Navigating the Uncharted: How Transformational Leaders Master Volatility and Lead Through Fear
Leadership Lessons Learned Under Pressure During a Red Sea Storm
If I were to ask you what the scariest day of your life was, could you tell me?
Take a moment and think about it. What moment pushed you to your absolute limits? When did you feel most afraid, most out of control, most uncertain about whether you’d make it through?
Now, if you asked me the same question, my answer might surprise you. Because the scariest moments of my life—and I mean truly terrifying—all happened on the same day. And no, it wasn’t when we were being chased by Komodo dragons in Indonesia (yes, that happened—15-foot-long, 400-pound prehistoric predators that can take down water buffaloes and run as fast as alligators). It wasn’t dodging pirates with machine guns in the Gulf of Aden, that stretch of water between Oman and Yemen that sailors call “Pirate Alley.”
It was something far more primal, more overwhelming, more completely out of my control: battling the worst storm of our lives in the middle of the Red Sea.
When Everything Goes Wrong at Once
Picture this: Our small sailboat flying off the top of a 30-foot wave—three stories high—then slamming down into the trough below, the whole vessel shaking and shuddering like it had been hit by a cannon blast.
The seas were bigger than anything I’d ever encountered. Steeper than I’d thought possible. And they were coming faster than my mind could process. I remember counting—1,001, 1,002, 1,003—and BAM, we’d be slammed by another wall of water.
The noise was absolutely relentless. Each approaching wave sounded like a rumbling earthquake, followed by a hissing sound as the wind tore the tops off the waves and sent them stinging into our faces like cactus needles. We’d been up all night. We were exhausted, shivering, soaking wet, and utterly alone. There’s no Saudi Arabian or Egyptian Coast Guard to call for advice or rescue in the middle of the Red Sea.
I was starting to hallucinate—seeing walls and mountains that weren’t there, hearing voices in my head (more than I usually hear, anyway). And honestly? All I wanted to do was crawl down below, climb into a bunk, pull the covers over my head, and wish it all away.
But then I looked over at my crew.
The Moment Everything Changed
Ken and CJ were staring at me with eyes as wide as saucers. They were terrified. And they were looking to me for answers.
Now, I should mention that this whole situation was technically CJ’s fault. As the wind had been building—20 knots, 25 knots, 30 knots—CJ had said with a grin, “Oh boy, I always wanted to be out in a big storm!” Ken and I immediately shouted, “No! Don’t say that! The wind gods will hear you!” But it was too late. The damage was done. Within an hour, the wind hit 60 knots.
So yes, I’m blaming CJ for the entire incident. I certainly don’t want to take responsibility for my own weather forecasting abilities or my questionable leadership decisions that got us into that situation in the first place.
Here’s what I want you to understand: Was I scared? Absolutely. I was terrified. I was afraid for myself, for the boat, but most of all, for the safety of my crew.
You’d have to be crazy not to be scared in those conditions.
The Leadership Paradox Nobody Talks About
Here’s the paradox every leader faces but few openly discuss: You’re human. You feel fear. You make mistakes. Your confidence gets shaken—sometimes shattered. But your team is looking to you for stability, for answers, for confidence.
In that moment, battling 30-foot seas, I faced the hardest leadership challenge of my life. Because fear, like all emotions, is contagious. The last thing I needed was a crew frozen with fear, unable to function, paralyzed by the chaos around us. I needed a crew who was motivated, focused, ready to do their jobs to keep us alive and the boat afloat.
I needed to instill confidence in them.
And that was incredibly difficult, because my own confidence had been badly shaken. I had gambled on the weather forecast and lost. I had made a mistake—a potentially catastrophic one—and we were all paying the price.
This is where most leadership advice fails us. The books tell you to “project confidence” and “stay calm under pressure.” But they don’t tell you how to do that when you’re the one who made the error, when you’re the one who led your team into danger, when your own inner voice is screaming that you’re an incompetent fraud.
At times like that, it’s incredibly easy to lose your confidence. And that loss of confidence often leads to compounding errors—making more bad decisions because you’re second-guessing yourself, rushing to “fix” things, letting fear drive your choices instead of clear thinking.
Slowing Down to Speed Up
So there was no crawling into that bunk for me.
Instead, I did something counterintuitive: I slowed down. I studied the charts. I took things in chunks—one decision at a time, one hour at a time. And I found a small anchorage we could reach, a protected spot 60 miles away where we could find safety.
It took us a full day to get there, fighting upwind the entire way. And honestly? The sailing wasn’t the hard part.
The hard part was dealing with my crew.
Because my crew wanted me to turn around. They wanted to run with the wind, run with the storm—which can sometimes be the safer choice. But not in the Red Sea. The Red Sea is so narrow that within a day you’d be on the other side, and you’d be in an even worse position than when you started.
I knew the right call. But my crew was scared, exhausted, and desperate for relief. They wanted the easy answer, the comfortable choice, the one that felt like escape rather than endurance.
The Three Pillars of Leadership Under Fire
This is where I learned—or rather, had burned into my soul—the three essential pillars of leadership in crisis:
First, you must maintain confidence in your vision. What do you see as the endgame? Where are you actually trying to go? In my case, it was that anchorage 60 miles ahead. Not behind us. Not some fantasy of calmer seas. A real, concrete destination where we could find safety.
Second, you must have confidence in your course. How do you plan to get there? What’s the path, even if it’s difficult, even if it’s slow, even if it’s not the path others want to take? For us, it was continuing upwind, hour after grinding hour, maintaining our heading.
Third, you must continually reevaluate your methods. This is crucial. Having confidence doesn’t mean being rigid. I was constantly adjusting our sail configuration, our angle to the waves, our strategy for each new set of conditions. The destination stayed fixed, but the tactics adapted minute by minute.
Your leadership is what inspires others—not through false bravado or pretending everything is fine, but through clear-eyed determination and the willingness to stay the course when everything in you wants to quit.
The Most Important Leadership Lesson of All
Here’s what I realized in those exhausting hours battling toward that anchorage: The most successful leaders know that leading yourself is where you start.
You begin with self-mastery—managing your own fear, your own doubts, your own mistakes. You develop the discipline to slow down when your instinct is to panic. You learn to make decisions from a place of clarity rather than desperation.
But then something shifts. You have a recognition, a fundamental realization: It’s not about you.
Real leadership isn’t about proving your competence or protecting your ego or being the hero of the story. It’s about lifting up others. It’s about instilling in your team the confidence they need to perform at their best, even when the seas are mountainous and the way forward is unclear.
That day in the Red Sea, I wasn’t battling the storm to prove I was a good sailor. I was battling it to get my crew safely to that anchorage. Every decision, every course adjustment, every word of encouragement or correction—it was all in service of them, not me.
And that’s when you become a real leader. When you stop asking “How do I look?” and start asking “How do I serve?”
What This Means for Your Leadership
You might not be battling 30-foot seas or dodging pirates or outrunning Komodo dragons. But you’re facing your own version of the storm:
- The product launch that’s behind schedule and over budget
- The key executive who just quit at the worst possible time
- The market shift that’s threatening your entire business model
- The tough conversation you need to have with your board or your team
- The decision only you can make, with incomplete information and high stakes
In those moments, the same principles apply:
Acknowledge the fear. You’re human. Of course you’re scared. Of course you’re questioning yourself. That’s normal, and it’s actually healthy—it means you understand the gravity of the situation.
Slow down to make better decisions. When everything is urgent and chaotic, the most powerful thing you can do is pause, study the charts, and choose your destination deliberately.
Maintain confidence in your vision and course. Your team will push for the comfortable choice. They’ll want to “turn around and run with the wind.” But you’re the leader—you have to see what they can’t see yet and hold the course even when it’s unpopular.
Remember it’s not about you. The moment you shift from protecting your ego to lifting up your team, everything changes. Your leadership becomes authentic, powerful, and truly effective.
We made it to that anchorage. After 24 grueling hours, we found calm water and safe harbor. My crew was exhausted but intact. The boat was battered but afloat. And I had learned lessons about leadership that no classroom or book could have taught me.
Your Turn to Navigate the Storm
What storm are you facing right now? Where are you being tested as a leader?
Maybe you’ve made a mistake and your confidence is shaken. Maybe your team is scared and looking to you for answers you’re not sure you have. Maybe you can see the right course forward, but it’s difficult and unpopular and everything in you wants to take the easier path.
This is your moment. This is where real leadership is forged—not in the calm waters, but in the storm.
Bring These Leadership Lessons to Your Organization
The stories you’ve read here aren’t just tales from the sea—they’re powerful frameworks for navigating the storms every leader faces. From boardrooms to crisis situations, the principles of maintaining confidence, managing fear, and lifting up others under pressure are universal.
Larry Jacobson brings three decades of CEO experience and real-world leadership lessons to audiences worldwide. Through vivid storytelling and practical frameworks, he helps leaders at all levels develop the clarity, confidence, and courage to navigate their most challenging moments.
Is your organization facing change, uncertainty, or high-stakes challenges? Invite Larry to speak at your next leadership retreat, conference, or executive offsite. His presentations combine unforgettable stories with actionable insights that leaders can apply immediately.
Contact Larry Jacobson today to discuss bringing these transformative leadership lessons to your team.
Because the best time to learn how to navigate the storm isn’t when you’re in the middle of it—it’s before the first wave hits.
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