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The "honeymoon period" is by no means unique to Japan. It happens anytime you decide to immerse yourself in a new and complex subject (like another culture) that has both good parts and not-so-good parts. It's only human to overlook the bad in search of the good but you can only filter out the other stuff for so long and then it starts to become more obvious. How that affects you depends on you more than the place. For me, the good parts of living in Japan outweigh the bad parts. But, at the overused saying goes: "Your mileage may vary."

Not being career-minded is a strike against you at this point. Not because the ordinary non-career jobs don't exist... because obviously they do. But there are plenty of Japanese also ready to take on those particular jobs and, all other things being equal, a manager would rather have someone he can talk to in his native language. So the only real hope of landing employment here is to bring something not that many Japanese can do (like computer programming or English fluency) or to become fluent in the local language so you can compete for the regular jobs along with Japanese natives who can do the job just as well as you can.

As for teaching... it's true that anyone with a degree (or provable equivalent experience) can teach English. But the market for English teachers is very poor right now. The books that claim how you can make a killing teaching English in Japan were all written 10 years ago, when every company under the Sun was sending their mid-level execs to English school in order to remain competitive. That market doesn't exist today. It's really hard to find a decent job if all you bring to the table is the ability to speak English.

I'd advise against just coming with the hope that you might find something when you get here. To say that Japan is on the high side in terms of cost-of-living would be an understatement. It may be possible to live like a king on some countries just by finding odd jobs here and there, but: (a) that's not as feasible here due to the cost, and (b) you won't get a visa to just bum around doing odd jobs. Information on visas is available if you search for it -- the new law doesn't change things that much (other than registration procedures, which don't affect you unless you show up here, the only real change is that visas are generally for longer periods than they were before -- but you still need to qualify in the first place).

As for cultural assimilation... that also depends mostly on you. You need to realize that no matter what you do, you'll never be Japanese. The difference is a lot more obvious here than it would be in melting-pot cultures like the US or Britain. That's not to say you can't make friends here. If anything, I found it easier to make friends here because many Japanese have a natural curiosity about other cultures (for much the same reason that you're interested in Japan) but that also means you'll have to tolerate a few inane questions every time you meet someone new. But if you're willing to work to get past that stage -- and if you learn enough Japanese to carry on a reasonable conversation -- you should have no problem.

Mostly I think it depends on whether you're willing to accept the fact that things are different that they were at home. If you come over with all your expectations intact and take offense any time things aren't done the way you think they should be done, you're not likely to last long. If you embrace the local culture instead of wishing it were more like your own, the "not-so-good" bits will eventually become "ok" bits. But that too is not unique to Japan. It would be the same no in matter which culture you decided to immerse yourself. The key is immersion in something other than that which you're used to. The only real difference is that Japan is more different for us Westerners than if we moved to some European country.

If you can qualify for JET, by all means give that a shot. Once you're here you can spend the first couple years making contacts that might help you find something else once your contract it up. If you have enough money to support yourself for a year or two, you might be able to get a visa as an artist (such a visa does exist but you need to prove that you can support yourself for the term of the visa and you would need to jump through additional hoops to get permission to work while you're here). Maybe you can convince your current employer to open a pastry shop here in Tokyo, which would qualify you for a visa if the business will also be employing a handful of locals. There are probably many other possible avenues but just showing up with "several thousand yen" to your name is a sure recipe for failure, IMHO.

Hope that helps...
 

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I've always assumed (and said so in previous threads) that it takes at least a year or two to really grok what Japan is all about. And not knowing the language masks a lot of the faults. If you needed evidence of a "honeymoon period" you need only talk to someone who's only been here a few months, doesn't speak the language, and hasn't yet landed a job.

BTW, when I say "faults" that's not to say I don't still prefer Japan as my home. It's just that I've gotten to the point where I realize that there's going to be things we don't like no matter where we live and, IMHO, people tend to carry these attitudes around with them wherever they go. In other words, if you think where you live right now is more-or-less OK, you'll probably like Japan. If you hate where you live now, spend two or three years here and you'll learn to hate it here just as much. It has less to do with the actual location than with the person doing the observing.
 
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