A talk with Simon Baumer on working remotely, island life, and cultural adaptions in Kyoto, Japan.


Simon Baumer and I have known each other for 15 years. He has been working remotely for the last 10 years: 8 in Oahu, HI and the last 2 in Kyoto, Japan...

Thanks for sitting down with me before the workday starts. You used to live here in the city, what brought you to New York?
After college, I lived in NY for about 3 years. For me, there was a lot of opportunity, because I went to high school nearby and college in the state. There was a confluence of all my different lives all in once place, so my network was pretty good. It was the place to go.

For sure, and what did or do you like about New York?
I like the fact that you can get world class cuisine within 30 minutes. And it’s not like there’s just one place, there's expensive fine dining and good cheap food. Compared to any other city in America, that's really important.

Also, I don’t know that there’s a more diverse place in the world, in a very small area there are a lot of people from different backgrounds and places, and it doesn’t interfere with everyone doing what they’re doing and how they’re living. It’s a nice feeling. You get used to fitting in. They say it never sleeps and it really doesn’t. You never forget you’re alive, because you have near death experiences every day but also there’s life all around you.

To counter, what didn’t you like?
All the people I knew, that network, was a challenge. My personality type is such that I’m terrible at saying no, and that’s problematic when you’re around people and a lot of asks. You end up living a life that isn’t really your own.

People work too much here. In general, I don’t think people have a healthy balance of life and work, especially with expenses. People work more to make more in order to afford what’s here.

So, you moved to Hawaii. Why Hawaii?
It was America, no new language, I didn't have to deal with visas or employment because I was freelancing. No winters. My grandfather lived in Hawaii, and my parents ended up retiring to Honolulu to be near him, so I could see them whenever.

You were there for 8 years, what did you love best about living there?
I loved it and I love everything about it.

Top 3 things about Hawaii, what would they be?

  1. The ocean in Hawaii because it’s everywhere, it’s warm all year round, and there’s a lot of life in and around the ocean. Ocean culture.
  2. Weather.
  3. I’m not sure what the right word is… the timing. People work to live, they don’t work to have. This is painting with a broad brush, but you work, it’s 5pm, you go to the beach. Money isn’t about getting more, it’s about enough to live.

What was the most common thing that people would say when they heard you lived in Hawaii?
“Aw man, you’re so lucky.” or, “Aw man I hate you.” Verbal jealousy.

For those who wished they could do it too, what did you say back?
I usually had a reply: You can buy a one way plane ticket and that’s a good start, or a roundtrip because it’s the same price.

Did anyone ever critique you in some capacity for moving to Hawaii and leaving life in New York?
Definitely people saw a selfishness in it. Though my parents and grandparents were there, I would have gone anyway. No one ever outright called me selfish but would elude to the fact that they had commitments that wouldn’t allow themselves to move. Some people thought I couldn’t cut it in NY, and I agree, I couldn’t cut it in NY. I absolutely could not. But it didn’t bother me, I didn’t want to live that way.

Olomana hike on Oahu, also known as "Three Peaks".

You initially worked remotely doing freelance?
Yes, the first 2.5 years I was 100% freelance for east coast nonprofits. People still piped me development gigs.

And you worked as...
At the time I was a frontend and backend web developer.

Would you say that working remotely is challenging?
Hawaii is 5-6 hours behind EST, so as a developer I would work with a project manager in the morning, and then would do developing at night. There are definitely the occasional odd hours.

For the first 2 months that I moved to Hawaii, I didn’t go to the beach once because I just wanted to work. It was important to me that the networks I had relying on me didn’t associate moving to HI as a distraction. So, I spent the first 60 days doing all the work as fast as I could so all their concerns would be discarded. It seemed like torture at the time but I think it was a good investment.

You worked from home all that time?
Yes, the whole time. About 6 years in, I rented an office space but ended up not using it enough to make it worth it.

Did you ever have to schedule time to leave your house?
No, the time difference was ideal because I’d work mostly in the morning so by noon it was 6pm EST and then I’d get lunch, eat on the beach, read a book, take the dog for a walk, and then in the evening I’d put in 4 hours of solid development time, working with zero distractions.

So then you moved to Kyoto with your wife, Voni. Can you speak to that decision to move. Why Japan?
I grew up in Tokyo from ages 8-13, when Voni and I went to Japan to visit, she really loved Kyoto. At the time she was a teacher’s assistant at a school in Hawaii and an independent contractor for skills development, and decided she wanted to work at an international school in Japan.

How was that process?
She found a posting looking for someone who was already living in Japan, so we pretended she lived there. They asked her for a test lesson and videotaped it with myself, my parents, and our friend Brian, all pretending to be 5 year olds.

I know that the transition to move wasn’t very easy, it was difficult to find a place that allowed dogs, and even getting wifi was incredibly hard. But you managed to find a beautiful, traditional Japanese house in Sakyo-Ku neighborhood. Tell us about your hood…
We live in a mostly residential area, close to Kyoto University and a 15 minute bike ride from downtown Kyoto, where most of the retail and business establishments are. Our house is 100 years old. We have a neighborhood pork butcher, beef butcher, 2 fishmongers…

It’s quaint, old school, quiet Japan, in the midst of a greater, more active and vibrant metropolis.

Are there many other Westerners?
We’re probably one of two foreigners within the 200-300 building area around us. We see foreigners more often in our neighborhood but they’re mostly university students commuting.

How are your Japanese neighbors?
They’re wonderful neighbors, very warm and welcoming. They’ve had us over for dinners, despite the fact that there’s a significant language barrier.

I remember a neighbor rang your doorbell and presented you with cooked sweet potatoes. Can you talk about the Japanese gift culture?Japan is a gift culture. If you travel anywhere, you typically bring back consumables that are famous from whatever area you went to.

We have a pretty informal relationship with our neighbors, like we’ll bring them chicken wings in saran wrap, which is very not Japanese. And yes, they brought sweet potatoes wrapped in tin foil because we’re foreigners. We can both break the social norms without losing face or shame. We aren’t expected to know any better, and the assumption is that we don't know either.

Why is it food? I mean I love food, but why is that the thing?
I guess other goods can survive traditional transport but food has to be brought immediately or it perishes, historically. Also in Japan specifically, a lot of food is regionally produced and it’s not distributed. They’ve been into “eat local” before it was a slogan in America.

What happens when you get a gift? Do you have to give a gift back?
If someone has traveled and brought you a gift - you don't have to give a gift back, no. The expectation is when you travel you'll bring a gift back. ​

"Mon" Simon's favorite restaurant in Kyoto. Here is the Chankonabe aka Sumo Wrestler Hot Pot.

Was there anything that you really had to adapt to? No feigning ignorance on?
We bought a house and had to do a lot of renovations. In the process of talking to the contractors, we’d ask if we could do something and many times the response would be “That would be difficult.” When I hear that, I think “That’s great, it can be done, there’s a way.” But what it really means is “No.”

They have a very hard time telling people no, so they look for other ways to say no. Saying no would bring shame to you. It took us a while to figure that out, we were in that situation many times.

So, before you knew it meant no, would you push them?
Absolutely. We’d say things like “Ok we’ll pay more.”

Would they then do it, what would happen?
In some instances, they would look for ways to do it. But usually they’d present all the caveats in doing it and we would just give up.

Do you think it’s important to adapt to the cultural norms where you’re living?
Absolutely. It’s the path of least resistance. If you stay the way you were, then why are you there?

What about Voni? Does she have the same mentality?
Yes, especially now when she is a tourist elsewhere, she’s more aware of herself in a foreign place.

As an American or as herself as a human?
Both. She has a tattoo sleeve, which she covers all the time because having a tattoo has a specific connotation for Japanese people that it doesn’t have in America. There are many times I’d say you don’t have to wear a long sleeve shirt, you’re not from here, but she feels that because she’s living there, she should treat that with observance.

Do you think you’ll ever move back to the States?

New York?


Do you see yourself moving back there?
I think pretty soon, I won’t live in just one place for the whole year. In my life, I’m 33, I think I know enough about my nature that being in one place for an extended period of time doesn’t help me thrive.

Thanks so much, Simon. Any pieces of advice to those who want to live the dream?
Yes. If you have a good family, they’ll love you no matter what so don’t let their guilt stop you from trying to live your dream.