Looking for Something More
The main topic of what I want to talk about is why I sail and why I started One World Sailing Academy. To really understand that, I need to go back many years, to when I first started sailing.
I was in my early twenties at the time. I had spent my teenage years and early twenties partying and having fun—skateboards, motorcycles, racing, chasing girls, and all that kind of stuff. Back then, I worked construction, and I found working with my hands and learning the trades very rewarding.
Although I was having a lot of fun with some of the more shallow endeavors of my youth, I was also getting older and starting to mature. I had reached a point where I was looking for something more substantial to do with my life. I guess I was looking for a higher purpose than what I had been doing up to that point.
I had always been interested in working with my hands and learning how things worked. Even as a kid, I rebuilt bicycles, and later I built little hot rods and did a lot of mechanical work. I went to school and became a structural mechanic and built airplanes in the aerospace industry. I also worked in building construction. I worked on framing crews and plumbing crews, both residential and commercial. I did masonry construction and pipeline construction, operated heavy equipment, worked as a painting contractor, did drywall, and worked for a plastering company. I did interior and exterior plaster and stucco the old traditional way, and I worked as a hod carrier.
There were a lot of different trades that interested me, and I was always interested in learning something new. I always needed new challenges throughout my life. Working with my hands, learning how to build things, fix things, and developing new skills was something I found very rewarding.
In the process of learning all these different skills, most of the reward came in the beginning. It was almost like a self-taught apprenticeship. I would start out knowing nothing, gain some knowledge, practice, and then get better and better at something until eventually I became a journeyman at whatever it was I was trying to do. There was a lot of satisfaction in that process.
The secondary reward was the income you could make doing these jobs. Once I became skilled at a particular profession or trade, the next goal naturally became trying to make as much money as possible doing it. Oddly enough, the money-making part was rewarding at first, but over time it began to feel shallow, similar in a way to some of my youthful endeavors—partying, chasing girls, and that kind of thing.
The financial part of what I was doing just wasn’t as satisfying as the process of learning had been. Working with my hands and learning the trades still meant something to me, but simply making more money from those skills wasn’t enough. I was looking for something new.
At the same time, I was applying for credit cards, buying material things, and chasing what I perceived society was forcing us to do. I fell into that trap—the idea that you’re supposed to make a bunch of money, you’re supposed to have a bunch of tangible things, and at some point you’re supposed to buy a house, get married, have kids, live the American dream, and then eventually retire and die.
That was what society seemed to be forcing us to do. But my inner voice was telling me something different. I enjoyed working with my hands. I enjoyed learning new things and becoming good at them. What I didn’t enjoy nearly as much was chasing money, although I wasn’t terrible at it.
So I was kind of cruising along, just going through the motions of day-to-day life—working your eight hours a day and trying to earn as much money as possible. As I learned different skills and became good at whatever trade I was in, I got less and less reward from accomplishing those skills, and eventually less and less satisfaction from the financial rewards as well.
The feeling of buying a new car, a Jet Ski, a motorcycle, or a boat wore off pretty quickly. Whatever excitement came with acquiring something new didn’t last very long. So after a while, I just felt somewhat empty, you might say.
Discovering Sailing
Then, purely by accident, I was introduced to sailing. A friend told me I should go down to the marina because a friend of his had a little sailing school. He had some small boats and taught basic sailing, so I went down there to check it out.
At the time, I really didn’t have any money, but the guy didn’t seem to care. He basically said, “Yeah, jump on this boat and go with these guys,” and he didn’t charge me anything. It was really nice of him. I think I was about 25 at the time.
Anyway, I went sailing and thought, wow, this is really fun. It was challenging, there was a lot to learn, and I was out on the ocean. Suddenly, I had this rewarding feeling again that had been absent from my life for a long time. It sparked something in me, and I wanted to learn more.
I did that for a while, but these were just very small boats, and I only went out a few times. Then I got sidetracked with work and life, and the next thing you know, I had a baby—a daughter I was going to be responsible for. Sailing just kind of got pushed off to the side.
I needed to focus, grow up, be a man, and be responsible for this child. So I worked very, very hard. I made money, I was a good father, I supported my daughter, and I did what I was supposed to do.
At the same time, not really knowing any better, I went back to pursuing financial success and material possessions. I went back to buying things in an effort to feel accomplished or rewarded, because at that point, that was still what I thought success was supposed to look like.
The Challenge That Pulled Me Back
Then one day, I ran across a sailboat for sale on a trailer in a neighborhood, and I bought it. The problem was, I didn’t really know how to sail. I had tooled around a little bit on smaller sailboats at this guy’s sailing club in San Pedro, but I didn’t really know what I was doing.
So I bought this boat and went out and tried to teach myself how to sail. I struggled, I had problems, and slowly I started figuring out the mechanics of it all—how to raise the mast, how to set the sails, what the different lines did, and how everything worked. I could figure that stuff out. But I still didn’t really know how to sail.
So the challenge was set. All of a sudden, I had this thing in front of me that I knew almost nothing about. And, by the way, it also scared me. I wasn’t comfortable with the ocean at the time. The ocean was a scary place to me. You could die out there. There was a lot I needed to learn.
So now I had this huge challenge in front of me, along with this deep fear of the ocean, and for some reason I was just pulled toward it. I was pulled toward sailing and toward this potentially dangerous thing that I knew absolutely nothing about but really wanted to discover.
Being a father to my little girl was incredibly rewarding—that part of my life was fantastic. But on a deeper, more personal level, there was still something missing. I still felt slightly empty, and sailing was beginning to fill a part of that emptiness.
From there, I took some sailing classes, started racing, and met a lot of people in the sailing community. I sailed a lot. I started going on bigger adventures, sailing out to Catalina Island, and gradually I became more and more comfortable with the ocean.
At some point, I even sailed to Hawaii with a couple of people. Looking back, it wasn’t necessarily the safest situation because the people I went with weren’t particularly good sailors. But I learned a lot from the experience, and I just kept going with sailing.
Learning to Take Care of My Own Boats
Over time, I kept buying bigger boats, and with bigger boats came another challenge: I needed to learn about boat systems and how all that stuff worked. In the beginning, I hired people to do some of the work, and they failed miserably at accomplishing what I needed done. I realized pretty quickly that if I was ever going to get ahead of this learning curve and really understand my own boats, I was going to have to learn how to do everything myself.
So then I basically taught myself another trade. The thing about working on boats is that there are so many different aspects to it. It’s really multiple trades all rolled into one. There’s plumbing, electrical work, rigging, sailmaking, paint and varnish, installing and refurbishing hardware, and using just about every power tool imaginable—which was something I already had a lot of experience with.
It’s an extremely multifaceted and challenging thing. You’re not only learning how to sail; you’re learning how to maintain, repair, and upgrade a vessel and understand all of the different systems that make it work.
At the time, I was still feeling somewhat empty, and sailing was just a really rewarding hobby. But almost accidentally, that hobby started turning into a career. I got hired to deliver a boat 1,400 miles to Puerto Vallarta, which was my first paying gig. During that trip, I remember realizing, wow, this is kind of cool. You can actually get paid to take boats from one place to another.
So I went and got my captain’s license.
Going
“ALL IN”
Sailing can be an extremely expensive hobby. I mean, you have to purchase a boat, maintain it, pay slip rent, insure it, and then, if you’re hiring people to work on it, you have the labor costs on top of everything else. The parts are extremely expensive. There’s really no aspect of sailing that’s inexpensive. It’s a very expensive thing to do.
There’s a saying: “Sailing is the most expensive way to travel for free.”
I was able to save a lot of money over the years by doing almost all of the work myself. But even with that ability, sailing has still basically taken every dime I’ve earned for decades.
But the flip side of sailing taking basically every dime I’ve earned for decades is what it has given me in return. It has provided me with this incredible level of fulfillment—rewarding experiences, memories, a sense of adventure and accomplishment, confidence, and really an entirely different lifestyle. And honestly, that was what I had been looking for all along.
I had always felt somewhat empty following what society said I was supposed to be doing. And let me tell you, living on a sailboat, traveling around on a sailboat, and learning all the skills required to do that is pretty much the definition of an alternative lifestyle compared to what most of society does, especially in this country.
Then there’s this incredible connection to history and exploration. You think about all the sailors who came before you, the places they traveled, and the stories you read about what they experienced. Then you go out there yourself and experience some of those same oceans and places. There’s just something incredibly rewarding about that.
Eventually, my career changed completely. I went from working in all kinds of construction and different trades to basically doing anything and everything that had to do with boats. I became a licensed captain. I became a sailing instructor. I became a marine mechanic. I became a yacht broker. I basically switched my entire life and went “ALL IN” on the marine industry.
Making a Living on the Water
Interestingly enough, though, some of those feelings of emptiness eventually returned within the marine industry itself. At the same time, there were also some incredibly rewarding experiences.
Running a whale-watching boat was a good example. Part of my job was to seek out and find whales, dolphins, sea lions, and other sea life. I got to mingle with these creatures and take people out on the ocean and show them this amazing sea life that exists right here in our geographic area. That part of the job was incredibly rewarding. Honestly, there has never been a time when I’ve seen a whale and didn’t enjoy it. I have always enjoyed seeing whales, dolphins, sea lions, and sea life in general. It’s fantastic.
The negative side was that I was doing it commercially. I was the captain of a 149-passenger vessel, and occasionally I would take a break and look around at the passengers. I would notice that quite a few of them were down below, sitting at a table with their heads down, not even paying attention to the ocean or enjoying the sea life at all. Others seemed like they were mainly there to drink. They could have cared less about the whales.
That was difficult for me to understand. Here we were, surrounded by something I found absolutely incredible, and some people weren’t even interested in looking at it.
On the flip side of that coin, there were also many people who were just awestruck and completely amazed by the sea life we were seeing. They were coming from their everyday lives in American society—working, going to school, raising families, and doing all the things that we do. Then, for a couple of hours, they got to leave all of that behind, go out on the ocean, and see some of the most amazing creatures there are to see. Some of them were just completely blown away by the experience.
I found that incredibly rewarding. Seeing people have that kind of positive experience on the whale-watching boat meant a lot to me. I started to realize that part of what made the work meaningful wasn’t just being out on the ocean myself. It was sharing that experience with people who genuinely appreciated it.
Running My Own Sailing Tour Company
Another captain’s job I had was running my own sailing tour company. We operated a 40-foot high-performance catamaran with daggerboards, kick-up rudders, and a rotating mast. We did sunset sails and snorkeling trips.
That was very rewarding because I was on a boat, I was on the ocean, and I was doing what I loved. For the most part, people really enjoyed the trips. Of course, on almost every trip there might be a few people who got seasick, got sprayed with ocean water, or ended up cold and miserable. But generally speaking, people had a great time.
It was also a big responsibility and a very expensive business to operate, especially in a place where the season was only about 100 days a year. But I had fun while I did it, and overall, it was a really rewarding experience.
Running Shore Boats
Another job I did during that period was running a shore boat. Both of these businesses were on Catalina Island. The sailing tour business was based in Avalon, and the shore boats operated around Avalon Harbor, Descanso Beach, and Hamilton Cove.
Basically, a shore boat picks people up from their boats—whether they’re on a mooring or anchored offshore—and takes them to shore. Maybe they don’t want to use their dinghy, or for whatever reason they just want a ride. You pick them up, take them ashore, and later, whenever they’re ready, you take them back out to their boat.
That job wasn’t particularly rewarding. It paid the bills, but for the most part, I was picking up people who were either too lazy to take their own dinghies in or who wanted to go ashore and drink and didn’t want to drive their dinghies back to their boats afterward. And let me tell you, a lot of them were drunk. On the return trips, I would say more than half were completely inebriated.
I did get to develop some basic prop-and-rudder boat-handling skills, which was kind of fun to add to my library of skills. But other than that, it wasn’t particularly rewarding.
Teaching Sailing
Another thing I did was teach sailing. I became an American Sailing Association instructor, and a lot of what I taught was basic sailing—first-time-ever-on-a-boat kind of stuff. I taught basic keelboat sailing, then more advanced keelboat sailing, and eventually bareboat chartering classes.
The bareboat chartering class, ASA 104, was my favorite class to teach. We would take a group of people over to Catalina Island, and it was really their first introduction to cruising. You’re making your first small passage, about 30 miles, and you’re anchoring or picking up a mooring, exploring different places, using the dinghy, and going ashore. It gives people their first real taste of what cruising is actually like.
That was my favorite class because I found the teaching side of it very rewarding. Financially, though, it was probably the worst-paying job I ever had.
I never forgot how rewarding teaching sailing was, though.
Driving the Catalina Ferries
I also spent many years driving passenger-carrying ferry boats back and forth from the mainland to Catalina Island. I worked for two different companies and drove multiple different vessels over the years.
That job was basically being a glorified bus driver. The rewarding part was that I got a paycheck, I was on the ocean every day, and I was taking people to this beautiful island where they were going to have a good time.
The negative side was that I wasn’t really having a whole lot of fun myself. I was challenged on a regular basis with mechanical breakdowns, and I had to be the guy who saved the day pretty much every day. The hours were long, and overall, it just wasn’t very much fun.
Trying the Private-Yacht World
I even tried my hand as a private yacht captain. At the time, I got hired to drive the biggest boat in Marina del Rey, which was a 120-foot Palmer Johnson. There have been many larger boats since then, but at the time, it was the largest boat in the marina.
That was a uniformed job on a boat valued at over ten million dollars, working for very wealthy people who turned out to have criminal backgrounds. I was the captain and the engineer, so there were some mechanical challenges, and figuring those out was rewarding.
But driving a fancy yacht around in a uniform for wealthy criminals wasn’t something I found rewarding at all. So after a short period of time, I quit.
People thought I was crazy because it was a good-paying job, but I could see that I was not going to enjoy it.
Becoming a Marine Mechanic
Alongside all of these different boat-driving jobs, I also kind of became a marine mechanic without ever really planning on it. I’m a diesel mechanic, and I’ve become very knowledgeable about vessel systems. I work on batteries and charging systems, complete lithium battery systems, diesel engine service and repair, generator service and repair, all forms of plumbing, and basically just about everything on a boat.
There are certain trades that I stay away from professionally, even though I know how to do them and have done them on my own boats. Rigging is a good example. I’ve re-rigged my own boat, and I’ve rigged plenty of other boats over the years, but today I leave that work to the riggers because it’s not something I want to do full time. The same goes for painting and varnish. I’ve done plenty of it on my own boats, but I don’t want to do it for a living. I’ve cleaned the bottom of my own boat, too, but I definitely don’t want to clean other people’s boat bottoms for a living.
So there are a lot of things I know how to do, and having all of those different skills is great.
As I became a marine mechanic, I eventually built a boat maintenance, repair, and upgrade company. Over the years, I worked on thousands and thousands of boats—just about every kind of boat you can imagine, sail and power, different sizes, different systems, everything imaginable.
In the beginning, probably 20 years ago or so, that work was incredibly rewarding because every day I was faced with a new problem. And back then, almost every problem was new to me. It was a real challenge to figure out what was wrong, understand why it was happening, solve the problem, repair the boat, and get everything working again.
Then you get to explain to the owner what was wrong and what you did to fix it. You were kind of the hero of the day. And let me tell you, it’s a great feeling being the hero of the day. You’ve solved a problem, you’ve helped somebody understand their boat, you’ve gotten them back up and running, and then you got paid for doing it.
In the beginning, that was very rewarding.
When the Challenge Disappeared
Unfortunately, after decades of doing this and fixing so many problems, my phone rings now and, oddly enough, it’s the third time, the fifth time, the hundredth time, or maybe the five-hundredth time I’ve had to solve the exact same problem. At some point, the reward from that starts to disappear.
It’s like, okay, great, I get paid to go fix something, but I already know what’s wrong. I already know how to diagnose it, and I already know how to fix it. There’s just not much challenge left in that anymore.
As I’ve gotten older, the challenge has become the incredible physical demands of working on boats. It’s not necessarily the heavy lifting. It’s fitting yourself into the hardest-to-reach places imaginable, crawling around in engine rooms, working in spaces where you can never stand up straight, bumping your head over and over and over again, and constantly getting cuts and scratches.
Over the years, I’ve torn the meniscus in my knee, herniated two discs in my neck, gotten stitches multiple times, and so far I’ve had three staph infections. There is a lot of injury, pain, and suffering that goes into working on boats, especially when you’ve been doing it for decades.
Once the challenge wore off—and at this point it has completely worn off—the reward went with it. Now it’s mostly just the boring repetition of fixing the same old things over and over again. So the work has really lost its appeal for me.
I’m 61 years old now, and physically I’m nowhere near as capable as I was when I was 40. When I was 40, I was unstoppable working on boats. I could crawl into just about anywhere, work all day, and keep going. At 61, that’s just not the reality anymore. I need help at every turn.
Fortunately, I have my sons helping me. They’re incredibly valuable, especially when I’m working in tight spaces. They can hand me tools when I’m wedged into some impossible spot, or if the space is simply too tight for me, they can crawl in there and I can hand the tools to them. So we’re still able to get the work done.
But the whole time, I know the work itself isn’t rewarding to me anymore. The challenge that originally drew me into it is gone.
And that realization is really part of what led us to start One World Sailing Academy.
The Cruising Life Changed My Perspective
Over the last five years or so—maybe even a little longer, although we had a pandemic mixed in there—we’ve gotten into a lifestyle where we spend about half the year sailing and cruising and the other half working. Of course, we have to work to afford the lifestyle. Boating is very expensive, especially when you’re trying to maintain and keep up a vessel.
During all those years of sailing and cruising, we’ve met many, many people along the way. And one thing I’ve noticed is that, for the most part, the people we’ve met out there cruising are pretty self-sufficient.
Many of the people we’ve met out there, or at least the ones I’ve developed friendships with, are people who can work on their own boats. They understand what they want, they understand what needs to be done, and when something breaks, they figure out how to fix it.
Those tend to be the people I relate to the most because they’re a lot like me. That doesn’t mean they won’t accept help—absolutely they will, and so will I. If somebody has a solution to a problem that I can’t figure out, I’ll gladly take the help.
But these are people who enjoy the satisfaction and get a real sense of reward from being self-sufficient. They want to understand their boats and be capable of taking care of themselves.
And that’s something I truly love.
Finding the Most Rewarding Part
So as I think about what I’m going to do as I get older, I keep coming back to a question that I need to ask myself: What’s the most rewarding thing?
I already know it’s not money.
Over the years, I’ve had many people express deep gratitude after I helped them solve a problem, understand their boat, or get out of a difficult situation. Being the hero of the day has always felt good.
But where I think I’ve shined the most, and what I’ve found the most rewarding, is helping people learn the skills they need to embark on their own sailing journeys.
I love getting somebody to the point where they don’t need me anymore, knowing they can always call. I’ve given them what I know, they’ve learned the skills, and now they can move forward on their own. They can figure things out for themselves and continue learning through their own experiences.
There’s nothing more rewarding to me than that, with the addition of cruising, discovery, sailing, and exploring the world under sail.
Why I Started One World Sailing Academy
So, yeah, that’s really why I started One World Sailing Academy.
My focus remains on teaching and sharing knowledge. But money is required, at least to a point, to take care of the vessel and keep doing what we do. I’ve bought new sails, new rigging, new batteries, and done all kinds of work to this boat. It seems like I spend $20,000 or $30,000 a year just keeping her up and continuing to improve things.
There’s a big financial demand that comes with operating a vessel and keeping it in good, safe condition. So I need to make enough money to properly maintain the boat, but I also need to balance that with living a life that I find rewarding.
For me, that means teaching people how to cruise successfully so that one day they can take care of their own vessel and build solid seamanship skills.
And in my opinion, the people best suited to become sailors are mechanics.
I don’t necessarily mean professional mechanics, either. I mean people who think like mechanics: people who want to understand how things work, who can solve problems, who are willing to get their hands dirty, and who want to become self-sufficient.
That’s really the philosophy behind One World Sailing Academy. The number one priority is to teach people how to successfully cruise a boat on their own and give them the confidence, knowledge, and tools to do it.
I can even help them find the right boat. As a yacht broker, I can help someone through that process, and if I do my job correctly and they purchase a boat, I can earn a commission from the sale, which is generally paid by the seller.
But that’s secondary.
The primary goal of One World Sailing Academy is to teach all the cruising skills required for someone to embark on their own sailing adventure, and at the same time make enough money to support the endeavor itself. We need to take care of the vessel. We need to make enough money to live and survive and continue doing what we’re doing.
I don’t care about being rich. I don’t care about packing a boat with as many people as possible just to maximize profit. My primary goal is to share the knowledge I’ve accumulated over all these years and help people accomplish their own goals.
If I can eventually get somebody to the point where they don’t need my help anymore, then I’ve accomplished what I set out to do.
Another Kind of Self-Sufficiency
There’s one other thought I have about sailing, especially in today’s world. You look at the geopolitical environment, the potential for wars to escalate and other countries to become involved, and all the doom and gloom that’s out there. I don’t spend my life worrying about those things, but I do think about them occasionally.
And sailing isn’t a horrible way to be prepared for a negative future, if there ever was one.
What I mean by that is, if you’re “ALL IN” on a sailboat like I am, you have a certain amount of freedom and mobility that most people don’t have. If war or some other conflict ever reached the area where you lived, could you potentially leave and sail somewhere safer? Of course you could. That’s something I think about occasionally.
I also think about weather and how extreme weather may affect sailing and cruising in the future. I don’t know how much worse it’s going to get, but from my own experience, I’ve certainly seen changes during my lifetime. That’s one of the reasons I sail conservatively. I try to sail in the appropriate season for wherever I’m going, and then even within that season, I still wait for the right weather window.
If the world ever truly fell apart, I’d probably wish I didn’t have a diesel engine and a diesel generator. I’d probably want an electric motor and a boat that could operate entirely on alternative energy. But that’s a whole different conversation.
Anyway, those are some of the other reasons I stick with sailing. There’s something reassuring about the self-sufficiency of it. A sailboat gives you the ability to move if you need to and isolate yourself if you need to. We can make fresh water from salt water. We can catch fish. We can generate our own power. And if we ever really needed to, we could survive for extended periods of time on the ocean.
Hopefully we never need sailing for those reasons. But I like knowing that we could.
“ALL IN”
I don’t know. I was just thinking about all of this today, and I thought I would write it down. Maybe someday I’ll do a video about it or talk about it in an interview.
But I think the simplest way to explain it is that I’m “ALL IN” on this sailing and cruising lifestyle.
I want to live it. I want to teach it. And I want it to be the way I make my living.
I don’t care if I get rich doing it. I just want to continue doing this for the remainder of my life, or at least until I’m physically no longer able to do it anymore.
I also want to share this lifestyle with my teenage boys. I want them to understand that there are alternatives to what society tells us we’re supposed to be doing in Western civilization. You don’t necessarily have to follow the same path everybody else follows. There are other ways to live your life, and there are other ways to measure whether that life has been successful.
Anyway, that’s kind of it.
If you feel like there’s something missing in your life, go learn something that challenges you. Go sailing. Go hiking. Get out into nature. Find something that scares you a little bit, something you don’t already know how to do, and learn how to do it.
For me, that thing was sailing.
And it still is.