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In This Episode of School of Talk


This episode features Jocelyn Hellested.

Jocelyn is a self-described travel junkie and education enthusiast.

She quickly realized teaching online gives her the ability to travel and create a lifestyle full of work she loves while still having lots of time to explore! 

She believes in the importance of pursuing careers that fill us with purpose and allow us time to spend with the people and things we enjoy.

She’s here to share a bit of her story as a travel lover and teacher.

Episode Highlights:

The Freedom and Flexibility of Teaching English Online

  • How getting a Teaching English as a Foreign Language (TEFL) certificate allowed Jocelyn to keep her options open as she considered getting an in-person teaching job abroad. 
  • Creating a flexible schedule as a traveling online teacher. 
  • Maintaining a consistent routine while having enough free time to travel and explore.
  • Enjoying freedom as an independent contractor, including the power to create your own schedule. 
  • Having autonomy over what and how you teach as an online teacher, including a range of subjects, ages, and class sizes.
  • The benefit of forming connections with students without being bogged down with the daily tasks of a classroom teacher.
  • The amazing companies Jocelyn has worked for, include VIP Kid, Cambly, and Outschool
  • What resources you can keep in your backpack as an online teacher.
  • Learn more about how China’s new private tutoring regulations affect foreign-based online tutors

Follow Jocelyn on Instagram.

Interested in teaching online or abroad?

Sign up for a FREE information session

TEFL 101: How to Qualify to Teach English Online & Abroad

Episode 7 Transcript:

Intro: You’re listening to School of Talk. We’re creating a world where every child experiences the power of a great teacher. We believe education is the answer. It has the power to conduct change, improve lives, unlock ideas, create opportunities, and build connections.

It’s the single greatest investment we can make today to create a better tomorrow. That’s why we’re on a mission to train, inform and inspire educators around the world.

Each week, we dive into a topic related to education, teaching, and learning.

Whether you’re an educator by trade for an educator by spirit, we’ve got something for you. Open up your mind, and get ready to soak in some new learning.

Class is in session.

Today’s episode is brought to you by Teach Away.

Teach Away offers a full suite of services to schools, aspiring and current teachers from helping travel lovers get certified to teach abroad to offering international recruitment solutions for schools to providing world-renowned professional development courses.

Teach Away is here to create a world where every student experiences the power of a great teacher.

Michelle: Welcome back to School of Talk. On today’s episode, I sat down with Jocelyn Halstead. Jocelyn is a self-described travel junkie and education enthusiast.

She quickly realized teaching online gives her the ability to travel and create a lifestyle full of work that she loves, while still having time to explore.

She believes in the importance of pursuing careers that fill us with purpose and allow us time to spend with the people and things we enjoy.

She’s here to share a bit of her story as a travel lover and a teacher. All right, Jocelyn, I was hoping we could just start off with a little bit about yourself.

What inspired you to become a teacher in the first place?

Jocelyn: Okay, well, that is a really good question. So I really enjoyed my time at school. But I definitely felt that I was stronger in certain subjects than other subjects.

One in particular math, I just really disliked. I always had like a hard time with the class.

It wasn’t until I was in high school that I had a really, really good math teacher. And she made the classes really fun and engaging. We played lots of games.

She was super patient with us and, you know, loved when we were able to ask her questions and things like that.

It just made me realize the power that a teacher has to really, you know, share and instill a love in a subject, whether or not the student is naturally inclined in that subject.

So kind of after having that experience, it just made me realize that that was something that I wanted to do for others.

I’ve really enjoyed learning languages myself, I love how it’s connected to culture and to, you know, all sorts of different things.

So I wanted to kind of share my experiences with my students and make learning languages fun in the online classroom.

Michelle: Thank you for sharing that Jocelyn.

And I love that the teacher that was so inspirational to you was your high school math teacher.

I think it’s just like an important reminder that an inspirational teacher can affect students at any time in their career.

Their learning career doesn’t necessarily have to be younger students.

Jocelyn: Which my perspective of it, I was like, ‘Wow, maybe it’s not that I dislike math.’ I just never had a teacher who was able to share the subject in a way that was interesting to me or relatable to me.

Michelle: She engaged you in a different way. Yeah. And opened your eyes. That’s fantastic.

Did you pursue online teaching right out of school? Like, did you go from high school to post-grad? Or how did that work?

Jocelyn: So after high school, I attended college and actually was a double major in art history and Spanish.

And so I didn’t pursue teaching more so because I had talked to teachers, being like, oh, you know, is this like a profession I want to get to, like, get into, and unfortunately, a lot of them were like, ‘don’t go into teaching, the hours are crazy.’

And, you know, there’s so much kind of like bureaucracy that gets tied up into it, that kind of prevents teachers from, like, doing the part that they love, like, forming relationships with students and, and doing the actual teaching portion.

So I was like, you know what, okay, I’m not gonna go into teaching. I’m going to go this other route, kind of a more unconventional way of teaching, whether it was like in a museum as a part of like a didactic program, where I was teaching in a museum or maybe teaching languages or with different volunteer programs or things like that.

So I did not pursue education. But I was always intrigued by working with children in sort of unconventional ways.

After I graduated college, I actually became a site coordinator for an after-school program. So again, still working with kids still in a school setting, but an unconventional way of, of teaching that something like during the school day.

Michelle: Yeah, I think that’s such a good point to bring up.

I myself was a teacher, a school teacher. And I think it’s so common to think of school teaching as only like one option like you have to be a classroom teacher, you have to, you know, do all of that. And, and that’s the path.

But there are so many other avenues to get into the world of education and be an educator.

I think oftentimes, we just don’t know about them. So I’m glad that you were able to find something that kind of like, connected your passion for working with youth or children, with your love of languages.

And sounds like art, too. That’s pretty awesome.

How did you discover online teaching?

Jocelyn: So that portion of it, it’s actually really interesting, because I was also very intrigued by traveling and traveling to Spanish-speaking countries because I speak Spanish.

The whole online teaching portion kind of came about as a desire to travel!”

I was thinking like, okay, like, I really want to travel.

And I really want to travel for an extended period of time. Like, I don’t just want to go on a vacation someplace like I really want to, like live there, I want to meet people, I want to be able to bounce around and you know, create my own schedule.

So what is going to allow me to travel but also earn some money because I need money for things?

What’re some different, you know, virtual positions, remote work?

I came across online teaching to students in China. So I looked at a bunch of different companies. And I finally settled with VIPKid.

That was kind of my first online teaching position.

And at the time, I had thought to that maybe I was going to go abroad, and maybe I would find a position in-person abroad, which is what led me to get my TEFL certificate.

So while I was still at home in the States, I began teaching with VIPKid. And then I was also at the same time pursuing that TEFL certificate as well with the intention of maybe teaching abroad in person which that part didn’t really happen, but, but the online teaching portion did it.

How getting a Teaching English as a Foreign Language (TEFL) certificate allowed Jocelyn to keep her options open as she considered getting an in-person teaching job abroad

Michelle: Did you need any type of certification in order to join VIPKid as a teacher? Or was that just you and your own skillset?

Jocelyn: So it’s changed a little bit, but when I first applied I did not need to have a TEFL certificate.

I could, I believe I could just apply with them.

And then they had their own unofficial VIPKid TEFL program that was like a few hours: you had to watch some videos maybe and like answer some questions about it.

So I think it definitely helped my chance, my chances having the TEFL certificate, but at the time, it wasn’t required.

I think that since changed, and a lot of things are changing with the online teaching world in China right now.

I’m not quite sure what it’s like now.

But yeah, at the time, it wasn’t required for me to have the TEFL certificate, but it was just something extra.

I was like, it’s not going to hurt and I’m interested in it anyways.

So it was something I was like, regardless of how I use it, I’m gonna get.

Michelle: You’re gonna get it and have that certification for your next steps. Fantastic. And where do you live now? And what and how do you teach?

Jocelyn: So I am currently teaching in Puerto Rico.

I arrived in Puerto Rico on Sunday, before that, I was in Ecuador for two and a half months.

So still getting acquainted with Puerto Rico but enjoying it.

I am currently teaching with VIPKid still. I’ll be teaching with them for at least one more week.

And then I am also working with Outschool and Cambly as well.

Creating a flexible schedule as a traveling online teacher

Michelle: So you’re with a few different education providers. And so how, how busy is your work schedule? Do you teach daily?

Jocelyn: I do. I do teach daily. The bulk of my classes is on Tuesday through Friday.

I try to leave Monday really open so that I can do lesson planning.

I have a few different side projects and like teacher training programs and things that I’m a part of.

So I try to keep my Monday kind of open and free and then do the bulk of my classes Tuesday through Friday.

And I’m teaching, like, I’m teaching for about five hours, four and a half, five hours, Tuesday through Friday.

Maintaining a consistent routine while having enough free time to travel and explore

Michelle: That seems like a really nice balance in terms of like, having time for yourself to travel and explore and just live in a different country that you’re you’re new to. But also having like a full enough scheduling kind of keep a routine for yourself.

Jocelyn: Yeah, and for me, I found it’s been very, very helpful to have more of a consistent routine, because when I first started teaching online, I was like, Oh, well, I want the flexibility to change my week, or, you know, to change my work week on the drop of a hat.

And you know, it’s always gonna be changing.

Enjoying freedom as an independent contractor, including the power to create your own schedule

Jocelyn: I’m a person who feels a lot less stress and a lot less anxiety when I have a schedule, and I kind of know, okay, this is my schedule, and then kind of work around it.

So it’s great because, with online teaching, I do have the power to create my own schedule, I’m an independent contractor.

So I have complete control over that. But I do enjoy having more of a consistent schedule, just for my own mental health.

And then also, it helps students find me, and then also stay with me, because they know they can depend on me to consistently have classes, they don’t have to think, oh, you know, well, we were with this teacher for two weeks, and then her schedule changed.

And you know, because with education, you want a consistent teacher to build that relationship and build upon that content.

So it is helpful to have somewhat of a consistent schedule.

Michelle: Great to know that, you know, if you are someone who enjoys a consistent schedule, you can keep it that way.

But if you’re someone who’s a little bit more maybe free-spirited, or you like the idea of keeping it up in the air, you can change it how it suits your style, which is cool, for sure.

Jocelyn: The platform kind of will dictate that a little bit as well.

So if you’re somebody who wants more of a schedule, then like, a platform like Outschool, might be really good for you.

Because you’re creating your own classes, you’re promoting your own classes.

And then you can have particular students, you know, for six months at a time or for a whole year.

But if you are a teacher that you know, wants more flexibility with your schedule, then definitely applying for a program or a platform like Cambly might suit you, because you’re not gonna have as consistent as students, you might have a few regulars.

But you can just go online and find students immediately, you don’t have to set a schedule, ahead of time, per see.

So there are definitely a lot of options, depending on your traveling style, your teaching style, the kinds of students you want to work with.

So definitely a lot of options and variety in the online teaching platforms.

Having autonomy over what and how you teach as an online teacher, including a range of subjects, ages, and class sizes

Michelle: That’s fantastic to know. Thank you for sharing all of that. And what do your classes look like? Do you have a group of students that you work with? Is it one-on-one with different age groups?

Jocelyn: It changes depending on which platform I’m teaching with.

When I’m teaching with VIPKid, it’s one-on-one.

And I’m generally teaching students as young as like 4 years old, to as old as like 11-12 years old.

My zone of genius is definitely the little ones.

I love being silly in my classes and just being way over the top.

So I love the littles.

But yeah, VIPKid, one-on-one, my Cambly classes are also one-on-one, and they have an adult platform as well as the kids platform.

I mainly teach on the kids’ platform. But that’s one-on-one with students from all over the world, which is really, really interesting.

And then my Outschool platform that I teach with, is pretty cool because I get to design my own curriculum.

I get to decide how many students I want in my classes.

So I, again, teach the littles because they’re my favorites to teach.

And the most students I’ll have in a class with me is six.

So usually it’ll fluctuate from like three students to six students.

But it’s nice because it’s a smaller setting, which is a little bit easier to navigate when you’re teaching online and you’re not in the same physical space as them.

I have so much respect for teachers, you know, within the past couple years who have had to teach like their full classroom of like, 28 kids, like, I don’t know how they do that.

Like when people are like online teaching is crazy. It’s so hard. It’s like, that’s a whole other ballgame.

I could never do that full-time. Like it doesn’t have to be that way. There are lots of other platforms where it’s a one-on-one or small group setting. That’s so much more manageable.

Michelle: I think that’s so true like such a good distinction. Having a full class of, you know, 25 plus 25 is actually a small class. 30-ish students is a much different wheelhouse than teaching a small group.

Jocelyn: Yeah. And when I do teach more than one student, it’s only for 30 minutes.

So, like, within 30 minutes, it’s like, no matter what age the student is, it’s very easy to be like upbeat, high tempo, like maintain that energy, which is gonna keep them more focus, keep them more engaged.

And then after 30 minutes, I say goodbye.

And they either go to another class or you know, go about their day, but it’s only for 30 minutes.

So the amount of you know, energy that you can bring to a class that you know ahead of time is only 30 minutes… is much different than having them for several hours a day.

Michelle: That’s a good point. And you’re teaching these kids English.

Jocelyn: Correct. So for VIPKid and Cambly, I’m teaching English, and then Outschool.

I’m teaching Spanish. And then I have like a random like arts and crafts class that I do at night.

Michelle: So you can teach arts and crafts virtually?

Jocelyn: Yes, yes, you can.

Like, there’s no limitations. They bring their own materials.

And yeah, so we keep it to really basic materials that I know most students will have around their house.

It’s the same two little girls that I teach every single week.

So I’ll send a supplies list like the week before.

But yeah, on this one platform, I know teachers who teach cooking, and they teach science, where they do experiments and things.

So of course, you have to, like send a supplies list.

Also keep in mind, you might have some students who don’t bring the right supplies. So you have to definitely be flexible if that happens, and still find a way to incorporate them into the lesson.

But yeah, it’s really amazing.

Like, since I’ve joined Outschool, it’s kind of blown my mind, like what we’re able to do in a virtual setting.

The benefit of forming connections with students without being bogged down with the daily tasks of a classroom teacher

Michelle: That’s pretty neat. For the students that you do teach English to, or perhaps all of your students, how is their level of English with you?

Like, are they able to communicate very easily? Or do you speak to them in Spanish, depending on where you’re teaching? Or how does that work?

Jocelyn: Yeah, so again, it kind of changes depending on the platform.

And also, of course, like the level of the students.

So for example, one of my Cambly students, she is from Brazil and uses Cambly as kind of like a supplemental course or class to what she’s doing already in school.

And she actually attends like, an in-person English school as well.

So with her, it’s just conversation. Her English amazes me, she’s 13 years old and can have like, really deep conversations with me about movies and books and what’s going on in her life.

So her level is definitely much higher. And I’m not giving her formal lessons, I’m actually just doing conversation.

So I might teach a few idioms or you know, some phrasal verbs that maybe she hasn’t heard of, or different expressions.

So it’s definitely not as structured.

But then for my Spanish classes, I’m generally teaching students like 4 to 7 years old, and some of them come from bilingual homes where they do have some exposure to Spanish already.

And I do try to give a good amount of my instruction in the target language, so in Spanish, but they’re, they’re beginner students.

So if we’re going over more of a complex grammar concept, I’ll slip into English so that they can understand me and have like a firmer grasp on it.

But I use a lot of like little flashcards. And I have a whiteboard that I draw on to show things in a visual manner so that they can make more of a natural connection so that they aren’t always feeling like they need to translate something.

I’ll have presentations and things with different photos as well, that kind of helps with my beginner students that might not have as much of exposure to the target language, whether that’s in my English classes or in my Spanish classes.

What resources you can keep in a (literal) backpack as an online teacher

Michelle: That’s fantastic. You sound like an excellent teacher.

You mentioned that you have some visual things like flashcards and whiteboards.

Are there any other resources that you typically use in your classes? Are there online resources, or do you typically use visuals like that?

Jocelyn: I have a few physical resources because I’m traveling on the go and I’m on the go.

Like I literally just have like a backpack that I bring with me, so I don’t have a lot of space for physical props.

I have some 2d flashcards that are just like on a piece of paper.

And then I do rely a lot on like online tools because like I just have to bring my computer it’s nothing like physical that I have to bring with me.

So I love Canva. Canva is a great tool for teachers and really anybody who wants to create visually appealing things. So I’ll create presentations with Canva. They have a wide variety of like pictures and different graphics and things like that.

I also use another platform called Nearpod, which allows me to incorporate interactive games into my classes that my students can log into an account. And then they can do it on their own device, either on a computer or using a tablet, or a phone. So there’s like drag and drop games they can do, they can draw on the screen, which is very cool. They have virtual field trips. So if I’m teaching a subject, or if I’m teaching a specific unit on a specific topic, like animals, I can like take my students virtually to the zoo, and they can like go around in this little virtual field trip and really, like experience it. So that’s through Nearpod, which is very cool.

And there’s lots of different resources and online tools that definitely make the classes more engaging and fun.

For the teacher who’s teaching them, but also, for the kids that are experiencing them.

Michelle: That’s amazing. And that’s definitely one thing about teaching, that maybe people don’t know all the time is that you don’t have to reinvent every single thing.

There are so many resources. And so many teachers are willing to just share things that they’ve created already for you to use and your classes.

And it’s just a matter of picking and choosing the pieces that work really well for you. And running with them. Like the fact that you use virtual field trips. It’s so incredible.

And I bet your students love that and have so much fun, and probably learned quite a bit too.

What would you say is the hardest part about teaching online?

Jocelyn: Oh, I think on like a practical side, if you are interested in teaching online and traveling, the hardest thing is sometimes the unknown when it comes to Wi-Fi and your working situation.

So for example, when my boyfriend and I arrived here in Puerto Rico, we were under the assumption that he was going to work in like, maybe the bedroom, and I would work in the living room.

And then I’d come to find out the bedroom is like a Wi-Fi dead zone area. There’s no Wi-Fi in the bedroom.

So like, now we’re positioned, we’re, we’re like at the same table, and he’s like, right next to me, and like I’m teaching, and I’m loud.

And you know, so just the unknowns, when it comes to like you kind of have something in your mind, like, Okay, this is gonna be the plan, we’re gonna arrive there, and then maybe the Wi-Fi is not strong enough, or you know, you need to find a backup or change where you physically are in this space.

So sometimes that unknown can definitely be a little bit stressful, and you kind of just have to, like roll with the punches, laugh at it, because you have no control over it.

So you just, you know, got to just keep chugging along, and then have backups and things like that, like hotspots and, you know, buy a SIM card if you’re international and things like that.

And then I think maybe something that’s more specific to actually online teaching unless just like remote virtual work, is sometimes there’s a lack of communication between you and you and the families or you and the parents.

Maybe this is something that all teachers might have to kind of work with as well.

But you’ll find you have some families that are very forthcoming with information where, you know, they might let you know, if the kids having a really rough day, or, you know, they might let you know, specifically what the kid has been working on before they even come to your classroom.

So you have an idea of, you know, what their strengths are, what some things they might need to work on.

And then you have other parents that you might send a message to and then never hear from.

So you’re like, okay, like, Is everything fine? Is everything not fine?

It’s sometimes hard not having full communication with families and then not always getting feedback regarding how you know families and parents are viewing your classes or seeing progress in the students and things like that.

That’s sometimes a little bit difficult to work with.

Michelle: That’s so funny. Both of those things that you mentioned are so typical for a typical traditional classroom as well like just constantly dealing with unexpected hiccups.

And of course, parent communication is sometimes challenging with you know, different families, different schedules, all those kinds of things, but you know, of course, you take the good with the bad and sounds like there’s a lot of good.

What would you say is the best or most rewarding part about your job teaching online?

Jocelyn: I don’t know if this is specific to like online teaching, it’s probably true for all teachers, but just when you are working with a particular student, and maybe it’s on, you know, a subject or a concept that they’ve been struggling with, and when it finally clicks, and they’re like, oh my gosh, like, I got this, like, just that, that moment where it’s like, okay, I’m doing my job like I could, I can totally see that, like, things are clicking.

They’re getting it. I feel really good about it. They feel really good about it.

We can like all celebrate this moment.

Yeah, I would definitely say those little lightbulb moments when things start to click, because there are also really hard days where you’re like, I just taught that lesson, and I’m not really sure how it went.

So when you do have those moments, it’s like, it just affirms like, okay, like, we’re doing fine.

Where are some places that you’ve gotten to live as a result of teaching online?

Jocelyn: So I’m in Puerto Rico now, and before I was teaching in Ecuador. I love Ecuador.

Lots of great things to say about I’ve been there twice now since beginning my online teaching traveling journey.

But I also spent some time in Colombia, and then Costa Rica as well.

Michelle: You’ve been to so many places! How long have you been doing this?

Jocelyn: Since we left in October of 2019. So yeah, we left in October of 2019.

And then we were traveling in Central and South America until March 2020.

Then we came home because borders were closing and we were like, Maybe we should be with family, we’re not really sure what’s happening.

We also spent some time in the US traveling. We spent some time in Massachusetts and Utah for about like five months. We went back abroad and went to Ecuador in August.

And now technically, we’re back in the United States here in Puerto Rico.

Michelle: You mentioned that you’re with your boyfriend, does he also teach online? Or is he doing something else?

Jocelyn: No, he’s doing something else. He’s a web developer. So he has the luxury of just needing his computer and working from anywhere.

Michelle: It’s great that you found a way for both of you to live that lifestyle. Because honestly, I don’t think too many couples would be able to do that. That’s incredible.

Jocelyn: It’s probably helpful he doesn’t teach online, too so that we don’t have to find two spaces where we’re both simultaneously teaching.

Michelle: For sure. Just before we hop off here, is there a message or recommendation? Or something that you’d like to leave us with today?

Jocelyn: Yeah, sure. So I think what I would want people to know, is to try and not get so bombarded by you know, what society expects of you. Or by what you see on social media because it’s so easy to get kind of wrapped up in this ideal picture of like, what teaching online and traveling is like or what online teaching is and the things that you need to be successful. It’s going to be different based on who you are as a person.

Don’t get wrapped up in all of that and kind of just do your own thing and know that that’s okay and that your journey doesn’t have to be the same as anybody else’s, and it shouldn’t be.

“Find your own path. Find what’s gonna bring you bliss and joy and just go with that.”

Michelle: Thank you so much to Jocelyn, for being with us today.

Thanks again to Teach Away for sponsoring today’s episode.

If you’re interested in teaching abroad, if you absolutely love to travel, or if you’ve been cooped up in your home for the last year and a half and are itching for an adventure, Teach Away can help you see the world while teaching English abroad.

They’re hosting an information session that will explain to you how you can teach English online or abroad. And by signing up for the session, School of Talk listeners will receive a 20% off coupon to use toward one of Teach Away’s internationally recognized TEFL courses.

So head over to to learn more about teaching and living abroad and find out where teaching can take you.

Outro: Thank you for listening to this episode of School of Talk. If you enjoy today’s episode, be sure you subscribe to the podcast. If you love today’s episode share this with a friend. Class is dismissed.


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TEFL 101: How to Qualify to Teach English Online & Abroad

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