A retrospective on working remotely 5000 miles away

I’ve recently returned to Philadelphia after spending a month in Argentina and Uruguay. I thought folks might find a retrospective interesting.

Why?

Last year, I quit winter for the first time with my friend Kelly, renting an apartment on an island off the coast of Belize. This year, especially because of the wonderful friends I made at Recurse Center, I wanted a longer trip. Especially since my door-to-door trip took about 18 hours, it was a swell idea to spend a while in the Southern hemisphere. Plus now the weather forecast here at home looks like this:

If you are in/of Philadelphia or the East coast, you will note that is unseasonable. I DON’T MIND.

How?

Well first you buy a plane ticket …

No really, the how is a lot easier done than most people believe.

I am not a freelancer, nor would I say I am a “digital nomad.” I am a person, with a full-time software engineering job, with a life partner, apartment, cat, and lots of friends in Philadelphia.

If you have the ability (some people would call it a “benefit”) to work remotely, you can work remotely in another place. Last year’s test run in Belize gave me the confidence to go for a longer span this year, and I think 4-6 weeks might be my optimal anti-winter span. I feel healthier, got to spend lots of time with friends abroad, and also you know, hanging out in Argentina and Uruguay was pretty cool.

Boring utilitarian things that you need to work remotely from not-your-home:

• VPN access if you have a restricted network (work at home ever? already have this!)
• Team willing and able to involve remote workers (work at home ever? already have this!)
• Consistent and reliable internet access

Note that 2/3 of these things are things you already have if you ever work from home; the third item largely depends on the location you visit.

Challenges & Lessons

Timezones!

Well, I feel like an idiot for this one.

I thought Buenos Aires was in the Eastern, if not the Central, timezone, because I “remembered” that “most of” Latin America was Central or Eastern. Oh ho, I was wrong, and only realized this 3 weeks before the trip started. No way to turn back really.

When working remotely, to make it very easy to pitch to the Powers That Be, I prioritize working in friendly timezones. For the US, that limits winter escapes to Central and South America.

Turns out, B.A. is two hours ahead of the East coast, so I started my days around 11am and finished around 7pm. This worked out fine based on when my friends were working (and that people eat dinner starting at 9pm in B.A.) but I wish I had known ahead of time.

Coworking and intentional workspaces are a great idea (but do research)

I joined a coworking space for some of my time in Buenos Aires and it was great! I was so productive when working in an intentional workspace. Easy access to water/tea/conference room was also nice. There were some downsides though.

For one, I didn’t email the coworking space ahead of time, mostly because I was embarassed that I’d have to write in English rather than Spanish. This was a mistake, as the coworking space (while nice!) that someone recommended to me was not prepared/welcoming to drop-ins, and they basically had to scramble and do a bunch of annoying work in order to get me a 5 day pass. Even as I enjoyed my time there, I felt guilty for imposing. PLUS the space was not as international as it was in the past, and so there was little opportunity to meet other people as I had hoped. BUMMER.

I would still recommend coworking spaces and more so intentional workspaces – when working in the AirBnB with my travel buddy, it felt like an impromptu coworking space. When working from my friend’s house, I worried about being disruptive to people at home. Have a place where you plan to work.

Remote machines are a great idea

This is a bit specific to my particular internet troubles, but last year much of my work involved web development. I could run my local server offline, work on some stuff, get connected to the network, push a changeset up, you get the idea. My current role involves a lot more of “let’s SSH into a server and do a thing!” which is sometimes … not great on the internet connections I was on. Another plus to the coworking space, but can also be a minus if the space was full.

I really wish more of our automated tooling was hooked up (it is now … that I’m back in Philadelphia) to do work on remote machines.

I suppose the lesson here is to think about the kind of work you do carefully so you can do it while you’re away.

Clear the country(ies) with your company

I only found this out this year because apparently my managers have taken care of it without my knowledge (thanks, managers!) but you might need to let security know that you’re leaving the country. For example, chances are very good you shouldn’t go work remotely in China, and it would probably violate your company’s security policy.

During my trip, we decided to work a week in Uruguay, which was complicated because er, I didn’t tell anyone I was changing countries until “bye! getting on a boat to Uruguay!” Don’t be like me!

Take enough time off

For one, it prevents people from badgering you when you get back over whether you “took time off” or not. People have a hard time believing me that I truly truly just want to work somewhere where it’s warm and NOT be in Philadelphia when it’s cold. Taking the first day or so to adjust to the local area and adventure around is a good idea.

Also giving this tip allows me to post the gratuitous picture of our trip to visit a glacier in Patagonia. For the record, it was actually fairly warm that day.

Summary

Anti-Winter 2016 was a rousing success!! I really like working remotely not-here and had really enjoyed getting to visit my friend Benni and his wonderful family in Buenos Aires. Extra bonus that Gonçalo came too and we were able to travel together and make the trip to Patagonia!

Also a side thing that I’m proud of: I didn’t make a budget, but I did track everything I spent, and in the end, the spend came in at about what I hoped, considering the extra trip to Patagonia (that is, an extra flight, hostel, and a glacier tour).