//
My sense of self-worth used to be tied to my job performance and I found I’d get frustrated and anxious if things weren’t going according to plan (even if it was beyond my control). I learned a lot about what really matters to me out there and I think I’m a more confident, balanced person because of that.
Ten years ago I quit my job, sold all my possessions, and decided to buy a sailboat (without yet knowing how to sail). It was the hardest decision I’ve ever made and it took me almost a year before I built up enough courage to take the leap.
I was looking for a grand adventure that would challenge me and stretch my comfort zone. While I had Chile in the sights of my mind’s eye, I wasn’t sure if I’d be able to make it. I didn’t let on to many people before or during the trip, but there were times along the way where I came really close to giving up. And there were times along the way when I was truly scared. It’s those experiences that have helped me grow the most.
You are in charge of your life. You can’t let the opinions or fears of others dictate your happiness.
What this “guide” isn’t meant to do is assuage the fear of venturing into the unknown. Nor is it intended to give you a step-by-step guide to sidestepping the hardest part, which is taking the first step of the voyage.
Consider it a journey of the imagination that gives rise to the actual journey. Perhaps it inspires you to delve a bit deeper into your own dreams of living a simpler, less frenetic life. It should also be noted that this guide was originally written for people like me at the time: educated, twenty-something, a few years out of college, building a career, making good money, etc. Not everyone is privileged enough to fit this mold, but I think anyone can take actions to make their dreams their reality.
Most folks have this notion that sailing is a wildly expensive activity reserved for elites and millionaires. Some people certainly spend fortunes on huge boats and electronic gadgets, but the Rascal and my way of life were pretty reasonable.
Unfortunately, a lot of people are complete dumb-asses when it comes to managing money. My parents were fairly frugal as I was growing up and they helped me to understand and control my spending. This doesn’t seem to be the norm in the US (or in capitalistic societies in general), so I’ll try to impart some of the mindset that allowed me to live off of savings for a couple years.
Over the course of my travels, I’ve met and talked with people that live on a couple of dollars a day and are totally satisfied with their lives. Their needs are met.
It is this perspective that can set you free.
If you’re constantly comparing yourself to pop culture icons and professional athletes, your hunger and consumption will be insatiable. This is what media and marketing twist your brain into thinking is the
“right path”. However, if you compare yourself with a Chinese farmer or a Chilean fisherman, you’re suddenly living a life of tremendous excess.
A good place to start is to take a hard look at where your money goes. How much do you spend a month at coffee shops? What do you spend every year on gas for your car? Do these financial expenditures bring you proportional amounts of happiness? Fulfillment? Add all these figures up and make pie charts and really wrap your head around where all of your money goes. A couple of dollars a day add up to substantial amounts of money over the course of a year. There are plenty of apps to help you with this.
Once you have a good understanding of where your money goes, start making decisions on where you can spend less. Maybe you’ll move into a smaller apartment. Maybe you’ll sell a bunch of the clothes you bought on a whim. Maybe you’ll trade your car in for an older one or start riding a bike to work. Cut out all of the expenses that don’t enrich your life!
These are the parts that won’t be fun or easy, but they’re also the parts that will enable you to live your dream in the end. Find a balance between austerity and happiness and don’t lose sight of the light at the end of the tunnel.
Make sure you have a legit parachute before you jump out of the plane. Quitting your job with just the vague notion that you’re going to “travel the world!” or “ride a bike through India!” would be a bit rash. Conduct some serious research, develop a budget, come up with a timeline, and know what you’re getting yourself into.
Read books, send emails, and learn as much as you can about your new life. People are always eager to share their experiences, so reach out to folks that have done something similar. You need to understand the nuances of what your new life will be like, especially the realities and difficulties you will surely encounter.
The next step is cracking open a spreadsheet to figure out the financial realities of your dream. What will your living expenses look like? Will you have any residual income from investments? How much does food cost in Tibet? How many kilometers can your motorcycle go on a liter of fuel? How much will health insurance cost? Will you have a monthly cell phone bill? What is rent on a beach cabana in Costa Rica?
Chances are your new life is going to be totally different (financially) from your old life, so there will definitely be some guesstimating and back-of-the-napkin calculations. Do your best, but be realistic and base your budget on research. Based on all of these costs, figure out either how much you need to save, or how long you’ll be able to unplug. Plan to have some cushion money stashed away for your return back into the world of work in case it takes a while to get a job again.
Once you know roughly how long you’ll be gone, give yourself some milestones—things you want to accomplish and a date to accomplish them by. My initial milestones involved buying a boat and learning to sail. Eventually they evolved to sailing to the Sea of Cortez before hurricane season and arriving in Chile before winter set in. I found it was really important to stay motivated and focused, because it is really easy to just veg and relax once you’re not working every day.
If at all possible, try to get a real taste of the life you’re contemplating. Take some vacation time to crew on a cruising sailboat. Spend a few weeks hiking the Pacific Coast Trail (PCT). Make sure you truly enjoy what you’re planning to do, as opposed to just the idea of it.
What you’re doing isn’t “normal”. Everyone around you probably thinks you’re going to keep busting your ass until age 65. Your boss, your friends, and your family are all making plans based on this assumption. When you break the news, you’ve got to do it gently. Hope they’re supportive, but don’t hinge your determination on their support.
The research you’ve done, the plan you’ve developed, and your realistic budget should help to persuade your friends and family that you haven’t totally lost your marbles. If they love you and care about your happiness, they’ll support you and help you succeed. Just remember: You are in charge of your life. You can’t let the opinions or fears of others dictate your happiness.
As far as the job goes: It took me a long time to build up the courage to actually hand in my resignation. It was scary and the finality of it is resounding. I figured the best route would be working hard before departing and being open and honest with my boss. This has the benefit of making for a less awkward conversation when you resign and also leaving a good taste in your employers’ mouth if you wind up needing a job again in a year or two.
After you quit, there is no going back. I was lucky enough to have a few friends as role models, and they gave me the confidence and support I needed to go for it.
My sense of self-worth used to be tied to my job performance and I found I’d get frustrated and anxious if things weren’t going according to plan (even if it was beyond my control). I learned a lot about what really matters to me out there and I think I’m a more confident, balanced person because of that.
If you’ve managed to make enough money to quit working for a while, you’re probably going to be leaving some money on the table (impending raises / bonuses / etc) when you go, which obviously makes it even harder. Take a step back, however, and think of all the experiences you’re not having as you continue to amass your savings. You can’t put a price on your time – especially when you’re in your prime.
Everyone is thinking (or has thought) about doing something like this and when they see you doing it, a little piece of them rejoices and they applaud you. It’s like a switch has flipped and the entire universe is conspiring to help you towards your goal. People will come out of the woodwork to lend advice, or introduce a contact, or just give you a pat on the back when you need it. Knowing that it will get easier definitely makes it easier to take the big step.
Don’t forget to celebrate. This is a big deal. Throw a fitting “retirement” party to thank folks and provide a symbolic end to your old life.
The first few weeks are kind of a rush as the reality of your new life sinks in. It’s good to leave your plans a bit open ended before you begin your quest toward your first milestone—this new reality will likely differ from your original plan. The most important thing, in the end, is to enjoy the flexibility of your new life – you’re not beholden to anyone! If you find that you need to alter your plans to realize the dream that you envisioned, leave yourself the flexibility to do that.
Take plenty of pictures and make sure you remember to sit back and smell the roses (or in my case, tropical flowers) occasionally.
It might be important to you to break away from your old life, but don’t lose touch with the things from your past that are important to you. Try to include your friends and family in your plans, as sharing your adventures always makes them sweeter and more memorable.
Each adventure will teach each individual something different. I’ll describe my experience to give you some idea of what you’ll get out of it in the end.
I chose cruising on a sailboat for a number of reasons. A sailboat seemed like it would allow me to explore some beautiful parts of the world. I figured it would challenge me and stretch me beyond my comfort zone. I also reckoned that it would reduce my impact on the world around me.
These precepts have all proven true over the course of those two years, but there have been other benefits as well.
You frequently hear people saying how unhealthy it is to be constantly stressed out. I’ve always quietly figured it was true, but it has also seemed like a bit of an abstraction. How, specifically, would my well being improve if all my worries melted away? After making a fairly abrupt change from a stressful job to a really slow-paced, relaxed lifestyle, I can honestly say that there is a night-and-day difference.
When I sailed away from the dock I immediately started losing weight and thus feeling healthier. I used to come down with a cold or something every 3-4 months, and in those two years, I only got sick once and that was only after a long stint of partying and eating in some pretty sketchy road-side food stands (which is to say, that was pretty much my own fault).
I think my mental health improved as well. My sense of self-worth used to be tied to my job performance and I found I’d get frustrated and anxious if things weren’t going according to plan (even if it was beyond my control). I learned a lot about what really matters to me out there and I think I’m a more confident, balanced person because of that.
My mind was free to wander when I was out on the open sea. I had the chance to ponder lots of things that I never would’ve taken the time to consider when I was working full time. I spent a lot of time reading and new ideas that I picked up along the way evolved my view of the world.
Along the way I met some fantastic people and built some friendships that I treasure. Most cruisers you run into are really warm and welcoming people, and I’m sure I’ll keep in touch with them for years to come.
Sailing across oceans in a small sailboat teaches you a lot. There are obviously the hard skills, like learning to be a navigator, diesel mechanic and an electrician. But more important than these hard skills are the intangibles that build within you along the way. It took a long time to cultivate my will power, manage my fear, and focus my concentration—to convince myself it was a good idea to cross the South Pacific in a 30 foot boat. The confidence and the sense of independence I gained are invaluable and will continue to serve me as I turn the next page.
Are you thinking of embarking on an adventure of your own? Don’t hesitate to reach out if I can be helpful in answering questions or guiding you to live your dream.
Ten years ago I quit my job, sold all my possessions, and decided to buy a sailboat (without yet knowing how to sail). It was the hardest decision I’ve ever made and it took me almost a year before I built up enough courage to take the leap.
I was looking for a grand adventure that would challenge me and stretch my comfort zone. While I had Chile in the sights of my mind’s eye, I wasn’t sure if I’d be able to make it. I didn’t let on to many people before or during the trip, but there were times along the way where I came really close to giving up. And there were times along the way when I was truly scared. It’s those experiences that have helped me grow the most.
You are in charge of your life. You can’t let the opinions or fears of others dictate your happiness.
What this “guide” isn’t meant to do is assuage the fear of venturing into the unknown. Nor is it intended to give you a step-by-step guide to sidestepping the hardest part, which is taking the first step of the voyage.
Consider it a journey of the imagination that gives rise to the actual journey. Perhaps it inspires you to delve a bit deeper into your own dreams of living a simpler, less frenetic life. It should also be noted that this guide was originally written for people like me at the time: educated, twenty-something, a few years out of college, building a career, making good money, etc. Not everyone is privileged enough to fit this mold, but I think anyone can take actions to make their dreams their reality.
Most folks have this notion that sailing is a wildly expensive activity reserved for elites and millionaires. Some people certainly spend fortunes on huge boats and electronic gadgets, but the Rascal and my way of life were pretty reasonable.
Unfortunately, a lot of people are complete dumb-asses when it comes to managing money. My parents were fairly frugal as I was growing up and they helped me to understand and control my spending. This doesn’t seem to be the norm in the US (or in capitalistic societies in general), so I’ll try to impart some of the mindset that allowed me to live off of savings for a couple years.
Over the course of my travels, I’ve met and talked with people that live on a couple of dollars a day and are totally satisfied with their lives. Their needs are met.
It is this perspective that can set you free.
If you’re constantly comparing yourself to pop culture icons and professional athletes, your hunger and consumption will be insatiable. This is what media and marketing twist your brain into thinking is the
“right path”. However, if you compare yourself with a Chinese farmer or a Chilean fisherman, you’re suddenly living a life of tremendous excess.
A good place to start is to take a hard look at where your money goes. How much do you spend a month at coffee shops? What do you spend every year on gas for your car? Do these financial expenditures bring you proportional amounts of happiness? Fulfillment? Add all these figures up and make pie charts and really wrap your head around where all of your money goes. A couple of dollars a day add up to substantial amounts of money over the course of a year. There are plenty of apps to help you with this.
Once you have a good understanding of where your money goes, start making decisions on where you can spend less. Maybe you’ll move into a smaller apartment. Maybe you’ll sell a bunch of the clothes you bought on a whim. Maybe you’ll trade your car in for an older one or start riding a bike to work. Cut out all of the expenses that don’t enrich your life!
These are the parts that won’t be fun or easy, but they’re also the parts that will enable you to live your dream in the end. Find a balance between austerity and happiness and don’t lose sight of the light at the end of the tunnel.
Make sure you have a legit parachute before you jump out of the plane. Quitting your job with just the vague notion that you’re going to “travel the world!” or “ride a bike through India!” would be a bit rash. Conduct some serious research, develop a budget, come up with a timeline, and know what you’re getting yourself into.
Read books, send emails, and learn as much as you can about your new life. People are always eager to share their experiences, so reach out to folks that have done something similar. You need to understand the nuances of what your new life will be like, especially the realities and difficulties you will surely encounter.
The next step is cracking open a spreadsheet to figure out the financial realities of your dream. What will your living expenses look like? Will you have any residual income from investments? How much does food cost in Tibet? How many kilometers can your motorcycle go on a liter of fuel? How much will health insurance cost? Will you have a monthly cell phone bill? What is rent on a beach cabana in Costa Rica?
Chances are your new life is going to be totally different (financially) from your old life, so there will definitely be some guesstimating and back-of-the-napkin calculations. Do your best, but be realistic and base your budget on research. Based on all of these costs, figure out either how much you need to save, or how long you’ll be able to unplug. Plan to have some cushion money stashed away for your return back into the world of work in case it takes a while to get a job again.
Once you know roughly how long you’ll be gone, give yourself some milestones—things you want to accomplish and a date to accomplish them by. My initial milestones involved buying a boat and learning to sail. Eventually they evolved to sailing to the Sea of Cortez before hurricane season and arriving in Chile before winter set in. I found it was really important to stay motivated and focused, because it is really easy to just veg and relax once you’re not working every day.
If at all possible, try to get a real taste of the life you’re contemplating. Take some vacation time to crew on a cruising sailboat. Spend a few weeks hiking the Pacific Coast Trail (PCT). Make sure you truly enjoy what you’re planning to do, as opposed to just the idea of it.
What you’re doing isn’t “normal”. Everyone around you probably thinks you’re going to keep busting your ass until age 65. Your boss, your friends, and your family are all making plans based on this assumption. When you break the news, you’ve got to do it gently. Hope they’re supportive, but don’t hinge your determination on their support.
The research you’ve done, the plan you’ve developed, and your realistic budget should help to persuade your friends and family that you haven’t totally lost your marbles. If they love you and care about your happiness, they’ll support you and help you succeed. Just remember: You are in charge of your life. You can’t let the opinions or fears of others dictate your happiness.
As far as the job goes: It took me a long time to build up the courage to actually hand in my resignation. It was scary and the finality of it is resounding. I figured the best route would be working hard before departing and being open and honest with my boss. This has the benefit of making for a less awkward conversation when you resign and also leaving a good taste in your employers’ mouth if you wind up needing a job again in a year or two.
After you quit, there is no going back. I was lucky enough to have a few friends as role models, and they gave me the confidence and support I needed to go for it.
My sense of self-worth used to be tied to my job performance and I found I’d get frustrated and anxious if things weren’t going according to plan (even if it was beyond my control). I learned a lot about what really matters to me out there and I think I’m a more confident, balanced person because of that.
If you’ve managed to make enough money to quit working for a while, you’re probably going to be leaving some money on the table (impending raises / bonuses / etc) when you go, which obviously makes it even harder. Take a step back, however, and think of all the experiences you’re not having as you continue to amass your savings. You can’t put a price on your time – especially when you’re in your prime.
Everyone is thinking (or has thought) about doing something like this and when they see you doing it, a little piece of them rejoices and they applaud you. It’s like a switch has flipped and the entire universe is conspiring to help you towards your goal. People will come out of the woodwork to lend advice, or introduce a contact, or just give you a pat on the back when you need it. Knowing that it will get easier definitely makes it easier to take the big step.
Don’t forget to celebrate. This is a big deal. Throw a fitting “retirement” party to thank folks and provide a symbolic end to your old life.
The first few weeks are kind of a rush as the reality of your new life sinks in. It’s good to leave your plans a bit open ended before you begin your quest toward your first milestone—this new reality will likely differ from your original plan. The most important thing, in the end, is to enjoy the flexibility of your new life – you’re not beholden to anyone! If you find that you need to alter your plans to realize the dream that you envisioned, leave yourself the flexibility to do that.
Take plenty of pictures and make sure you remember to sit back and smell the roses (or in my case, tropical flowers) occasionally.
It might be important to you to break away from your old life, but don’t lose touch with the things from your past that are important to you. Try to include your friends and family in your plans, as sharing your adventures always makes them sweeter and more memorable.
Each adventure will teach each individual something different. I’ll describe my experience to give you some idea of what you’ll get out of it in the end.
I chose cruising on a sailboat for a number of reasons. A sailboat seemed like it would allow me to explore some beautiful parts of the world. I figured it would challenge me and stretch me beyond my comfort zone. I also reckoned that it would reduce my impact on the world around me.
These precepts have all proven true over the course of those two years, but there have been other benefits as well.
You frequently hear people saying how unhealthy it is to be constantly stressed out. I’ve always quietly figured it was true, but it has also seemed like a bit of an abstraction. How, specifically, would my well being improve if all my worries melted away? After making a fairly abrupt change from a stressful job to a really slow-paced, relaxed lifestyle, I can honestly say that there is a night-and-day difference.
When I sailed away from the dock I immediately started losing weight and thus feeling healthier. I used to come down with a cold or something every 3-4 months, and in those two years, I only got sick once and that was only after a long stint of partying and eating in some pretty sketchy road-side food stands (which is to say, that was pretty much my own fault).
I think my mental health improved as well. My sense of self-worth used to be tied to my job performance and I found I’d get frustrated and anxious if things weren’t going according to plan (even if it was beyond my control). I learned a lot about what really matters to me out there and I think I’m a more confident, balanced person because of that.
My mind was free to wander when I was out on the open sea. I had the chance to ponder lots of things that I never would’ve taken the time to consider when I was working full time. I spent a lot of time reading and new ideas that I picked up along the way evolved my view of the world.
Along the way I met some fantastic people and built some friendships that I treasure. Most cruisers you run into are really warm and welcoming people, and I’m sure I’ll keep in touch with them for years to come.
Sailing across oceans in a small sailboat teaches you a lot. There are obviously the hard skills, like learning to be a navigator, diesel mechanic and an electrician. But more important than these hard skills are the intangibles that build within you along the way. It took a long time to cultivate my will power, manage my fear, and focus my concentration—to convince myself it was a good idea to cross the South Pacific in a 30 foot boat. The confidence and the sense of independence I gained are invaluable and will continue to serve me as I turn the next page.
Are you thinking of embarking on an adventure of your own? Don’t hesitate to reach out if I can be helpful in answering questions or guiding you to live your dream.
Dwyer Haney
“Grabbing life by the horns and tickling it behind the ear.”
Before and during his time studying engineering, Dwyer built skis in his garage, tinkering and learning the process. Soon after he landed an outdoor-lover’s dream job – working with Black Diamond Equipment. He put his head down and got to work. The next thing he knew, he was building a ski manufacturing facility from scratch, in China, for Black Diamond. After leading a team of engineers to reach mass production, he returned home, satisfied with his work, but with wanderlust in his heart.
The book, Across Island and Oceans by James Baldwin—a book about a youngish guy who quits his job, sells his stuff and sails away—became a companion on his flights halfway across the world. He took the book as a beacon, a call to arms.
Then, in his mid twenties, he bought a 30-foot sailboat. He learned to sail it in the San Juan islands – west of Bellingham, Washington. Then, with the goal of skiing directly from his boat, he navigated it more than 12,000 nautical miles down the west coast of the Americas—to Chilean Patagonia. A good bit of adventure ensued along the way – from hurricanes to volcanic eruptions and more than a bit of ice-breaking.
In the time since his voyage, Dwyer has focused on building a homestead in the hills of Vermont. He and his wife live in a 500sf timber frame with their dog Spruce. They’ve planted several hundred fruit and nut trees and are looking forward to growing their family, surrounded by an abundant food forest.
Dwyer Haney
“Grabbing life by the horns and tickling it behind the ear.”
Before and during his time studying engineering, Dwyer built skis in his garage, tinkering and learning the process. Soon after he landed an outdoor-lover’s dream job – working with Black Diamond Equipment. He put his head down and got to work. The next thing he knew, he was building a ski manufacturing facility from scratch, in China, for Black Diamond. After leading a team of engineers to reach mass production, he returned home, satisfied with his work, but with wanderlust in his heart.
The book, Across Island and Oceans by James Baldwin—a book about a youngish guy who quits his job, sells his stuff and sails away—became a companion on his flights halfway across the world. He took the book as a beacon, a call to arms.
Then, in his mid twenties, he bought a 30-foot sailboat. He learned to sail it in the San Juan islands – west of Bellingham, Washington. Then, with the goal of skiing directly from his boat, he navigated it more than 12,000 nautical miles down the west coast of the Americas—to Chilean Patagonia. A good bit of adventure ensued along the way – from hurricanes to volcanic eruptions and more than a bit of ice-breaking.
In the time since his voyage, Dwyer has focused on building a homestead in the hills of Vermont. He and his wife live in a 500sf timber frame with their dog Spruce. They’ve planted several hundred fruit and nut trees and are looking forward to growing their family, surrounded by an abundant food forest.
info@HenceSupply.co
Park City, Utah 84098