I would take a gamble and bet that “more travel” is pretty high on most everyone’s bucket list, but with a full-time job and only a couple of weeks of vacation a year, it can seem like an unrealistic dream. I believe it’s possible to make “more travel” a real possibility. With a little advance planning, some discipline, and a small leap of faith, here’s how I’m making it work.


Rice Paddies in Bali, Indonesia

Damnoen Saduk Floating Market in Thailand

Whether you call me a “digital nomad”, “location-independent entrepreneur”, or the more straightforward moniker “working traveller”, my travelling work life started long before I even knew that I was setting myself up for it. I had always been an explorer. The first time in my life I was free to do as I pleased was at the naïve age of 18. I had worked like a dog for over a year, then took myself on a 6-month journey to Europe and Africa. I was hooked! There was so much to see out there. I continued like this, working hard/travelling, for three years until I decided it was time to further my education. Through my studies I continued to travel. I was broke, but I was young and full of energy.

 

Then life interrupted. Kid, mortgage, real job. Travel was still a part of my life, but not like it used to be, and I missed it. Before I knew it, my boy had grown up. I still had the mortgage, and the real job turned into one I loved and was not willing to walk away from, so I tried an experiment: 10 weeks travelling through Southeast Asia, working 2 days per week.


A Cave in Ao Nang, Thailand.

The Flower Market in Bangkok, Thailand.

As I mentioned, my years leading up to becoming a working vagabond set me up quite nicely. When my son was young, I worked from home in the evening, which later turned into full-time work. I had a sick relative in Ontario and flew back and forth several times, working late in the evening in the hospital, hitting production deadlines on pure adrenaline and coffee. Then in 2010, I moved from Vancouver to Ontario. Working remotely was my new way of life. I was regularly dealing with a three-hour time zone difference. I was already living the life of a remote worker, just not with the nomadic up-sides one imagines.


Georgetown Street Art in Penang, Malaysia.

When I decided to hit the road, I approached my employers. Working at Line 21, I’m uniquely lucky to work for a company that not only values travel, but more importantly, recognizes the benefits of having happy, healthy staff. In doing so, they’ve built a staff of loyal, life-work balanced people. In a world where few people work with a company for life, we have several staff members that have been around for well over 10 years, some closer to 20. When they said, “Go for it,” I was off and running.


Wild Monkeys Roam the Streets of Lopburi, Thailand.

While you can run off with your carry-on and laptop on the next flight to Bora Bora, a bit of pre-planning is recommended before you board the plane:

  • Beware of time zone differences. If you’re travelling around a lot and hopeless with the math, try using a helpful app like Every Time Zone or World Time Buddy.
  • Make sure you have a plan to communicate with clients or the office. For audio and video, try Skype or Google Hangout, or Hipchat for group chat and instant messaging.
  • Download Dropbox or something similar so you can save and share files on the cloud. This is important so documents are available to those who need them in your off hours, and backing up will come in handy if your equipment gets stolen.
  • Speaking of stolen equipment, insurance is a must. And it doesn’t hurt to encrypt your hard drive to protect your data.
  • And speaking of insurance, make sure you’re covered for any health-related expenses while you’re at it. One of the most popular companies is World Nomads. Typical employee packages max you out at 30 days and may have limitations. Credit card coverage typically limits you to 14 days and the scope of coverage isn’t usually very broad.
  • If you’ll be needing large files transferred and don’t use an FTP client like FileZilla, make sure you have file transfer software. Try Hightail or WeTransfer.
  • My work laptop is heavy. If you can get away with it, why not consider purchasing a smaller, lighter travel computer? I did and loved it. It had a few limitations, but I was able to work around them, and I really appreciated being able to toss my tiny laptop in my bag and cart it around all day if I wanted to.
  • When you get to your destination, get a local SIM card right away. You can often find them at the airport. The most I paid for a month of data on my iPhone was $12 in Indonesia. Thailand and Malaysia were even cheaper. Alternatively, you could opt for a voice/text/data package for a bit more money. Use Wi-Fi when you can to save even more.

Office for the day at the Singapore Botanical Gardens.

Office on the Island of Gili Air in Indonesia.

Join us next month for practical tips on how to make a work/travel life a reality, and how it can benefit you and the company you work for!

 

 Leslie manages the script and transcription departments with Line 21. She’s been loving her job for 18 years and counting! When she’s not working, she likes to drive fast, dance slow, and she has an insatiable sweet tooth. Leslie love to explore—people, places, food, music. She loves live jazz, road trips, and laughing till her head hurts.

You can find more of Leslie’s travel stories at thebugthatbitme.com! Follow her on Instagram. See her staff profile here. This is part 1 of a 2-part series. Don’t miss part 2!


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