The Many Faces of Success: Japanese Vagabond – Fighter and Freelancer

“We think of success as only measured by your money. / But, money never lasts. / In fact, it’s only last / on the list of impactful things you can ask for / …So, with that – we need us a plan…” – Wale, The Perfect Plan

Welcome to The Many Faces of Success Interview Series: a reoccurring interview series focusing on success in many forms. From entrepreneurs to writers, to travelers who are just living the life they want to live…in this interview series I sit down with people who are living and defining their own success on their own terms, people who I find inspiring, and whose stories I find interesting enough to share here.

In today’s post I sit down with fellow traveler and blogger, Masafumi Matsumoto. Masa is originally from Japan, but has been travelling and living abroad for over a year now, mainly in Southeast Asia. His blog at is a place where he shares his writings: “writings on life and love.” He describes himself as “a Brazilian Jiu Jitsu fighter, vagabond, translator, copywriter, lover of life and beauty, and curious learner.”

I caught up with him while we were both staying in Taipei and he was willing to be the “guinea pig” in the Many Faces of Success Interview Series.


Masafumi Matsumoto

Masafumi Matsumoto

Here is his story:


William: You’ve been traveling for awhile now. What initially inspired you to leave Japan and live on the road?

Masa: That’s a tough question actually. Somehow I was interested in living this kind of lifestyle. If I think about it, when I was a high school student one of my teachers asked me what I was going to do when I finish University. I was planning to study Philosophy. That was in 2001, so about 12 years ago. I hadn’t heard of digital nomads or anything like that, and I don’t think there were many then. But, when he asked me that question, I thought that maybe in 10 years or so the internet will be much more available. So, maybe I will be able to work from anywhere and maybe I will be a writer or something.

So I had a kind of vision, but I didn’t take it seriously really.

I think my first real inspiration was Chris Guillebeau when he published his free ebook, A Brief Guide to World Domination. I think it was 2007, 2008 maybe. I got to know about about Chris and what he was doing and it made me realize that that kind of lifestyle was a real possibility  There’s someone doing it!

So, I think Chris was my first real inspiration to make this kind of lifestyle happen. I think it was also around the time when Tim Ferriss published his book, The 4 Hour Workweek.

Ok. So you mention in 2001 you thought about it, then in 2007 you heard about Chris and that’s when you really got inspired. What where you doing between that time?

Well, I was in Australia. Thats where I went to University. Around that time I was trying to become a freelance translator. I mean that was the only thing I knew I could freelance and make money and I knew I was at least okay with my translation skills.

You got into translation because you were bilingual?

Yes. To be honest, I didnt think much about other possibilties, like copywriting for example.

Right now I’m starting my own copywriting service. I think I have a very good background for it, and once I got started, and got a little experience I could see that I would actually be quite good at copywriting. And I actually do enjoy copywriting a little more than translation.

Yeah, I guess copywriting allows you to be a little more creative, allows you to tell a story through your copy…

Yeah, and of course being a freelance translator gives you flexibility and freedom without the pressure of time. Well, that’s not always the case sometimes you have a tight deadline and you have to submit before the deadline. So you have irregular work hours.

How long have you been doing translation?

Almost 4 years now.

Ok. And, how long have you been traveling and living on the road?

I started traveling extensively since February last year. But I did a “mini-travel” for one month in 2011. So, I think that was a good test for whether I could support myself with translation and live this lifestyle.

So you’ve been doing freelance translation to support yourself and now you’re doing copywriting as well. Is there anything else you’ve tried along the way? Any other ventures to make income you attempted while you’ve been traveling?

Not really. Well, I kind of did. I tried to some affiliate marketing and those kinds of things. But, I guess the thing is I wasn’t really intersted in – well, I was interested in making money to support myself – but I wasn’t interested in selling someone else’s products that way.

It’s not as exciting as copywriting or even translation. I mean some poeple are interested in affiliate marketing and these kinds of things – but for me, not so much.

Now, I know another thing you are very passionate about is Brazilian Jiu Jitsu. Do you train in every city you stay in while you travel?

Yes, that is the case. And, I know I mentioned Chris Guillebeau as an inspiration earlier, but another inspiration when I started travelling was Christian Graugart. He wrote a blog called BJJ Globetrotter, and when I saw that I thought it would pretty cool to incorporate into my travel and lifestyle as well. Because Brazilian Jiu Jitsu is something I have practiced for 11 years now.

Ok, yeah I have heard a lot of good things about martial arts and Brazilian Jiu Jitsu in particular. How do you think BJJ has affected your approach to life and affected your thought process?

Well, I think it’s really helped actually. It’s given me the discipline of working on one skill and one particular thing over and over, every single day in order to be good at it. And, I think this applies to other skills as well, and is something I have used for other skills. I have currently been working on copywriting and I handwrite ads by hand, every day, in order to build the skill. So, it’s similar I think.

Also, the point of Brazilian Jiu Jitsu is you want to be calm. Completely calm and execute effortlessly while your opponent struggles. And I think it helps to apply this to life as well. You want reach the point in your skills where you are calm and things are effortless.

Yeah, that’s a really good point. That’s something I’ve noticed a lot and something I agree with a lot as well: working hard on your skills daily until you reach the point where its simple and effortless. I can see how Brazilian Jiu Jistu would help with that. It makes perfect sense. Anyway, let’s change gears a bit and talk a bit about your writing. You write your own blog. How long have you been writing?

I’ve been writing my blog since the beginning of 2010. I started it on January 1, 2010 actually. That’s my birthday. And when I started writing I did a 12 week course – a course I got from a book I read, called The Artist’s Way by Julia Cameron. It’s a really good book actually and her premise is that you can rediscover your creativity in 12 weeks.

So, I did that, and I kept doing what she calls The Morning Pages, which is every morning after you wake up, you handwrite 3 pages of uninhibited thought. You just write for 3 pages. I did that for awhile. Not the whole time that I’ve been writing the blog, because I stopped doing it, but I’ve recently started doing it again.

Ok. So it sounds like you have a pretty good morning routine going now. You wake up everyday, handwrite 3 pages of uninhibited thought, then you handwrite copy…

Yeah, and actually, that is how I learned English as well. I mean I went to English school, but when I really improved my English, I did it by handwriting English everyday and saying what I was writing out loud. It really helped me get familiar with language and internalize the grammar and structure, ways of saying things.

And, now you write a blog in English. So what is that like: writing in your second language? Do you ever find it difficult, seeing as its not your native tongue?

Actually, I find that when I write I express myself better in English. Well, you know I went to University in Australia and I studied Philosophy  so I had to write a lot papers. I’m at a point now where I’ve been writing in English for a long time, many years. So, I can express myself better when writing English versus Japanese. I never really write Japanese actually. Only when I email my mother or something like that.

Okay. So what about speaking? Do you find it easier to express yourself when speaking in English as well?

Well, yeah, in a way. Because when I speak Japanese, I have a Japanese mind. So, I have to think about who I’m speaking with and whether I have to be very polite. Not that I’m not polite when I speak English, but its different.

Yeah, that makes sense. So, I’m curious what are your future plans? Where is this all going?

Well, I plan to continue traveling. And, I plan to be great at copywriting.

As far as travel plans, well, I’m going to Philippines soon to compete in a Brazilian Jiu Jitsu tournament. After that, I’m traveling to Europe. I’m flying to Sweden and then I plan to go to Poland, and start my own “Euro Trip” from Poland. I haven’t been to Europe yet, so I am pretty excited.

Yeah, that sounds good. Sounds like an exciting trip. Well, you have done a bit of traveling, what was your favorite place so far?

Favorite place? Oh, that’s a hard one. Cambodia was quite impressive. But as far as living? I have to say Taipei has been really good to me. Obviously when I’m travelling one of the most important things to me is that there is good Brazilian Jiu Jitsu training where I go and Taipei has been really good in that respect and there is a lot to do here as well. Yeah, Taipei has been good.


Taipei. Photo by: William Peregoy.

Taipei. (Photo by: William Peregoy.)



For more on Masa, please check out his blog at

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