Leading Through Uncharted Waters: What Icebergs Can Teach You About Market Vision

Image by @Dan Raz

Captain Ben Lyons at the helm. Photo by Reeve Jolliffe

In the frigid expanse of Antarctica, Ben Lyons learned to see differently. During his early days navigating polar waters, he was mentored by veteran captains who taught him how to see icebergs. Not as objects to merely avoid, but as markers for the unseen.

“Back when I was piloting the Queen Mary 2 across the Atlantic, we’d have to stay 20 miles south of iceberg limits. But then I went down this expedition road and all of the sudden you’re getting so close to these big icebergs that you see the ship’s shadow on them. And that’s the point so that the guests get an amazing experience! But to do so safely, you have to learn to look at your environment differently.”

Sounds like pivoting from corporate to entrepreneurship, right? And where you’d think Ben would find uncertainty and risk in expeditions, lessons from his mentors gave him a new understanding of his world and how to read it.

“I very clearly remember the captains saying to me, “Okay, we’re gonna go into this bay and it’s not particularly well charted. We’re not entirely sure what the depth is everywhere, but we’ve been in here before and, you know what? See that huge iceberg right there? If that has a height of 50 or 60 meters above the water, then we know it’s gotta have hundreds of meters below the water. So if you actually steer closer to that iceberg you know that it’s gonna be deep enough for the ship, right? ”

In many ways, leading a business through shifting markets requires the same kind of attuned vision. Below the surface of every market shift are signs, signals, and second-order consequences that rarely show up on spreadsheets.

As Lyons shows, this kind of perceptive leadership is learned, and it’s essential. So, here are three lenses and key practices you can develop to improve your ability to lead over the long haul.

1. Interpreting the Surface Clues

Develop a Regular Market Sensing Routine
Create a system for listening to the quietest signals in your industry. Every week:

• Scan two niche forums, subreddits, Discord groups, etc.

• Talk to two users or customers about what’s changing for them.

• Watch what early adopters are doing.

• Document your observations in a tool accessible by all employees

Just as Lyons was trained to read the icebergs, shoreline, and sonar with more nuance, founders must develop their own radar: scanning niche communities, emerging platforms, even complaints on forums. Often, it’s not a loud trend but a subtle tension.

Before sustainability became a buzzword, a quiet shift was underway. A handful of founders noticed that modern consumers were becoming more interested in carbon footprints than logos. The team at Allbirds paid attention to those signals. Instead of doing more of what already worked in the fashion world, they tuned into a deeper current: people wanted to feel good about what they wore, ethically, environmentally, and emotionally.

Market sensing is the ability to pick up on faint changes in mood, demand, or values before they become obvious. It’s the entrepreneurial version of spotting “growlers”—low-lying chunks of ice that can wreck your ship but are nearly invisible until you know what to look and listen for.

2. Evolving With the Conditions

Conduct Decision Debriefs
Explorers dissect every journey to prepare for the next one. After all major decisions, gather your team to ask:

• What signals did we respond to?

• What did we miss?

• What can we systematize for next time?

Run Scenario Loops

Regularly choose a current challenge and ask:

• What’s the most likely path forward?

• What’s a worst-case scenario we’re not prepared for?

• What’s a totally unexpected shift we haven’t even discussed?

  Practicing this builds “if-then” muscles—like training your body to shift weight quickly while climbing.

In expedition travel, no plan survives contact with the real environment. You adapt, or you turn back. The same goes for founders.

Take the case of Airalo, a young company providing eSIMs to travelers worldwide. When the pandemic hit, international travel collapsed. Many companies in the space folded or froze. But Airalo’s leadership team didn’t cling to their original model. They drew on outside expertise from telecom and SaaS, and retooled their platform to serve business partners and expand domestic use cases. They turned a crisis into an opportunity by flexing, not freezing.

This is adaptive expertise. It’s the ability to execute and change the strategy when the winds shift. Lyons learned this from seasoned captains who helped him develop instincts that textbooks couldn’t teach. Similarly, the best founders surround themselves with advisors inside and outside of their industry who help them see more clearly, think more fluidly, and adjust their grip on the wheel.

3. Second-Order Thinking: Seeing Beneath the Ice

Build Your Second-Order Thinking Muscle
Before making a major decision, pause and ask:

• “And then what?”

• “What happens if this works too well?”

• “What are the unintended consequences?”
  Map out two or three layers of ripple effects—not just for your business, but for your team, customers, and competitors. Writing this out forces your brain to go deeper than instinct.

Most people react to surface-level outcomes. Great explorers and great business leaders look deeper. They ask, “If we do this, then what happens next? And after that?”

Second-order thinking is the mental model that separates reactive decision-making from visionary leadership. It’s the difference between staying 20 miles away from icebergs and understanding how its position reveals a deeper current below—then, using that to your advantage.

Using last night’s binge watching as an example: Netflix’s pivot from DVD rentals to streaming wasn’t just about consumer convenience. It was based on a cascade of anticipated changes: broadband infrastructure would improve, content licensing would become critical, viewer habits would shift from scheduled programming to on-demand bingeing. Each of those required betting not just on the first move, but on the ripple effects of that move. They didn’t just react. They read the future by studying the deeper structure of change.

Business leaders need this same lens. When you change a product feature, how does it affect customer behavior? What does a shift in pricing signal to competitors or partners? How will today’s acquisition impact your brand trust two years from now?

The water may look calm, but the current below will shape your journey.

Seeing the System

The Systems Thinking Iceberg Model from EcoChallenge.org

When Ben Lyons was learning about icebergs in Antarctica, he was learning to the value of reading the entire system—wind, current, pressure, radar, sky. Everything was connected. And each part influenced how the ship moved through the world.

This is the essence of systems thinking—the ability to zoom out and see how small events are connected to larger patterns and structures. And it’s a skill every founder should cultivate. (I highly recommend reading Thinking in Systems by Donella Meadows. Also, check out @TheRossHarkess’s video takeaways from the book.)

Heck, they even call it “The Iceberg Model!” When you train yourself to think like a systems navigator, you begin to ask:

• What patterns led up to this?

• What structural decisions created this vulnerability?

• What assumptions are we operating under that no longer serve us?

  By examining these layers, organizations can move beyond reactive solutions and address root causes for sustainable outcomes.

Thanks to Ben Lyons and EYOS Expeditions for sharing these and other insights from the world of exploration.