beautiful color of the water, gentle waves that lake makes and the fact that I know there’s always land somewhere beyond that horizon feels strangely grounding.

Every summer, I watched people dive in and float in the lake, and at some point I thought, “Why not learn sailing?” So I signed up for a class. (Surprisingly, I was back again this year, my second year of sailing!)

When I first signed up, I honestly had no idea what sailing really involved. I imagined that if I had white sails and a boat, I could go anywhere. But sailing requires paying attention to far more things than I expected, and because I found it all very interesting, I wanted to write it down.

So first of all, when you sail, you will always go through uncertainty. The direction of the wind is hard to read, waves are unpredictable, even though in the situation when the destination you need to reach is somehow clear.

I mainly learned on a two person small size sailboat called “420” : it fully operates only with lines, no intuitive steering wheels or handles to change the direction, and a skipper who controls the main sail at the back, and a crew who manages the front jib(smaller sail).

To move the boat correctly, both have to communicate constantly:

  • The skipper watches the overall route and adjusts the main sail
  • The crew pays attention to nearby risks and adjusts the jib in response

There are absolute references, of course: east, west, north, south, and fixed landmarks. But unlike a car that can drive straight south, a sailboat can’t. You have to read the shifting wind in real time, adjust your heading, and work your way there, sometimes zigzagging, sometimes catching the perfect angle.

Zigzagging and adjusting to the wind—sailing isn't a straight line.

During my first session, I didn’t understand that constant adjustment. I was the crew, and the skipper didn’t have much experience either. We kept turning left and right or sometimes going in circle without knowing why. I didn’t understand why I had to release the left line sometimes and the right line at other times.

I left that first class with a giant question mark.

During the second session, a woman who had sailed her whole life joined our boat. She calmly explained everything:

“Let’s point the bow toward the Northwestern Kellogg building. What direction do you think the wind is coming from now? It’s shifted from northeast to north, so we’re going to go upwind first, then tack, and aim the bow toward that buoy.”

That was the moment it clicked.

The wind direction is a real-time variable, the boat can’t just go straight toward a destination.

Once I understood that, I could finally read the shifting wind and plan a route. When the wind changed again, we reassessed, made a new decision, and kept moving.

I’m someone who always wants to understand the underlying principles. I ask “why?” a lot. Once I understood the mechanics, I felt more confident.

But then I wondered: Does everyone learn best this way? Just because this works for me doesn’t mean everyone needs to start with principles.

I realized there are three factors that matter:

  1. Psychological Safety (Trust): The level of trust between the skipper and the crew
  2. Environmental Stability (Risk): How stable or risky the environment feels
  3. Cognitive Style Alignment: Whether they share the same communication style

Once, I went sailing with my other friend. Because I get comfortable after understanding the system, I started explaining our movement using landmarks and the overall route instead of giving direct instructions while we are at the water:

*“We’re going to point the bow toward downtown.”

“Now let’s angle toward Kellogg, so release the left line in 5 seconds”*

But every time I mentioned a landmark or cardinal points, she panicked.

“So should I release the left line or the right line?”

She didn’t want the big-picture route and She wanted direct instructions.

That made sense. There can be many reasons for that, but usually when you’re drifting away from land, it’s easy to panic before trying to understand principles. I felt relatively calm because I knew how it works and we could get back, but she didn’t have that level of understanding yet.

So I said, “Okay, then I’ll just tell you left or right. And since I understood how the boat works, I knew we could always make our way back. So don’t worry about that part.” And after that, we aligned.

Once we were back on land, we talked again about the principles of how the boat moves. She seemed to understand them. And later, I asked her, “How do you want me to communicate on the water? Do you want only the immediate actions you need to take - left or right - or do you want me to talk about our heading too?” She said, “Just tell me left or right. If you talk about the big direction on the water, I panic.”

And that made perfect sense.

In that situation, we had trust (factor 1), but the environment didn’t feel stable for her yet (factor 2). So the best communication style (factor 3) - which will depend on the person I’m communicating with was simple, direct commands—which may change as she gains more experience.

That’s something I’m starting to notice beyond sailing too - in teams, in products, and in how we design systems around people.

The challenge isn’t just handling uncertainty, but designing for how people experience it.

What a fun world!