Alternative Work in Japan: Freelancing in Tokyo [Interview]

Today I'd like to introduce David Chester, who wrote Freelancing in Tokyo: A Unique Guide to Achieving Financial Success in Japan's Most Expensive City. I'm frequently asked about "other types of work" in Japan aside from teaching English, and though it varies, especially depending on where you go in Japan, not everyone has to get locked into teaching English if they don't want to.

I first heard about David's book through his interview on Tokyo Podcast and found it really interesting, so I bought and read the book. I also recommend you check out the Tokyo Podcast interview (after reading this one, of course!), since I heard about David's book there first.

freelance, Tokyo, Japan, book,

Ashley: First of all, where are you from, how long have you been in Japan, and what do you do?

David: I’m from Los Angeles (California, USA). I came to Tokyo in April 1993 as a musician/songwriter. I am still a musician but have become a screenwriter/filmmaker along the way.

Ashley: Teaching English is commonly believed to be one of the few ways a foreigner can find work in Japan, but your experience has proven otherwise. Do you think freelancing in Tokyo (or another large city in Japan) is a viable option for anyone?

David: I can only speak of Tokyo, because that’s where I’ve applied my skills. Freelancing in Tokyo is best suited for a native English speaker with a college degree and some legitimate work experience. If that work experience is in the field of teaching, writing, editing, acting, singing, or narrating (voiceovers) all the better. Film editing, photography, translation and interpretation are also valuable assets. And as much I do not want to say this, it’s better if you are in your 20s or 30s. After that, it becomes more challenging (but not impossible).

Ashley: What characteristics, skills or knowledge do you think, in your experience, are best suited for this type of work/lifestyle?

David: That’s a broad question and one of the reasons I wrote Freelancing in Tokyo. Again, if someone is seeking freelance work in Tokyo and has interest in following some of the paths I’ve taken, they would need to be a native-English speaker and have some work experience, preferably white-collar. Also, it is really essential that they have a positive outlook on life, because the Japanese respond well to “cheerful” people.

One must also be able to quickly grasp new skills as you are sure to be thrown into situations where any number of things will suddenly be required of you (not to mention expected of you) simply because you are a native-English speaker (e.g. teaching, editing, rewriting, proofreading, voiceovers, etc.). In addition, one really should have a strong, strong desire to understand/appreciate/accept the Japanese culture, language and food, because without that desire, it could be quite difficult to live here.

Ashley: Can you give us some examples of the types of jobs you've had over the years as a freelancer?

David: They are all detailed in my book and the list is extensive, but I’ve done everything in Tokyo from teaching English in all situations imaginable (from private students to politicians), doing voiceovers for corporate videos and anime, acting in commercials with Japanese film and pop music stars, writing for The Japan Times and Metropolis Magazine, and organizing screenwriting/filmmaking events with special guests from Hollywood.

Ashley: To your knowledge, how easy/difficult is it to obtain a work visa as a freelancer for those who don't have one already or aren't in Japan on a dependent visa? Briefly, what is the best way to go about it?

David: In brief, you will need to find a visa sponsor who has a legitimate company who needs your services (teaching, writing, etc.) badly enough to be willing to sponsor you. I've also covered all of this in my book. But every foreigner I’ve met in Japan has a different story about how they “got in,” so I cannot give one clear answer. For some, it seems to be a breeze–for others, a challenge.

I’d also suggest people interested in coming here do extensive research, which is easy to do thanks to all of the resources on the Internet—something unavailable to me when I came here in 1993.

Ashley: Do you feel that the way you network and go about finding jobs is different now with the prevalence of the internet and, in particular, social media?

David: Yes. Gone are the days of scouring The Japan Times on Monday morning in hopes of finding an interesting job (although, on rare occasion, they still have them). Anyone who uses the Internet on a regular basis can find numerous sites with information about jobs and networking opportunities in Tokyo.

In addition, there are networking groups and special interest groups or clubs where people can network to their hearts’ content. Perhaps more importantly, one can start one’s own group through Facebook or Meetup and create their own networking opportunities.

Ashley: Your book is full of incredibly useful resources for anyone potentially looking for work in Tokyo (or other parts of Japan). Would you mind briefly sharing a few of those resources with our audience, just to give us a taste of what Freelancing in Tokyo has to offer?

David: It’s difficult to say which site offers the most help, but and sites connected with Metropolis Magazine seem to offer a lot of links that have value for people who are seeking full-time or part-time jobs, apartments, roommates, and more. I’d start with those two sites.

Ashley: Finally, what are your best "living in Japan" tips for SiJ readers?

David: I would say that it’s essential to learn as much Japanese as you can. This is the key to living here successfully as communication quickly becomes an issue if you can’t express yourself and/or get what you need. Yes, there are many Japanese people who can speak English, and yes, they all have to study it, but generally speaking, they are shy and reticent, and if you have made the effort to speak Japanese to them, I find they relax and are more willing to assist in whatever way they can. This makes living here so, so much easier. Even for those who only think they’re going to be here for a year or two, commit to learning the language as much as you can. Trust me, you’ll be glad you did.

David, thank you so much for sharing your knowledge and experience with us! 


Freelancing in Tokyo contains a wealth of information, not just for freelancers, but other living in Japan tips, resources and links. I definitely recommend it if you want to pursue similar types of work and need ideas and suggestions for how to get your foot in the door.

You can find Freelancing in Tokyo on Amazon in Kindle or Paperback formats. Also be sure to check out the Freelancing in Tokyo website for more information.

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