Teaching English online with Wall Street English: Sarah’s story

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Sarah Di Paola sat down for a chat about her experiences as an online English teacher with Wall Street English. As an event planner, an online ESL teacher for adult learners and an artist, Sarah is the first to admit she doesn’t always get enough sleep, but she wouldn’t want it any other way.

She says that online teaching gives her life meaning and purpose, and gives her time to pursue her other loves. Throughout our conversation, the words “meaning” and “purpose” crop up a lot and I can’t help feeling that Sarah’s attitude will inspire other online English teachers.

So...if you want to know what it’s really like to teach adults online, have questions about the cultural issues that might crop up in the online classroom or are just curious about how anyone can juggle three jobs and retain a sunny disposition, keep reading.

How did you end up becoming an online teacher?

In one way, I’ve always taught people, but as a career choice, it took me a while to make the teaching plunge. I come from a long line of teachers. My mom, her mother and her mother’s mother were all teachers. I kind of rebelled against the idea of just following in their footsteps.

I’ve been teaching, in one form or another, since college. During my time at York University, I was the co-vice president of the Visual Arts Student Association for two years and the president of United Through Worship for one year. I mentored a lot of other students in leadership positions.

I took that a step further in my graduate degree at Seneca College. A lot of my fellow students didn’t have English as a first language so I would help edit their papers. I didn’t charge, but occasionally someone would buy me a cup of coffee. That was teaching for the love of it (or maybe for the love of coffee! ☕💚).

After college, I wasn’t in a great place. I ended up working three jobs (a bit of a theme for me!). The first as a barista, the second was as a keyholder at a retailer, and the third was as a waitress. It was a tough time because I didn’t really like what I was doing and I wasn’t sure what I enjoyed. Eventually, I quit my jobs and took some time off to take care of my grandparents for 3 months.

During my time off I talked to a friend about her time teaching abroad in Korea. I started reflecting on my time in college and realized how much I loved teaching. The idea of teaching became more and more attractive, but I really wasn’t sure about teaching abroad so I realized that online English teaching might be a better fit - and the rest, as they say, is history.

What drew you to teaching English online initially?

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Getting to make a difference and help others. I get really excited when something clicks for a student. That moment of realization is a big pay off.

I value the connection with others, it’s very fulfilling, and I think some of the one-on-one tutoring online gives you that in a way traditional teaching might not. This one time, I was teaching a one-on-one for fluency. A low-level student came on, and she was so discouraged. I gave her a pep-talk and took the time to encourage her. We had a little moment before moving on with the class.

It stands out for me because I saw her transform from a reluctant learner - into an enthusiastic one. All she needed was that extra little boost of confidence.

But I guess in broader terms, I teach because I want to live a life that has meaning and purpose. We will all die, so we have to make a mark. With art I always try to think about what is archival, y’know will the material last? For me, teaching is the same. You have to think about what sort of imprint you’re leaving on students. I still remember my art teacher Mr Andrew McClure, he inspired me to where I feel he has influenced me to this today. And that’s something I want to do for my students too.

How long have you been online teaching?

I’ve been teaching with Wall Street English for 5 months. It’s a new program so I was part of the first batch of employees when it was first launched in Canada. A lot of my coworkers are similar to me. We all have a lot on. There’s a couple of Masters students who are juggling their full-time studies with online teaching.

We still usually find time to hang out for an hour after work though. I think a lot of online teachers could miss the connection of an office of people, I feel like I get the opportunity to connect with coworkers. I live by myself, so I value the community and connection.

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Why did you choose Wall Street English?

I’m growing a lot teaching with Wall Street English at the moment, so it’s where I need to be. I think as long as you can feel yourself growing in a job, it’s a good fit. Toronto is so expensive that this is really the only option for me as they provide the office space. I would need to have a devoted space at home if I were to teach with other online programs. I’d have invest in a map and a whole backdrop.

I’ve got office lighting and a professional backdrop, as well as a community of teachers to bounce ideas off every day. As someone who lives alone the community aspect appeals to me, I’m 95% extroverted, so I really value coming to work and getting to know my team.

Note: Sarah is an unusual online English teacher because she works regular hours from an office where there is an online teaching team. This gives her the added advantage of having a supportive work environment and gives her a sense of community, but the challenges she faces are the same as those people will meet working from home, she just doesn’t have the advantage of rolling out of bed and walking 30 cm to work. 🤷

Is there any reason why you picked online teaching over teaching abroad?

I might still teach abroad someday, but it’s just not the right time at the moment. I guess I had a few concerns. I knew I wanted to teach English to non-native speakers, but I really wasn’t sure about shipping my life halfway across the world. There are four main reasons why teaching abroad wasn’t a good fit for me, right now:


  1. If I did want to go, it would be to Asia. My top two destinations would be Japan or Korea, and that feels like a long way to go right now.

  2. The 1 - 2 year contracts for teaching abroad in Japan and Korea were daunting. It’s a big commitment, and I wasn’t ready to take the leap.

  3. I could easily do art overseas, but it would be hard to do event planning. I would really miss that. One of the best things about online teaching is that it gives me space and time to do everything else.

  4. I want to spend time with my family, particularly my grandparents, so living abroad isn’t a great fit right now.

Not that teaching abroad is out of the question, if I do go someday it will be because of the adventure, potential earnings and a chance to develop my skills in a new environment!

What qualification did you need to land your job teaching online?

I think my background in teaching and mentoring throughout college helped! But that didn’t stop me getting properly qualified. Once I made the decision to teach, I knew I wanted to invest in the right TEFL/TESOL certification.

It ended up costing me just over $1,000 CAD, but it’s been worth the investment. If anyone is looking to get a TEFL qualification for online teaching, I recommend going with a course at about this price point. I don’t honestly know if I could teach some of the grammar without it, because so much of what I knew before taking the course was innate. I struggled through the grammar portion of the course, and I’m glad I did. At least now I feel prepared in my online classroom.

Also when I think about the price point, I compare it to my undergrad/graduate programs, where I could easily spend $1,000 CAD on a class. Some of those were taught by MA students. At least with the Oxford Seminars TEFL course, I was paying for a fully-qualified teacher.

What did you like about your TEFL course?

What I really loved about the TEFL course was the in-class components. They were very honest, which I value. They didn’t shy away from any of the tough questions and made sure to go over concerns for teaching abroad if you were LGBTQ+ or had tattoos.

There was a detailed section on what to do about contracts and how to know if the contract is too vague or dodgy. There was a bit on how to research jobs and protect yourself, which I found useful. They also posed important questions about the cultural difference: like what should a teacher do in a country where it’s considered okay to discipline with a ruler?

Were there any parts you didn’t like?

Although it was a necessary evil, I wasn’t a big fan of the grammar portion of the TEFL curriculum. It was online, and I felt like I’d have absorbed it quicker in a classroom setting.

It depends what kind of a learner you are, I’m extroverted, so I really value being in a class and bouncing ideas off other people. I used to have to go to a cafe with a friend just to get through some of the tougher grammar sections.

What skills from your background in art do you think help with online teaching?

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I took several courses in theatre in college  - I think it helps a lot. A mixture of being dramatic and being Italian definitely means I use my hands a lot when I am teaching online which helps the students.

Art helps too because I can draw on the slides, and upload pictures. My coworkers are always laughing at the number of pictures I use, but pictures are so helpful when it comes to generating natural conversation.

What do you think are the advantages of teaching adults online?

There are a lot! The focus is more on fluency so you can have some really interesting conversations. A lot of the topics can lead to philosophical or political chats which are always fascinating. For example, the environment is one of the subjects. Right now, that’s a necessary conversation. We should probably all sit down and talk to someone for an hour about what we can do to help the environment.

I am often inspired by my students and their ideas! I think you’ve to go in with an open and creative mind. I’m not sure everyone would consider this an advantage, but sometimes it can (especially one-on-ones) feel a bit like a therapy session. I don’t mind, because I genuinely love to connect with people and check-in. The biggest benefit is probably that you’re being paid to have this hour of connection with someone halfway across the world. I love getting to speak to so many different sorts of people.

It’s an endless education. I love asking questions - so my job is an excuse to probe people. I love that I never know what my students are going to tell me. I could be talking about anything on any given day. Recently my students told me about Singles Day - which is like Black Friday in China. I had no idea!

What are the challenges of online teaching?

Usually in group classes - there’s a lot of time management and some students want to hog the class. It’s my job to interrupt them and make sure everyone has equal talking time. That can be tough because as a Canadian I feel rude interrupting someone, just culturally that’s not something I’d normally do. So I’ve to balance fairness with politeness. And in the context of a classroom of Chinese students, fairness is most important.

In a normal classroom I might have more time to hone in on weaker students or give stronger students a chance to do some advanced work, but online you’ve to balance the class and talking time.

Their names can be challenging too, I try to learn these in advance by getting Google to pronounce them - that normally saves me from messing up!

I guess the hours can be hard to adjust to, starting work at 5 am is rough. It means I’ve to plan my social life well in advance.

Is it hard to navigate cultural difference with Chinese students online?

I think it’s easy for me to avoid any big cultural faux pas as I became a part of the Chinese club in university. It started out with just helping them with events, but by graduation, they had made me an honorary member!

That experience means I’m already familiar with a lot of the cultural things. For someone teaching Chinese students for the first time, it’s valuable to do a bit of research around their culture, just so you don’t make any blunders.

Any issues or horror stories?

It’s not really a horror story, but once a student doctor came into a group conversation class just after she told a family that their loved one had passed away. She started crying in the class and was clearly very emotional.

Instinctively I wanted to reach out, but culturally in China, it would have been considered unprofessional to spend extra time with her in a group class. Navigating that from a Canadian perspective is tricky, how do you show empathy without making things worse or letting a student lose face? That’s probably the hardest lesson I’ve had online.

What is the single best thing about teaching online?

Without a doubt, it’s the students. I’ve so much respect for them.

One thing that stands out to me about adult learners is that they want to learn. Occasionally their boss is making them, but it’s not like kids being forced by their parents. They are so motivated. I think anyone who learns a new language is extremely brave, but I have a special respect for my Chinese students because they come from a culture where losing face and making mistakes is a big deal. With learning a new language, the risk of losing face is high because you’re going to make mistakes…that’s how you learn.

There are so many obstacles for Chinese (Mandarin) speakers trying to learn English. In their language they don’t use tenses or pronouns, so explaining some of that can be tricky. It’s interesting to hear about their culture too. I love telling them about Canada, and they love to tell me about China.

What kind of person would you recommend online teaching to?

At Wall Street English, all my colleagues are very different, but I do think there are a few common traits that help. Pretty much everyone has an adventurous spirit, we’ve all been on crazy adventures. We’ve all traveled. It’s so important to be curious about other cultures and want to learn about your students, so having that sense of adventure and a desire to connect with other cultures helps.

We also all value education and learning, so that we all have a sense of purpose. A growth mindset too, online teaching isn’t as easy as it might sound, and you really need to love working with the students and want to improve your teaching. Another big one is patience, you cannot get stressed out easily. You’re balancing classes with small groups of adults and need to be able to manage all the different personalities.

Being creative helps, if you’re genuinely interested in teaching and have a creative spark, it’s amazing how many little games, pictures and diagrams you’ll find yourself creating. Students love that. It gives class that extra spark.

Read this: Everything you need to know about teaching English to adults online