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I've gone through several cycles of dirt poor and stinking rich in my life. I understand the joys in life are given by God not bought but money makes can make you comfy not happy.
At first thought I was a check writer but now realize I'm in the middle group. This middle group would be the 1 to5%ers back home.
Simple things are difficult and require much thought when you are by yourself. Things like dropping the genny to get at the turnbuckle under the furling drum so you can tune the rig. Working on the top of the stick. Getting the engine on of off the dinghy to put it on the push pulpit.
The absence of a car always at your disposal creates its own set of headaches.
You have upper middle class highly educated people dependent on a population whose main source of income is tourism. Beyond issues of theft causing concern the role reversal is problematic for some on both sides of the equation.
Still I like the blunt reality of this life.
And
Something's broke you fix it.
Something's needs work you do it.
Some thing is drop dead gorgeous you ooo and aaaa.
Some one offers knowledge or friendship you try your best to reciprocate.

Sun comes up you wake up. Sun goes down. It's time wind the day down.
And I like it enough to see myself doing this for years to come.
Next projects are learning Spanish and French
 

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A most unique mindset.
And hard? Can't get a girlfriend and ostracized by part of the community? Yes thats bloody hard!

The videos excellence touches on those two points: "If people think I am a dirt-bag..." and lack of relationships is a delightful, tender way intermixed with beautiful 'enviable' lifestyle shots. But remember those 'enviable' moments, like thee scrubbing of the frying pan over the side ain't so enviable in real life. Or having worked hard all our lives to be able to, in retirement, cast off the lines only to be thought of as 'dirt bags'.

Good on him and lets hope his cruise goes well and he utterly enjoys it... but lets not take this video as a "What to Expect" 101 because its not, the video is a glorious piece of art depicting a unique person, thats all.


Mark
two things i think you are missing:

1) i don't get the impression that he gives two hoots if some people look down at his life choice....anymore than i would. that kind of thing is only an issue if you judge yourself by the judgements of others. i am sure he meets plenty of people that don't think he is a terrible person. i noticed he was socializing with locals in the video.

2) he didn't say he couldn't find a girlfriend. what he said was that he was afraid that, if he did, she wouldn't like the lifestyle and try to drag him back ashore. in other words, he chooses not to get a girlfriend, at this point in life. there are women that love living aboard. one of them posts videos on youtube.

this guy just needs to find one of those women. but, is that really different than any lifestyle you live? if you are a biker, you find women who like motorcycles and motorcycle events. if you are any kind of sailor or boater you find a woman that also enjoys that.

the guy who does the pirate lifestyle videos on youtube used to be a successful business guy with a big house, nice cars, a motorcycle, and even his own small plane. he was married and his wife was used to that 'successful' lifestyle. he gave it all up and they moved onto a sailboat. last i watched his videos, they'd been doing it for 10 years. he didn't have to give up female companionship to follow his dream lifestyle.
 
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What I've found interesting is that last year I was in the process of buying a class b RV and discovered a whole group of people living in them.They call it boondocking,the class b isn't much bigger than a conversion van so it can be parked on the street legally.A lot of them posted videos on youtube and while it isn't the life for me I can understand people doing it,Now with the amount of people looking into or living on boats added I'm wondering if there is a small but growing move to downsize and live more simplistically in these stressful times and if there are other ways people are trying to live.
yes. there does seem to be one. if you go searching youtube for live aboard stuff you tend to see other related stuff. tiny houses. peole building actual small adobe houses. go to netflix and watch "tiny".

we have all been trained to be good little consumers. you just can't live without the biggest suv, the biggest house, a wall size tv, and two harleys in the garage. but, in our failing economy, many people are finding that they can't live with those things and that trying to do so is making them miserable. they are finding that living without them is easier and happier.

that's the course i have plotted and am working towards. material good don't make you hapy and not all hardships make you unhappy. most of the hardships presented to people in our modern world are enduring hardships that are becoming insurmountable. on the other hand, hardships you can face and, with a bit of work, overcome, leave a person with a sense of accomplishment that let's you sleep at night. better than sleepless nights worrying about problems you have no idea how to solve.
 

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reading over everyone's comments, i get the feeling people didn't really hear what he said because of how he said it. he did talk about cons. he spoke of heavy weather, no baths or showers, no fridge, and only having two days of ice (if he chose to sail to austrailia). he said that every day he is faced with challenges.

i think the reason it sounds as if he didn't speak of cons is that he didn't speak with the down trodden bitterness most people, who live the land bound life we are 'supposed' to live in the modern world, have when speaking about the negatives in their lives. it's a different perspective. not all hardships are bad, as he kind of says in the film.
 
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