By Dan Foley
Over the last few years, I’ve been able to work remotely from Spain, Sri Lanka, Japan, South Korea, London, Jordan, Canada, Germany, Ireland and the UAE. The best part is, I didn’t have a single client in any of these places (although I managed to pick up a few while in Dubai).
But this isn’t exclusive to me. By 2020, experts are predicting that half of all jobs in the U.S. can be remote. And remote work means freedom: Freedom to set your own hours, freedom to dictate your productivity and (my personal favorite) freedom to travel.
So why not travel? After all, it’s been proven to be good for your mental and emotional health. It keeps things fresh and exciting. You gain a new perspective while you work your 9-to-5 job (in whatever time zone you wind up in).
How did I do it? It was a combination of logistics, discipline and timing.
Creating the Plan
- Aim for Tuesday. I love Tuesdays. Not only is it frequently the cheapest day of the week to travel, it’s also one of the best days to book travel as well. Most work travel is at the beginning of the week and most vacations are at the end. That means the middle of the week is the best time to fly. And with less crowded flights, it gives you more breathing room. Trust me, an 18-hour flight is much more doable when you have a row of seats for yourself.
- Choose the right destination for you. Want to hit the beach? Try new and exotic cuisines? Or learn about a new culture? Believe it or not, you can do all three on a budget. Starting at $850 per month, you can live, work and experience beautiful destinations the world over. And yes, that includes food, accommodations and fun. In Chiang Mai, if I spent more than eight dollars a day for food, I felt like I got ripped off. After a long day, nothing beat a $20 hour-long Thai massage. Then I could disappear into the jungle for a two-night weekend trek and be refreshed come Monday.
- Stay connected. Wherever you go, make sure you’ll have a stable internet connection. Some countries, like South Korea, have blistering fast internet rates. But there are other nations that have frequent internet blackouts. My advice: OECD countries are your best bet for stable internet, but most countries will have connection speeds good enough to send emails and work on Google Docs. In less-developed nations, streaming videos and downloading large files can be tricky, so plan accordingly.
- Timing is everything. Deadlines matter more when you’re halfway around the world. It may seem like you have an advantage when you start earlier in the day than your colleagues but don’t forget: They’ll also be working well after you finish. In some places, you might be going to bed as they’re starting their workday. Dubai was a double-edged sword in that regard. Because it’s a Muslim country, their workweek was from Sunday to Thursday. Coupled with the time difference, I had an advantage of two full working days before anyone in New York started their week. Conversely, New York had two full days after I was already finished for the week. Usually, it worked to my advantage, but when a last-minute deadline came up, it meant spending part of my weekend working.
- Make it your home away from home. If you’re price-conscious, avoid hotels. Airbnb can offer a great way to simultaneously experience a culture (especially if you just rent a room) and lessen the impact on your wallet. Plus, you can now write off Airbnb stays as a business expense. Last month, in Jordan, I was able to stay in clean, comfortable hotels for $30 a night, with breakfast, dinner and tea included. (I wish my rent in New York was that affordable.)
Staying Productive
- Mitigate your expectations. Travel does not equal a vacation. It’s easier than you think to confuse the two. On the plus side, while you are going to be working, you’re also going to have nights, weekends and days off. Just think of it as an office that you choose in another country. As long as you can accept that, you won’t be frustrated. For this reason, I try not to go anywhere “relaxing” during work trips. Resorts, beaches and island drinks are too tempting for me. Save Hawaii for a proper vacation; hit a famous city instead.
- Work while you're in the air. Want to spend more time enjoying your destination? Working on your flight is one of the best ways to do just that. So many airlines offer Wi-Fi (especially if you’re on a long-haul flight), so it’s worth paying a bit more for. If your flight is eight hours or more, consider it a workday at 30,000 feet. I like to turn off emails and focus on internal company stuff. The isolation of being in the air surrounded by strangers calms me down and lets me think about things in a different way.
- Work and explore (at the same time). There’s no reason you can’t embrace a culture while working. Set up shop in a local coffee shop. Instead of surfing the web during your breaks, take a stroll through some new streets or look up a good lunch place nearby. In Dublin, any pub with Wi-Fi is a great way to spend your time. You’re bound to get at least some work done before you find yourself immersed in conversation with a total stranger.
Being Free
The combination of travel and remote work is surely liberating, but you need to have the right mindset. Frustrations will arise and there will always be situations that are much easier to fix when you’re living in the same country.
But if you can make your peace with these things, there’s no reason you can’t work from a bungalow in Thailand, a cottage in Stockholm or an apartment in Capetown.
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Dan Foley is the proud Co-CEO and Co-Founder of Tailored Ink, a boutique copywriting agency based in New York City.