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Ralphs. Fresh for everyone. Radical Personal Finance is a community-funded project. Listeners directly support the show. If you'd like information or details on how you can get involved in that, and thank you for those of you who do, go to radicalpersonalfinance.com/patron. Picture this. You are sitting on the back deck, or I guess probably it's better to say you're sitting in the cockpit of a beautiful white sailboat in the middle of a protected, secluded anchorage, surrounded by tropical green jungle on all sides, beautiful crystal clear water underneath your hull, white sand beaches, just a short boat ride or swim away.

Is that the lifestyle that you've dreamed of day after day after day? Is that type of lifestyle compatible with working? I just finished a book that says it is. It says that it's entirely compatible. And so today I've prepared for you some thoughts on how we can use some of the financial models of long-term sailing, what's called cruising, as inspiration for our own financial plans.

Welcome to the Radical Personal Finance Podcast. My name is Joshua Sheets, and today is Monday, April 27, 2015. This is episode 184 of the show where we dig into cruising. I've had a few sailors on. They've talked a little bit about it. But today I'm going to give you some ideas from my perspective, not about the lifestyle, but rather about how to actually make the lifestyle happen, whether you want to sail or not.

Cruising and sailing is something I've had a long-time interest in, but never really actually done much of it. I've got interest in all kinds of things. I remember when I was a kid I used to get dozens of books on sailing and dozens of books on flying and all these things from the library, and that usually satiated my curiosity without ever having to go farther than that.

But over the years, this is an interest that's continued on. But it's more of an academic interest. I actually don't really love the idea of boating. I'm intrigued by the idea of learning how to sail, but I've never really pursued it. I enjoy boating every now and then, but it's more like going out for a day or two here and there rather than something I'd want to do long-term.

But I'm fascinated by it from the perspective of lifestyle design because long-term cruising and long-term sailing is something that many people really dream about. All you need to do is just look at the sailing magazines and then go and figure out what percentage of the people who read sailing magazines are actually sailing versus the ones who are wishing to be sailors.

But this is a common thread. I'm not sure why. I think some of it is a bit of escapism. It's nice to think about just being out on your own. It harkens back, I think, to an independent spirit that is hard to achieve in modern culture. After all, as a sailor, especially on a sailboat rather than a powerboat, there's this idea that you can come as you go and go where you like, and you're the captain of your ship.

You're not really accountable to anyone. If you don't want to be somewhere, you just pull up anchor and sail away for free. Now the reality of it may or may not be close to that, but I think there's some of that romantic idea and image to it. But I'm always fascinated by how people actually achieve the lifestyle.

I love talking to cruisers. I think that's what they often are called, probably the right name, or sailors. I like talking to people who go out and live on their sailboats and travel for long periods of time. I've never really had a long-term friendship with someone, but I've always gotten along well – someone who lived that lifestyle, but I've always gotten along well whenever I run into people.

I just love talking to them. Half of them are – the majority of them are just plain weird in the sense that they don't follow society's script for what they should do. I sympathize with that. I empathize with that. I consider myself a bit of a weirdo. So I get along well with weird people who march to the beat of their own drum and kind of set out and say, "I'm going to do something different." Oftentimes, at least the people that I meet hanging around docks here in South Florida and when they come in on their little dinghy off of their sailboat, they're different.

They – obviously. But they're all kinds of different. I've met people from – one time I did a Craigslist transaction. I sold a bicycle to a guy and he reached out to my – reached out to me for the sale of the bicycle. I took it to him. It was kind of unusual.

He asked me if I could deliver it and he asked me if I could deliver it with an air pump. So we renegotiated the price and I tossed in a bicycle pump that I had sitting around. When I met him, I think he was 18 years old and he had bought a sailboat and sailed it down from the northeast of the United States down the intercoastal waterway.

I think he'd gone out in the ocean a little bit, but primarily he'd stuck with the intercoastal. Then he was hanging out in Jupiter, Florida. He had found a little secluded place to anchor and he was planning on getting just some part-time work here to fill up his bank account and get ready to go off and sail around the Caribbean for a few years as an 18-year-old.

He needed the bicycle from me that he bought cheap off of Craigslist to be able to get to his job and back. I thought, man, good for you. I didn't have the guts to do that at 18. Even if I wanted to, I'm not sure I would have had the guts to do that.

But here was a guy who did that. You meet all kinds of couples out cruising together. I met a boy and his father one time that were cruising together. I even had a fascinating experience with an old rich guy on Palm Beach. He was a boat guy. He went by the name of Captain something.

I won't give away his name. But as I started talking to him, I found out that he was living the Palm Beach lifestyle, but he didn't really quite have enough money to fully fit in in Palm Beach. But what he'd worked out is he had a very nice power yacht that he kept anchored right over on Palm Beach.

He had an apartment that he owned right off of Worth Avenue. He invited me out to the boat one time and we sat there and we're having some drinks together sitting up on the deck of his boat, he and his girlfriend and me and my wife. We're sitting there talking with him, hearing all about his story.

But basically, he couldn't really afford to live the Palm Beach lifestyle, but he liked living the Palm Beach lifestyle. So, he lived on his boat during season and he rented out his apartment and he was able to rent out his apartment for enough during season to be able to keep him living the Palm Beach lifestyle and then he would move into his apartment during the summer when the rents in Palm Beach when it's not during season here where the rents are much lower.

And kind of doing this back and forth thing allowed him to continue doing his boating thing and his land thing. And he was kind of just this awesome crusty old guy involved in all these local organizations and all these local community things that he loved to do and he'd figured out a way to finance his life with almost no work just by bringing in the boating lifestyle as an option for him.

And I don't remember how much those anchorages cost, but he was doing exactly the same that some people do – same thing that some people do on a $1,000 a month budget but just with a few more zeros behind, but kind of living the lifestyle. And what's amazing to me is as you start to talk with people, you start to realize that there's not necessarily one path that people take.

Some people are very wealthy and they've built up – I loved in Palm Beach where I live – it's near where I live in West Palm Beach, in downtown West Palm Beach a few years ago, they redid all of the docks here in Florida and they put in these very nice municipal docks.

They redid the whole waterfront and they provided with all these public docks a much better option for sailboats to come in from around the world. So now if you go down pretty much any day down to downtown West Palm Beach and you start walking along the waterfront, you'll see large sailboats from everywhere.

And so I love talking to New Zealanders who have sailed up from New Zealand or Australia. Those are the two flags that I always get my interest. I've never been there and they kind of appeal to me as far as destinations I'd like to travel to. And you just find these people out cruising for a couple of years and they got fancy boats and they're out doing their around the world sail.

And so when you start to meet these people, you start to see that they're very wealthy people is my point in talking about them. Or I remember meeting a guy that I attempted – he wanted to buy a life insurance policy from me one time who was living on – he said all he had was social security disability.

But he was living on a sailboat down in Boynton Beach and we met at a friend's house and he tried to buy a life insurance policy from me and wasn't able to make it go through. But he was just living on – I think it was under $1,000 a month.

And he would basically – when he ran out of money, he'd stop eating for the month and he'd try to pile up a little bit to get down to the Caribbean during the sailing season. And the rest of the year, he'd bring his boat back up here to South Florida and anchor out on the intercoastal.

It's just fascinating to meet people at all different ends of the spectrum. And over the years, I've started to notice though some themes and that's what I want to share with you is just some themes that make this type of lifestyle work for certain people. And I think there are themes that are useful to apply to other areas of life whether or not you – they're obviously useful if you want to go cruising.

If that's one of your dreams, then maybe this will be helpful to you. Or if you just simply want to learn the lessons and like I do, I don't want to go live on a sailboat. But you just want to learn lessons, then in this case, maybe we can learn them.

And as I've looked at it, I've come to the conclusion that there are a few things that really make a big difference that make cruisers be able to live this independent lifestyle. Number one, you own your shelter and the ongoing costs of owning your shelter are significantly diminished. If you think about the concept of a sailboat, especially a sailboat that's not just a day sailor where you're going out on the lake and cruising around for a little bit.

But actually a sailboat that's an ocean-going sailboat that's meant to be lived on. Whether it's large or whether it's small, whether it's basic and Spartan or whether it's luxurious, the purpose of the sailboat is almost a – it's almost as a life pod. It's a living system that's designed to meet your needs and to get you from one place to another.

It has a roof over your head. There will be a bed of some sort that you can sleep in, a place of some kind for you to sit. Maybe there will be a sail to get you from one place to another and a place to store some food and a way to provide or collect some water.

And that's basically it. But because you own your shelter, you have a place to go back to every night. Now, sailboats or boats in general can be very expensive types of shelter or they cannot be. They certainly require maintenance. You're going to be scrubbing the barnacles off the bottom.

You're going to be fixing the equipment because a lot of the equipment because of the nature of the housing is very important for keeping you alive in difficult times. But the point is you own your shelter. Now, think about this. If you're trying to build a financial plan for yourself, if you take out the concept of what you pay for your shelter and you can switch all of the things that we consume from shelter, rent that you pay, mortgage payments that you pay, taxes and insurance that you pay, if you take all those consumption items and you drop them out and say, "I own these," so they're not an ongoing cost, how much of your budget does that take out?

For most of us, that's a very large amount of our budget. But there's another advantage to owning your shelter, especially that type of shelter. Because of the constraints of your shelter, you largely stop consuming except for your own personal living needs and some relatively small or at least usable consumption items.

If you're living in a sailboat, there's not nearly as much space as there is living in a stick frame construction house or a block concrete construction house, whatever your scenario is. Because of that, you're limited on all of the things that you can have. There's no garage or a place for you to park your car.

Now, you need a dinghy to get you back and forth to the dock. You might be able to have a bicycle, but you're not going to have four of them. There's no place to park the quad or to hook up the RV or whatever it is. You might have some toys.

You might have a surfboard. You might have a kayak that you use to get around. But most of the toys are limited based upon the amount of space that you have. Because of those forced constraints on consumption, that drops off a lot of the amount of money that needs to be spent.

Now, obviously, there are plenty of options for personal consumption. There are plenty of beverages that can be purchased at a beachfront bar. There's plenty of food that can be bought, and it's often not inexpensive. There are plenty of tours and points of entertainment and recreation that can be participated in.

But cost to cost, as far as living on land versus living on the water, you're probably going to be forced to minimize your consumption. That's going to be the case whether you're on an 80-foot sailboat or on a 40-foot sailboat, which leads me to another thing that happens. It seems to me most of the sailors that I talk to and at least the ones that I read about, the need to impress other people is substantially diminished.

It often seems like cruisers already feel like a part of a club because they have taken the risk of shoving off from the dock and tossing the lines and going and setting sail. That puts them into a different type of person, and it's kind of an independent spirit. And once you're out of the normal everyday mainstream trappings of society, then the need to impress other people diminishes.

Now, obviously, you can still admire another guy's boat or still admire another guy's fancy gear, but a lot of the things that we do in life, a lot of the ways that we live are about impressing other people. And as long as you've got a bathing suit or two, it doesn't matter much what the brand name is.

And as long as you've got a dinghy to get you from the boat to the shore, although you might admire someone else's super fancy one, it's not quite the same way we run so many other things in life. That drops a lot of cost out. And then if you look at the ongoing costs, you would largely eliminate and reduce transportation costs.

There's a lot of costs that fall out. Now, there are also a lot of costs that come in. Maintaining boats is not necessarily inexpensive, and so you've got to plan for that. But it's an interesting mental experiment to look at it and say, "Could I recreate that lifestyle?" Once you own your shelter and once you have some of your basic needs of a roof over your head covered, a lot of your need for money is at least reduced if not eliminated.

So your primary need for money is just simply to fund some ongoing needs, some basic food, some basic entertainment, keeping your boat in working condition. So how do you do that? Well, there are obviously a couple of different ways to do that. One of them is you could save a bunch of money and then live off of the income from that money, investment income from the money.

Or you might have other sources of income, a retirement fund, a settlement fund, a disability payment, something like that that you could live off of. Or you can always work. And the cruising lifestyle is not necessarily antagonistic toward the idea of working. But it's a different style of working.

And that's where the inspiration for today's show comes from. I recently read a book called Financial Freedom Afloat and picked it up at the library. I like reading these types of finance books. And it's a fairly detailed, exhaustive outline of ways that cruisers or sailors can live while they're cruising and earn money.

I'm not going to go through all of the different specific ideas. That would be a good book for you to pick up if you want to get some practical tips if you're interested in actually pursuing this lifestyle. Rather, I'm just going to look at the front end, the back end, and what the authors are actually proposing through it.

And if we pick that up, you might find that you could apply this to your own financial plan and find something that works for you whether or not you want to go cruising. If you set out the lifestyle of cruising as a retirement plan, which is what many people do with their financial plans, they set out this lifestyle and say, "I have to accumulate all this money and then I can go live the life of my dreams." It's doable by some people.

But it's much harder for everyone to achieve that. But if you set out the lifestyle of cruising and you plan to work while you go, then it's much more doable. And that's the major thesis of this entire book. The author makes the point that you probably don't want to just sail around for the rest of your life.

There's a great comic in the book that illustrates his point. It's a man and his wife that are sitting in the cockpit of their boat. At the beginning, they're sitting near a shore with the sunshine over, with a drink in their hand, just hanging out and talking. And in the next picture, it's the same.

There are a total of six frames on the comic. And the only thing that changes from one to the next is they get fatter and fatter and fatter. And eventually, at the sixth frame, the smile is gone and they're just sitting there staring at each other. He talks a lot about that as far as the cruising lifestyle.

If you're just out there, we're just going to go sail, you get bored, fat, and drunk constantly. That's his version of the cruising lifestyle. So into that, he inserts this. He talks about some of the reasons for working and some of the reasons it gives you things to do.

And it gives you a way to A, fund your trip so you can leave earlier. And he also gives you some more engagement with life. It's not just sitting around and sitting in the cockpit of your boat under the sun every day drinking and reading a book. But listen to some of these other reasons for working and think if these might not be applicable to your life now.

There are many reasons other than the quandaries faced by these three couples that he just profiled why someone would want to work while cruising. Some people may be looking for a new or second career. Others might want to explore some skill or talent they just don't seem to have time for lately.

In our competitive, success-oriented society, there is often too much emphasis on visible results and not enough time to pursue nonproductive occupations. One can't simply leave a job as, let's say, a bank manager, take a few years off to play the saxophone, then expect to come back to any sort of career.

Not to mention the financial drain incurred from trying to support a traditional lifestyle ashore without the income of a "real job." However, if one has decided to live a cruising lifestyle, many concerns are lifted. With even a small, regular income, the money that you need to generate from your "new" career is minimal.

The sailing life simply does not require the same kind of overhead as a traditional modern existence. Also, concerns of maintaining a career path, a respectable resume, or keeping up with the Joneses all vanish. This can be a profound freedom for one accustomed to the rigors of the modern workplace.

Our friend Bob had been trained as a dentist and worked in that career for 10 unsatisfying years. It was not until he went sailing and started exploring his talents, however, that he found that what he really enjoyed was repairing sails. While his family and friends back in New York were aghast that he would throw away his expensive education, the sailing community was happy to have a new artisan.

He found that with a low stress workload, he was able to support himself comfortably and the adventurous, nomadic life that he loved. There are also people who may have budgeted enough money for a cruise of a certain duration, but find that the restraints of always sticking to a rigid budget limit their enjoyment.

Having some source of extra income while you're sailing can often mean the difference between just existing and really living. Often it is that extra little bit that allows you to take advantage of cultural offerings, local restaurants, or entertainment that you would have otherwise gone without. When we recently spent the winter in Lisbon, I was luckily able to keep a small income coming in by teaching English to local businessmen.

It allowed Maggie and I to take advantage of concerts, restaurants, and classes that made the winter much more enjoyable. It would have been a different story had we spent months cooped up in the winter rain, unable to spend money on anything but the essentials. We have met many people on a round-the-world sail who have missed what were probably once-in-a-lifetime opportunities because of the necessity of sticking to a fixed budget.

Finally, there's no better way of learning or using a language than having to make a living using it. There are many would-be cruisers who study a language before leaving, often Spanish or French, only to find that through laziness or just normal inhibition, they hardly ever use it. Getting out and working with a language quickly overcomes these barriers.

Our friend Russell was a diesel mechanic by trade and hardly a language scholar when he arrived in Guatemala. He saw, however, the opportunity to make serious money working on the sport fishing fleet of the local Spanish-speaking businessmen, so he quickly boned up on the language. Never one for learning out of books, he acquired most of his knowledge from his assistant, who spoke no English.

Soon he was speaking like a local and enjoying his contacts with the new culture immensely. In fact, within a few years he had successfully wooed, courted, and married a beautiful Spanish-speaking woman from one of the local families. While many people we've met have fallen into their new careers, there are many others onshore who are just not interested in stepping off the cliff without knowing what waits at the bottom.

Certainly, having some idea in advance of what might realistically be expected from the sailing job market would lift a lot of anxiety from people's minds. That, in essence, is what we aim to do with this book. If you think about the ideas and the concepts there, you recognize a little bit of the quiet desperation that so many of us live under, the sense of feeling like we're stuck.

If you start searching around, you often find that the fear that most people have is, "How do I transition? How do I transition not from working to not working, although that has its own questions, but how do I transition from something that I feel stuck at to something different that I want to pursue, that I want to try?" I'm convinced that the biggest challenge of this transition is the mental transition.

To be able to mentally cast off what we've been taught to always be thinking about our resume, to always be thinking about enhancing our employability, and be willing to try something different. I continually find myself confronted and challenged by this and never like to do something different just for the sake of trying to be different.

But on the other hand, I continually challenge myself to say, "Follow your own idea. Create what you want to have created." That's the guiding line of radical personal finance. Sometimes it works great. Sometimes it doesn't. But at the end of the day, I'm proud of what I've created because I'm creating what I wish existed.

It's kind of a unique feeling to do that. Now, it doesn't have to be done in the form of a media. That's just where I experience it because I spend a lot of my time thinking about it, working on it, etc., etc. But it's kind of fun to venture out into a little bit of adventure, into something where the waters are not quite so well charted, where you've got to figure it out as you go.

I'm convinced that we need to be thinking about this more and more because the world, especially the world of the job market, is changing quickly. Some of us, it's changed more quickly than for others. But the rate of change is increasing. As we continue to experience the application of the electronic revolution, Moore's law, and things, computing power consistently gets cheaper and better and faster and cheaper and better and faster.

Many of our jobs are changing. I think it's important that we focus on building the skills and the mindset to be able to lead the change instead of sit back and wonder what happened. What's interesting is the perfect parallel between that in general in life and the cruising lifestyle.

If you look at the cruising lifestyle, what do you need? Well, you need a boat. It's probably best if you own the boat debt-free because that brings in more flexibility. Now, if you want to live on a boat, go live on a boat. If you don't want to live on a boat, you need something similar, some way of providing for a bit of your overhead, providing some shelter over your head.

It could be as simple as a tent for some of you more rugged individuals, and it could be more mainstream like it is for me, relatively mainstream middle-class house. It's up to you what your boat looks like. Some people are happy with a 30-foot – I'm not a sailor, so I don't know all the right nautical terms.

Some people are happy with a 30-foot boat and some people need a 90-foot boat. That's up to you. A lot faster and easier to get on the water if you're happy with a 30-foot boat I would imagine than if you need to figure out how to find the 90-foot version.

But for some people, that's the lifestyle they want is the 90-foot version. I'm not prepared myself to go out and live in a tent in the Florida wilderness and take my family out there. If I need to, I would, but that's not going to be my plan A. You also need some skills, and it's good if these skills are varied.

The author of Financial Freedom of Float goes through a checklist and talks about what are the skills that you have making an inventory of them. Now, specifically, he profiles a bunch of skills that are specific to sailing occupations. I'll read them to you. But as you think about this, consider what skills do you have.

He has these listed in categories. Working with your hands, skills such as sewing, cooking, carpentry, electrical, mechanical, painting, home maintenance, craft work, artistic areas of skill, painting or drawing, decorating, music, professional skills, medical, computer, accounting or financial, teaching, sales, writing, restaurant work, and language skills. Now, that's a very simplified version of the skills, but what's interesting is if you actually look at that, I can look at many of those and recognize that I have a basic level of skill here, maybe a more competent level of skill there, maybe an expert level of skill in certain things.

And then you could start bringing those things together and crafting new potential ways of earning income. One of the keys that he stresses is the need for flexibility, and there are multiple aspects to flexibility. One way of flexibility is that if you need less money, then you have more flexibility.

For example, if you are continually working as you travel, instead of waiting until you run out of money, but rather just continually going instead of waiting until you have to get a job, then you have the option. You're flexible and you can pick and choose the employment options that you have.

It's a good point when applied to the sailing lifestyle, but don't you look around and see that oftentimes? The people that we need to help the most are oftentimes the people who don't seem to be able to ever generate any flexibility in their lives. Flexibility is key. That's why I encourage save money that's not in a retirement account.

Build up money that allows you to transition from job to job, place to place, career to career. There's also a willingness to be flexible with new opportunities and new ways of earning an income. One of the biggest benefits of this book – and this show is kind of a half book review and half kind of just using it as inspiration for some other ideas.

But one of the biggest benefits of this book is he lays out the career path, which is largely accidental. He uses three couples that he and his wife knew well over their years of sailing, and he shows they're almost accidental paths from what they thought was going to happen to something that ultimately wound up working well.

And there can be fortuitous circumstances that lead you from one thing to the next if you're willing to be flexible. In sailing, I think one of the unique things about sailing as a metaphor is that to be a good sailor from my outside observation, I think you need a willingness just to take life as it comes and not try to control everything.

Winds change. Storms happen. And you're not at the control of those things. Sometimes you're going to sit and wait and wait and wait for the winds to change. Then the winds are going to change. You're going to head out, and they're going to change back, and you got to go back and sit and wait.

Sometimes the winds change in your favor, and you need to draw a banker and leave in an hour because you're dependent on the winds. That's often how life is. But I'm guilty of usually trying to make life happen instead of just allowing life to happen. There's probably a happy middle ground, a sense of being direct and trying to control certain things, but then a sense of being willing to go with things and experience the adventure.

And if you're blown off course, enjoy the sail, and then try to get back on course if you can. When going through the inventories of skills, you find different things that can be put together. And one of the biggest benefits that I see from his book is the idea of not being so focused on one specific career, but rather being flexible.

Now, partly as inspiration, let me just read you from the table of contents here of the different types of trades and jobs that he outlines in this book. And he outlines them very carefully with details on advantages and disadvantages of each of these trades. And if you want to go sailing, maybe this will be useful to you.

If you don't want to go sailing, think about this in your own context. So he starts with a category called boat work. The idea is you can work on other boats. If you're living on a boat and you're in a boating community, there's work that needs to be done on boats and other boaters can pay you money.

That's the basic essence of any economy. So marine sewing, marine carpentry and fiberglass work, marine mechanical, electrical and air conditioning or refrigeration work, marine mechanic, marine electrician, marine air conditioning and refrigeration. If you have an ability with one of those basic things, let's say that you work as an air conditioning in the air conditioning trade on land and you want to go sailing, shouldn't be that tough for you to learn the skills that you need to apply that to your new sailing career.

A lot of us have parallels. There's something that we're very good at in our current life and that we really enjoy in our current life. And then if we look to what the ideal lifestyle is that we'd like to do, maybe there's an option there. His next category is behind the scenes in the charter and delivery industry.

So the idea here is just some people want to come in and sail boats on a short-term basis. What could you do? So you can work for a bare boat charter company. Working as a skipper is an option, a captain for hire. Working as a mechanic or maintenance person or housekeeping or work in an office for a charter company.

Working for a private charter boat or private yacht has options as a captain or cook or maid or engineer, advantages and disadvantages of that. But the point of this is there are marine-connected occupations that can be transitioned into. So is there a marine-connected occupation for you that you have interest in that you would like to transition into?

His next category is talking about the concept of just doing casual work on shore. So basically bringing your boat into a harbor and finding an anchorage and then getting a job at the restaurant or doing some kind of construction work, maybe managing a resort, these types of temporary contracts where you're just working part-time.

This is a strategy that could be pursued for just about anybody's travel lifestyle or for any retirement lifestyle. Work for a time, travel for a time. Work for a time, travel for a time. He moves on into some of the professional occupations, academic teaching, casual teaching, teaching English as a foreign language.

That's a time-honored tradition of a way to travel. Just go where you want to travel and teach English. Working as a medical doctor or a nurse or working in other aspects of healthcare. Every place in the world has a need for healthcare. So if you have certain skills that could translate over, it could be useful.

He goes into a section of entrepreneurship, of people making crafts on board and selling them or working in the yacht brokerage business or freelance writing or communications options, working with computer work. Now, what's interesting about this job is it was written in 2000. This book was written in 2000.

It's amazing to look back over the last 15 years and see how many more options have opened up than what this author profiled in the year 2000. Then he goes on and talks about other work opportunities, doing volunteer work or other entrepreneurship opportunities. So I'm not going to go through all of those details.

That's specific to you if you have an interest in sailing. My point today is just simply to challenge you to say, "Is there a job that you could transition to that would give you a greater degree of lifestyle freedom to do the things that are important to you?" Some of you might transition from job A into job B because that job B better fits your lifestyle.

There might be somebody else who transitions exactly from job B to job A. I'm reminded of in my mind the job of teaching school. I've worked with a number of teachers as clients and I have a number of teachers in my family and friends. I have some friends and family who are looking to get out of teaching into another occupation because the characteristics of the teaching profession are not suitable to what they want to do.

They can't make enough money to meet their lifestyle needs. But then I know other people. I had a client of mine who was an amazing guy and he – specifically in the middle of his life, he decided to close his business. He had a fairly successful business. He went back and finished some of the professional education that he needed to be admitted into the school system and went back and took on the job of a teacher because it perfectly fit what he wanted to do as a lifestyle.

He loved to impact the lives of young people and he wanted to travel. And so he and his wife were planning to both of them teach for a period of time in the US and then once their kids were grown and out of the house, they were going to start teaching abroad.

Same job, two different people. Every job is like that. Every career has options around it that are interesting that can be pursued. Money is not necessarily the deciding factor. If you ever find yourself looking at money and saying, "I can't do this because of the finance," I'm not saying every one of those things can be solved without money.

They can't. I'm a realist with that. But usually it can be solved with a smaller amount of money than many people seem to think. If you sit down and make the list, make the shopping list, figure out what it is, you might need to work a little longer doing one thing to have a specific plan to transition from A to B.

But it's probably not millions of dollars. It's probably a few thousand or a few tens of thousands. And remember, you can often make up in skill what you lack in money. I enjoyed reading some of the stories in the sailing book about people that are completely broke, young people, two young lovers that get together and decide they want to go sailing, buy some piece of junk boat for cheap, live on this boat in primitive conditions and go on and build up and fix the boat up and get things going.

They're completely broke, but they got a working boat. And they went on and took simply the skills that they learned from fixing the boat up for themselves and applied it and were able to start earning money on the water. And were able to build their life from the beginning with almost no money other than a few thousand dollars to buy this piece of junk boat and then a little bit of money from part-time work to fix it up and buy the needed materials to get it seaworthy.

They were able to get started, though, and not wait forever to achieve certain things. That's the basic account of what I wanted to share with you from the concept of sailing. But I want to wrap up with reading two excerpts here from the end of the book. I thought these were very well-written excerpts.

I love hearing themes in different parts of society that most people don't hear and don't see. And I thought this was a well-needed reminder, this first section here, where it says, "Don't expect one job to do it all." It's from page 185 of the book. "Time and again, we have seen that diversity is the key to financial freedom for sailors who have successfully married work and cruising.

In all probability, it will be several talents, not just one, that allow you to support your cruising lifestyle. A portfolio of skills and a wide range of experience will give you the best chances of securing work wherever you go. As a cruiser, however, you do have several things working in your favor when it comes to exploring different alternatives.

First, you should have the time, space, and freedom to look at yourself and decide what you want. Buying a boat and setting sail may have its drawbacks. It may at times be uncomfortable, even dangerous. It may be cold, wet, and miserable, and more hard work than you envisioned. But one thing you will gain when you step off the land is the space and freedom of the sea.

This freedom is both mental as well as physical. Night watches and time spent alone are invaluable assets for someone who wants to learn more about himself or herself. Anyone who uses this time creatively will find that it can provide the opportunity for significant personal growth. Second, as a member of the sailing community, you have a tremendous amount of psychological liberty to indulge your interests.

There simply is not a career mentality among sailors. This is what John and Paula found in their very first jobs in Northern California. The lack of societal or peer pressure was a liberating and refreshing change. The sailing community, by its very nature, freely accepts eccentrics, free thinkers, and square pegs.

Third, and perhaps most important, as you cruise, you will learn very quickly that you, and you alone, have control over and responsibility for your actions and their consequences. Few lifestyles will give you such control. As a nomadic, cruising sailor, you control everything from how you make electricity to what laws you live under.

You determine your own budget, whether it be lavish, miserly, or in between. You decide which boat and gear are best for you. Should you go high-tech or low-tech? Should you put comfort or cost as your top priority? Where will you cruise? How long will you stay? And what will you do in your new location?

The very nature of a modern shoreside life, with its technological interconnectedness and necessary dependence on the "system," tends to deprive people of many of these options. Although as a cruising sailor you will still be dependent on technology and modern infrastructure, you may have many more options to choose as to when, where, and how much you make use of it.

These three things—the freedom and space to examine your desires, the lack of expectations or pressures from your peers, and the power and responsibility to take control of your life— give you, the cruising sailor, the opportunity to construct the best possible synthesis of earning money, helping others, and having a good time.

So don't limit yourself to just one or two options. Be creative and explore. Use those long night watches and lazy tropical days to daydream and ponder, to come up with not just one or two but many ways to enjoy your freedom. I would argue that's specifically applicable to sailors and cruisers, but it doesn't have to be limited to that.

You can build time and freedom to think into your life no matter where you are or what circumstances you're in. You can look for freedom and space and you can take the responsibility back over your own life and chart out a course that's appropriate for you. So don't limit yourself to one or two options.

Be creative and explore. And you'll build the type of resilience that I believe is going to be more and more necessary in the future for all of us to have. And in closing, I'll read the last section here from a section entitled "Real Security in Life." Finally, let me address a point some people have raised in the past with my wife and myself.

"Okay," they've said, "there may be a lot of possibilities for supporting myself while cruising. But you say yourself there's no one magic solution and things are always changing in a cruising life. I've got a steady job now. Maybe it's not the greatest, but it's a job. I'd like to go cruising, but I don't want to give up the security of this stable life until I've salted away enough to live on.

If I went sailing, how would I deal with the constant insecurity of not knowing how I would support myself from one year to the next? It all sounds like a prescription for ulcers to me." Let's take a look at some of the fallacies inherent in these assumptions. The first assumption is that a steady, shoreside job or career provides you with security.

This may have been true years ago when people could be reasonably sure of a lifetime job with one company, although I question if trading your most productive years for a pension and a gold watch was ever really that good of a deal. Nowadays, however, I don't think that even the most naive employee is under any illusion about a company's loyalty to its workers.

The wave of downsizing, outsourcing, and laying off of employees, perhaps to rehire them as independent contractors that has occurred during the last 15 years, has shown the transient nature of the modern workplace. The second fallacy is that because you have a stable life, you can predict what will happen next year or the year after.

The ability to extrapolate the future from the past is a convenience that people have evolved to allow themselves an illusion of security. In truth, we don't know what the future will bring. You may be hit by a car tomorrow. A loved one may die, or your house may burn down.

There's no telling what changes might occur in your life next week or next month, let alone next year. In fact, the only things you can be certain of about next year are that you will have aged a year and that you won't be able to get it back. Finally, where does this assumption that a sailing life is inherently less secure than a stable shoreside one come from?

If one looks at real security, that is, having control over what will happen to you in the short and medium-term future, there are few lifestyles more secure than that of a self-sufficient cruising sailor. The key word here is "self-sufficient." For a sailor to have real security, he or she must be self-sufficient in three ways.

He must be a competent seaman, able to navigate his boat safely wherever he sails. He must be able to maintain the boat in seaworthy condition at all times. And he must be financially self-sufficient, able to support his lifestyle anywhere. Hopefully, with the aid of this book, you will be able to find ways to achieve this last.

As you do, you will find, like Paula did in Panama, that soon you will have confidence in yourself and your ability to support yourself anywhere, anytime. This is real security. If you are reading this book, obviously you are interested in a long-term cruising life. If so, ask yourself this, "Is it just money and security issues that are tying you to your present life?" If you could be guaranteed financial security, would you opt to try cruising?

If the answer is yes, consider this. Over the years, my wife and I have met literally hundreds of cruising sailors in dozens of countries around the world who were managing to support their lifestyle as they went along. Although their methods and solutions were as diverse as those seen throughout this book, there was one common thread.

Everyone, once they evolved their own personal approach, was surprised at not only how easy but how enjoyable it was to combine working and cruising. Many times, what had begun as a break from shoreside life ended up as a whole new and unexpected lifestyle. It's amazing to me that the author does a good job of laying out within one specific lifestyle the themes that I believe are applicable to all of us, no matter the lifestyle.

As I said in the beginning, I don't particularly aspire to go and be a long-term cruiser. That seems to me, for me, in my enjoyment and the types of things I like to do and my situation in life, it seems quite boring. But to some people, they love it.

If you love it, check the book out and read it and see if there's some ideas in there. But if you don't love the idea, still put yourself there mentally and say, "If I were going to approach that lifestyle, how could I do it? How could I use the themes and lessons from that lifestyle and apply them to my own lifestyle?" That ability to look at another lifestyle and try to put yourself there and then come back or however you do that, you can do it with world views.

That's how I often do it. You can do it with lifestyles. That's how I often do it. I find coaching and helping clients has always been the most useful thing to me because I'm personally entrenched in my own lifestyle. I don't see a lot of my own personal problems and biases.

But then when I'm helping a client, I see the options. So put yourself in that other lifestyle and you'll be able to coach yourself to the lessons that you need for your own situation, whatever that is. Hope it's been useful to you. I was going to do a show today on the importance of keeping a job and how to plan for that for the long term as far as how to plan for the job and how to build it.

I think that's something we need to cover. But I decided to do something different. So I hope you enjoyed that. Look at the sailors. Talk to the sailors that you meet. Ask them how they do it. If you're living in, I don't know, Minnesota or Kansas or Colorado or something, if you don't have a lot of sailors around you, go online and talk to the sailors.

The amazing thing that we have in the year 2015 versus the year 2000 when that book was written is we have the ability to talk directly with people no matter where they are in the world and chart out your own plan. So I hope it's useful to you. I wish you a lovely week.

That's it for today's show. If this has been useful to you. If you have any desire to support the show financially, I would be thrilled for you to go to RadicalPersonalFinance.com/patron and sign up for that. Let me give you an update while we're here on how we're doing. We're primarily focusing right now on our goal of if by June 1, which is the goal of bringing on up to about $6,000 a month of support from the Patreon campaign.

That way I can keep the show ad-free. At the moment, we have a total of 163 patrons and $1,625.50 per month of monthly support. So at the moment, I'm starting to look for advertisers. I'd love to keep the show free of advertisers, but at the moment, I'm starting to look for advertisers.

If you would like to keep the show ad-free and help support me in the work that I'm doing, I would be thrilled for your support. You can sign up at RadicalPersonalFinance.com/patron. If not, I just thank you for listening. The best thanks that I get is when you just simply say an idea that I've shared with you has been helpful and you go out and apply it.

To me, that's one of the biggest things. Obviously, I have my own financial motivations, which are one component of why I do this show, but it's not only financial motivations. I'll deal with that on that side. But my favorite form of compensation is actually just hearing that you've taken the ideas and the concepts and applied them to your life.

I wish you success and we'll talk with you tomorrow. Thank you for listening to today's show. If you'd like to contact me personally, my email address is Joshua@RadicalPersonalFinance.com. You can also connect with the show on Twitter @RadicalPF and at Facebook.com/RadicalPersonalFinance. This show is intended to provide entertainment, education, and financial enlightenment.

But your situation is unique and I cannot deliver any actionable advice without knowing anything about you. Please, develop a team of professional advisors who you find to be caring, competent, and trustworthy, and consult them because they are the ones who can understand your specific needs, your specific goals, and provide specific answers to your questions.

I've done my absolute best to be clear and accurate in today's show, but I'm one person and I make mistakes. If you spot a mistake in something I've said, please help me by coming to the show page and commenting so we can all learn together. Until tomorrow, thanks for being here.

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