Working Remotely In Software: 8 Months, 5 Countries, 4 Timezones

Joshua Saunders
Sep 10, 2019 · 7 min read
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Image for post
Photo by my wife, Jordyn. Maskeliya, Sri Lanka.

This past April my wife and I came back from a whirlwind trip around the world that we’d been on since September. My wife was working with various organizations in each country and I was given the opportunity to go with her and and work remotely full-time.

During that time I worked in the Philippines, Greece, Cyprus, Italy and Sri Lanka for 1–2 months in each location. It was my first experience working remotely for anything close to this length of time, so I wanted to outline what I learned and hopefully answer any questions you might have about working remotely as well as improve working life for both remote workers and their team members back at home.

I’ll leave a short section at the end for chatting about what we got up to in on the trip outside of work if you’re curious, but for now let’s focus on working remotely as a software developer. I’ll go through each stage of being away and what lessons I learned about working remotely there.

Feel free to skip to each “Lessons Learned” section in each segment — I won’t be offended!

Before Leaving

The biggest concern was how hard it would be to communicate. I spent the time before I left trying to figure out the hours during which the team collaborated most. It turned out to be the about 10am-1pm, so I made sure that even if I wasn’t going to be available during full regular hours, I’d be available during those core collaborative hours.

Lessons Learned

  • Start discussions well in advance. It may take time and work to get your team on board with the idea.
  • Going remote is stressful for your team. Have plenty of discussions about what you have in mind beforehand and ask what they might be worried about and make a plan for addressing their concerns.
  • Consider working during home hours. One of the hardest things about working remotely is communication and being available during their local time can really soften the blow. If it can’t be the full hours, try to determine what the most impactful hours for availability would be.

On The Road

The Philippines is also a full 12 hours ahead of home in Ottawa. I wasn’t going to be able to work full Ottawa hours of 9pm-5am, but I did do 7pm-1am and finished the remaining work during the following day. The sleep schedule took a little while to get used to but it actually wasn’t too bad. Having the day time free ended being really nice since there was much more happening in the town during the day than the late evening.

One other aspect that became apparent was that with those hours I would do during Manila day (Ottawa night), I was able to take care of critical issues during Ottawa night. In one instance, a bug was released on Ottawa Tuesday day, I noticed it and addressed it during Ottawa Tuesday night, and it was possible to ship it right away Ottawa Wednesday morning.

It was my first experience being away from the team and I definitely did miss that chatter that’d happen around our desks. Having casual conversations over Slack, having calls to sort out issues instead of text-based communication, and hopping on video when possible did a lot for bridging that presence gap.

Lessons Learned

  • Be ready for poor connection. Mobile data is pretty cheap in a lot of places outside of North America, so that’s a great backup for if wifi fails you. I don’t recommend using portable wifi services — didn’t work out for me! Using an ethernet cable instead of wifi and turning off video during calls (and audio when you’re not talking) can all really help speed things up as well if needed.
  • Be ready for having just a laptop monitor. Unless you land some special accommodations, you’ll probably be working with just your laptop. I forgot how limiting it is having just the one small screen!
  • Take advantage of timezone difference. There may be something that you can uniquely bring to the table being able to work during the local night time.
  • Use a time tracker. It’s easy to lose track of if you’ve completed your full “day” of work while working split hours. Using a time tracker like Timeneye can really help you maintain a work/life balance.
  • Be intentional catching up with the team. Ask what’s going on in the office and what they’re up to outside of work to make sure you’re maintaining a personal connection.

Mid- to End-Trip

There were many lessons learned quickly in the Philippines which continued to apply to the rest of the journey, but there were certain things I ran into as the months went on.

It became clear that I wouldn’t be able to be deeply engaged in meetings or real-time events like discussions about sudden critical issues. As time went on, though it was expected, I definitely became more out of touch with was what was going on socially in the office.

I did however find that I was actually more focused most of the time. When I came back, I noticed that there was a lot more context-switching and parallel discussions happening around me when in the office.

Lessons Learned

  • Collaborating and support is hard. You can’t go over to someone’s desk and ask if they’ve seen a particular error message before. I found it super helpful to hop on a screenshare call over Slack at times like these. If I ever had environment issues, I’d give a coworker control over my machine and have them click around just like they would in the office!
  • Leading remotely is hard. Leading an in-office team on a project from outside the office is not easy. Frequent check-ins over messaging or calls is vital to being a remote leader.
  • Figure out a consistent audio/video setup process. Instead of losing five minutes every time there’s a meeting because audio/video isn’t set up properly, book 30 minutes with your team lead to figure out how to set things up properly and write down a process to follow going forward.
  • Use video when possible. Getting some face time really helps bridge the personal distance that can grow over time.
  • Take care of your hardware. Thankfully I didn’t have many issues, but I realized that I’d be pretty out of luck if something happened to my work laptop at any point along the way!

Dear Managers Of Remote Workers

  • Check in often. See how they’re doing both in and out of work — it’s definitely much easier to have struggles go unnoticed while remote.
  • Give them talking time in meetings. Lag makes it super hard to identify when it’s a good time to speak, so calling them out for opinions is very helpful.
  • Work actively to keep up the personal connection. Have a few minutes at the end of meetings to allow for catching up with the whole team and make sure to switch between a screen share and their video call every now and then. Make a point to keep them up-to-date with office happenings as well!

Bonus: Travel Tips

  • Airbnb offers significant discounts (even up to 60%!) if you stay somewhere for 28 days or more.
  • Try packing less. We traveled with just a 35L carry-on backpack and a personal item (laptop bag) each. We didn’t even up using everything we brought!
  • Knowing someone where you’re going opens up so many opportunities for when you get there — dig up some contacts in the area if you have any and see what they’re up to!

Bonus: What We Were Doing

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Joshua Saunders

Written by

Senior software developer at Klipfolio. I love writing about all things dev and faith. linkedin.com/in/jksaunders to connect!

The Startup

Medium's largest active publication, followed by +752K people. Follow to join our community.

Joshua Saunders

Written by

Senior software developer at Klipfolio. I love writing about all things dev and faith. linkedin.com/in/jksaunders to connect!

The Startup

Medium's largest active publication, followed by +752K people. Follow to join our community.

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