Work and Travel

What is it Like to be an Online Teacher and Freelancer?

Am I living the dream? Not mine, I hope. I’m pretty awful in my dreams. 

Do I take my laptop to the beach? Of course. Sand and salt water work wonders for my electronics—I mean, writing.

Seriously, though. It’s been a tough week. Lacking inspiration for work today, I found myself instead drawn to write my narrative of what it’s like to be an online teacher and freelancer.

“Work from anywhere.”

“Be like us!”

“Travel the world!”

“All you need is a laptop and internet.”

It is indeed all very possible. Here, then, is a look at my reality.

I’m a teacher (these days, I call it English communication coaching) and a freelance writer. Two different kettles of fish. Though personally, I think they’re much better grilled.

So I’ll start with the humble beginnings of my digital nomad career, as an online English teacher.

What is it like to be an online teacher?

I stumbled into the world of English teaching as a young adult, looking for a part-time job to fund a hyper-extended gap year of volunteering in the Philippines. 

Over time, dissatisfaction with the language schools I’d been teaching at turned me to private tutoring, and tutoring turned into launching a business. From there, red tape, personal life changes, and a relapse of the travel bug drove my transition to online teaching. 

Moving my work online allowed me to relocate several times as well as make extended trips abroad—with work and income as carry-on. But the mobility is not stress free.

Depending on the platform you work for, you will have to meet varying standards for internet connection speed, work space, and backdrop. These standards will dictate your schedule and itinerary.

You’ll also often have to make a trade-off between flexibility of schedule and stability of income:

  • Companies that offer a dependable income tend to require more commitment to a fixed schedule. 
  • Platforms where you have control of your schedule generally don’t come with any guaranteed amount of classes or income. 

You can read more about what specific platforms have to offer in this post: Is Teaching Online Worth It?

The first thing that I can say on the subject is that I’m very grateful to have had an income from online teaching that I can take with me around the world. 

Having said that, there have certainly been times when I struggled with the stable connection, quiet work environment, and appropriate backdrop video classes demand. These factors have played a role in my travel choices and added varying amounts of weight to my freedom.

My preferred classes are self-managed through Verbling, giving me flexibility to reschedule with my students at my own discretion, as well as the option to simply propose an occasional class without video when I’m on the road. 

However, another platform I’ve been working with—for the income stability side of the equation—is much more rigid. Which is exactly what I’ve wanted to move away from and why I decided to broaden my online freelancing portfolio.

Plus, I love writing. Teaching is a pleasure; writing is a joy.

The Ups and Downs of Online Freelancing

Regardless of what you’re doing, every coin has two sides. So it is with online freelancing

On the one hand, you have the freedom to live anywhere you like and manage your time as you please. On the other, you’re bound by cost of living. 

On one side, you can pick and choose from a variety of interesting work. On the other, you can worry about having either too little or too much on your plate. 

Yes, your time is your own and you’re blessed with a flexible schedule. But you can also find yourself rigidly tied to project and stressed out by a lack of boundaries.

Work from anywhere: does it mean your work is everywhere?

Here’s how I’ve experienced—and attempted to balance—these contrasts.

Free to Move, Bound by Cost 

Yes, working online provides freedom of movement. But let’s be real, nobody takes their laptop to the beach. 

Currently, my daughter, partner, and I are based in the Philippines. Taiwan is on the horizon, though, so we’re working on our Chinese. 

Blessed with strong passports and an online income, I can relocate my family to just about anywhere in the world.

Well, anywhere?

Of course there are limitations. Cost of living is one of the biggest. 

I have a huge preference for being based in a country with a lower cost of living and more structural freedom. (By that, I’m referring to governments that don’t constantly have you on their radar and won’t fine you when a local election goes under yours.) 

All jesting aside, such things allow me to capitalize on my freedom as a freelancer.

When cost of living is low, I can get everything I need for $1,000 a month. That means, technically, I only have to work 12 hours a week.

“My riches consist not in the extent of my possessions, but in the fewness of my wants.”

—Joseph Brotherton


In Southeast Asia, I can do that. And I know travelers and Worldschoolers who do so in other parts of the world such as Eastern Europe and Central America.

But US$1,000 in Australia? You’ll spend every penny just renting a room—preferably near a Sikh temple because that’s where you’ll be having your meals. (That being said, visiting a Sikh temple is a truly unique experience and absolute must.)

Of course, my workload fluctuates. There are times when I can take off for a few weeks of travel and others where I work from Monday through to Sunday. 

Generally, I work at least 20 hours a week. Sometimes it’s close to a full forty. And even when traveling, I can still fit in a good 16 hours. But that still leaves so much room for freedom—especially with the option to work from (almost) anywhere—and for that I’m awfully grateful.

What do I do with the extra time? Primarily, I try to spend as many quality hours a day as I can with my daughter: having breakfast together, getting her off to school, going to the park, having a swim, doing extracurricular activities—beautiful things like that. 

Flexible Schedule, Rigid Requirements

My schedule can be both entirely flexible and extremely rigid. 

With the live classes and English coaching, as well as the writing and editing I do, some work can be moved and some cannot. For example, I have regular students with classes at set times during the week, and live group classes that happen at a fixed hour no matter where I am or what I’m doing. 

Much of that work is in the evening, starting around dinner time. So I can enjoy breakfasts and afternoon snacks with my family but typically not an evening meal.

Writing and editing work, though it can in principal be done at any time, tends to come up on short notice and with imminent deadlines. That regularly means changing plans in order to get it done. (Though I have to say I’m generally one to thrive on and even enjoy being put under the pump in such a way.)

In short, with the flexibility of online freelancing, you may find yourself lounging in the pool one fine Tuesday morning and chained to your computer all day Saturday. 

Endless Variety, Absence of Boundaries

You’ll have your finger in a lot of pies and boundaries will be tough.

Part of the freedom of being a freelancer comes from not relying on a single source for your income. At least, that’s how I’ve seen it so far.

Because once you rely on a single company or client to make a living, well, you kind of belong to them.

Then they make the rules, and you have to follow them. Eek. (That’s not to say I have any problem with rules; I simply value having a say in them.)

I’ve found that having a variety of clients means not only that I don’t depend fully on any one in particular but also that there’s a lot of diversity in my work. 

Currently, my clients come from:

  • Referrals and word-of-mouth. The way to go and reason to build your brand on LinkedIn as well as have a strong personal landing page or portfolio website. Biggest plus: you won’t lose any of your earnings to platform fees.
  • Verbling. Specifically for live classes and English communication coaching (job interview prep, resume editing, etc.) Also great for networking! However, the platform takes a 15% cut of everything you make.
  • UpWork. If you want to get started as an online freelancer, you’re sure to find something on UpWork. After about two years on the platform, I have to say that much of the work offered is low in terms of quality and pay. Plus, the platform takes a pretty steep initial cut of about  20%. However, once you have your foot in the door with a strong profile and land a solid clients or two, you’ll find that it’s a well-managed platform with strong work protection. Additionally, the cut UpWork takes from your earnings reduces the more you work with a single client. 

This is by no means a comprehensive list of where you can find work opportunities online. I can say that it’s all about getting yourself out there. To that end, here’s a little anecdote. 

Whether it’s intended for it or not, my Verbling profile is also how I’ve been recruited for other teaching work. One such “recruitment” came about in a pretty interesting way, through my first regular student on Verbling. He was an intern at an investment company in Silicon Valley and one day he told me about this startup that was being called the “Uber of language learning”. 

His company was considering making an investment in this platform and he was curious to know if I’d be interested in checking it out and giving him my opinion. I thought it sounded interesting and gave it a try. Though I didn’t end up teaching many regular classes on the platform, I became a member of the community and joined the live classes team—and I still enjoy hosting some very fun group classes with them. 

But this mobile teaching platform also lead me to projects of a much larger scale, such as writing for the CEO’s other two companies. Moral of the story: get out there, start doing things, build up and show your skills, and see what happens.

Always Learning

One of the things I’ve been loving most about being an online teacher and writer is that I’m always learning something new.

Through Verbling, I help people from all around the world improve their English communication skills and in doing so I myself discover the most interesting things. Knowledge gained includes how kimchi is made, how a pilot builds her own home simulator, how the kitchen god flies to heaven on a carp, and how amazing candombe is—and I didn’t even have to book a ticket to discover it.

When it comes to writing, I find myself learning about and researching new topics with every client—constantly growing in knowledge, both relevant and entirely abstract. 

I’m constantly expanding my skill set and knowledge base as I explore new tools and platforms with various clients and veer into the specializations they require. 

On the flip-side, having your work and clients spread around the globe and across different time zones means work can keep going around the clock. 

Thus, one of the first and most obvious-and-obviously-overlooked things you have to do as a work-from-home freelancer is create boundaries.

The Balancing Act: 3 Tips 

1. Get a big fat permanent marker and draw boundaries.

If you work hard and put everything you’ve got into meeting your clients’ needs and deadlines, you must also draw lines. 

Say no when you have to say no. Or say, “Heads up, I’ve got plans for the coming weekend. So if you have work to spring on me, spring it now.” 

Recommended boundaries: 

  • Have a cut off time at some point in the evening or night, depending on your usual work hours, at which you disconnect completely from work—and ideally devices.
  • Better yet, let clients know right off the bat exactly what your available work hours are so they know when they can count on you and when they can’t.

Remember, you’re living the dream. Don’t forget to take a couple days or even weeks off every now and then—just because you can—and explore the world around you or do something you’ve always wanted to do.

2. Think positive; be grateful.

It’s what I tell my daughter every day. And in doing so, I have no choice but to obey this sage counsel myself.

So it’s Saturday and I’m slaving away. But how great is it that I’ve had so much time to spend with my daughter throughout the week instead of being away at work all day?

3. If you’re not happy with the way things are, change them.

If you find that focusing on the good has become more of a “I’m saying all of this to convince myself I’m happy because I’m actually not,” you need to stop.

Stop what you’re doing and change. Were you happier at your regular job? It’s totally OK to admit that. You don’t need to prove anything. You need to find the life that makes you happy and live it. 

What I love about being an online freelancer

I’ll close with the things that seal the deal for me:

  • I typically get to spend as much time with my family as I do working.
  • I can wear whatever I like. No blouses, no pants. No make up if I don’t feel like it. No pinchy shoes! 
  • I can go to the gym whenever I like. Midday boxing? Sign me up! (Actually, I’m looking for a sparring partner so it’s more like, hit me up!)
  • All I have to own for work is a laptop and headset. No car, no briefcase or purse. Did I mention no high heels? Freedom!

If you’re interested in working with me, feel free to explore my portfolio, UpWork page, or teaching profile.

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