Career Hack Guide to Japan

Japan is a common destination for people looking to live and work overseas. It also serves as a nice gateway to Asia where you can get your feet wet as an entrepreneur or career hacker in a foreign country.

Below are some interviews and advice for living and working in Japan.

Working as an entrepreneur in Tokyo


Below is an interview with Chris Kirkland about his experience as a digital nomad and entrepreneur in Tokyo.

Please give us a rundown on who you are and the ventures/sites you are currently running.

To briefly summarise, I have a long freelance tech background but for the last 7 years have been running ArtWeb which is a hosted platform for artists to build their own website, promote and sell their own artwork online – a bit like a niche for artists. More recently (last year) I co-founded TokyoCheapo, which is a popular blog about living in or visiting Tokyo on the cheap.

Plus I also blog and podcast on – my musings and philosophical ramblings coming from a life of business and hobodom.

How did you become a digital nomad entrepreneur? Did you make a decision or did it happen organically?

I’d been working as a freelance web designer/programmer for a few years and some of my clients were already long distances away. So I started to think about some kind of SaaS or product instead of a purely service based business I already had at the back of my mind the idea of being a digital hobo.

And so about 1 year after I founded ArtWeb I booked a 5 week return flight to Tokyo. I skipped the return flight and lived overseas for the next 5 years straight.

You base yourself mostly out of Berlin and Tokyo. Why do you like these spots specifically? What other spots do you suggest people check out?

Tokyo is a fascinating place to live on so many levels especially if you’re not from Asia, if you can afford it (or are a commited cheapo!) it’s a great place to live. It’s not all roses though, it’s expensive, there’s very little nature, most people only speak Japanese (read as “you need to become fluent in Japanese”) and it’s a double edged sword being a foreigner. But if you can handle the downsides it’s well worth it.

Berlin is my antidote to Tokyo – cheap, lots of nature, lots of space, beautiful old European buildings and borderline anarchistic undertones. It’s also got a budding young start up scene so plenty of tech people floating around too.

I’ve also enjoyed Chiang Mai, Thailand and Ho Chi Minh City in Vietnam, I rate both as excellent places for working remotely.

Tokyo is not a digital nomad haven due to its exorbitantly high prices. Please tell us about Tokyo Cheapo and how a person can live frugally in Tokyo.

My co-founder Greg Lane and I were both complaining about the Mercer report which labels Tokyo as the most expensive city in the world. Whilst it certainly can be expensive, the criteria they used seemed to be based on importing an American lifestyle into Japan.

There’s lots of ways to save money in Tokyo, here’s my top three cheapo living tips:

Save on rent by sharing an apartment, living in older places, living in tiny apartments and living less central. Also there’s a government sponsered cheap housing scheme anyone can get on UR Rental Housing – Apartments Without Stupid Fees in Tokyo.

Don’t try and import a “western” lifestyle – leave the organic berries, sheeps cheese, pregnancy yoga, high ceilings and golf. Stick to Japanese cuisine and lifestyle options, they are generally far cheaper

Learn from the locals – follow the salary man for cheapo lunch, learn Japanese and or make friends who guide you, don’t just do what other expats and tourists do.

More at of course…

You are building a brand out of the “Cheapo” ideology. Please tell us about your plans for this and what your vision is for the brand. Who is your target market? What are they getting from Cheapo that they aren’t getting from Lonely Planet or Frommers?

Well our plans are top secret…

Kidding. We like the idea of unashamedly identifying ourselves as “cheapos”, kinda like laughing in the face of the “must have” culture of status through tacky show of wealth (label clothes, watches etc etc). We’re more interested in true value, avoiding wasteful spending and I think we’re not alone. But idealogy aside, I think there’s always demand for information for both budget travelers and expats new to expensive (and often enigmatic) cities. We differ from more traditional guides line lonely planet, rough guide etc in that we focus only on good value, low cost and travel hacks – we’re not going to do any reviews of the Grand Hyatt (unless they have a $10/night special offer).

Please tell us all about Art Web and becoming a coder. Did you become a coder to become an entrepreneur or were you already naturally drawn to coding? How and why did you develop the digital skill sets that you did?

I started fiddling with computers since in the early ‘80s (my dad worked at IBM) so IT skills were always easy for me. In the late ‘90s I picked up a few apple macs and started on freelance design, but over a couple of years transitioned to web programming which I ultimately found more interesting.

Shibuya Crossing, Tokyo, 1991

I didn’t exactly set out to become an entrepreneur, but as soon as I finished at Uni I decided that I didn’t want to work for anyone else, so I just naturally slid into doing various freelance jobs and a string of failed business ideas.

And statistically on target (only 20% of new businesses survive) I eventually I had some success with my 5th business ArtWeb.

How can people with student debt take a leap and become digital nomad entrepreneurs? What skill sets do you think are most important to acquire to adapt to and thrive in the 21st century economy?

Firstly, you are safe and have nothing to worry about, you have supporting family, friends, food and shelter, plus most of your adult life ahead of you. 80% of the world have absolutely nothing in comparison with you.

Learn how to hustle

Learn how to inspire and influence people

Get out of your comfort zone

Take calculated risks

Stay fit and healthy

Find a mentor doing something you want to do

Hang out with people who are already doing what you want to do.

And above all take responsibility for your life

Specifically for being a digital hobo:

Hit up some people already doing it and offer to go out to where they are and give your skills as their gimp for 3-6 months if they pay your board and lodging.

Sell or give away to charity everything you own.

Don’t listen to any of your friends or family, most likely they will just hold you back. Actually don’t even tell them you want to be a digital hobo, just leave.

If you want an “in between” step, book a return flight for a few weeks to a digital hobo hotspot, like Chiang Mai, Ho Chi Minh City. There’s a good chance you’ll just find a way to stay.

If you could start from the beginning, what would you have done differently as an entrepreneur?

I’d have studied some basic business principles, I really had my head in the sand when I started.

Plus I’d have sought out a mentor and connected with fellow entrepreneurs from the beginning (I didn’t really do this until years after I started).

Let’s say that I want to pick a cool second tier or third tier Japanese city in which to teach English and save some money – potentially to pay off student loan debt. What cities would you suggest? Why?

I’ve only lived in Tokyo, so I’m a bit short on experience alas. I hear Fukuoka is nice, it’s got a beach, the founder of Ruby lives there and the people are friendly. Apart from that I’d say stick to the large cities, like the Osaka area or the Tokyo area. Most the young people flock to Tokyo and are leaving the smaller cities, plus you’ll not be such a spectacle in Tokyo since theres more foreigners there which makes life a little easier (still very few though).

The Tokyo Metropolis is a huge area, so you can live in one of the outer areas like Kanagawa and still have the Tokyo experience, e.g I’d suggest Yokohama, Kamakura.

In the 21st century will it be more important to be a polyglot or a hacker? What are the relative pros and cons? What are the advantages of having both?

I take it you mean Hacker as in the tinkerer/coder sense?

I don’t think either is that useful on it’s own, there’s plenty of hackers and polyglots around now, so it’s not a particular competitive advantage. For example there’s a host of bilingual people out there, but it doesn’t give them much of a career (apart from translation) unless they have other skills.

In particular each language you add after two becomes increasingly less useful: Speaking 1 language is massively more useful than speaking 0, speaking 2 is a lot more useful than speaking 1, speaking 3 is a bit more useful than 2, 4 slightly more than 3 etc. It’s only when you get up to 40 do you merit being included in the Guinness book of records or something and any notable increase in value occurs.

Never-the-less, being a polyglot is proven to be great for your brain (bilingual people don’t go senile or something), and hacking is a great approach to business. I’d say these two skills work well to leverage other skills – e.g. if you are good at presenting, sales and have lived in China, then speaking the extra languages is going to leverage those skills further.

Teaching in Japan

Let’s start with the obvious: Japan isn’t a cheap country. Especially if you compare it to it’s much, much cheaper Asian alternatives, Japan is definitely on the pricier end of the spectrum. That being said, however, Japan is an amazing country unlike anywhere else. Below are some cities besides Tokyo, naturally the most famous, where teaching English is a possibility and you might save some more cash than in the expensive capital:

The Saitama/Chiba/Kanagawa prefectures

Saitama Temple In Japan

So these places aren’t exactly “cities” but they’re definitely worth mentioning. Many Japanese people who can’t afford to live within Tokyo itself opt to live in some of its surrounding prefectures – Saitama, Chiba, or Kanagawa – instead. Why? Rent is considerably cheaper in these surrounding areas and the commute is easy with Tokyo being less than an hour away. The public transportation system is extensive in these areas, meaning you won’t be living in the big city, but you also won’t be living in the middle of nowhere. Some English language schools have expanded into these areas as well (especially Kanagawa) so you might not even have to commute too far everyday.


Nagoya Subway

Located in Aichi prefecture, Nagoya is the third largest city in Japan. For those of you who still wish to live in a city, Nagoya could be a great option. It’s bustling with life, has great sightseeing locations, and is well known within Japan for its unique cuisine. Of course, being a city, it will still be somewhat more expensive than living in a more remote area of Japan. But that being said, it would still be cheaper than Tokyo or Osaka, and English language schools are abundant.

The Kansai region (Kyoto/Osaka/Kobe)

Teach in Osaka

I’ve clumped these three cities together, mostly because they pretty much can be seen as a continuous metropolis. Of course, living in the center any of these three cities can get pricey, especially Osaka or Kyoto. However, a little known secret is that living in the suburban areas between these cities can cut your living costs substantially. It might be a bit (okay, a lot) quieter than living in the exciting heart of Osaka, one of the liveliest cities in Japan, but the subway and railway systems stop frequently in-between the cities as well, making it easy to commute or visit any of the exciting areas nearby within the hour by local transportation.


Teach in Sapporo

For those of you who prefer a quieter lifestyle, perhaps more immersed in nature, Sapporo could be for you. Sapporo is the capital city of the Hokkaido Island up north and is known for its fresh seafood, great produce, and skiing resorts. Though winter can get chilly, the island itself is beautiful and full of nature – and much, much cheaper than the other cities on the other Japanese islands. Sapporo itself is the fourth largest city in Japan, which means English teaching jobs are still possible to find.


Fukuoka Temple

The southern city of Fukuoka has been gaining popularity over the past few years both in and outside Japan as an overall cool city to live in, and was even ranked this year in lifestyle magazine Monocle’s “Most Livable Cities” at #13. Though it might be a bit far from the well-known cities of Osaka or Tokyo (you’d have to fly there), Fukuoka has much excitement to offer, known for its yummy cuisine and fun festivals. Though it is a fairly populated city, it’s known for it’s generally cheaper costs of living; for example, the locals enjoy grabbing a bite at one of the many, many street stalls, which can definitely cut your daily expenses.