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 w