Financial Case Study: Sasha and Rachel, Grateful Gypsies

Sasha and Rachel are a married hippy couple from the US who met at a music festival and got engaged at a Phish concert. They write about life in China, teaching English, gap year travels, and of course live music on their site Grateful Gypsies. They earn their living in a variety of very interesting ways (getting paid to study Balinese culture? Sign me up!); read on to see how they do it!

In this series, we’re exploring the various careers of world travelers, and how they make ends meet financially while living abroad. Yes, financially sustainable full-time travel is possible!

This post was originally published in 2016. It has since been updated for accuracy of links and content.

How long have you been living/working on the road, and where have you traveled to?

I [Sasha] moved to Beijing in the summer of 2008 to teach English, and then after a year back home Rachel decided to join me in early 2010. We spent 3.5 years living in the Chinese capital, during which time we traveled to Japan, South Korea, Thailand, Laos, Indonesia, the Philippines, and even Mexico for a music festival (yes, we flew all the way there from China).

During our gap year trip, we revisited some countries and tacked on a few others along the Banana Pancake Trail across SE Asia. I’ve also been to a few European countries and Rachel has been Down Under, but all of those trips came when we were much younger.

Please describe what you do for income.

I’ve been an on-again, off-again ESL teacher in China since I first moved there in 2008. I also took on so many random side jobs it’s laughable, including acting as a “white guy in a tie.” I was paid to simply put on a suit and sit in on business meetings, even though I had no idea what was being said in the meeting and had no actual business there.

Since 2010, I’ve also been running a handful of language and culture blogs for a big language company back home. I’m also currently taking part in a scholarship program, where believe it or not the government of Indonesia pays me to live in Bali and study the language and culture (it’s not much, but that’s pretty awesome, isn’t it?).

Rachel busted her butt teaching English the last five years, so she’s currently enjoying an extended honeymoon as a Bali housewife. It isn’t all just sitting on the beach, though – she’s actively working on our site Grateful Gypsies and making strides towards monetizing it.

How many hours per week do you work on average?

At the moment, I spend about 20-25 hours a week working on all of the blogs I run and their accompanying social media pages. I also go to class from time to time, which counts as work since they pay me for it. We’re on a quest to never work 40-hour weeks, and we’ve done well so far. Even at our busiest times in China, we never worked more than 35 hours a week. We very much value our free time and try to have as much of it as possible!

How much money do you make?

This is a tricky question because it has varied so much over the years, so I’ll give a few answers.

When we were living in China, we were both teaching basically full-time and I was blogging only a couple of hours a week. For those years, I’d say we made about $4-6,000 US/month total from teaching, and my checks from blogging were only a few hundred bucks. We managed to save enough money teaching to allow me to join this program in Bali and be able to survive the year.

Thanks to our travels and my newfound mediocre skills in a few other languages, my blogging work picked up quite a bit, and I currently get checks between $1,200-1,400/month for that. My school gives me a small stipend every month, which amounts to only about $150. It’s not much, but it helps cut our rent in half (yes, it’s that cheap to rent a place in Bali!).

Do you make enough money to support your lifestyle?

We’re not very extravagant people, so it’s not that hard to support our lifestyle. We live very modestly here in Bali since the job prospects for foreigners aren’t exactly great and thus Rachel doesn’t have an income at the moment. We brought enough money here to get through the school year along with my stipend, and my checks from blogging just go straight into my bank account at home to be saved for the future.

We’ve also got investments at home that are off-limits and are being saved in case we ever want to “settle down.” I should note, though, that when we were living in Beijing, we lived a rather epic lifestyle for a couple of part-time teachers – nice apartment, lots of traveling, fancy meals out, days at the spa, lots of partying. Plus we saved enough money there to take a 14-month trip around the US, SE Asia, and China and even had enough saved at the end to pay half a year’s rent when we moved to Kunming.

What do you like most about your career and lifestyle?

Teaching English is great, as you can take on one contract for a year, take a break, and then move somewhere else. We’ve only taught in China, but we’re considering lots of other options for our next move – Thailand, Brazil, Taiwan, and Chile amongst others. It’s also a fun job, especially when you get to teach adults. You’re not only teaching the language, but you’re engaging in a cultural exchange every day.

As far as my blogging work goes, I get paid to write, share photos, and edit videos about my travels and my experience learning new languages and cultures. It’s what I love to do, so the fact that it doesn’t pay a whole lot doesn’t bother me at all. I can work wherever there is an internet connection, and I can schedule the work however I want. For example, I recently managed to finish a whole month’s worth of work in just ten super busy days – that freed up almost three weeks to do whatever I wanted, and I still got a nice paycheck at the end of the month. I don’t know many jobs that afford you that kind of freedom.

What are some of the challenges you have with this career and lifestyle?

While it’s awesome that our jobs as teachers are portable, it’s not so easy to pack up and move and get adjusted in a new place. This is especially true when you take an extended travel break in between jobs. We had a rough time getting back to work after our crazy gap year trip – I think we were tired for six months after that one!

As far as the blogging goes, it gets harder and harder to come up with enough topics every month. I write about 15 posts and edit around 10 videos each month, so it’s challenging to keep it fresh, interesting, and relevant.

Finally, we’ve spent so much time and effort building up our website, but we haven’t seen any money from it – just a few free/discounted trips. Building a site is fun and it’s a good challenge, but it gets harder and harder to get excited about when you’re not seeing much of a financial reward.

(Nora’s Note: Amen! Monetizing a website is tough stuff. Here’s a way to reduce the learning curve and increase income: Want to Make Money Blogging? This is For You!)

What is your vision for the future of your lifestyle on the road?

We’re really focusing on developing our site right now and coming up with ways to monetize it. This may be offering some services like travel planning or coaching, or through e-books on topics that we’re pretty knowledgable about (like living and teaching in China).

I’d also like to branch out and get some more freelance work with other outlets. I love the company I work for and will continue to provide content for them, but I’d like to cut back a bit so as not to get burned out.

Rachel is looking into online teaching jobs so we can pad our income without tying ourselves down to a place with another year-long contract, so we’ll see how that works out.

We’re also hoping to take on some seasonal holiday work back home in the States this fall to save enough money for another extended trip. This time we’re eyeing Central and South America, hoping to take our time and really dig in. If a place really grabs us and we find that there are good teaching jobs there, chances are we’ll plant some (temporary) roots and work for a while. Of course, as soon as we get Phish’s tour dates and the summer music festival lineups, we always get the pull to get out there and dance…

Any advice for the aspiring traveler about living and working on the road and managing finances?

For those who would like to travel but don’t think they can afford it, I highly advise trying out the ESL world for at least a year. In countries like China and South Korea, you can earn enough to live a comfortable life in a big city, do a fair amount of traveling, and take some money home. Without our experience working in China, we wouldn’t have been able to do even half of the traveling we’ve done. I also wouldn’t have gotten my blogging job, and I would have had no idea about this program in Bali. It’s amazing the kinds of doors that open to you once you’re out of your comfort zone and in a different part of the world!

When it comes to managing finances, we try to stick to a tight budget when we’re working/settled down, and focus more on saving money for travel. We also form a monthly budget for travels and do our best to stick to it. If two silly hippies like us can manage to travel as extensively as we do while working as little as we do, then there’s hope for everyone!

Is there anything else you’d like to add?

Don’t be worried about what others say or think if you choose to take a leap of faith and move abroad or travel long-term. Doing these things are not easy, and that’s why most people don’t do them. It’s much easier to be “normal,” get a desk job, buy a car and a house, and wait until you’re 60 to travel. If you’re really feeling the urge to explore, to experience a new culture, or to change your life, then just go for it. The worst that’ll happen is that you’ll end up back where you were, but at least you’ll have some stamps in your passport, some photos, and some cool stories to tell. Those people who thought you were crazy for leaving will most likely still be hanging out in the same places, doing the same things. As we say on our site’s motto – Improvise your life! You’ve only got one (unless you believe in reincarnation, I guess), so why not make it as awesome as possible?