Today I had the pleasure to interview Gwendolyn from the USA who is another great example that digital nomads aren’t all in their 20’s and that it’s always possible to venture into a new life. Thanks for being an inspiration, Gwendolyn.

So here we go:

Gwendolyn is an online English teacher with the Chinese education company VIPKID. She became a digital nomad in 2014, at the age of 39, after deciding that there must be more to life than spending 70 hours a week as a marketing manager in investment banking. She grew up in Glasgow, Missouri, but has lived in London, England and Daegu South Korea. She has travelled extensively – to over 55 countries. Find out more about Gwendolyn on her blog and social media accounts:

Blog –
Facebook –
Instagram –

You had a corporate marketing job in the UK. What made you quit it and why did you decide to become an ESL teacher instead?

I became very depressed with life. I remember one day early in 2014 when I thought ‘If this is my life for the foreseeable future, then I don’t want to live anymore.’ My corporate marketing job was stressful, required long hours, and was unfulfilling. I hired a life coach who made me fill out a pie chart before our first meeting in which you had to rank what you spend your time on and what is most important to you. It turned out that I was spending nearly 90% of my time on the things I put zero importance on. And the things in life that were very important to me, I was only dedicating around 2% of my time on. This was a wake up call.

Three months later I resigned to spend a year traveling the world whilst I tried to contemplate my next move. During my travels, I had a lot of opportunities to ‘teach’ English to foreigners and children in informal settings. I loved it. When my year was up, I still didn’t really know what I wanted to do, but becoming an English teacher won out over all the other options because the career transition wouldn’t take me long or cost me much. A TEFL certificate only cost me a few hundred dollars and a month of online study to receive. Also, I wasn’t ready to settle down yet. Being an ESL teacher would provide me with an income whilst still seeing the world. I also thought teaching would be a very rewarding career that also has a lot of options for advancement. I could volunteer to teach in a remote village in Sri Lanka or I could later get a Master’s Degree and teach at a University in the US. The varied opportunities were really appealing to me.

Did you travel a lot before you became a digital nomad?

Technically, I’ve only been a digital nomad for three months, since May 2017, but yes, I have travelled a lot in my life! After leaving my corporate job, I traveled around the world for a year, visiting six continents and 26 countries. But even during my regular working years, I always travelled extensively. I’m at 57 countries visited and counting, and most of those include exploring a country for a week or more.

How did you land your job as an English teacher in Korea? What did you like about it? Did you also have bad or difficult experiences?

I just googled ‘English Teaching Jobs in Korea’, and was led to a recruitment company called Teach ESL Korea. They helped me with the application and interview process. I found it comforting to have someone ‘hold my hand’ and help me through the process. Also, they approached all the companies on my behalf. It would have taken time to do all that leg work on my own.

I loved living in a totally foreign country. It was great to spend a year in one place to get to extensively know a culture and to build up personal relationships. I also had a lot of time to travel around the country.

Maybe it is just me, but I found that it could be lonely at times. Part of that is due to my older age. But I did make some lifelong friends whilst there, and there is so much exploring to do you are always busy so that helps. Probably the worst thing that happened to me in my year there was that my favourite uncle passed away whilst I was there. No one really talks about what to do when you lose a loved one whilst abroad. I had heard that some Korean employers wouldn’t allow personal leave for a death unless it was a parent. I was prepared to quit, but luckily my employer let me have a week off to fly home for the funeral. It cost me a lot, and that amount of international travel in such a short time was hard on me physically, but my family is important to me and I wanted to be home.


You’re now working for VIPKID, a Chinese company. Could you tell us a bit more about it?

Sure! VIPKID offers online English language classes to Chinese kids. It started in 2013, and already has 15,000 teachers hired to teach its growing database of 100,000 students. I teach remotely for about 2 to 3 hours a day and earn $20/ph. I love working for them as I can work anywhere and set my own hours. Also, one advantage of this company is that the lessons are prepared for you, so I just log on and start teaching. No prep is bliss! If you want to know more, read my blog here:

What are the main challenges of combining a digital nomad lifestyle and working for VIPKID?

There are two challenges. Neither of them are that big though. First, peak teaching hours during Chinese school term is 6pm to 10pm Beijing time. Depending on where you are in the world, that can mean VERY early starts. It works for me though. Right now I am in Arizona, US. I am up at 4am but finished with my day by 7am. The rest of the day is mine to pursue personal interests or take a nap.

The other challenge is transporting props. VIPKID likes you to reward students when they do well. Some teachers have puppets, and elaborate reward incentives, like a jar that fills up with marbles. So not practical on the road. My rewards are all flat and magnetic that can attach to my small portable whiteboard. For example, I have an ice cream cone, and each time you do a good job, you get a colored ice cream scoop. I’ve learned to adapt. It’s fine.

Where can we find you in the next couple of months? Do you plan much ahead?

Right now, I’m only planning my life about 3 months in advance. I finished my teaching contract in South Korea at the end of April 2017 and decided to spend three months back in the States catching up with my family. At first, I applied for a job with the Peace Boat as a web reporter on their next around the world voyage (HINT: They hire English teachers too! It’s a volunteer job, but you get the voyage for free and they go to over 20 countries in 3 months.) I got to the interview stage, but didn’t get selected.

So Plan B, was to continue teaching with VIPKID and go to Medellin, Colombia for three months. The first month I will be on a digital nomad retreat with a company called Unsettled. I am looking forward to co-working and co-living with some like minded professionals.

I’ll be back to Arizona at the end of October to catch up with my family again, but beyond that, I have absolutely no idea!

Is your work for VIPKID your only source of income at the moment? Do you have any plans for own projects?

I am extremely fortunate to have been able to get on the property ladder in my early 20s. I have a home in England that I rent out which provides me a very stable income.

I am in early stage negotiations with a former colleague on a new networking app for financial professionals. He needs some help with content marketing – i.e. providing blog posts, crafting blast emails. Not sure if anything will come of that opportunity, but with my background digital content marketing is certainly an area I might consider exploring more.

Ultimately, I want to be a writer, so I want to spend some time working on my travel blog. I need to start monetizing that and I’d love to have an travel article or two published.

Where and how do you see yourself in 10 years?

I love traveling, but I do also miss having a home base. I expect that within 10 years, my wanderlust will have subsided some and I will have found a place in the world to have as a permanent base. I’d love that to be with someone special, but life has no guarantees. The travelling won’t stop though, it will just be for shorter periods. As for what I’ll be doing, I don’t know, but I’m pretty positive it will be a location independent role. I never plan to return to corporate life.

Thank you very much for the interview Gwendolyn and good luck for your future plans. 

Author: Daniela

Hi! I'm Daniela - a native German who's living as a digital nomad in Latin America. Besides making a living teaching German, I'm constantly trying to improve my Spanish and Portuguese. On my blog, I write articles for (aspiring) language teachers to help them get started and for people who want to travel the world and make some extra cash teaching offering quality language lesson.

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