What I Learned My First Year Freelancing

And why I’m never looking back


Rachel Wayne

3 years ago | 7 min read

In January 2019, I joined Upwork and a bunch of content mills to try to make some extra money to pay down debt. (Thank you, ever-inflating college tuition that laughed its head off at my scholarships and stipends.) Little did I know that freelancing would soon cease to be merely a bit of extra dough in my wallet. By fall 2019, it would become the whole damn loaf.

Freelancing indeed gave me freedom: the freedom to take the sick days that had been cruelly denied to a chronically ill person throughout her career. The freedom to walk away from abusive clients rather than put up with horrible bosses. The freedom to work when I was most productive rather than hauling my ass out of bed at 6 am and leaving my energetic evenings wasted. And most of all, the freedom to work on any project that struck my fancy.

If I’ve made freelancing sound glamorous, that was not my intent. There were plenty of rough patches and some hard lessons learned. And despite all my research going into freelancing, I still manage to make every newbie mistake in the book.

Here’s what I learned during my first year of freelance work — and why I’m never looking back.

Don’t Sell Yourself Short

One of the biggest, most famous benefits of freelancing is the ability to set your own rate. No longer do you have to sift through the crap, literal or figurative, and wonder why you’re not paid more. You tell the client what your time is worth, then you get paid a fair rate for your labour and creativity — plus all your overhead costs.

By the same token, if you’re unhappy with your rate, you have only yourself to blame. But it’s all too tempting to lower your rates to try to win a client or fall victim to prospective clients’ promises of “better-paying work later on.”

No. It’s all a lie.

“But what if I’m not that good?” our inner critic whines as our imposter syndrome whispers in our ear to lower our rates.

Three things:

  • You’re better than you think.
  • Your work is worth more than you think.
  • Your rate doesn’t just reflect your experience, but also what you need to make.

All creative people I know suffer from the same disease: the tendency to doubt themselves and be extra critical of their own work. Our bias dually blinds us to our best work while convincing us that something we spent extra time on is our Sistine Chapel.

If I look at my top-performing and purchased articles, none of them are things that I felt were extraordinary after I wrote them. Meanwhile, the stuff on which I spent literally weeks fizzled into the night. If I’m such an unreliable judge of my own work, perhaps I’m discounting myself when I shouldn’t be. As with any business, customer demand is what matters. Someone wanted to purchase my work at $500 per article — that’s what matters. Let the market determine your rate.

Still, there is a psychological trick you should exploit to ensure that you are paid fairly. It’s called the Veblen Effect and it’s the idea that people want to be “conspicuous consumers.” They will pay more if they think they’ll be getting higher quality work for their money — or at least be able to say that they afforded something higher-rate.

Witness the Art Basel Banana, which is objectively a terrible work of art. But the buyers who coughed up six figures aren’t buying the banana — they’re buying the idea.

Similarly, when you market yourself as a $12/hour writer, you’re not telling the buyer that you’re going to deliver gold — even if you’re more than capable of doing so. You’re telling them that you’re the writer equivalent of a dollar-store product.

However, if you market yourself as a $60/hour writer (for example), you’re telling prospective buyers that you have value to offer and that their payment to you is an investment. Sure, some may baulk because they just want a cheap product. But those aren’t clients you want anyway. The clients who will make freelancing a worthwhile experience for you are those who will constantly give you work because they have bought into what you promised them: high-quality work that makes them feel like a success.

Finally, you simply can’t neglect the expenses of being a freelancer. You no longer have an employer subsidizing your computer, software, phone, office space, healthcare, retirement… the list goes on. Add in the fees that freelancing platforms charge, and you’re looking at potentially paying other people to work. Not good.

For me, the cost of working from home amounts to about $20 per hour. If I want to cover that and make a decent wage so I’m not living hand-to-mouth, I need to charge $60/hour.

Once I started charging more, I got more work, not less. That’s the lesson every freelancer needs to learn: You will never lose work by charging more, but you’ll definitely lose money by charging less.

Always Establish a Fair Scope of Work

Often, as a freelancer, you’ll be working with agencies or hired by other freelancers. I’m sorry to say that even people working in communications are not always the best communicators. And because we tend to work within a casual, flexible environment, it can be challenging to keep everyone on track or know who’s doing what.

Also, a private client sometimes thinks that by hiring a copywriter or graphic designer, they’ve gotten themselves a virtual assistant — which is also a thing. Sadly, there aren’t any universal standards for this type of work, which leads to confusion. That means that copywriters find themselves being asked to perform work that’s out of scope, while the client either promises to pay later or ropes it into existing duties.

The problem with these anything-goes arrangements is that they’re ripe for abuse of the freelancer — even if the client or agency doesn’t mean to do so. Without a clearly defined scope of work, the freelancer often feels compelled to perform related tasks, while the client figures that the freelancer can simply add it onto their current workload.

That’s why I recommend to you that you use proposals and contracts to clearly define the scope of work and exclude anything that you will not be provided. Implement rush fees and conditional costs, so that if the client suddenly realizes they need help with accessory tasks or to meet an undeclared deadline, you’re not losing out on income trying to keep them happy. This technique also teaches clients that they need to set their project budgets accordingly and that freelancers’ time is valuable.

Dump Toxic Clients Sooner Rather than Later

No client, no matter how well they pay you, is worth mental anguish. I learned this the hard way. For several months, I had a client who acted as my manager. That was my first mistake, to allow her to play that role.

Repeat after me: clients are not your employers. As the freelancer, you are in charge.

The whole point of freelancing is that you provide a service that clients need with no expectation of them establishing an employer-employee relationship that would confer certain protections. As soon as they start pretending they’re your boss, they’ve violated this arrangement.

Think about it: even a long-term client is limited in what they offer you. You’re not showing up to work for them every day. You’re providing them with temporary services, even if on a regular basis, to meet their business goals. They have no claim to mentoring or training you — in fact, they should be hiring you because you’re already an expert.

What’s Next?

Now that I’ve learned to value and respect myself, I need to embrace the next step, which is to celebrate my achievements and look for ways to grow! Freelancers won’t succeed if they stay passive or never look beyond their current situation. With a year’s experience under my belt, I can look beyond the status quo and truly start to promote myself. And with each year, I should continue to elevate my work and establish my reputation.

Keeping my rates low or continuing to work for bad clients is a great way to ensure that I never improve as a freelancer. It may seem scary to ask for more or take risks in your work, but it’s well worth the lucrative relationships you’ll form with clients who are worth your time. One great thing about 2019 for me was that I found some of these clients who regularly trust me to take care of their needs, and that’s a great feeling. In 2020, I hope to fill my docket with such clients — because that’s the best part of being a freelancer, to be able to support yourself through a variety of fulfilling business relationships. As they say… variety is the spice of life.

Rachel Wayne is a full-time freelancer and coach with Free Ring Circus and Lyra Creative Studios. Follow her on Twitter at @freeringcircus. A version of this article was originally published on


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