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In the Spotlight: Jay Riley from ESL Gypsy

All online English teachers offer a unique skill set from our previous experiences and backgrounds. Each of us also must continuously reflect on our teaching practice and invest in professional development for online English teaching in particular. We at Promise Opens Doors ask - What steps are you taking to ensure success for yourself and your students in the online ESL classroom? We encourage you to seek out professional development specific to this field, such as the TESOL/TEFL Certificate for Online Teaching (, available for trainees to register tuition-free for only one more week.


In this article, we share the story of one person’s journey to the online EFL classroom, the importance of mentorship and community along the way, and the steps he has taken to ensure success for himself and his students over the years. Today’s spotlight teacher Jay Riley from ESL Gypsy started down the path of his teaching career over fifteen years ago, and remembers it well:

I actually went to school for business. My undergrad is in economics (from the University of Hawaii). Then, I got my MBA from St. Leo University and went to Australia to get a Master’s in Accounting. I came back to the US in 2005 and worked in a bank in Florida doing basic, entry-level accounting work- and I hated it! I needed to do something I enjoyed and something that I felt would make a positive impact. I started tutoring first and second grade reading at a local YMCA. It was a volunteer position twice a week after work, but I loved it. I’d come home and I couldn’t stop telling stories about my kids and the progress that they had made. My mother was a teacher, so when she saw how enthusiastic I was, she encouraged me to pursue teaching as a career.


Along our path to teaching we make connections with people who influence our practice for years to come. It may be someone we meet on social media, a relative, a supervisor, or a senior coworker whose encouragement and wisdom speak to us. You can see the importance of mentorship as Jay made his transition from accounting to the classroom:

My first paid teaching job was in the Florida public schools. Since I was coming from a non-traditional teaching background, I needed to pass some state tests and also take part in a mentor program with more experienced teachers. I was lucky that I had a terrific mentor! She was a huge asset in helping me adjust to teaching as a profession! I still think one of the best ways to develop as a teacher is to work with other teachers- especially those who have experience doing whatever it is you’re trying to do. After teaching for a few years, I went back to school to get my Master’s in K-12 ESL, and eventually my Education Specialist degree in instructional technology.


Then there is the day we begin our online TESOL career. It may be a way to earn pocket money while staying home and caring for loved ones, a complement to other work we’re doing, a temporary position that steadily becomes full-time, a way to fund extended traveling, or any mix of the above. Some start teaching English abroad and then pick it up online when they return to their home country. Jay’s experience was unique:

Ironically, my first ESL teaching job was as an online teacher! After I left the Florida public school system, I went abroad and began teaching online for a company called Englishtown. They had a center based in Bali. I have always loved Indonesia, so I jumped at the chance. I wanted to continue to build my resume and it was hard to resist the opportunity to work in Bali, so I ventured into online teaching. I didn’t have any background in ESL/EFL, so I took an online TEFL course with Bridge TEFL to learn the basics on teaching English as a foreign language. Undoubtedly, having great colleagues was the biggest asset in helping me to transition to teaching English online. I can’t stress enough the value of reflective practice with other teachers.


Once we start teaching online, we find a whole set of challenges particular to this field. For those with experience in the brick-and-mortar classroom like Jay, there are added hurdles. Below Jay describes how he responded to three common online-teaching challenges:

1. Adapting teaching practices to the online space

It was definitely a transition moving from the classroom to a virtual environment. I think one of the things that made it easier for me was that I had only been in education for two years when I made the switch. My own classroom practices hadn’t really become ritualized yet. I was still flexible enough to make the change. When I moved to Korea, I taught in the public schools for two years and then at a university for seven years. Of course, that was all face-to-face. When I had to transition back to teaching online, it was a lot easier because I had that initial experience with Englishtown. I would definitely encourage new teachers, or those new to online teaching, to remain as flexible as possible. There are unique challenges to virtual ESL teaching, but if you remain open-minded, the benefits are well worth it.

2. Building rapport with students

Now I teach entirely online. I think the biggest challenge, or the thing I miss most about being in the classroom, is seeing my students in person. It always makes it easier to develop relationships with your kids when you see them face-to-face. That doesn’t mean it’s impossible to do in a virtual environment, I just think that teachers need to be committed to building rapport with their students. I think it’s important to take a few minutes to get to know your kids AND REMEMBER what they tell. Build on what you’ve talked about in previous classes. When possible, make connections between the materials you cover in class and the students’ own lives. Not only does this help the students learn, but it really fosters strong relationships. It’s not easy and it does take time, but the results will show in their learning.

3. Building Personal Relationships with Colleagues

When I was working at the university, if I had a tough class, it was always easy to find someone who could offer me feedback. I worked in a shared office and someone was always around to bounce ideas off of. I also had a great boss whose door was always open. Being in a virtual environment, it’s more difficult to connect with colleagues, but it is not impossible. There are tons of Facebook groups, other social media platforms, and websites where you can connect with people who are working as online English teachers. If you work for a school, inquire about how you can connect with other teachers. Many schools may offer professional development opportunities as well. It definitely requires a more proactive approach, but you can find ways to network and build relationships teaching in an online environment.


As we overcome initial challenges and continue our online teaching career, it is important that we find ways to keep growing as teachers. Jay has made this endeavor both enjoyable and affordable:

I’m fortunate because I love learning. Since I run my own business, I’m able to invest in my own professional development. I plan something every year that I feel will help me improve as a teacher, and I invest my time and money into whatever it is that I’ve chosen. Over the last two years, it was getting an Education Specialist degree (EdS). This year, I am completing my K-12 teaching license with the state of Florida. I am doing a series of online classes with the University of West Florida and then I do some field experience work. It’s awesome because it can be done anywhere in the world and it is something that I can directly apply to the classes that I’m teaching now!


We stick with this career because we love it, each of us for our own reasons. It may allow us to stay at home with those we love while doing what we love, or it may allow us to continue our travels while doing what we love. It isn’t always easy, but as Jay describes below, it is always worth it.

Without a doubt, my favorite part of this career is the flexibility to teach from anywhere in the world. When I first connected with Promise this interview, I was in Indonesia. Now, I’m writing this from Europe. In a few weeks, I’ll be back in America. I really can take my life and my career on the road. That can be challenging sometimes because you’ve got to hustle to get things done and sometimes have to work at uncommon hours, but for me, it’s a dream come true.


Most importantly, as the field of online teaching grows and matures, the community of online teachers becomes richer and better connected. Regardless of our background or amount of experience, we all have something to bring to our fellow online teachers. Here are the final words that Jay offers today.

Teaching in an online environment definitely has some unique benefits and challenges. I always encourage people to do what they love. If I had all the money in the world, I’d still be a teacher. It’s what I love to do. If you feel you really want to be in this field, commit yourself to it over the long-term. Engage in professional development and build long-lasting relationships with your colleagues. Don’t expect everything to happen overnight. Teaching is a hard job! It’s also a job with rewards like no other. Start small and work your way up the ladder. My first online teaching job (in Bali) paid me $750 a month! Of course, I had to struggle on that type of money, but I always gave my job 100%. I wanted to grow as an educator as much as I could and do the best job for my students. Everyone has to start somewhere. If this is what you want to do, commit yourself to it and go after what you want with everything you have.


Jay has recently launched a new website, ESL Gypsy, which can be found at

His site includes blog postings related to online ESL teaching and living & working as a digital nomad. Jay also blogs about topics related to helping teachers reach their financial and professional goals, such as a recent series on the best way for online teachers to prepare their taxes. The website includes a job board, links to free teaching materials, and much more. Check it out!

Thank you Jay, and all the best to you!

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