I didn’t start off in Tokyo, but in Hamamatsu, a little to the west in Shizuoka prefecture. It’s kind of a small city that for some reason was the birthplace of Yamaha, Suzuki and Honda, and is now the musical instrument capital of the world (seriously, something like two-thirds of all electronic instruments in the world are made there). Anyway, I started off as a teacher at a tiny English conversation school in summer of '95 when I was 23 and taught there for about 2 1/2 years. The reason I chose Hamamatsu was because that school was willing to hire me and sponsor my visa before I’d even come to Japan. All the other schools (I’d sent applications all around the country) only hired people already living in Japan. The lesson I came away with (although I know others here have had better experiences) is that if a school is willing to hire from overseas, it’s because their reputation is so bad that nobody local will work for them. Come here first as a tourist and then look for a job.
Anyway, you asked about Tokyo. After teaching for a couple of years, I decided that while the money wasn’t bad and the students were fun, it wasn’t really what you’d call a career and I was starting to get burned out. Looking around Hamamatsu, the only career option for western foreigners (non-Brazilian, but that’s another story), besides working at conversation schools, was marrying a Japanese citizen so you could get a spousal visa which would allow you to start your own business, and most of the folks I knew who’d done that were either running restaurants, import shops or their own conversation schools. None of these really appealed to me at the time (and I was lacking a prospective spouse), so I decided I had to move to greener pastures. Looking through the want ads in the Japan Times, the overwhelming majority of jobs for foreigners were in Tokyo, so that’s where I started sending applications. I got a job as a creative writer with Interbrand Tokyo in '97, spent a couple of years at NEC, went back to teaching for a year out in the suburbs (much better experience this time), and most recently started working as a copywriter for an ad agency in the Tsukiji neighborhood (near the big fish market) about two years ago. I also got married about the same time I started with the ad agency, with one of my former students from Hamamatsu. Overall, I have to say I really like it here, athough if the job market in Hamamtsu had been better, I wouldn’t have minded staying there, especially now that the spread of the internet, Amazon and Citibank mean I’d no longer have to make special trips to Nagoya to buy English books.
As for the whys and the hows: I went to Japan mainly because I had no idea what I wanted to do after college, and thought this would be good way to strike out on my own, get some work and life experience, and then maybe figure out what I’d do from there. I guess I also had some unexplained deep-seated thing for Japan, maybe rooted in all the hours of Battle of the Planets, Force Five and Star Blazers I watched when I was little. Anyway, that’s why I went to Japan; going to Tokyo was simply a career move.
I’d already decided to go to Japan in my senior year, so I spent a year after graduation studying Japanese at night school. As a result, I could speak and read enough when I arrived to ask for directions and handle basic survival stuff. Since then, I’ve studied off and on, and while I’m still far from fluent, I can generally handle myself.
Being Japanese, my then-SO (she moved here to live with me about three years before we got married) didn’t find Tokyo that much of an adjustment. In fact, she’d gone to college and worked here for a few years before returning to Hamamatsu to help take care of her father, which is when we met. She didn’t have too much trouble finding a job here, either. She’s addicted to the city now and would probably raise hell if I suggested moving to a more rural area.
Woo, this turned out longer than I expected. Guess I just like talking about myself.