Working 9,000 Miles From Home

On a three month work/pleasure trip to Thailand, I learned some important lessons as I maintained a software project alongside a team based in the U.S. The benefits and drawbacks of typical remote work were amplified, and helped me settle on a number of ways to improve remote work culture for colocated companies.

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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:

  1. 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.
  2. 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.
  3. 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.
  4. 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.
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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:

  1. 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.
  2. 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:

  1. 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.
  2. 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.
  3. 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.
  4. 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.
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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:

  1. It can be very difficult to attend any meetings. Again, just to clear the air here, I hate meetings. Most wander aimlessly with no resolution and everyone ends up wasting an hour of their life that they will never get back. It’s not a company-specific problem. I can actually hear you nodding your heads collectively. Of course, it doesn’t have to be this way, but that’s another article. So, as much as I generally try to avoid meetings, some are actually important. There are even some that I enjoy attending, or rather some that produce notable value. But when I was working from Thailand, I had a very small window of time to attend meetings due to the 13-hour time difference. Inevitably, that rare important meeting was scheduled for 2pm central time, which was 3am my time. And believe me, I was thrilled to have an excuse to miss all of my meetings, at least for the first few weeks, and maybe even for the first month or so. Sorry, that’s like the middle of the night for me, can’t make it, but do send me the minutes. ~Ding!~ . “Re: Meeting about the meeting about the meeting.” Delete. But then something strange happened. That feeling of being disconnected set in. I felt like I had no idea what was going on with my team, or my project, or my company. I found myself going out of my way to attend meetings. I even called in to several meetings at 3am my time. Multi-hour-long meetings. While running away from packs of angry rabid dogs on the streets of rural Thailand. The attendees on the other end can vouch for this.
  2. Most communication is out-of-band. This becomes more significant as you venture further away from home base. In my case there was often a significant delay between question and response. I’d send out a message at 9am Bangkok time (8pm central) and wait for a response, which wouldn’t come in until about 12 hours later (9pm my time, 8am central), which I would not see until the next morning. The time difference alone made it very difficult to carry on an effective “conversation”. And this was compounded by the fact that digital communication is commonly terse. If a response to my question came in devoid of appropriate detail, I’d have to wait another day for clarification. The importance of gathering my thoughts and all important information into a single response was apparent to me, but less so to everyone else back at HQ. Not that I blame anyone. It’s hard to empathize without an appropriate frame of reference.
  3. Possible internet issues, depending on the location. Internet stability and speed can be critical. Outside of exceptionally remote locations, I’ve found mobile, and especially wired internet access, to be reliable and fast across my home country. In Thailand, this is also true, but to a lesser extent. Bangkok, Pattaya, Chiang Mai, Udon Thani, and areas outside of bigger cities have acceptable mobile and wired internet. Mobile internet is very cheap, but outside of those larger areas, it’s often unbearably slow, at least in my experience. 4G is very hard to come by, and even when my phone reported “4G/LTE”, I was often only seeing speeds of 1 Mbps down, and many times even less. Even wired internet can be hit or miss, but this may have been partly due to my reliance on shared WiFi. Latency was much higher, and general network reliability seemed to be worse as well. This, of course, made video conferencing, an already awkward and touchy medium, much more frustrating.

Remote work can be very rewarding and convenient, but in the longer term, and with more distance from the home office, cracks start to appear. Some of the issues I covered above are substantial ones. They’re even big enough for some to consider avoiding longer-term (or permanent) remote work. In fact, I was in this camp after returning from my trip. My experience, as I saw it, was a failure. But after the dust settled, I began to ponder and investigate solutions to these problems. Good news: there is hope. Bad news: it may not be easy to make the required changes, especially for companies with colocation firmly entrenched in their culture. As part of the post-mortem, I identified five specific ways in which remote work culture can start to thrive, or at least improve:

  1. When one team member is remote, everyone must be remote. This is not my original idea, but I honestly can’t recall the source. Regardless, this is crucial. I noticed that I felt much more connected when the entire team was working remotely. Our Slack channel was lively. One-on-one video conferences were more abundant. JIRA cases were updated with details and comments more frequently. On days where it was just me, quite the opposite. Now I’m not suggesting that everyone on a team has to actually work remotely if one member chooses to do so, nor should colocated employees have to avoid speaking to each other outside of Slack or group video/audio chats. This is all about state of mind. If colocated employees are able to empathize with the remote ones by taking the time to ensure important information and conversations are accessible to everyone, most of the problems outlined above simply go away. The rest of my list focuses more on specifics, but they all tie back to this first general concept.
  2. If you really want to promote remote work, focus on documentation to share information. Slack is a very good step in this direction. Encourage everyone to share information on Slack. Ensure your team has its own channel, but make it easy for anyone to join any channel and get answers to questions quickly, or simply observe. Ban private channels, there’s no need for group secrets in a distributed organization. And if email works better for you (for me, it most certainly does not) then I suppose mailing lists à la Google Groups are a reasonable choice. But important information tends to get lost in chat rooms and mailing lists. So is may be helpful to maintain an easily searchable, browsable, and editable repository of documents. Google Drive doesn’t really fill this need in my experience. Some sort of wiki such as Confluence or Crowdbase is probably more appropriate. Another frustration I had while working remotely was lack of cohesive documentation of project feature cases. We use JIRA to track project features, bugs, and tasks. Sometimes, during story pointing sessions, important details discussed among team members were left out of the notes or not organized in a readable manner. Even worse, later discussions that ultimately influenced the direction of stories often did not result in appropriate updates to the underlying JIRA case. For those already in the know and part of these conversations — no big deal. But for remote employees, plenty of time is wasted sorting out the details later. In short, it’s fine to have actual conversations, but leave a paper trail. Not only for remote workers, but for people like me with terrible memory. As an added bonus, taking the time to properly document cases gives you time to reflect, and, in my experience, this tends to reveal flaws that would otherwise have not been discovered until later on in the process.
  3. Record everything. Well, maybe not everything. No need to turn the office into The Truman Show, but certainly record the important stuff — meetings, presentations, and announcements. Use a decent camera, and a good mic. Make sure it’s easy for individuals and teams to record their own presentations and meetings. Uploading and searching for these recordings should be trivial as well. Post links to these recordings in the appropriate Slack channels or mailing lists. Automate this. Automate as much of this as possible so it just happens. Remote employees can then have the freedom to at least observe important discussions on their own schedule. This seems especially crucial for widely distributed teams.
  4. Work tirelessly to make video conferencing painless and natural. I honestly don’t exactly know how to perfect video conferencing. It’s an unsolved problem in my mind. At the very least, a fair amount of research is in order to find the proper technology for your organization. And it all has to be insanely easy to use. Click something or press a button, and the conference starts. Screen sharing must be easy too. Use auto-tracking video cameras for meetings and events with Q&A. Make sure you have access to exceptional microphones too. We use this Blue Omnidirectional Yeti mic at Widen. It’s amazing — buy several now. The mic built into your laptop is shit for meetings. Please don’t cheap out on this.
  5. When in the office, communication “just for the hell of it” can normally be a distraction. But it really helps to keep remote employees connected. I personally (even more so than usual) looked forward to one-on-one video chats with my boss while I was overseas. It was a rare opportunity to re-connect to the home office. And this is coming from someone who isn’t particularly social and generally avoids small talk and general pleasantries. Interestingly, when I discussed my remote work experiences with another employee, I received confirmation on this point based on this person’s recent long-term remote work venture. Any sort of welfare check is helpful, from a boss or even a team member. This is especially hard for me to do, but it’s much more top-of-mind now.
Nothing more refreshing after a long absence to find that your desk has been relocated to the coat room.

I’ve given you a lot to think about. Actually, I’ve given myself a lot to think about, as I’ve been somewhat delinquent in pushing required changes inside my own company. Offering the ability to work from home, beach, or tuk-tuk is a compelling one for many employees. But it’s never as easy as saying “it’s ok to work remotely.” If your company’s culture revolves around colocation, you may find that this previously vibrant and compelling atmosphere actually alienates your remote workforce. But fear not, you can patch the holes and make your office much more remote friendly, as long as you and all of your coworkers have the same goal in mind.

Benevolent Dictator For Life of @FineUploader. Author of ‘Beyond jQuery’ Read more of my writing at

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