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The Wolf of Upwork

By Matt Cates

Dear Readers,

Clearly I don’t know what I’m doing. Most EFL teachers aren’t in this for the big bucks, but at least they churn out a living. Not me. And yet I’m writing to lecture you how to make extra income!

Two years ago I was working in the Pentagon, and out of pocket $1,500 for my CELTA tuition, plus another grand for my flight to Istanbul, where I did my in-person teaching practice. Last year, I was out $3,000 more, for the English scholarship I gave away to a Turkish barista.

Yep, I paid someone to take English lessons from me. Sad, huh? Not really! You can read about the Mad English Lab project here.

In part, it was an internship, a step towards my next ill-conceived goal…

It Never Got Weird Enough for Me…So I Made It Weirder

My Next Ill-Conceived Goal

What do we do when teaching isn’t turning a profit and we’re operating in the red? We move on, or we take on something new to supplement our income. Lucky me, I do get a military pension and disability comp, so I have a safety net of passive income, and until last month, I was living overseas, maximizing on geo-arbitrage (getting paid in dollars and exchanging for lira at a rate of $1 = ~3.50TL).

So I can afford to be an unpaid neophyte when it comes to teaching, but I still need to work and supplement my pension, and I have in fact found a way; I now do some writing on the side. There may be teachers out there who love their jobs but find it hard to make ends meet. For those teachers, here’s how I make money… Actually, first? Here’s how I don’t make money!

I did a MFA Creative Writing, but couldn’t sell my novel to save my soul, nor my screenplay. My second fiction book made a nickel, before tax. So I moved on, got my teaching certification, retired from the Air Force, and moved overseas to Kusadasi, Turkey…and that’s when I saw. The horror, the horror…!

I saw the dismal teaching wages and the dreadful hours being offered. Why hadn’t I done my homework prior to all this?

Freelancing for Fun and Profit

So I didn’t take a teaching job, but I tried a few private students and they quit. So I got the idea to form a Limited Liability Company in the US to offer a philanthropic scholarship to a local university student, who had impressed me with her energy and enthusiasm to learn English. My intention was to improve her English and to train her up to be a type of intern.

An intern to what, asks you? To my future freelancing agency of course!

Necessity is the mother of invention, but I had no need to do anything. In Turkey I was rich(ish) but bored. So I began freelance writing on and learned a few things, and one thing I learned? Freelancing pays cash and it pays quickly. Unlike, say, novel writing.

Ah, freelancing, where the rainbow ends and the pot of gold gleams under the rays of dawn. Where a digital nomad can be a digital nomad, and tear off to any of the four corners of the globe on a whim.

I have made over $7,000 from 65+ little gigs, and I did that that just to learn how to do it well. It was my own little self-imposed internship. And I did those gigs at a cafe facing the Aegean Sea.

And that $7,000 exchanged to 26,000 Turkish Lira (the exchange rate slid), more than the annual income of a full-time worker. Added up, I made it in under 180 hours, offering a virtual service to international clients, doing jobs I wanted, working on my terms.

You can read specifics from my in-depth article here, How to Make Money on Upwork Fast!

In fact, I did a little YouTube explainer about how to build your account and craft a killer profile!

So yes, freelancing. This was but one of the skills I wanted to train my intern up on, but it was a crucial one. Why? Foreplanning.

My Virtual Freelance Company

I’ve returned to the US, the prodigal son embraced back into the meaty capitalistic arms of my country. Good to be back. And now I have an English-speaking intern who knows the Upwork ropes, so I can reach back to her. She acts as an independent contractor, doing research for me.

Here’s how I do that, and how you can do it, too.

  1. I created a profile on (but you can use any freelance site)
  2. I crafted a killer profile, after reading the profiles of some highly-rated freelancers working in my categories (creative writing, etc.)
  3. I made my first bid, lowballing it so I’d get it…and I did. $30 to write a ghost story!
  4. I put my heart into that first job, and the client left a great feedback…and hired me again, for $40
  5. Over time I did little jobs like that, then started to bid on jobs I had less experience on, like slogans and branding and market research. I learned by doing
  6. After a while, I earned a “Top Rated” status on the site, and now clients sometimes come to me instead of me searching for jobs to bid on. In fact, Upwork sometimes recommends jobs for me, acting as a liaison…because when I make money, they make money!
  7. I introduced my friend/English student to the site, and she became my intern and later my research assistant, so I could focus on the writing parts
  8. I moved away, but maintained contact with her so that we could continue to work together in tandem. We formed an agency on Upwork (with the same name as my actual LLC company in the US)
  9. We’re pulling in a fair amount of work, and we share the workload and profits 50/50. For her end, living in Turkey and making dollars, her share is enough to almost be considered a full time salary, despite only working a few hours a day…from home!
  10. As my little virtual agency continues to grow, I am looking to bring on more talent and form virtual teams…hopefully so they can eventually handle most of the work themselves and I can manage the bidding and build relationships with long-term clients

So, essentially I am a teacher with one student, but her subject isn’t only English…it’s more transformational than that. As a creative writer breaking into the lucrative trade of brand naming as well as copywriting, I need help to keep up and as she continues to help me, she continues to learn herself. Soon she’ll be training up others, and then her role and responsibility will increase to that of virtual assistant (unless she decides to break off on her own, which I actually encourage!).

So yes, currently I do this part-time but I’ve registered an LLC, with the intention of scaling up by contracting virtual hires in the near future, in order to build an online agency specializing in brand marketing, content creation, and graphic design. My teaching did not give me the dream job but it gave me travel, time to think and plan and eventually it brought me an assistant to help me in future work; not the path I had planned but an interesting path all the same.

What about you? Let’s swap stories in the comments below!

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