For 10+ Years The @Gratefulgypsies Have Been Traveling The World Together Teaching English And Attending Phish Concerts
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21st Jul | 7 min read

Rachel and Sasha are two live music lovers with a passion for traveling and experiencing new cultures. Since 2010 they've lived abroad in China, Indonesia, and Mexico and traveled to a lot of places in between. These days they're living the digital nomad lifestyle by teaching English online and blogging about it. You can follow their adventures on Instagram @gratefulgypsies and on YouTube by subscribing to the Grateful Gypsies

How We Met And Started Traveling Together

We met at the Rothbury Music Festival (now known as Electric Forest) back in 2008. Sasha moved to China to teach English the next month (talk about bad timing, right?), so we just kept in touch online. When our favorite band (Phish) got back together, he cut his contract short and came back to the US.

We spent the entire summer traveling the country together seeing Phish concerts and going to music festivals. Due to the “Great Recession” that year, we had a tough time finding jobs and a suitable place to live that fall. After our house and car both got broken into, we made the decision to abandon ship and move to Beijing together. We haven’t looked back since!

How We Manage To Work & Travel At The Same Time

For the past 4 years, we have been traveling as digital nomads. Our primary source of income is from teaching English online. We both teach young Chinese students very early in the morning since we’re on the other side of the world now. Rachel has another job teaching mostly adults from Europe, which is usually from 10 AM-2 PM. Sasha usually spends his afternoon doing freelance writing work for other websites or creating content for our blog or YouTube channel. Rachel also has an online course where she teaches others how to become an online ESL teacher and take the job on the road as a digital nomad.

Our work never seems to stop during the week, as we always have something going on. We like to take breaks to do yoga, go to the gym (if possible), take a long walk, try a local restaurant or brewery, check out a museum, or whatever else seems interesting where we are! No matter how busy we are, we try to take at least one full day off a week, and we take a week or more off several times a year to fully enjoy our travels. 

Our Travel History So Far

It’s different for both of us. Sasha has been to more (pretty close to 30 countries at this point) and Rachel has been to 24 or so. When we lived and worked in China, we took several short trips to different places around the country. Whenever we had a week or more off, we traveled to neighboring countries. We’ve also done two extended backpacking trips (7 months each in Southeast Asia and South America). 

We like to mix it up when we travel - big cities, historical sights, natural areas, small towns, and so on. As digital nomads, we usually spend more time in cities and bigger towns where we can find reliable fast internet and places to work. We like to do walking tours, visit museums, art galleries, parks, and all that good stuff in the cities. We’re music lovers and night owls, so we also like to check out the music and nightlife scenes. What we really love, though, is putting the computers away for a few days and going off on epic adventures.

Our favorite travel experiences have been things like trekking to Machu Picchu, camping out in Patagonia, and riding motorbikes in Thailand. We’ve met so many amazing people from all corners of the world in our travels and had some great experiences with locals as well. One that comes to mind is visiting a friend’s remote village in the mountains of Yunnan, China to celebrate Chinese New Year.

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We Travel All The Time

We are always traveling! We haven’t moved back to the US since we left in 2010. We spent 5 years living in China, 1 year living in Bali, nearly 2 years just backpacking, and the past 4 years we’ve been digital nomads.

Our strategy in that time has been to spend 6 months out of the year in Mexico, usually in Puerto Vallarta. We’ll take short trips during that time but mostly settle into a routine here. Then we spend the other 6 months of the year traveling, both back to the US to visit and exploring new places like Guatemala and Costa Rica. We like to spend at least 3-4 days in a place but sometimes we move a bit quicker. There have also been many times where we spend a week or even a month in a place so we can slow down, explore more leisurely, and still get work done. It all depends! We love music, so we usually end up planning our travels around when the next Phish concerts are or if there’s a really cool music festival somewhere that we’d like to check out. 

One Of Our Favorite Travel Experiences Together 

There are way too many to count! We’ve had some pretty unforgettable travel experiences over the years. One that comes to mind is traveling overland from the Atacama Desert in Chile to the Salt Flats in Bolivia. We saw some other-worldly landscapes along the way and ended it with a sunrise visit to the amazing Salt Flats. It was such an incredible experience and one we talk about all the time.

How We Manage To Keep Costs Low

We definitely try to travel on a budget, but usually go over it! We use an app called Trail Wallet that was made by travelers for travelers. It helps us keep track of our costs broken down into different categories. We try to keep costs down by finding deals, especially on accommodation and airfare. We also use credit cards responsibly to accrue points that we can use to score free flights or hotel stays.

We book places with a kitchen most of the time, so we can save money by making coffee and some meals at home. We’re always looking for free or nearly free activities, we love street food, and we appreciate a good Happy Hour! We cut corners with most things so we can have money to do the big epic adventures we love so much, like spending a week in the Galapagos Islands.

Some Things That Prevent Us From Traveling More

Our teaching jobs are great, but they limit when and where we can travel to an extent. We need reliable and fast WiFi to be able to teach our classes successfully, so it’s not like we can just go anywhere. That’s why we spend so much time in cities and bigger towns. We can take time off whenever we want, but we try to keep a consistent schedule most of the time in order to keep regular students coming back. We’re pretty confident as backpackers these days (after making all the mistakes our first time!), but traveling as a digital nomad is a whole new ball game.  Having to worry about things like upload speeds isn’t fun, but it’s what keeps us on the road!

Tips For New Digital Nomads

We always recommend that you start out small. It’s quite intimidating to take the leap and go full-time as a digital nomad. If you already have a job, see if you can work remotely for a few weeks or even a month and try it from a different city in your home country. Not having a drastic change in time zone, culture shock, or a language barrier makes a big difference! If that works out for you, then the next time you can take the show on the road and try a nomad stint in another country.

We recommend spending at least a month or more wherever you go so you can be productive and still get to explore the place. If you want to work for yourself, there are lots of options out there - teaching online, blogging, being a virtual assistant, graphic/web design, affiliate marketing - the list goes on and on. Definitely make sure you have some money saved and something to fall back on if you’re going all in, though. Being stressed out about covering your day-to-day expenses will likely result in a negative experience!

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