How sailing across the Atlantic Ocean prepared me to lead in the COVID Era | Joseph Imbriano
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How Sailing Across The Atlantic Ocean Prepared Me To Lead In The COVID Era

Talk presented to an organization of advisors in Denver CO (July 2020)



Good morning! Thank you for giving me the opportunity to share with you a powerful story in my life, and what I learned from that story.


I help leaders through crisis. You could say I’m an emergency room doctor for organizations. I help leaders make tough strategic, operational, and hiring decisions when they feel overwhelmed - by the changing landscape, or melting assumptions, or were left blindsided by shifting markets or the effects of bad decision making. Or in the middle of a pandemic.

I’ve been doing it since 2004. I started in the desert of northwest China, putting out fires for European companies that thought that the best way to expand into China was to copy and paste what worked in, say, Belgium.

Take a moment, and think about that, copying a business model that worked in Nebraska and pasting that model in say Serbia, or Pakistan. Needless to say, I had a lot of clients.

After building a reputation across China, I took this show on the road, helping leaders in countries in Asia, Southern Africa, Latin America, Europe, and the U.S.

Looking around the Zoom, I think we all would agree that it’s important to spend the necessary resources to make the best decisions we can. And yet, time and time again I’ve found that in crisis, when the ground is shifting beneath the decision-making table, that is not what happens.

And it’s those moments - those stormy seas - where we need to be the best leaders we can be.

Right now, we live in a perfect storm, where leaders are fighting strong headwinds in their pursuit to grow profitable, sustainable, and impactful organizations.The ground is shifting below us, and to meet those challenges, we need to be strong, adaptable, and resilient.

Since the pandemic began, I been working with leaders to adapt to this new world, and build organizations that can thrive within the uncertainty and emerge stronger on the other side.

And when I go home – or more realistically, when I end the Zoom call – and reflect on what gives me the strength and resilience day in and day out, one experience in my past comes to mind.

And in this story, there’s no decision-making table, no room where it happens, no suits or ties, no water cooler…no fame or glory or money. No, I learned these lessons along the precipice of endless seas and multicolored skies.

And I want to share this story with you, along with 4 leadership lessons I learned on that journey that better prepared me for the challenges the world faces right now.

Perhaps it will help you better face this perfect storm. Perhaps it’s nothing more than a good story. But what I hope more than anything, it unlocks your curiosity as a leader.

When the ground shifts beneath us, and the headwinds bring unfamiliar and powerful challenges, our previous wins don’t matter, previous models we have come to depend upon can become useless in a flash. And without a mindset forged by crisis, something as simple as dancing in your kitchen at home becomes much more difficult – and much less fun – than, say, dancing on the deck of a sailboat…in a storm.


On May 22, 2008, I boarded a sailboat in South Africa headed west to the Americas. Some of you may be thinking, sailing around the world sounds amazing. Count me in!

But before those rose colored lenses get too comfortable on your face, let’s look closer at my situation. The goal for the trip was simple - deliver this brand-new boat to its owner in Florida. The owner, whoever he was, would then tow it to his private dock on the Great Lakes.

Lakes…yes, the boat was made for lakes. Think about the last time you were, say, spending an afternoon on a sailboat on a lake. Can you visualize it?

Now imagine that same little lake boat – crossing the ocean. Imagine that instead of enjoying time with your friends or family, you're with 3 strangers. Imagine that instead of spending a glorious afternoon on that boat, your onboard for 33 grueling days.

Oh yeah...imagine that the boat had never been tested.

So to sum up, boat made for a lake, crossing thousands of miles of ocean. Never been tested in either. Still in?

I was! I weighed the risks, and made the decision to do this. When we drifted from the dock and through the harbor, it still hadn’t dawned on me that as risky as the situation already was, there was a much more dangerous factor, a significantly higher predictor of the success - or failure - of our mission.

This guy [Pointing to Joseph on the screen]. I know, he doesn’t look like too much trouble, but here’s the thing. I was at least 1/4 of what it would take for our tiny lake toy boat to cross the ocean. And, well, how should I put this….I had never sailed before.

Now, obviously, this wasn’t news to me. When I decided to join the crew, I weighed that detail with all the usual suspects I consider when making big decisions. My ability to craft solutions in crisis. All the wins I’ve had in the past. I was confident that if I could do it in all those other places, then surely, I could do it on this boat. Right?

Well, Wrong. Making decisions on land is different from making decisions at sea.

When I consider all the crises I’ve led through, and have guided leaders through, no matter how high the stakes, no matter how much the ground seemed to shift underneath us – the actual ground always remained stable.

This was a different world, a world where every decision had to be made on ground that actually moves – all the time. I could no longer depend on stable ground. And that is a significant distinction.

We aren’t even out of the harbor yet, and I can share with you my first lesson learned:

1. Accept the reality

That shift – from the world of certainty to one we feel is profoundly uncertain – well, that’s what makes a crisis.

It’s human nature to think of crisis as a blip in the journey of what is “normal”, and instead of adapting, we tolerate it. And because we view this as temporary, our goal is to navigate it to be able to Go BACK to normalcy. The path forward is actually anchored to yesterday.

And yet, we must focus instead on how today’s changes create tomorrow. The world we find ourselves right now is shifting in profound ways. And we will continue to feel the effects years from now. There is no return. The only way out of this crisis is through it.

As leaders, we must accept the world has changed. And a fundamental shift requires fundamental changes in how we lead. When we move from solid ground to stormy seas, our skills are transferable, but our confidence is not. Our winning streaks no longer matter, because a leader who may be strong in certainty does not always translate into being a strong leader on stormy seas. Often, the reverse is true.

So be humble. You may not even realize that not accepting the reality, like me on that boat, may be the biggest risk to your organization.

So Lesson 1: accept and adapt to the reality.


I had no choice but to accept my reality. The boat had already set sail! We could no longer see Table Mountain dominating the Cape Town skyline. Currents and Tradewinds that were outside our control propelled us into the blue unknown.

With each day, we worked to understand our new environment. We read the manuals, from the guidance system to the refrigerator, and learned the ins and outs of our new home.

We got to know each other. The four of us had never worked together before. In fact, we barely knew each other. Now we were spending 24 hours a day together in a space about 8 ft long and 8 feet wide. I focused on narrowing the skills gap as fast as I could. In particular, I wanted to be the best navigator on the boat.

After a few days, we adapted to our new life. My sea sickness died down. I started playing my guitar on the deck. Once, a large whale swam perpendicular to the boat, it’s long dark shadow gliding below us. At night during my 2-4am shift, I would enjoy the cool breeze and gaze up at the stars.


One evening, we all sat and watched the sunset. The sky was divided into two by this thin low hanging layer of clouds. Below the clouds, a blood orange sun dipped its toes in the water, before majestically disappearing into the vastness of the sea.


As vibrant colors danced across the sky before turning to night, I couldn’t help but feel alive.

The next day, we sailed into our first storm. And what a storm it was. The waves rose over 20 feet in height, crashing onto the boat head on.

Imagine with me my new normal: For what feels like an eternity, the boat rises with a wave. As we hover on the crest, for a split second, the world is calm and tranquil. And then, BAM! we plummet downward, like a terrifying rollercoaster, along the back of the wave.

The whole rhythm took about 20 seconds. These were the most frightening 20 seconds of my life. Ever. By far. And they repeated, 20 seconds after 20 seconds - for 13 hours. I was so afraid that I couldn't even process what was going on around me.

Fear was the lens with which I interpreted the world. And Fear was the consiglieri, the trusted advisor I turned to to guide my decisions. That made me useless. But we needed all hands on deck. The storm didn’t care about my feelings, and we still had to get through it. Skills were transferable, not confidence, right?

But no matter how hard I had worked to become better at sailing, 5 days was not enough. It didn’t matter anyway, since because I was looking at the world through the lens of fear, I couldn’t even apply what I had learned.

I made one wrong decision after another. One of them almost capsized the boat.

Like I said, the worst 20 seconds of my life, over and over for 13 hours.




We’ll come back to this storm a little later.


Anyway, We survive, Some days go by, and we spot our next storm. It was also a large one, and there was no sailing around it. The only way out was through. Round two, right? 


Except this time was different. We had some time before we sailed into the storm. Instead of freaking out, we made dinner, checked our equipment and told jokes over instant coffee. When the storm came, we were calm and ready.

2. Remove your lens of fear

Two storms, just days apart, with two completely different responses. What changed?

I often reflect on that first storm – and all that fear - and how I made decisions based on that the perceived reality that I saw wearing those fear glasses.

And then the second one – the calmness that came after accepting that situation - and the freedom to face real dangers in real time.

I think of the risk I was to the crew during the first storm. And the important role I played in the second one. In fact, I was asked to navigate the boat through most of the second storm, after only having sailed for a little more than a week! How’s that for building trust?

So what was the difference between the two? Well that’s the next lesson I want to share.

In the second storm, I refused to view the crisis through the lens of fear. I accepted the reality for what it was, and now that my mind wasn’t preoccupied with fears, I could focus on the real dangers that we faced.

As leaders, it's important to take off our fear glasses, and make decisions based on what is, rather than how we fear it to be.

So Lesson #2: take off those fear glasses, and see the world as it is.


Let’s go back to that first storm. Well, right after the first storm. The storm had passed, it’s late at night and I’m alone on the deck. It was a looooooong day. And even though we survived, our dinky lake boat still above water, we didn’t celebrate. Because a question still loomed large over the boat.

“Where are we?”

And we had a bad feeling about the answer to that question. It was obvious we had been pushed off the current. I could clearly feel our boat was rocking around slowly, in a circle. Like a rubber duckie in a bathtub.

Back in Cape Town, our plan was simple: ride the currents from Cape Town to Ft Lauderdale, Fl. You can see in this picture how. Let’s google maps it: take the Benguela, then take a left on South Equatorial, and at the fork, take the exit for the Counter. Follow the current and you’ll see the Caribbean. You see it right?

That was certainly the most reliable way for a boat designed for a lake to cross an ocean. We had a plan. The plan…was to stick to the plan.


The morning after the storm, our calculations confirmed what our intuitions told us. We had been pushed westward, way off the current. Looking back at the map, we were stuck in the circle between the arrows, a little north of the “g” where it says Benguela. And keep in mind, [on this map] each letter in Benguela represents a lot of miles.

It was bad news. Getting back on the current was going to take several days, minimum. And that was if we could avoid another storm. The thing is, with no current under us, no dependable winds in our sails, and equipped with a lake boat motor, we couldn’t really control how we got there. We could barely influence if we got there.

Now, When I get to this part of the story, many people will say things like “oh this must have been terrible” or “how frustrating.” The truth is, it was a beautiful experiment. Where we were heading hadn’t changed. That’s the most important part. Our challenge was finding how to get there from where we were now.

Every 6 hours or so, we would establish our location, plot it against our destination, and recalibrate. We were totally off plan, so there was no pressure to get that right. Instead, we stayed oriented to our goal.

Slowly but surely, after a few days, we caught a favorable wind, we managed to merge with the current. ironically, just in time to run into that second storm…

That brings me to one of the most important guiding principles for leadership:

3. Don’t plan. Orient.

When we plan, and then crisis hits, we tend to respond by fighting hard to preserve the plan. What we should do instead is orient ourselves to our mission.

What I do is: Imagine my organizational mission is a star in the sky. A star I can see no matter where I am. No matter where I find yourself – even if I’ve just being battered our my course by storms – I am not lost. As long as I can see that star, I can set a new course to get there.

As you navigate this pandemic, it may feel like you are lost. Like you are in a storm that just seems to get worse. It may feel comfortable to cling to the illusion of control by clinging to the plan. Often, by clinging to our plans we forget our destination.

When we orient, grounds can shift, but as long as we have clarity in where we’re headed, we can adapt our course to get there. Remember, as long as you see the star, you’re not lost. So don’t plan. Orient.




Let’s go back to this picture. This is day 32 at sea. Look at my smile. A month ago, I had never sailed. About 27 days ago, I had the most frightening day of my life, still to this day. A day after that, our boat ran the risk of being stuck off the current. And in this photo, we are headed to Brazil to make an emergency landing.

And I’m smiling!

Sounds like a hero’s journey, doesn’t it? The purpose, the mountain, the struggle, the triumph, right?

But as leaders, we can’t be fooled. There is never a singular hero in crisis. The words “I” and “hero” never belong in the same sentence.

We got there together, as a team. The mission was more important than anything that divided us.


And there was a lot that divided us. Values, belief systems, work ethic, skills, and don’t get me started on the personalities. Take me and the first mate. All I will say, diplomatically, is: We weren’t ever going to be friends. But after a few weeks in, we didn’t have to be. We developed a system. That worked best when working together.

The first mate probably knew everything there is about sailing, but he lacked the ability to zoom out and see the bigger picture. He was a sailor, not a captain. Also, he had a negative, cynical viewpoint of the world.

I couldn’t match his sailing skills, but I thrived in the big picture, and I could think steps ahead. And my view of the world trends positive.

And we made better decisions – meaning the boat was safer - when we combined forces. Part of that is the team bond that came over time, working together in the trenches, building trust. 


But another key part is that our captain – the leader – chose each of us to be on that boat. He had 20 years of experience sailing around the world. He knew what it would take, and he hired who he thought it would take to accomplish that goal. Not only that, when he realized how inexperienced a sailor I was, he could’ve made my life a living hell. Instead, he gave me the trust, the space, and the direction to grow into my new role – even in stormy seas.

Here's the fourth lesson:

4. Choose your team wisely

You see, the Captain was a leader. And good leaders choose teams wisely. We trust our team members to make the right decisions. That’s why we hired them, right? We delegate responsibilities to the right person. And we hold the space for new members to grow and become a valuable part of the team.

Leaders often ask me: but how can we lead that way now, in a pandemic? When we need to act now?

The truth is: you can't afford not to.

I get this question often. Perhaps too many times. That question comes from a place of anxiety or fear, or the strong desire for control. We need to remove those fear glasses and accept that in a crisis - like that first storm I just told you about, like the pandemic we face right now, we can’t afford not to.

There is no singular hero in crisis. A leader cannot navigate the storm without a strong team. The autopilot option is no longer an option. So it’s critical that leaders delegate and trust that together, they can face the challenges ahead.

There is no better predictor of success than your team. So choose wisely, delegate and trust.



It was a mechanical issue that forced us to make an emergency landing in Brazil. And it was there that I decided not to continue. In 33 days, we had crossed an ocean, and I decided the time was right to retire. 


I oriented to my next adventure – graduate school. I received a master’s degree in conflict resolution. I studied some of the biggest conflicts in our history, and even participated in some of our present conflict. I was sent to talk to officials in Syria just months before the civil war broke out.

And still, I believe that of all the experiences in my life…it is this sailing trip that best prepared me to lead, and to guide others, through the challenges we face in 2020.

Because what I learned there – to accept the reality for what it is, the reject the fear filter, to orient towards instead of steadfastly planning for, to choose my team wisely – meant that even now, as we navigate the pandemic and uncertainty, I can dance to the changing rhythms, lead with a clear mind, and continue to build organizations that thrive on stormy seas.


Thank you.

Joseph Imbriano is the Founder of Omnikai.

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