Simple life, or Wealthy life?

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Hey guys, I was talking with a buddy last night about one of my former classmates. I went to school with a kid named Joey that was always a very happy dude. Kind of lived life by the seat of his pants and did what he enjoyed. After graduation we all went off to college/work/whatever and gained new friends etc.. Here we are, quite a few years later and Joey has moved to Hawaii. He is now a surf instructor with no car and no real responsibilites. Just a single dude, living in a paradise and teaching tourist to surf.

Now here I am, same amount of years later with a good job, own my home and many things I am proud of (cars/guitars/guns etc..). I am thrilled with the way things are going and am generally always a happy panda.

I see a post on facebook last night from joey that says. "taking a solo dirt bike ride through the island to get a pinneapple, life is easy". I'd be lying if I said I wasn't a tad jelly. I can't imagine living in a shack in paradise.

I do enjoy "nice" things and like living in a city but I seriously wonder how green the grass is on the otherside. Maybe if I am still single when I am 40 I will just take all my money and do something similar. Life is all about being happy, and it seems that a simple life would be a straight blast.

What do you think misc? Would you rather live in a shack on the beach with no real responsibilites or be a succesful businessman with a nice car/home/bank account etc...??