{2020} How to Start Freelance Writing & Quit Teaching English Online

Want to know how to start freelance writing in 2020? Learn how you can quit teaching English online for good.

This is the true story of how I started freelance writing and stopped teaching English online.

To be honest, despite a lot of people asking me about this, I’ve been a bit hesitant to share how I am able to make a living freelance writing.

Freelance writing is so broad, and because everyone approaches it with a different background, it’s tough to provide any kind of road map.

So, that’s my little disclaimer.

I’m just going to share my experience and pass along the tips/resources that worked for me.

After this post, you should have a better idea of how to break into freelancing and make this transition for yourself.

Before Starting Freelance Writing

When I moved to Mexico in Oct. 2018, my only source of income was teaching English online with VIPKID.

I was teaching from 3:30 a.m. – 8 a.m. six days a week, which came out to 25 hours per week.

You’re probably thinking that those hours sound horrendous, and yes, they were.

But, I was (and still am) grateful for VIPKID because I don’t know how I would have moved to Mexico without it.

Between the steady hours and solid paycheck, it felt like I’d found the golden goose.

Had what I’m about to tell you not happened, I might still be waking up at 3 a.m. to teach Chinese kids English online.

Why I Decided to Quit Teaching English Online

In April 2018, I woke up to teach only to find that the power was out.

No lights. No internet.

Even though it was basically the middle of the night, I went out into the street to investigate.

Around the corner from my house, I saw that a telephone pole (which had been leaning precariously for months) had finally fallen down.

With the power out until further notice, I wasn’t going to be teaching that morning.

I had to cancel my classes…which was no small thing under VIPKID’s strict policy.

Even though the situation was out of my control, there was a chance it would still count against me if I couldn’t provide adequate proof.

Too many cancellations and I could lose my job. To make matters worse, VIPKID deducted $10 from my paycheck for every class I canceled.

It was a nightmare.

Sick with stress, I knew something had to change.

It wasn’t the first time the internet had been an issue, and I was tired of relying on something so unpredictable.

The situation forced me to really look at my life. I was wandering the streets at 3 a.m. looking for the source of a power outage!

I came to the conclusion that, despite giving me the means to move to Mexico, teaching English online was no longer sustainable.

Because of the hours and the stress, I wasn’t enjoying my new life in Mexico.

When I started brainstorming other ways to make money, looking at my background, pursuing writing was the obvious choice.

Breaking Into Freelance Writing

While I didn’t major in journalism in college, I have significant experience writing for publication.

In addition to being editor in chief of my college newspaper, I interned at the local paper where I went to school.

With those experiences in my back pocket and my blog serving as my “writing portfolio,” I started looking for places I could write online.

Don’t get it twisted: I was still teaching 25 hours per week with VIPKID when I started to look for a way to break into freelance writing.

Having heard from basically everyone and their mother how hard it is to earn a steady income freelance writing, I was scared to give up my steady paycheck from teaching.

The Truth About How to Get Paid As a Freelance Writer

Now, I know freelancers love to wax philosophical about “charging what you’re worth,” but if I’m being honest, most people aren’t worth SHIT when they’re first starting out.

Myself included.

When you’re starting out, you need samples. To get them, you’ll likely have to do some unpaid work.

The first two articles I wrote were for female-focused travel websites: Pink Pangea and Travelettes.

Doing unpaid work is about more than just showing you can write for the web. It’s also proof that you can work with an editor and follow-through/meet deadlines.

With three unpaid pieces under my belt, I started looking for paid travel writing opportunities.

My first paid assignment was for Matador Network. In the Matador Marketplace, I saw a job post looking for a writer with extensive knowledge of the Midwest.

I emailed the editor and told him I’d grown up in Michigan. He emailed me back the same day asking if I could do a piece about underrated small towns in the region.

The job didn’t pay much ($40), but it did pay.

When the article went live a week or so later, I guess I could have started calling myself a freelance writer, but in reality, I wouldn’t embrace that label fully for another seven months.

After that first article with Matador, different editors from the website started reaching out to me with assignments. In all, I wrote 10 articles for Matador and made $60 per piece.

Not exactly enough money to quit teaching.

With the help of Sonia Weiser’s newsletter for freelance writers (“Opportunities of the Week“), I successfully pitched Fodor’s and World Nomads.

But, pitching for each and every story is a lot of work.

Plus, it’s beyond frustrating to spend time crafting an email to an editor only to never hear back from them.

If I was going to start making a living freelance writing, I had to find a steadier source of income.

With that in mind, I put travel writing aside and hit the job boards.

Using Job Boards to Break Into Freelance Writing

Hands down, the best two job boards for anyone trying to make a living as a freelance writer are ProBlogger and BloggingPro.

Over the course of several weeks, I responded to a dozen or so listings on these sites. I tailored my cover letter and resume to fit each position.

In Oct. 2018, I responded to a posting for a contract job writing blog posts about Instagram for a social media management company.

The director of content marketing got back to me almost immediately and asked if I would do a paid sample (a VERY good sign).

I wrote the post, and later that day, he told me I got the job. I wrote for them for more than a year.

To date, all of the contract gigs I’ve had came from that two-week blitz I did back in 2018.

Some gigs I heard back from right away (the social media management company). Others, I heard back from months later (a quiz-writing gig).

One job, for a link building company, I interviewed for in Jan. 2019. But, due to a hiring hold, I didn’t start writing for until July 2019.

I have been very fortunate in that I’ve gotten responses to nearly every resume and cover letter I sent out. The contract jobs I’ve accepted have provided steady and continuous work.

That’s not to say freelance writing has been all rainbows and butterflies…

How NOT to Make a Living Freelance Writing

In Jan. 2019, I accepted a contract gig as an entertainment and gossip writer with a Bustle-esque website.

At first, it sounded great.

I was writing five to six short articles per day about trending topics. If fans were going off about something in Kim Kardashian’s Instagram comments, I was doing a story on it.

The work was fun, and even though I wasn’t make much per story, the sheer number of articles I was writing made my paycheck seem alright.

I cut way back on teaching and thought I’d finally made it as a freelancer.

But, it didn’t take long for me to realize the position wasn’t a good fit.

Based on the editor’s demands and expectations, the website clearly wanted a full-time writer on a freelancer salary.

For me, the best part of working for myself has always been setting my own hours. As much as I liked not teaching, I wasn’t happy having to sit at my desk from 7:30 a.m.-3:30 p.m. every day constantly refreshing my feed to see if Kylie Jenner posted new pics of baby Stormi.

Websites, companies, editors: If you decide to pursue writing, you’ll quickly see how many people want to take advantage of freelancers.

After six weeks or so, the editor said they wouldn’t need me anymore (I’m guessing it had something to do with the not-so-happy camper vibes I was giving off).

Even though I hated the job, it still hurt to get let go. As a freelancer, one of the best skills you can develop is not taking things personally.

I know it’s hard (writing, no matter what you’re writing about, is so personal), but the sooner you learn not to take what an editor says to heart, the better off you’ll be. Separate yourself from the work.

Looking back, I should have walked away from that gig myself, but in the back of every freelancer’s mind, there’s the worry that you’ll never find more work.

That couldn’t be further from the truth.

There’s always more work.

Leaving Teaching English Online For Good

In Sept. 2019, I was still teaching English online despite having more than enough work writing.

It was hard for me to let VIPKID go because, after so many years of doing it, I was essentially teaching on auto-pilot. It required a lot more bandwidth to pick up and complete writing assignments.

Even on auto-pilot though, teaching at 3:30 a.m. requires a lot of energy. I knew that if I wanted to really make a go of freelance writing I had to save my energy for that.

After figuring out exactly how many articles/quizzes I would need to write per week to match my teaching income, I stopped working for VIPKID in Oct. 2019.

As of May 2020, I’ve been a full-time freelance writer for seven months.

Factors That Helped Me Break Into Freelance Writing

So, there you have it. That’s the true story of how I transitioned from teaching English online to freelance writing.

Before I dive into tips that will help you get started freelance writing, I want to touch on a few factors I know helped make the transition possible for me.

• Background in writing
  • I had experience writing for publication both online and in print.
  • Before I had a lot of samples, I leaned heavily on this in my cover letters and pitches.
• Affordable cost of living
  • I will be completely honest: If I was living in the U.S., I probably would have never pursued freelance writing.
  • The affordable cost of living in Querétaro meant I could do unpaid work/lowing-paying gigs.
• No timeline
  • When I decided to try to break into freelance writing, there was no pressure.
  • I could look for work at my own pace without burning out.
• Job security
  • I never worried about not being able to pay my bills because I always knew I could go back to teaching with VIPKID.
  • Even after I started making most of my income freelance writing, I renewed my contract with VIPKID just to have it as a backup.

8 Tips for How to Start Freelance Writing in 2020

Whether or not you’re transitioning from teaching English online, these tips will help you get started freelance writing.

Tip #1: Have Another Source of Income

I think the main reason I was able to successfully transition from teaching English online to freelance writing is because it was just that: A TRANSITION.

If the pressure is on and you’re freelance writing because you need money right this second, well, that’s tough.

I’m not saying it’s impossible, but you’re really going to have to hustle and that could quickly lead to burnout.

Instead, have another source of income that you can scale back as you pick up more writing work.

Tip #2: Tailor Your Resume & Cover Letter to Each Gig

You can find this advice on pretty much every article ever written about breaking into freelance writing, but it’s popular because it works.

People aren’t going to respond to your pitch or application unless it’s tailored to the publication or gig.

Use names whenever possible, and don’t be afraid to inject a little personality into your email. It’s important to be professional, but it’s even more important to stand out.

Tip #3: Check Job Boards Every Day

When you start looking for work, you need to check job boards like it’s your job.

I mentioned them earlier, but here are (in my humble opinion) two of the best:

• ProBlogger
• BloggingPro

If a posting is more than a day old, it’s pretty much irrelevant. Anyone still looking for writers will re-post the listing.

Found a gig you want? Make sure to read the whole job description and do everything it asks.

I got my first contract gig because I was the only applicant who included “brownies” in the subject line. These instructions were hidden in the job posting to weed out people who couldn’t be bothered to read the whole thing.

Tip #4: Pay for “Opportunities of the Week”

It costs $3 per month, but this weekly newsletter is an invaluable roundup of what editors are looking for at the moment.

Rather than cold pitching publications that may or may not be accepting work, pitch editors on the topics they’re looking for.

Plus, you know what a piece pays before you even bother crafting a pitch.

Tip #5: Be Open-Minded

When I decided to pursue freelance writing, I thought I just wanted to write about travel.

If you resign yourself to a single niche, you could be missing out on some good gigs.

Two years ago, I would have never believed you if you said I’d make tens of thousands of dollars writing personality quizzes like “Who is Your Emo Husband”?

Tip #6: Keep Your Work in Perspective

Of all the lessons I’ve learned while living abroad, one of the most important is that work is just work.

So many Americans base their self-worth on what they do for a living, and that’s a recipe for unhappiness.

I did not change the world with my listicle ranking the Disney princes by hotness. My article with step-by-step instructions for how to curate the perfect Instagram feed *probably* didn’t change anyone’s life.

But, the money I earned writing them allowed me to live a life I love.

To be able to support yourself with the words in your head (whatever those words may be) is pretty cool if you ask me.

It’s helpful to have another creative outlet where you can write about whatever it is you’re most passionate about. For me, that’s this blog.

Tip #7: Don’t Be Afraid to Walk Away

I know I just said “work is work” and whatnot, but don’t continue with a gig that’s not a good fit for you just because you want the money.

You will know when you’re being taken advantage of as a freelancer.

Listen to that little voice in your head and walk away.

There will be other work. I promise.

Tip #8: Don’t Take Rejection Personally

Not getting a job or having your pitch turned down is just part of freelancing. So is not hearing back.

Something that really helped me was this story about my favorite author, Stephen King:

Before he was the wildly successful author you know today, King had a nail above his desk where he used to collect rejection letters. Eventually, he had so many that he replaced the nail with a spike.

Rather than getting discouraged, he saw every rejection as one step closer to getting published.

Set a goal of how many rejections you want to collect. On your way to achieving that, you’re sure to collect a lot of yeses.

Final Thoughts on Making a Living Freelance Writing

My time with VIPKID showed me that I’m a person who likes working for herself. But, teaching English online wasn’t the digital nomad dream job I initially thought it was.

I’m so grateful for the circumstances that pushed me to pursue freelance writing.

I feel like I finally have the freedom to work from anywhere, and I’m excited to see what the future brings. This longtime expat is thinking about trying out the digital nomad lifestyle.

If you have questions about how to start freelance writing in 2020, leave a comment below.

How to Start Freelance Writing 2020