10 Life Lessons In 10 Years of Sailing
This past March marked 10 years since I started in the sailing and yachting industry. Realizing that made me take a quick trip down memory lane, which quickly turned into a deeper reflection on all the lessons this alternative lifestyle has taught me.
Sailing will always be a part of my life. I’ve tried to pull away from it twice and both times it slowly pulled me back in. I know for me, it’s here to stay, I just think I’ve worked out some of the kinks over the years and I’ve figured out what works for me and how to make the most of it. I’d like to share that with you.
I think any reader will quickly realize there’s an unintentional theme to this post, and it shouldn’t take long to figure out what it is.
1. Who You Go With Matters More Than Where You Go
For the longest time, my mind was fixated on sailing to distant places. First it was a circumnavigation, then it narrowed into the South Pacific. For years, every move I made in life was to get me closer to that goal. It consumed me. It drove me. It was my “why.”
I could probably write 10 blog posts about my trips to the South Pacific and it still wouldn’t be enough. But I’ll say this:
I had the highest of highs and the lowest of lows.
And what it taught me, over and over again, was that where you go does not matter nearly as much as who you go with.
At some point, if you sail long enough, where you are starts to matter a little less. The activities you do in these places are nearly the same. The conversations start to sound familiar, the rhythm repeats, and you realize… this could almost be anywhere.
And maybe that’s the point where it starts being less about the place, and starts being more about who you’re sharing it with, and what you’re actually doing out there.
2. In Order To Be Good At Anything, You Need To Suck At It First
In the context of becoming really good at something, learning new things, changing careers, and overcoming fears, this is something that sailing absolutely taught me.
This lesson comes from the fact that when I started my first job working on a yacht I felt like I knew so little about boats, but I was determined to remain curious, ask questions, read books, watch videos, etc. Within a few years I felt like I was in the upper tier of knowledge when it came to boaters. And although I’m the first to admit that I’ll always have a lot more to learn, I am proud of how far I’ve made it and it has taught me that in order to be really good at anything, you need to suck at it first. And it helps if you do it with a smile on your face!
3. Happiness And Experiences Are Best When Shared
What’s one of the first things we do after something meaningful happens? We tell someone. A partner. A parent. A friend. Why?
Because we need a witness to our lives. We want someone to see what we saw, to feel some version of what we felt. An accomplice to our adventures, our triumphs, and our failures.
Sharing something with other people can also completely magnify an experience. Imagine you’re sailing alone and come across a pod of whales breaching, birds diving, dolphins weaving through it all. It’s incredible. Unforgettable.
But it’s quiet.
Now picture that same moment with someone else, or a group. The energy changes instantly. You’re turning to each other saying, “Did you just see that?” “That was insane.” There’s excitement, laughter, disbelief. The moment isn’t just happening, it’s being elevated by the people around you and you get to talk about it and relive it together, long after it has happened. To me, that makes it more meaningful.
Being around other people also reflects us back to ourselves. Through them, we gain a lot of understanding about who we are, what we value, what matters, and what’s worth remembering. Without that reflection, even great experiences can start to feel empty.
And maybe just as importantly, being around others helps the baggage we carry around with us feel a little bit lighter. The weight of life, stress, a difficult situation, and uncertainty all feel a lot easier to manage when it’s shared. Not because the problems disappear, but because we’re not holding on to them alone. When my boat Raindancer was struck by a whale and sank in the middle of the Pacific Ocean, somehow within the first hour of being in our liferaft 1300 miles from land, the 4 of us were laughing hysterically. Maybe laughing was our coping mechanism, but I’m pretty sure I wouldn’t have been laughing if I was alone!
4. The Most Important Things In Life Are Not What You Have, But Who You Have
This is something I feel like I’ve always believed, but sailing has reinforced it over and over again. I’ve seen people on some of the nicest boats in the world who are completely unhappy. Divorced, disconnected, just kind of going through the motions. I’ve worked for yacht owners who seem to want nothing more than to be a part of the crew and fit in. And it all makes you realize pretty quickly that having more doesn’t fix anything underneath the surface.
I’ve had my own low moments out there too, and I’ve caught myself realizing that this would not feel any different on my “dream boat”. Not even a little bit. In fact, it may feel worse!
The best moments I’ve had on the water have had absolutely nothing to do with the boat itself. It’s never been about how big it is, how new it is, or how nice it is. It’s always been about who I was with.
The moment that this fully resonated for me was when my dad passed away. Him and my mom had just started their own sailing chapter. He was mostly retired, and they bought a catamaran and were making their way down to the Caribbean. They made it as far as the Dominican Republic, and while they were sitting in a marina, he had a heart attack and passed away within moments.
I remember just feeling completely helpless. Your brain is searching for some loophole to bring him back, some reassurance that you will see him again and that this could not be real, but unfortunately, there was nothing anyone could do.
It didn’t matter if you were a billionaire or a janitor, if you owned a megayacht or a kayak, it didn’t matter how many resources were available, nothing in the world could bring him back. That kind of moment wakes you up and resets your life and your priorities.
5. Being In The Right Mindset Is Everything
I had to think hard on if I even wanted to share this one, but here goes. I will never forget being anchored off a remote Fijian island in the Yasawa Group, in one of the most beautiful, stunning places I’ve ever laid eyes on, and being so miserable that, well, I don’t even want to say. I was going through a change in my life that had hit me harder than I’d like to admit publicly. There was not another soul anchored in that bay or on that island. It was myself and thankfully one of my best friends who was doing his best to restrain me from throwing myself overboard to the shark feeding frenzy that was happening underneath the boat. Wow, it’s so amazing that I can LOL about that now. But, in that moment it was impossible for me to recognize the beauty in anything. That made me feel even more guilty. How much of a prick am I that I can’t even enjoy a place that looks like it could be the screensaver on gods laptop?
Those dark moments in Fiji revealed so much about my life, the decisions I had made, who I was, and what was truly important to me. I saw these beautiful places through a totally different lens. It made me realize that no amount of raw nature was going to help me. I needed to be around people and community, and I needed time.
I left Fiji, got my head right, and I went back to the boat 6 months later when I was feeling great about myself. I had the most wonderful time. The Fijian people are some of the most hospitable and simple people you will ever encounter. And this time, with a clear head, I was able to see what a special place it is.
Ironically enough, those tough times in Fiji are some of the times I’m most grateful for, because they taught me the most.
6. Take Care of Your Neighbor
The sailing community is by far the best community I’ve ever been part of. When Raindancer sank, people went out of their way to rescue us, feed us, clothe us, and support us. It brought everyone closer. And it goes both ways.
I once saw an unattended catamaran dragging anchor toward a beautiful Hylas 70. I raced over in my dinghy and placed my inflatable bow on the side of the catamaran and gave the engine full throttle. That was able to push it out of the way just enough to avoid collision by a few inches. Within minutes there were 3 other dinghies there and we all boarded the drifting catamaran and re-anchored it safely. All while its owners were ashore pounding margaritas.
Last week I borrowed a pair of dog nail clippers from a boat that was leaving the anchorage the next morning. It was 9pm, pouring rain, and I realized I had not yet returned them. I put on my fowl weather gear, hopped in the dinghy and went over to return them. When I got there the owner asked if I had used the large or small pair of clippers for my dog, I told her that I used the large pair. She told me to keep them because they only use the small pair for their dog. But wait, it gets better. On my dinghy ride back to my boat I noticed a group of people on a catamaran yelling and waving their arms in the air like they were in distress. I turned in their direction and slowed down as I approached their boat. Then I heard, “Hey man, we were just wondering if you wanted to come have a drink with us”. I had never seen these people in my life.
I’ve lost count of how many times I’ve seen people step in to help complete strangers and I think it’s something that should be carried out to all aspects of life.
7. Be Five Steps Ahead Before Something Happens
For those that don’t know my boat Raindancer was struck by a large whale while crossing the Pacific Ocean to French Polynesia and it sank in less than 20 minutes.
Ever since then I’ve received lots of praise for being a competent captain and for “thinking quickly”. But that’s honestly all a bunch of BS. There are many things I did wrong but generally speaking there were two things I did right.
- I had the right emergency gear on board, and I knew how to use it.
- I had previously played out what I would do in my head in these scenarios over and over again. Including briefing the crew before passages. And even then it was still organized chaos during the abandon ship.
This brings me to something I’ve been doing for a long, long time. During offshore passages, throughout the day and especially before going to bed off watch, I imagine emergency scenarios like collision, man overboard, fires, dismasting, etc. and I play out in my head what my first move would be, then my second move, and so on. Getting these mental reps I’ve found is crucial because when disaster strikes you are ready for it and you have a plan. Your reaction time is much faster not because you are a quick thinker, but because you are a forward thinker.
I find this particularly applicable before going to bed offshore. I always make sure that I go to bed knowing that I can reach over and grab my headlamp, then I can put of my pfd, then I can take the next steps to address whatever situation might be occurring.
This type of forward thinking I’ve found can also be very useful in our careers, relationships, and day to day life.
8. True Character Is Revealed in Tough Times
In April of 2016 we were departing Belize City for Newport, Rhode Island. We had a delivery crew fly in who I’d met before and I knew to be a good sailor but he was fresh off of being on land for 6 months and didn’t have his sea legs.
While passing the western tip of Cuba and getting into the Gulf Stream the seas were big and very confused. He got extremely sea sick for nearly 48 hours. He could not keep anything down and would spend his watches dry heaving. But he was tough. Not once did he let anyone take his watch, not once did he complain.
Another friend of mine joined us on the notoriously rough passage from New Zealand to The Kingdom Of Tonga. She had never sailed before but wanted some experience and wanted to get back to Tonga where she had previously worked as a humpback whale guide. The last 3 days of that passage were tough upwind miles. The forward part of the boat was basically underwater for days which revealed lots of leaks and her entire cabin, bed, and closet area had become soaked. But again, she was tough. She never complained, always showed up to watch happy, and was always willing to help with whatever needed to be done.
It’s not as sexy as a story to tell, but I’ve seen the opposite happen to people, and not just on passages. At some point on a boat things will get uncomfortable, you’ll probably be sleep deprived, you’ll have been in close quarters with the same people for too long, and that’s when your character, patience, and self control will be tested. That is when you are likely to learn the most about yourself.
9. You Can Probably Figure It Out On Your Own
I don’t think its necessarily healthy to have the mentality of “I can do this on my own”. I think most great things happen because good people help us, give us opportunities, and push us along the way. But if the confidence of doing and figuring things out on your own is something that you struggle with, then learning to sail, repair, and maintain a boat is a great way to get into that mentality of being able to learn any skill you want to.
One of the biggest lessons sailing teaches is self-reliance. Things break. Plans change. Weather shifts. And most of the time, there’s no one coming to fix it for you. You often have no other choice other than to figure it out on your own. And once you realize that you can figure most things out the same way, you begin to build confidence that carries into every other part of life.
10. The Slower You Go, The More You See
If you’ve ever been snorkeling you’ve probably swam right over coral while just observing what you see from the surface. Maybe its a unique shape or color that your appreciating. But if you take the time to stop, dive down and put your eyes just a foot away from the coral you will see things from a completely different perspective. You’ll see small fish living in parts of the coral, iridescent colors, anemones, and a miniature neighborhood of activity.
Here is another example. Do you notice your surroundings more when you are walking or on a bicycle? How about when you’re on a bicycle vs in a car? Or in a car vs an airplane? I think you get the picture.
Sailing slows everything down so that you are able to fully take in everything around you. You notice things you wouldn’t notice on a quick vacation, you may reflect on things you normally wouldn’t, you’ll interact with locals in a way that doesn’t make you feel like a tourist but instead a peer. You feel the changes. You experience the transition from one place to another instead of skipping over it. The slower you go, the more you see.
Final Thought
Paired with the right person or the right people, sailing is still one of the best lives you can live. And, if you happen to get a taste of how good that life can be, then hold on because it may just capture you.
These days, my relationship with sailing feels a bit like a volcano. It might not be erupting right now, but it’s still very much active, and at any moment, it could come back to life.
In summary, I truly believe that life isn’t about the places you go. It’s about the people you share it with, the challenges you go through, and the meaning you create along the way.
The ocean just has a way of making that impossible to ignore.
