5 Things I Wish I Had Known Before Starting My Online English Teaching Business 5 Years Ago

Cara Leopold
10 min readJul 26, 2021
Looking back with a 5-year perspective

I’ve been trying to build an online English teaching business, without burning myself out on 10-dollar-an-hour Skype lessons, for the past 5 years.

Sometimes, if I had known how hard it would be, it might not have started.

But given what I’ve been able to create, the amazing people I’ve met and the personal growth I’ve experienced, I wouldn’t change a thing.

That said, I’d still like to pay some of what I learned forward so that if you’re just starting out, you don’t make the same missteps. And if you’ve been going for a while, maybe you’ll recognise yourself in some of my story.

# 1 Creating a business from scratch is hard

And it’s not what most people do. Or necessarily acknowledge. Think about it, there are ways into business that are much quicker and easier:

  • Become a franchisee. You literally have an instant business — just add water! Although when head office is telling you want to do, how to do it and when — is it really a business?
  • Buy an existing business. I see this happen all the time in my town — people buy a “fonds de commerce”. They now run the business, but the previous owner gives them the client list. That doesn’t mean you can’t expand or change things if you buy a business. But you’ll hit the ground running.
  • Retire early and create a business to tide you over. I’ve seen late-career colleagues do this. They’re in their late 50s or early 60s and they’ve had enough of their jobs. So they decide to make a break for it and start a business. This is starting from scratch in a sense. At the same time, given how long they’ve been working, their experience and reputation in the field and the sheer number of contacts they have, it’s going to be easier to get going. That’s assuming that the business is connected in some way to the previous role.

When you start from scratch however, you really do start from scratch. Particularly in online business which is like our ever-expanding universe. When you start, you’re in a dark corner, millions of light years from anyone, apart from your mum!

And if you’ve never been in business before (my case), then it’s even worse. Not only do you start from sub zero, you have no idea what you’re doing either!

So be realistic about the work involved and the timescale. And be incredibly gentle with yourself and your business. Putting pressure on yourself and your business to make money fast could burn you both out.

I’ve been going for five years and it’s only really in the last 2 and a half that things have started coming together. And I still freelance on the side. Plus, I almost abandoned my business completely in 2018, after 1 and a half years of false starts and disappointments.

This is a pattern for me connected to my issues with perfectionism. I walk away because anything less than perfect makes me think I’m doing a a bad job. The universe keeps bashing me over the head with the lesson!

Fortunately when I was ready to get back on track, things came together relatively quickly thanks to the foundation I had already created, but perhaps didn’t recognise. So much of our impact is invisible — all those people quietly watching and waiting for the right offer to come along.

I’ve often beaten myself up about the time things have taken. But then I look at other colleagues who started around the same time. And after a while, things just start to come together, like there’s a kind of natural time frame that you can’t necessarily “hack”.

After a certain number of blog posts, emails, live videos and social media posts put out there. After a certain time spent honing your message and communicating your vision, things just seem to come together.

But your timescale will likely be different to mine. Asking how long it takes is like asking the proverbial “how long is a piece of string?”.

#2 Don’t sabotage your success through impatience and ignorance

Know what to expect. I mentioned that I almost abandoned my business completely in 2018. That’s because I was fed up after 2 years of hustle and not a lot of results (at least as I perceived it anyway).

Things would sell (or not!), especially initially but then would dry up. People would stop working with me. After a while, no-one seemed interested in my offers.

I realised I was hardly teaching and was so fed up that I started working elsewhere, just to have some teaching work. I took on work at the university as well as with a couple of language schools and with another language website. I took on so much in fact, that I had little time for my business.

I was also panicking about the redundancy money I had coming in and assumed it was going to dry up sooner rather than later. I was wrong about this! But mostly because I didn’t run the numbers and check with the unemployment office.

Redundancy money was a big help, but it just ended up being another stick for me to beat myself with because I felt pressure to bring in a full-time salary before the money ran out.

At the same time, when you’re not worried about money, you can just end up watching webinars all day, especially in the early days.

Looking at how close I came to almost completely walking away, I realise now how I would have disappointed my current clients and subscribers.

Here’s what you can realistically expect in business

A long, messy experimentation phase. Your first product will not be your last. It’s only in the last two years that I’ve been able to create two offers that bring in relatively consistent income. But they’re built on all the previous experiments.

Expect to have a hard time gaining traction until you have a core message or a why down.

Beware overnight success stories — behind every one are usually years of toil. And no-one is telling the whole truth. This post might read as honest and vulnerable and open. But you’ll never know the full story. And neither will I.

Luck and timing playing such a big role in “success”. But of course, people tend to downplay these factors, especially if they have something to sell you. The healthiest way to look at things is to not let your ego trick you into believing that success or lack of it is all on you.

Money feels like a tangible way to measure progress, but a lot of it is intangible.

My dad almost completely sabotaged things for me early on by saying — you’ve been posting on Facebook, do you have clients? If people know about business, then they’ll know that putting a few posts on Facebook is not enough to get a full roster of clients!

#3 Do you want fast cash or long-term sustainability?

If I had wanted to, I think I could have created a business much faster had I gone all in on finding clients locally.

Given how many people know me from the gazillions of jobs I’ve had in the past, it would have been fairly easy to find a dozen or so people to give lessons to, especially if I had been ok with tutoring people’s kids.

But what I do now is a million miles away from that initial vision that I could see in my immediate environment. I now run a movie club for English learners — it’s fun and I love it and my students are amazing to work with. It’s so different to what I thought I’d have to do. And so much better.

Going down the route of tutoring local kids would have been a fast path to cash. But not a path to fulfilling and meaningful way of working.

It also had the potential to be a fast path to burnout given the pressure on prices for language tuition. And the number of clients required to sustain those prices. University students here will happily give an English lesson for €10, cash-in-hand.

So figure out what it is you want. If you just want money, then maybe a job is a better option. I know that the job market isn’t always easy though, especially if you’re teaching languages. More on that in a second.

#4 Despite their marketing and your investment no course, or coach will give you the magic key to success

So let me qualify this first by saying that there do seem to be some business fundamentals.

You’ll need to know why you’re doing what you’re doing and communicate this. You’ll need to get to know your ideal client and what they need. And you’ll need to have a way to collect email addresses, which you can start doing, even if you don’t have a website.

One of the most dangerous things for online entrepreneurs is the number of people trying to sell you on how to build a business with their “proven strategies”.

Proven by who or what I don’t know. As far as I know, there’s no academic research on online business or its strategies or how successful most businesses are. All you have to go on is people’s marketing and testimonials. And of course they’re not going to tell you about disappointed customers!

When I started my online business I was lucky in that I avoided much of the “online marketing”/ “internet marketing” crowd. To the extent that I didn’t even understand the backlash to this type of marketing in other people’s work!

But of course, as a business newb, I knew I needed help and sought it out. I didn’t try to figure it all out myself because I knew my incompetence would just waste my time. So I’ve had my fair share of courses and coaching.

Every course you take or coach you work with will be a piece of the puzzle in creating your business. But no-one can lay the path out in front of you and tell you exactly what steps to take.

People can share what they did. And you can test those ideas. But ultimately you’ll have to experiment. And to accept that someone’s “proven process” may not work for you.

I got coaching in my first year in business. And then for some reason I got it into my head that I shouldn’t need coaching after a year. So I went off and did a course instead. Thanks to this course, I created an offer that sold a bit then stopped working. But because of sunk costs, I didn’t want to let it go.

Other approaches I like are learning how to trust your intuition. And also working with people in your field. My coach, Elena Mutonono, teaches online language teachers how to create more time because there is terrible downward pressure on prices. She knows because she’s been there.

The language of coaches working with other types of business people doesn’t help us, because we’re in competition with people charing 5 USD an hour, not 100 USD.

In the current marketplace, it could take a language teacher years to get their prices up to 100 USD an hour, whereas that’s seen as a starting point for life coaches and other professions. So our industry needs a completely different approach.

#5 Why are you doing this?

If you’ve decided that you don’t just want some cash quick, then you’ll have to figure out why you’re going down this path in the first place.

I bypassed some of this because I had got it into my head that creating my own business was the only way to make money. Hence why I put so much pressure on myself and almost quit!

This story isn’t necessarily true, but my career history has been pretty patchy up till now. I’m not one of these entrepreneurs who walked away from a glittering 6-figure corporate job to follow my true calling. I’ve always followed a calling.

I’ve been reading Celeste Headlee’s book, “Do Nothing” recently and in it she quotes the labour historian Nelson Lichtenstein who says that “most self-employment is involuntary”. Yup, that’s me.

Since graduating from university in 2007, I’ve had trouble finding stable employment (full-time, permanent contract). And when I finally did, in a field outside teaching, after a master’s degree and 10 months of internships, I ended up leaving.

After so many years or underemployment, working multiple gigs, struggling with both lack of job stability and low pay (earning less than minimum wage despite working multiple jobs), I felt like there weren’t many options left anymore, especially because I’m not willing to move or get a job in a school.

So it felt like self-employment was the only route left for me that would mean being able to make a living while continuing to live in France.

So my business “why” initially was — I’m out of options and I need money. And I didn’t know how hard it would be to make money this way.

I came up with my niche when working with my first mentor who encouraged me to do an in-depth interview with an ideal client to create it. I did this, and then I met Elena Mutonono, who stresses the importance of a core message.

If I had met Elena first would my niche have been the same? I don’t have a clue. In any case, for a while it was a bit of a Frankenstein’s monster.

A lot of people teach the whole getting to know your ideal client thing. Of course, it’s important. But when I first worked with Veronika Palovska years ago, she asked me a more important question: what is it that you and your ideal client both believe?

It took me years to get these things to line up. And I got very mixed up in the meantime. So my message didn’t necessarily resonate well. After starting in summer 2016 it took me till 2019 to link my personal why — living abroad — to the why of my teaching niche — understanding fast-talking native speakers.

So don’t end up like me in this messy soup of niche and why. Do some introspection and figure out what’s important to you and why from the outset. Then go looking for ideal clients who believe the same thing.

You’ll save yourself a lot of headaches and everything will get easier because people will know if you’re for them or not.

This is about more than helping someone with something specific. You can still teach business English or medical English or help beginners start speaking.

But we need to know why you do this. You could have the most magic and effective teaching method ever. God knows our industry loves magic language learning methods. But if we don’t know why, why should anyone care?

Working on your why will mean that your marketing feels a lot less like trying to bash people over the head with your message.

Over To You

So what about you? Have you been in business for a while? What lessons have you learned? What have you learned from mistakes or things that didn’t go according to plan? Let me know!

--

--

Cara Leopold

Binge watcher. French speaker. Introvert. Online English listening teacher and head subtitle freedom fighter at Leo Listening: https://www.leo-listening.com/