Sailing Through Life: 7 Lessons from 7 Seas
What I Told a Room Full of Sea Scouts About Life, Sailing, Storms, Crew, Purpose, and the Journey
A recent keynote Speech to Sea Scouts in Texas:
by Grant Headifen,
Global Direction of Education,
NauticEd International Sailing & Boating Education
Recently, I had the opportunity to speak to a group of Sea Scouts here in Texas—young sailors, parents, and leaders. It was a great group, and I remember thinking beforehand that I didn’t want to stand up there and lecture them. I didn’t want to tell them what to do or try to sound like I had everything figured out. What I wanted to give them was something simple—something they could actually carry with them and use.
So I told them this: life is not a road. It’s a voyage. Because once you start thinking about it that way, things simplify. In sailing, you don’t control the wind, you don’t control the weather, and you don’t control the conditions you’re given. What you control is how you respond to those conditions. And over time—through building businesses, failing at a few, sailing all over the world, and just having what I call a bit of “time on planet”—I’ve learned a few things about how to navigate that. I shared seven lessons and titled it: Sailing Through Life: Seven Lessons From Seven Seas.
Life Lessons from Sailing
Grant Headifen, founder of NauticEd, shares seven life lessons from sailing, originally delivered as a keynote to Sea Scouts in Texas.
- How failure can become the start of something new
- Why changing direction is not failure
- How competence builds judgment
- Why storms, fear, crew, and purpose are part of the voyage
1. Build Another Boat
There’s a moment in my life I can trace almost everything back to. I had just failed a restaurant, and I mean completely failed it. I was a mechanical engineer with a master’s degree from UT, and for some reason I thought that qualified me to run a restaurant. It didn’t. I didn’t have the competence, the knowledge, or the experience. What I had was confidence, and it turns out confidence without competence is not enough.
So I lost everything I had put into it. I was broke. The cat was looking at me like, “You gonna feed me or what?” Then I got a notice from the state of Texas: 30 days to pay $5,000 in property taxes or I was going to lose the house. That was the wind I was given. I couldn’t undo the failed restaurant. I couldn’t make the tax notice disappear. I couldn’t magically create money I didn’t have. But I could choose how to respond.
Someone suggested I go to a seminar, so I went, and one idea stuck with me: build something based on what you know and what you’re good at. So I thought about it. I knew technology, and I knew just enough about restaurants to have failed one. This was 1995, when the internet was just starting, so I had an idea: I’m going to build websites for restaurants. One problem: I didn’t know how to program a website, and I couldn’t afford a $10 book. So I went to Barnes & Noble, sat down in the aisle, read the book, took notes, and put it back on the shelf. Then I went home and started figuring it out.
I got in my truck with no air conditioning in the middle of a Texas summer, drove to restaurants, cooled down in their bathrooms just long enough to stop sweating, and then went out and pitched them. I needed to sell 10 websites to make $5,000. I sold 30. So here’s the point: when your boat sinks, and it will at some point, you’ve got a choice. You can sit there and complain about the wind, complain about what happened, complain about the situation, or you can start building another boat. You can’t change the wind, but you can change your response. You can learn. You can move. You can build again. It takes time. It takes effort. It takes scrappiness. But it’s always an option.
Lesson: You can’t control the wind, but if your boat sinks, you can build another boat.
2. Tacking Is Progress
From there, things started working. The restaurant website business grew, we raised money, and from the outside it looked like everything was going exactly the way it should. But I had this realization that surprised me a bit. I didn’t want to do it. It was working—but it wasn’t the direction I wanted my life to go.
So I stopped. I gave the money back, shut it down, and walked away from something that most people would have told me to keep going. That decision ended up putting me on a completely different path. It led me into the sailing world, first building a boat-sharing business that grew into 30 locations across the United States, Canada, and Europe. And then again, I tacked—seeing an opportunity to revitalize boating education, which led to NauticEd.
In sailing, if the wind is coming straight at you, you can’t go directly where you want to go. You don’t get to change the wind. You have to tack. You head off in one direction, then you come back, then off again, slowly working your way forward. From the outside, it looks inefficient. It looks like you’re not making progress. But in reality, it’s the only way to get there.
Life works the same way. You don’t go in straight lines. You change direction. Sometimes the wind forces that change. Sometimes you choose it. But either way, you are still responsible for your direction.
Tacking is not a failure. It’s progress.
And sometimes progress is not about continuing forward on the same path. Sometimes it’s about having the judgment to say, “This may be working, but it’s not taking me where I want to go,” and having the courage to change direction anyway.
Just because you have momentum doesn’t mean you’re headed in the right direction. At some point, you have to take responsibility for that.
Lesson: Don’t confuse momentum with direction. Progress sometimes means choosing a better tack.
3. Running Aground Happens Slowly… Then Suddenly
I’ve run aground three times.
One time I saw a lifejacket floating in the water and thought, “Free lifejacket,” not realizing someone had tied it to a rock to mark shallow water. I went right over to it — bonk!
Another time I was sailing into a beautiful bay in the British Virgin Islands. Boats were lined up on both sides with a nice open path down the middle, and people were waving. I thought, “Wow, friendly place.” They weren’t waving hello. They were waving, “Don’t go there.” Too late — bonk!
Another time, the charts said it was deep. It wasn’t — bonk! And then in Belize, both the chart and the depth meter said we were fine, but there were sticks in the water ahead — locals marking shallow ground. That time, we turned just in time.
Looking back, each grounding taught me something different. The lifejacket was temptation. The BVI was distraction. The chart error was over-reliance on one source. The sticks in Belize were local knowledge and judgment. But in each case, if I had checked the depth meter, checked the chart, looked outside the boat, and used better judgment, I could have avoided the problem — or at least seen it coming sooner.
In life, we run aground the same way. We chase something that looks easy, we stop paying attention, we trust the wrong information, or we ignore signs that someone else has already placed in front of us.
What I’ve learned is this: running aground doesn’t happen all at once. It happens slowly, with all the little mistakes and lack of better judgment, and then suddenly — bonk!
That’s why competence matters. At NauticEd, we define competence as knowledge, skills, and experience — which together build better judgment. Without those, sailing and life become risky.
And here’s the truth: there are two types of sailors — those who have run aground and those who are lying. You will hit bottom at some point. The goal is to learn the lesson, so you minimize how often it happens.
Lesson: Running aground happens slowly, then suddenly.
4. Storms Are Part of the Voyage
Every life has storms. Some are small, and they pass quickly. Others are bigger, and you remember them for a long time. And then there are the ones that don’t really go away at all.
If you’ve spent time on the water, you know how a storm works. Wind builds, energy transfers into the water, and waves grow. But what’s interesting is that even after the wind dies down, the energy doesn’t just disappear. It keeps traveling. You can be hundreds or even thousands of miles away from the original storm, and you’re still feeling its effects in the form of a swell. Life is like that. Some storms end, but the swell remains.
Some of you haven’t experienced your biggest storms yet, and that’s a good thing. You’re early in the voyage. But at some point, you will encounter something that hits hard. Something you didn’t plan for, didn’t want, and wouldn’t have chosen. For me, that storm was what I would call a Level 6 hurricane.
Four years ago, I lost my 13-year-old daughter to brain cancer. And if you’ve ever been through something like that, you know it’s not something that just passes. It doesn’t come and go like a summer storm. It changes the water you’re sailing in. You don’t wake up one day and say, “Okay, I’m past that now.” What you learn instead is how to sail in it. You learn how to move forward when the water isn’t flat, when things feel heavy, and when the conditions are not what you would have chosen. You learn how to sail in the everlasting swells.
Storms are not personal. They happen to everyone. Everyone gets hit by something eventually. So the question is not really, “Why is this happening to me?” That question can keep you stuck. The better question is, “How do I learn to sail in the effects of this one?” I used to say, “Everything always turns out for the best.” I don’t really say that anymore. Some things do not feel like they turn out for the best. Losing Alexandra and children to cancer is simply a loss to humanity and a flaw in the workings of the universe. Some things just happen, and then you have to learn how to live and move forward in the water the storm leaves behind.
That doesn’t mean you ignore it. It doesn’t mean it doesn’t affect you. It means you adapt. You adjust your expectations, your balance, your mindset, and you keep going. One thing the ocean teaches you is that waves are not random chaos. They have rhythm. They have pattern. Once you understand them, they become something you can work with instead of something that just knocks you around. Life is the same way. Even the hardest experiences eventually become something you learn to read, to anticipate, and to navigate.
So don’t expect life to be storm-free. It won’t be. And don’t think something is wrong when a storm shows up. It’s part of the voyage. The goal is not to avoid every storm, because you won’t. The goal is to become the kind of person who can continue the journey while living in, and still sailing through, the effects of the storm.
Lesson: You don’t get over everything. You learn to sail with it.
5. The Boat Heels
I was once sailing with a father and his two daughters, and every time the wind picked up and the boat heeled over, they screamed bloody murder. To them, it felt like the boat was about to tip over and they would die at an early age. It felt out of control. It felt dangerous.
Now, if you’ve sailed before, you know that’s actually when the boat is working properly. The heel is part of the design. It’s supposed to do that. But if you’ve never experienced it, your brain tells you something is wrong. So I told the daughters, “Next time the boat heels, look into my eyes. If you see fear, then scream. But if you see me smiling, then you’re okay. Deal?”
The point is that we were both in the same situation, but we had completely different perspectives. That’s when it really hits you: fear is often not reality. It’s unfamiliarity.
And the way you deal with that is not by avoiding it. It’s by gradually increasing what you’re comfortable with. The first time you sail, the boat heels a little and it feels like a lot. The next time, you let it heel just a bit more. Then a bit more. Over time, what once felt extreme becomes normal.
That’s how your comfort zone expands. It doesn’t happen in one big jump. It happens in small steps, each one stretching you just a little further than the last.
And this applies to everything in life. If you stay in the harbor, nothing ever grows. It’s safe, predictable, and comfortable, but it doesn’t change you. It doesn’t build confidence. It doesn’t build competence.
Growth happens when you put yourself into situations that are just slightly uncomfortable. When you volunteer. When you raise your hand. When you say yes to something you’re not completely sure you’re ready for. Because here’s the truth: most of the time, you’re more capable than you think you are.
And even when you’re not fully ready, there are people around you, your crew, who will help you, catch you, and guide you. You’re not out there alone.
So don’t wait until you feel completely comfortable. That moment never really comes. Ask yourself: is this dangerous, or is it just unfamiliar?
Step into it a little at a time. Let the boat heel a little more each time. And over time, you’ll look back at things that once scared you and realize they don’t anymore.
Lesson: Growth happens just outside your comfort zone—so don’t stay in the harbor. Go. Participate in life.
6. Build Your Crew
You don’t sail alone, and you don’t go through life alone either. But here’s the interesting part: your crew forms in two directions. First, there are the people who choose to be around you because of who you are. They choose your energy, your values, your attitude, your direction. Then there are the people you choose to bring close because of who they are. Over time, those two things become your team.
That means who you become matters. If you want good people around you, you have to become the kind of person good people want to sail with. And if you want to go somewhere meaningful, you also have to be thoughtful about who you bring aboard. Because your crew will shape your direction, your culture, your confidence, and your experience.
On a boat, you’ve got different roles. You’ve got someone navigating, someone trimming sails, someone watching systems, someone managing food, someone at the helm. Everyone has a part to play, and the boat only works when those parts come together. It’s the same in life. No one is good at everything. The goal isn’t to try to be. The goal is to build a crew where strengths complement each other.
At NauticEd, I’ve been incredibly fortunate to build a crew like that. We have people from all over the world, from different backgrounds, different cultures, and different skill sets. Each person brings something I don’t have, something someone else doesn’t have, and together it works. It’s not about one person being the best at everything. It’s about a group of people who care about the mission, who support each other, and who are all moving in the same direction. When I look at what we’ve built, I don’t see a company—I see a crew. And I’m grateful for every single one of them being part of this voyage.
But building your crew also means protecting the crew. I learned that very directly on a sailing trip in Greece. We had several boats, and one person on the trip was creating drama everywhere they went. It was affecting the whole team and the whole energy of the trip. We tried moving them around. We tried making it work. But at some point, it became clear: this person was draining the life out of the experience, and they needed to go. Fast.
So I made the call. I put them in the dinghy, took them ashore, pointed them toward the ferry terminal, gave them the timetable, and said goodbye. It wasn’t about being cruel. It was about being responsible for the rest of the crew. Sometimes leadership means making the uncomfortable decision that protects the whole voyage. And you don’t get to delegate that decision. That’s yours.
And that is true in life too. Not everyone belongs on every leg of your journey. Some people lift the crew. Some people drain it. You need enough judgment to know the difference, and enough courage to act when it matters.
Lesson: Who you become attracts your crew. Who you choose shapes your voyage.
7. The Journey Matters
The destination gives you direction, but the journey gives you meaning. That’s something I’ve learned more and more with time. When you’re young, it’s easy to think life is all about getting somewhere: getting the job, getting the degree, getting the house, getting the boat, getting to the next goal. And goals matter. A destination matters. You need something to steer toward. But if you only focus on arriving, you miss the best parts of the voyage.
I’ve been fortunate to sail in over 30 locations around the world: the Mediterranean, the Caribbean, the Pacific, South Africa, Tahiti, Tonga, Thailand, and plenty of places in between. And what I’ve learned is that the ocean is the same everywhere, but everything else is different. Different cultures, different food, different harbors, different ways of thinking, different ways people solve problems, different ways people live their lives. And every time you experience that, it changes you a little.
The journey is where you meet people you never expected to meet. It’s where you make mistakes you didn’t plan to make. It’s where you find yourself in situations that stretch you, humble you, scare you a little, and then teach you something. That’s where life actually happens. Not just when you arrive, but in everything that happens along the way.
One of my favorite examples of that happened in New Zealand. We were about 20 miles offshore, just moving along, when the captain suddenly pulled the throttle back and jumped straight into the water. I thought, “What are you doing?” “Whale shark,” he yelled. So I grabbed my camera, jumped in, and there I was in the water with a 30-foot whale shark, hanging on and getting pulled along. I didn’t plan that. It wasn’t on the itinerary. But it became one of those moments I’ll remember forever.
That’s the journey. It’s the unexpected moments, the people, the places, the stories, the mistakes, the fears, the storms, the laughter, and the beauty you didn’t see coming. And over time, all of it starts shaping you. You don’t become who you are only by reaching destinations. You become who you are by what happens while you’re trying to get there. And over time, without even realizing it, you become someone stronger, wiser, and more capable than the person who first left the harbor.
That whale shark was not the destination. It was the unexpected gift of the journey. I didn’t leave the harbor looking for that moment. But because I was on the journey, I was there when it appeared.
I know a lot of young people struggle with the question, “Why am I here?” I remember struggling with that question myself. But I’ve come to believe the answer usually does not arrive while you’re sitting still. It appears in pieces as you participate in life. You put your hand up. You volunteer. You start the voyage. You take one purposeful tack, and that leads to another. Each new experience gives you another part of the answer. In fact, there can be a risk in thinking you have the whole answer too early, because then you may stop tacking. You may stop exploring. You may stop letting life reveal the next destination. The real answer to “Why am I here?” is not always one fixed thing you discover once. It is something that unfolds as you live, learn, serve, fail, adjust, and keep moving. If you never leave the harbor, the answer may never appear — or worse, a comfortable but false answer may appear because you never gave life a chance to show you the real one.
So yes, choose a starting destination. Set a course. Head out with purpose. But don’t lock yourself so tightly onto one finish line that you miss the voyage, because the voyage may reveal the next tack, the next destination, and the next part of why you are here.
Lesson: Purpose rarely appears in the harbor. It reveals itself as you sail through life.
Final Thought
So as you sail through life, build another boat, choose your direction, pay attention, endure the storms, question your fear, build your crew, and embrace the journey. Because in the end, you can stay in the harbor… or you can go. And everything you’re looking for, and more, is out there.
About Sea Scouts
Sea Scouts is a co-ed youth program that helps young people build leadership, confidence, responsibility, and maritime skills through hands-on boating experiences. Local Sea Scouts units, called Ships, give youth the opportunity to learn seamanship, service, teamwork, and safe boating while being mentored by experienced adults.
Learn more at: Sea Scouts
If you’re a Sea Scouts Ship and want to sign up for NauticEd’s program, learn more here >
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NauticEd is a fully recognized education and certification platform for sailing students combining online and on-the-water real instruction (and now VR). NauticEd offers +24 online courses, a free sailor's toolkit that includes 2 free courses, and six ranks of certification – all integrated into NauticEd’s proprietary platform. The USCG and NASBLA recognize NauticEd as having met the established American National Standards. Learn more at www.nauticed.org.
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