I’m Peter Roberts, immigration attorney who does work for YC and startups. AMA

Edit: It's also not clear at first glance what counts as "work experience" - if you have first and last paycheck + contract it's easy, but if you don't it's fuzzy. Open source or hobby programming is no good.

One thing I will say up front, though: you need a bachelor's degree from a recognised university to have any chance of working in Japan normally. If you don't have one, that will have to be your first stop. This will help for getting visas in practically any country.

Anyway, here's what I learned at the time. If you have a university degree in an "engineering" field and can get a job offer for an IT job, you can fairly easily get sponsored by a company. There are some big companies, especially in Tokyo and Osaka that regularly hire foreigners (Rakuten is probably the biggest, but there are others). There are also a lot of US companies that do development in Japan. If you get a job for one of those US companies and work for them for at least a year, you can get an inter-branch transfer visa (I forget the Japanese) to work in Japan. Since you have American citizenship, that's a relatively easy way to get into the country -- you just need to join large companies that do development in Japan. There are also some big Japanese companies that have offices around the world: Hitachi is a big one, but for example, I have a friend who used to work for Square-Enix doing IT work in the UK.

Finally there is a points based system. If you are hoping to live in Japan long term (without a family member who is a citizen), this is by far the best route to go. http://www.immi-moj.go.jp/newimmiact_3/en/pdf/171110_point_c... You need 70 points to qualify, which is fairly difficult, depending on your age and accomplishments (best return of points for time invested is probably a Master's degree, which will give you 20 points... If you apply yourself, you can probably pass JLPT N1 language test in 2-3 years which will give you 15 points -- after that, you need to make sure to get a high salary). The main advantage to this system is that it's gives you a fast track into permanent residency for you and also allows you to sponsor family members.

Finally, for citizenship, it's really just a matter of time. If you stay continuously in Japan for 10 years, you can appy. You would have to renounce all of your other citizenships, though, so it's a big deal. You also need to show that you can fit in well in Japanese society. This is through a series of interviews as well as a written essay that you have to do. There is a lot of hoop jumping, but if you are unhappy jumping through hoops, then you are not Japanese :-)

Would you happen to know anything about the H1B1 visa for Singaporean nationals? In particular, if I'm Singaporean (and hence qualify for the H1B1), would that still count as 'needing sponsorship" when applying for jobs? I'm currently finishing up a non-STEM PhD, and will be eligible for the 1-year OPT; I plan to apply for both academic and non-academic jobs.

Thanks in advance for your time!!