Being a self-employed contractor in Japan
If you are wanting to continue being self-employed, the first challenge to overcome will be getting a visa. Unless you are eligible for a spouse visa, or maybe a working holiday visa, I think self-sponsoring a working visa is pretty challenging, and would probably involve setting up your own company here.
If you already have a working visa here though, changing to be self-employed isn’t such a big deal, so from a visa perspective, one thing to consider would be to get a full time position here, then sometime down the road switch to working for yourself.
Additionally, securing contract-based work here pretty much requires you to already be living in Japan with a valid visa. Both because these contracts tend not to be advertised, but go through word of mouth, and because the reason companies hire contractors in the first place is to minimize overhead, so having to bring someone to Japan wouldn’t make sense.
Finding a DevOps job in Japan
There is certainly demand for DevOps professionals in Japan. My background is coming from the development side of things, and the less I need to touch servers the better. Because of this, I haven’t been so involved with the community. I know the Japanese AWS community is very strong. Docker also has gotten a lot of buzz recently.
My impression is that the companies doing the most interesting DevOps stuff here are established web services companies like Rakuten, Gree, CyberAgent, and Cookpad. I think those companies are interested in using the latest DevOps technologies, so you would be at an advantage with them over the more traditional enterprisey companies here, which are probably still using some proprietary Hitachi solution developed ten years ago.
Another option would be to look for international enterprise companies operating within Japan. With any international company, you’ll have the advantage that you both better understand the international culture and speak English, both things that most Japanese DevOps can’t do. One thing to do would be to look at your own network to see if you have any connections to companies with subsidiaries in Japan.
Japanese outsourcing companies and hiring foreigners
Japanese outsourcing companies sell to Japanese clients. Because there is no international component to their business, I think these companies would not perceive a non-fluent Japanese speaker as much of an asset. It wouldn’t necessarily be impossible to get a job working for one of them, but it would be an uphill battle and would probably only be possible if you were willing to work in substandard conditions - think long overtime and low salary.
In addition to larger Japanese outsourcing companies, there are also several smaller international agencies here like Tacchi Studios and AQ. Companies like these are willing to work with non-Japanese on a contract basis. However I’m not sure that their projects often call for a DevOps professional, as I think the projects they focus on are building new solutions, and can get by with simple deployment strategies.