I’m Frustrated with Working While Traveling

This entry is part 3 of 4 in the series Frustration Week:

  1. Frustration Week and a Travel Update
  2. I’m Frustrated with Travel Blogging
  3. I’m Frustrated with Working While Traveling
  4. I’m Frustrated with Dar es Salaam

We have been really “lucky” during our entire trip to have enough money to sustain traveling. While we saved and behaved financially responsible in the months leading up to our trip, the main reason we are still on the road is because I’m working while we’re traveling.

As you may have remember, a few months before we started traveling I was laid off from a well-paid tech job. Immediately, we had to freeze our retirement contributions and excess student loan payments and reconsider whether we could afford to travel long-term at all. After a lot of soul-searching, we decided that it would be best for me to get a short-term contract job, save what we could, and hit the road as soon as possible (but you know this already). I was lucky enough to find a programming assignment with a small startup in California that needed someone for two months.

What you may not know is that I was able to negotiate an extension to the contract that would let me work while we were traveling. In general, it worked out well. I could do a lot of the work by myself, sometimes without wifi, and work just enough hours to sustain our lifestyle. For instance, in Asia, when we were only spending $55/person/day, 5-10 hours a week of work seemed like more than enough. In South America, where we were closer to $75/person/day, 10-20 hours was more the necessity. In Europe and Africa, things got real. We were spending close to $100/person/day, so we essentially had to take 1-2 week breaks in between trips where I could just stop and work full-time. And it worked! We’re here, 16 months later, and we aren’t going home penny-less.

Most travelers dote about how lucky we are to have a source of income to make traveling easier. And don’t think for a minute I’m not grateful and fortunate that things have worked out the way they have. But it doesn’t mean that it hasn’t been frustrating.

When You’re Working, You’re Not Traveling

When you’re traveling, you certainly have down-time: long bus rides, days when you feel like doing nothing but sitting around, or days when your travel companion is sick. Those times are perfect for working – no one is missing out on anything, except for maybe some views of the country-side. But unfortunately these moments are fewer than I ever expected.

We typically spent 3-5 days in any given city. For some places, like Singapore or Hong Kong, this time was packed from dusk until dawn with exciting sites to see and food try and activities to do. My job didn’t care where I was, as long as I got the work done, which is a great perk. Except when you’re in Singapore or Hong Kong or a beautiful white-sand beach where you just want to relax all day. But instead, you’re stuck inside your hotel room or at a café, writing code or troubleshooting a customer problem. Or you get notified about a critical issue you need to fix that happen to occur at 4 AM your time. And all of this is time lost. Am I ever going to come back to Singapore or Hong Kong or that white sand beach again? Not sure – but I’ve enjoyed it a lot less because part of it has become just another remote office and no longer a travel destination.

Only One of Us is Working

This was the biggest surprise for us, especially in Europe when I was working nearly full-time. Sara has a medical job that requires seeing patients, and she simply can’t do it while travelling. Sure, it’s fine in Bangkok, where there is so much to see and do. But on those days in Frankfurt, when I was spending 8 hours/day on the computer, what was she expected to do? It’s unfair to ask her to plan everything for the trip to compensate, or to be my personal assistant, or to do anything other than enjoy the time off and watch The Mindy Project. But that’s what happened. She got really stir-crazy. I got really jealous. We were both frustrated that more wasn’t getting done. And it really wasn’t healthy for either of us. The best thing we did was decide to come to Tanzania, where Sara and I could both work full-time while traveling on the weekends. It balanced the scales, and put the obligation to plan and take care of other things back on an even keel. But that was a really hard lesson for us to learn – equality in the marriage matters, even while travelling.

Can You Really Depend On This Forever?

I should explain that in the IT/startup world, a contract job doesn’t typically mean your employer is contractually obligated to pay you a certain number of hours for a certain period of time (I thought that’s what it meant when I first started looking, but quickly realized no employer that would let me work this flexible of a schedule would agree to such a thing). As a result, we never knew for sure that there would be work for me next week, so could we really depend on this job forever? How dramatically would we need to adjust our travels to compensate for the lost income?

Fortunately, for the whole 16 months, this never happened, until last week, when I got the call from my boss that our company was shutting its doors and could only pay me through the end of the week. What?! You always expect it to happen, but you still never expect it to happen. So this left us in a tight spot – we are leaving Africa next week, and neither of us have jobs to go home to. I guess I’ll spend my 31st Christmas unemployed, living in my parent’s basement. Happy holidays.

Before you worry, Mom, we’ve worked it out. One of our company’s clients has hired me for a support contract, full-time through March and part-time through 2015. So we’ll stay afloat while we find new jobs and determine where we want to go and what we want to do next. But man, working while travelling has been a way bigger roller coaster than I ever expected it to be. I’m grateful for all it has provided us these last 16 months, but looking back, I’m not entirely sure it was worth it.

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