I write to you from a friend’s house in Los Angeles, taking in the sunshine and warm weather. It’s a stark contrast to the bitterly cold Chicago winter I’ve been enduring for the past few months, and a primer for the tropical heat I’ll experience in Malaysia next week.
Starting with studying abroad in university, I’ve had my heart set on being in foreign lands. A mixture of new language, foods, smells, and culture makes every day an adventure. Even a transaction at the grocery store can be interesting.
However, an opportunity for experience and a steady paycheck presented itself after graduation, and with it went all hope of my expat dreams. With student loan payments looming, as per normal in the US, I was left with little choice but to accept.
It didn’t take long for me to realize that commuting on the same train every day to work, to eat at the same places and sit at the same desk, was a lifestyle I wasn’t interested in. Some folks take comfort in its predictability, but I loathed it at the time.
The weeks went on and so did my desire for change, until eventually I realized that I might be able to take my job with me and again experience the joy of living overseas — without sacrificing a paycheck.
I was 23 when I negotiated a remote work agreement and started my life abroad. Since then, I’ve traveled primarily at my own cost, but sometimes at client’s expense. I’ve procrastinated on things, made mistakes and poor choices along the way, but like anything it’s been a learning experience.
Hopefully I can pass along a few nuggets of wisdom I’ve picked up on my journey.
I began searching online about traveling and the idea of an unconventional lifestyle. It didn’t take long to find other folks who had an itch to travel and did something about it. I probably read just about every travel blog I could find.
Reading them helped fill my head with travel stories, but also with an understanding of how people started on their journeys. I took particular interest in those who maintained their professional life, and those who found a way to sustain it.
In between these lines, blog post by blog post, I began to read my story… or at least the one I wanted to write.
Create a Plan
It didn’t take long until dreams started to become plans. I began saving money and selling off my things. I decided that I’d have the negotiation with my boss around the time the lease was up on my apartment.
It was around that time I projected my savings would exceed $20k. In the event that everything went wrong, I could still leave and travel for a year on my personal savings, a “plan B” of sorts.
In the months leading up to the negotiation, I thought about some of the pros and cons of my job working abroad. In IT, we could leverage the timezone difference between our clients and my location.
You can’t take down an email system in New York during the business day for maintenance, but you can do it during business hours in Italy.
I could drop the company health insurance, which would save my boss a good chunk of change. I could help our company seem somewhat bigger by providing support coverage across multiple time zones.
There are obvious cons. With differing time zones, it makes it harder to work with colleagues or clients that are on a different continent. Your boss will need reassurance that you’re actually working, so you’ll need to provide a mechanism to record that.
I played the conversation out in my mind, trying to predict everything that could be asked. I even role-played with friends to help discover new questions my boss could ask that I may have missed. I wrote it all down, and reviewed it every so often in the weeks leading up to our conversation.
In the months leading up to the negotiation, I was working hard and kicking as much ass as possible. I handled a crisis exceptionally well, and executed a large project with precision that landed me a raving review from a client.
I also worked diligently in recruiting staff for the company. Being a small shop, it didn’t take long before half of the staff were friends and old classmates that I’d recruited!
All of these things helped me gain a level of importance in my firm, and would help in negotiating for something I wanted: in this case, travel. Seth Godin has a great book on this topic called Linchpin. It helps that I work for a small company, and my boss is generally very accommodating. Your mileage may vary.
It’s quite clear that some jobs cannot be done remotely. Careers like carpentry and masonry come to mind. Many knowledge worker positions today, however, can be done in the office, at home, or from a cafe in Stockholm.
I work in the IT consulting industry, and over 90% of the work I perform is done remotely. As such, there wasn’t too much of a need to convince my boss that working abroad could be technically possible.
I didn’t want to be a jerkbag, so I made sure to negotiate 8+ weeks before my departure, not 2 weeks beforehand. This helps your management have time to think about how to handle staff and clients with your potential transition.
You’ll want to do everything you can to reduce the apparent difficulty of your change in location, so it doesn’t appear as a burden.
It wasn’t really until being on the road that I realized just how important my work schedule was. Sometimes you’re required to be on a conference call or perform work at a specific time, which can be inconvenient when your client is in Seattle and you’re in France. Keeping track of the time differences becomes paramount to being available when you need to be.
It also means that your work schedule often doesn’t match the timezone you’re living in. This has lifestyle implications that you’ll ultimately have to plan around. There have been several times where I came back from the pub or dinner with friends a little early to help a client or be on a conference call.
Clearly it’s better if the work can be done on your own schedule, or at least a schedule that’s appropriate for the timezone you’re living in. Sometimes though, you have no choice and will need to plan around it. Every job differs, but it’s important to think about.
Along with time zones, connectivity can be a problem. When needing to be on a conference call, you’ll need a comfortable, quiet space with a stable internet connection. The meeting could be at 8 am or 10 pm — whenever it is, you’ll need the proper environment.
Your apartment may be quiet, but the internet connection is reminiscent of a dial-up modem. Your favorite cafe is quiet with blisteringly fast internet, but it’s closed at 10 pm when you need it. Know your environment and plan accordingly.
I almost always have fail-safes in place in the event that my connectivity situation goes awry.
The first item on my agenda in a new country is purchasing a SIM card from the largest local telco. Often times it’s the most expensive, but since it provides my livelihood, I’m willing to spend more for extra coverage and faster speeds. This way, when all else fails, I tether off my mobile phone.
I do my best to keep our company phone system updated with my foreign mobile number. Clients and staff continue to call my same extension in my home country, which forwards to my mobile. Regardless of my whereabouts, it’s a no-brainer for staff and clients to reach me because, to them, nothing changes.
When placing outbound calls, it’s often important that a client doesn’t see your crazy-long foreign phone number. I typically use a softphone on my computer to dial via our company phone system, but sometimes the connection is poor or I’m on the move. In these cases, instead of making the outbound call directly, I use a callback service to mask my phone number.
In coming up with and executing your plan to take your job on the road, keep in mind that you’ll want to keep the burden low for your company and clients. That means being available when you need to be, and having the right systems in place at your end so that little needs to change at theirs.
Always be mindful of your environment. Having the right workspaces and internet speeds are key, especially when making phone calls or doing any other real-time work.
In constructing this kind of life, it’s clear that you’ll make sacrifices. You’ll be away from family and friends back at home. You’ll have to work at odd hours, and internet connectivity will dictate where you go and when.
Ultimately though, you’ll be living a privileged lifestyle many others only dream about. While it’s not all puppies and rainbows, for me at least, it sure beats commuting to a 9-5.
This post is part of Digital Nomad Month on Too Many Adapters.