What I Learned From Launching a Freelance Writing Business

And why freelancing isn’t as great as it sounds

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Photo by Green Chameleon on Unsplash

When I started writing on Medium at the end of 2018, I didn’t really have any plans to write professionally. I had worked as a technical writer back in the day, but I rolled my eyes at the prospect of making money as a “blogger”. Until I did it.

I went from making pennies a month to around $1,000 a month on Medium in just a few short months, and slowly began picking up freelance clients.

It wasn’t terribly difficult to get started, but I noticed that all of my new clients had been finding me through existing clients, or though my writing on Medium — not through my inquiries. In other words, reaching out to blogs and trying to be a paid writer didn’t yield results, but writing on Medium and building up a big audience did.

When I did the math, I should have been able to pull in $3,000 a month as a freelance writer, working for just a few hours a day. And, if I could pick up a few more clients and devote 6–8 hours a day to my writing, I could turn it into a full-time income.

Now, it’s worth noting that I live in NYC, where finding an apartment for less than $2000 a month is almost impossible, so $3,000 a month before taxes is really not a viable full-time income.

But if I worked hard and doubled or tripled my output, I could have lived comfortably.

It didn’t work out that way.

Here’s what I learned.

1. This is a business based on referrals.

It sounds wonderful — your previous clients refer you to new clients, or someone stumbles upon your work and decides to hire you. Nice! But this means that there are very few ways to increase your workload without waiting for someone to “find” you.

You won’t find too many freelance writing jobs on job boards.

You can query hundreds of companies and hope that someone will like your work, but in general, people who weren’t already planning on hiring a writer are not likely to splurge.

Sending hundreds of query letters is a lot of work to do in exchange for being commissioned for one or two articles, unless you end up with a repeat client. It’s hit or miss.

Writing for content mills does nothing other than build your portfolio; you might as well write for free.

If you’re good at what you do, and if you make the right connections, someone will hire you on a retainer basis (X amount of articles per month for Y amount of money), but you’ll need to secure a handful of clients like this in order to make a good living.

In other words… this is not a business that will scale overnight. It takes months to establish a full-time workload, and due to the nature of the industry, the amount of work you receive can (and will) fluctuate.

2. Your rate is negotiable. Sort of.

Your rate is negotiable, but in many cases, if you aren’t willing to accept a lower rate than you think you’re worth, the work will go to someone else. There are plenty of people who are willing to write for 5 cents a word, and when businesses are simply looking for articles to boost their website’s SEO, they’ll cut corners to make it happen.

Take a look at Fiverr; freelancers offer to write blog posts for pennies, and some of them have been hired dozens of times.

As a freelance writer, you eventually have to decide whether you want to go for quality or quantity. There are a few magazines that pay up to $1 per word, but these opportunities will make up only a small fraction of your total work. You need to decide whether seeking them out is worth it.

You’ll also need to decide whether to charge for revisions.

Let’s say you write a 2,000 word article for $0.15 cents per word. You’ve just made $300. Nice. But now the client wants pretty extensive revisions.

Do you charge $300 for the original work, plus an hourly rate for revisions? A per-word rate for revisions that gets added on to the original price? Do you revise for free? What if extensive research is required? If you didn’t think about this ahead of time and put the details into your contract, you might not be earning as much as you thought you’d be earning.

3. Payment and taxes.

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Photo by Michael Longmire on Unsplash

Assuming your clients pay on time, you’ll need to choose (and agree upon) a payment method. PayPal is a common one, but PayPal charges fees that you are responsible for paying unless the client sends the money as a gift, which they probably won’t.

Then, there’s an additional fee if you want your money right away instead of waiting a few days for it to show up in your bank account. When you have bills to pay, sometimes you can’t wait.

THEN you pay taxes on it. And don’t forget about those self-employment taxes, too!

You don’t get paid time off or health insurance. If you get sick, injured, or have a family emergency, missed deadlines and the inability to delegate work to a teammate could cause you to lose a client, reducing your income until you find a way to fill in the gap.

Remember what I mentioned earlier about rent? Try finding a landlord that will accept your freelance income and not make you find a guarantor. The same is true for other creditors; you’re not getting an auto loan without a co-signer if you’re self-employed, unless your credit is over 750 and you have a documented history of high income over the past few years. There are some Uber drivers who make over $90,000 a year in NYC and still can’t get auto loans without co-signers, because their month-to-month income cannot be predicted.

This is the primary reason that freelancing is not all it’s made out to be. If you’re the sole earner, and if all of your income is self-employment income, it can feel demoralizing to be told that you can’t even get an apartment on your own.

But beyond feeling demoralized, for some people, it’s just not feasible to find a co-signer for every major purchase or change in living situation.

4. Marketing yourself is a skill that you need to develop. Like, yesterday.

We often market our writing to other writers because it feels good to be praised, but this is a mistake. Other writers aren’t going to hire you to write. You should be making connections within your niche, or with business owners and marketers in a variety of fields.

This is not only true for freelance blogging, but for those who self-publish books as well. I’ve seen countless authors promoting their novels to other authors, who promote their own books in return. The result is a group of 10 or 15 authors who buy and review each other’s books instead of marketing them to their intended audiences.

I learned very quickly that I needed to market myself to business owners. And for my upcoming book, I need to market myself to people who are exploring the possibility of working in software development. Not to other writers.

In the end, launching a freelance writing business helped me land a full-time job as a technical writer.

I realized that freelancing is a great thing to do on the side, but it isn’t an easy way to replace a full-time income in a short period of time, and it isn’t a great way to achieve a healthy work-life balance. Not when you have rent and bills to pay, at least.

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✨ serial questioner • technical writer/devops • editor of Diary of an SRE • thank you for connecting 👩🏻‍💻 kerisavoca.com

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