Vagabonding to Nomading.

Travel Wolves
3 min readSep 17, 2018

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A backpacking trip morphed into a few months working remote in Asia.

Well it happened. In an ironic twist of fate I got my first remote job offer just 6 weeks before we were to head to Asia. Bad timing? Good timing? Who knows. It happened. And somehow, deep in my bones, I knew it was going to happen. It was that big thing I wanted, but it was unfolding in a way I didn’t necessarily want.

I am lucky in that before accepting the offer I told my future employer about my upcoming trip. I gave them dates and details. I mentioned that I needed the first two weeks of the trip off, for our short time in Tokyo/Kyoto and Bangkok. I mentioned to them that I would like to work on South East Asian time. GMT+7. To my surprise they were completely understanding. I had no decent reason to turn this opportunity down. After all it could bring future journeys for Abby and I.

To my relief I was able to put my two weeks in with my current employer early. I was able to tell friends and coworkers of our plans which was a real relief for me. I had felt this whole experience was driving me half insane. However, my burden of keeping my travel plans secret seems to have been replaced with self-doubt and dread.

In a single day, one phone call and one e-mail changed a whole nine week trip, a trip which for me was most likely to include wandering about and getting lost. Now, most-likely, it will include slower explorations and weekend excursions. What was once a budget trip full of hostel dorm rooms now will most likely include private room hostels and hotels. Where I was once going to get lost in nature or in a South East Asian city, is now replaced with searching for stable wifi.

In a way I can’t help but entertain feelings that my decision has somehow cheapened this trip for myself. Indeed there is a possibility this could happen if I’m unable to keep the original intentions in mind. However, thinking about this trip more as an adventure and less of an extended vacation has made the thought of this trip even more exciting and worthwhile. In many ways, this new opportunity isn’t simply the beginning of a trip. Instead it helps give life to a whole new chapter for Abby and me.

It extends the adventure past this trip in Asia and into the future as we no longer need to stay rooted in one location. If it wasn’t for our pets, we could roam freely as long as we paid our rent and bills back in Chicago. This is by far the biggest luxury of any job I’ve ever had! This really is the future of office working.

It’s now been a month of working from home here in Chicago and I couldn’t be happier with the job. I’ve had about a month to get my bearings about me and from what I can tell I’ve done decently well and my confidence is starting to build. I think this is something I could handle working on from half-way across the world while most of my coworkers sleep. We shall see.

Tomorrow we take off for Tokyo to begin the “vacation” portion of the trip. We are taking a 13 hour flight to Tokyo where will we most likely take the subway to our humble airbnb in Shinjuku, Tokyo. As we prepare for the beginning of this trip I’m reflecting on life and how in just a few short months both travel and opportunity can become available if we’re truly open to it. The adventure most certainly begins at home, and as this first leg of our journey draws to a close, I’m happy I never turned down a single opportunity. Onward!

Previous: The Zen and Stress of Pre-travel Planning

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