Regardless of the fact that I’ve been to “The Land of Smiles” many times before, the nightmarishly long flight from the midwestern United States (18–21 hours) is always the most unpleasant part of my experience. Perhaps the only unpleasant part. Well, that and the occasional misunderstandings that can be chalked up to cultural differences. There’s a common saying in Thailand — ไม่เป็นไร. Some pronounce it “Mai Pen Rai”, others “Mai Pen Lai”. There’s this thing with “L”s and “R”s in the Thai language that I haven’t been able to completely understand. Mostly because I suck at languages. My four-year old speaks better Thai than me. Anyway, it means “don’t worry about it” or “no problem,” which expresses the national sentiment perfectly. In my experience, Thais are very much laid back, happy, and optimistic people. As a visiting foreigner (also known as a “farang”) you should attempt to adopt this way of life as well. I’m still working on that myself. But it really helps you manage day-to-day life. For example, take the following experience I had at a beachside restaurant on Kho Samed. This exchange is not exaggerated, nor is it unique:

⁠Asks server about several different shake flavors on the menu, none of them are available.

⁠⁠⁠Orders the one shake available — pineapple.

⁠⁠⁠Server returns with a shake.

server: Banana shake?

me: Uh, I ordered a pineapple shake.

server: Yes, pineapple. This is a pineapple shake.

⁠⁠Shake tastes like neither pineapple nor banana. Another server returns.

me: This shake doesn’t taste anything like pineapple.

server: We don’t have pineapple shakes.

Ah yes, mai pen lai your frustrations away! It really does work. But honestly, is this sort of thing worth getting frustrated about? Is this how we should spend our lives, getting angry about drink mishaps? And that leads to why I enjoy visiting Thailand, and why I miss the country terribly when I leave. In addition to the awesome weather (especially compared to the god-awful shit weather I’m used to back in Wisconsin) Thais really get it. People are important. Not to say that Thais don’t like things. Of course they do — just like everyone else. But I always feel this overwhelming sense of community, especially in the less touristy areas, such as the Northeast where I spent most of my time during a three-month trip that ended in March of 2016. So that’s why I’m going to focus a good portion of this article on how I spent 2+ of my 3 month stay pushing ones and zeros across continents. Because that’s what’s really important in life, right?

I think some lessons can be learned from my experience working remotely from such a faraway location. And my most recent trip was not the only occasion that involved remote work, though it was certainly the longest. Back in 2008–2009, I worked remotely from Thailand for about 7 weeks. At that time, I was working on a one-man-project for Avid. And this time, I was employed by Widen, developing a web-based project on a several-person team. I was the only remote member, save for a work-from-home day here or there for others. I came to realize that working on a team project while residing 13 time zones away in an area with spotty mobile (and even wired) internet service was much, much different than anything I had ever experienced before. I laughed, I cried, I hurled (don’t drink the water). But most importantly, I came away with a degree of empathy for remote team members that is hard to otherwise acquire.

So, why exactly did I do this? First off, my wife and I wanted to enroll our (at the time 3-year old) son in Thai preschool. We felt it would help him to learn the language and culture. My wife is from the northeast area of Thailand, also known as Isaan. She was looking forward to spending an extended period of time with her very large extended family. And me, well, I just needed a change of scene. I always came back from Thailand with a fresh new outlook, and figured this could perhaps have a positive effect on my work. Maybe it could even reverse my increasingly cynical outlook. But also, I had a feeling that this experience was going to be different enough from previous trips, and maybe I’d come back with some useful wisdom to share with others.

One of many co-working spaces I visited in Chiang Mai, which is considered to be one of the top places to work remotely in the world.

The benefits of working from home back in the states were already well known to me. Good things include:

Less distractions. At least distractions are easier to control. Unless you count packs of rabid dogs, passing elephants, and karaoke bars that shake the walls of your residence until morning. Well, I don’t. That’s part of Thailand’s charm that I find so enthralling. Sure, you can head to the office and grab an empty room to work without distractions, until someone finds you, or needs to use the room. And, sorry, but it’s kind of awkward to move my laptop into a meeting room. Why do I have a desk anyway? When you’re remote, it feels natural to work whenever and wherever. Communication happens on your terms, and interruptions seem to be easier to avoid. More freedom to see the fam. When I drive to work, I see my son for about 30 seconds before he gets on the bus for preschool. And when I return at 6:30pm, I see him for another 45 minutes before he heads to bed. So yea, 45 minutes a day, tops. When I’m remote, I get to see my son hop off the bus at 11:30am. I get to take a break and read him a book. I get to talk to my wife at lunch not via text messaging. I can even work from Chicago and hang out with my parents or sisters after work. And while in Thailand, I get to spend time with my in-laws, even if I don’t understand most of what they say. Working in a comfortable location and being able to switch locations is compelling. If I’m stuck in an office, my choices are my desk, or that one room with the beanbag chair. Or maybe the one with the kegerator. Because the dull hum of a fridge does wonders for my productivity. In all fairness, it’s hard to care after partaking in a few beers from said fridge. My point is, I have many more options outside of HQ. I can work at a coffee shop, or my basement, or the passenger seat of a car while my wife dodges dogs, samlaws, weaving motorbikes, and meth-fueled truck drivers on the Thai countryside. I can even work from the middle of a field, so sprawling that I lose my sense of direction. Or perhaps the table of a roadside restaurant (a full meal + a soda for a couple dollars). The choices are endless, and the freedom and flexibility is refreshing. No lost time traveling — unless I want to travel. My commute from Johnson Creek, WI to Madison is nothing to write home about — 30 minutes of open road with little to no traffic, many people have it much worse. But then there’s also the 3o minutes on the return trip. That is an hour wasted in transit. An hour is an hour. Oh, what I could do with that extra hour. When I’m remote, I’m already at the office. And Widen makes this even easier by giving me one of these. My Verizon hotspot doesn’t work so well in Thailand, but who cares? Data is dirt-cheap, so I can tether to my phone from a table next to the street in front of my wife’s cousin’s house. And every establishment seems to have WiFi, so I’m able to roam from shop to shop. I can work from almost anywhere, even far outside of the big city.

I could never get this sort of “perspective” back home. Only in Pattaya!

There are even more benefits when working from a faraway location. Such as:

New perspective(s). There’s something different about debugging a web app from the back of a pickup truck next to a group of people cutting papayas with machetes as the truck careens over bumps and swerves across lanes of traffic. It makes you think about shit. Being surrounded by individuals completely different from yourself in every conceivable way, this gives you perspective. It makes you realize that there is more to the world than your own sanitized and choreographed daily routine. Perhaps this makes you a more well-rounded person, and certainly this has some effect on your career. When you move from a 1 Gbps synchronous internet pipe with 20ms latency to 1 Mbps down and god-knows-what up with 300ms+ latency, you start to realize that the extra 200 KB for that badass parallax effect may not be a great idea after all. Even less distractions, since most communication is not realtime. This gives you the opportunity to respond to messages on your own terms, at your own pace. If you hate meetings (like me), guess what? You’ll miss ’em all with a time difference of 13 hours. Yes, this can be bad, but this is the “good things” section, remember? We’ll cover doom and gloom shortly. Until then, take respite in this short-lived win. You don’t have the constant dinging of your inbox when it’s 3am at the home office. Now you can focus on actually getting something done, right after your hour-long $10 Thai massage.

For each good thing, there is a matching bad thing. Occasionally working from home gave me glimpses of the potential perils of remote work. Working remotely for three straight months fully exposed and magnified each and every one:

Disconnected from in-office employees. This breeds frustration, lots of frustration. Instead of a team member, you’re more of a consultant. All interactions with other employees are scheduled and filtered. I’m not exactly a social butterfly myself, but even I felt like an outsider after the first few weeks. The coldness only increased with time. It’s tough to feel sorry for someone working in a tropical paradise while you’re stuck battling the snowpocalypse. And this can be a big problem with long-term remote working arrangements. There’s very little empathy from the in-office employees. They simply can’t relate unless they’ve been on the other end. Constantly behind everyone else in terms of “what’s going on”. At Widen, our teams are grouped together in “pods”. Three or four desks facing each other. And while pods do occasionally communicate via Slack, it’s only natural to start an actual conversation with the rest of the team. You know, like with your voice box and such. Even for us introverts (INTJ) it’s only natural to resort to hallway conversations when sorting out a critical issue or working through details of a planned product feature. It’s a quick way to get everyone on the same page, except for the remote employees. They have to find out that the planned implementation has changed the hard way. It seems like a game of 20 questions is required before necessary information can be extracted from the in-office employees. And often, the remote employee may not even know that something has changed, because no one documented the agreed-upon pivot. I speak from experience, being both a victim and a perpetrator myself. And the lack of information isn’t limited to project work. When you’re remote, you lose out on all of the hallway conversations. I remember only hearing about an employee’s planned departure quite a while after it was announced. An extra generous Christmas bonus, given to all employees, was also a bit of knowledge that I acquired only by accident. Constantly being behind the rest of the office, and your team, is frustrating and demoralizing. This, as I learned, was another downside to long-term remote work in an otherwise centrally located company. Text is not enough to communicate, but video discussions can be awkward and inconvenient. It’s now almost 2017 and we still haven’t figured out video conferencing. Self-driving electric cars? Check. All the knowledge in the world throughout all of history accessible via a device that fits in your hand? Check. Getting two $3,000 laptops with HD cameras to communicate via video over a pristine internet connection? Not even close. We’re decades away from the technology needed to solve this problem apparently, because I have never been in a meeting where half the goddamn hour wasn’t spent screwing with Goto Meeting, or Google Hangouts, or (insert one of the other 10 million video conferencing services, none of which actually work). Can you hear me? No, obviously not. Restart the computer. Now everyone in the room can’t hear me. Can someone do something about that feedback? I can’t see your screen. Wait how do you share your screen? Hmm, that didn’t work. Oh, now I can’t hear you again. Can everyone speak louder please?! Sigh. All of this fiddling with technology slows down the meeting and frustrates everyone. Honestly, one-to-one communication via phone or Slack calls seems to work well enough. But group conferences? Good luck. Sense of being a burden to everyone in the office. Thanks to you, all meetings you are invited to must include a hangout, which requires prep time, and as we already discussed, video conferences never go smoothly. Don’t get me started on that one again. Also, extra effort is required of in-office employees to communicate with you. More documentation is required. Again, word-of-mouth or hallway conversations cause problems, so we can’t rely on those alone. All of these little (or sometimes big) inconveniences build up, and suddenly you seem like the problem. If you would just come into the office, life would be easier for the rest of the team. Well, wouldn’t it? The relationship becomes adversarial, or so it seems. I can remember feeling bad about enjoying my time working from Thailand. You shouldn’t feel like a bad person for exercising your right to work from home (provided your employer has already given you this opportunity). But you’re only human.

This sometimes felt like my internet connection, narrow and unstable.

Just as there are even more benefits when working from a faraway location, this arrangement also introduces unique problems. For example: