How to Land Better Freelance Writing Jobs on Upwork

I’ve been a freelance writer since 2016 and have found many of my clients on Upwork.

For a long time, I avoided talking about this with other freelance writers because of the negative reaction the word “Upwork” often elicited.

Freelance writing jobs on Upwork

Other freelancers couldn’t wait to tell me how Upwork is for bottom-feeders and clients who only want to pay $5 an hour.

Another freelancer stated that Upwork is a place for “freelancers who don’t respect their work.” (Someone actually said this to me in a Facebook group once.)

One some level, I understand the Upwork hate. I mean, I can’t deny the fact that there are tons of low-paying clients on the platform. I have certainly encountered my share of them.

But I have found a lot of good clients on Upwork too. Clients that pay well and that I still work with to this day. 

So the question is, how do you cut through all the noise and find the really great clients that are hiding on Upwork? 

Why I looking for freelance writing gigs on Upwork 

I like Upwork for the same reason that many freelancers probably hate it -- because it’s a level playing field.

On Upwork, it’s doesn’t matter if you have a Master’s degree in Journalism. 

It doesn’t matter whether you were an English teacher for 10 years or if you spent the past decade as a stay-at-home mom, like me.

We all pitch the same clients and we all get to set our own pricing. 

And that’s what is so funny to me when people complain about Upwork.

You get to set your own pricing and pick who you work with! No one is making you write a 3,000-word blog post for $10.

I don’t know that Upwork is the best solution for everyone. And I would never recommend that you only look for clients on Upwork — I regularly find clients through LinkedIn and other job boards.

But it always surprises me when I hear of other freelancers who can barely find clients yet they’re unwilling to give Upwork a try. 

I’ve spent a lot of time thinking about my Upwork experience and why it’s so different from what most freelancers experience. And I think it comes down to a few key things.

Expect to find good clients

Freelance writing jobs on Upwork

I hate to break it to you but if go on Upwork only expecting to be paid pennies for your work, that’s probably all you’re going to get.

You have to approach Upwork believing that there are good clients there and if you do the work, you’ll find them. 

Of course, this is easier than it sounds. Beliefs aren’t simple things to change, especially since we aren’t always aware of them.

This is where it can be really helpful to get feedback from other freelancers who are a few steps ahead of you. 

For over a year, I charged a per-word price for blog posts. I thought that was a pretty good rate and I was easily able to find work.

But over time, I became frustrated because I could never seem to break past a certain level of income. I tried several times to raise my rates but I always seemed to scare away prospective clients when I did. 

Finally, I had a phone call with another freelancer and I explained to him my problem. He told me that my rates were incredibly fair and I could charge a lot more than what I was currently charging. 

Shortly after our conversation, I received an email from someone who was looking for weekly 500-word blog posts. He asked me what my rates were. I quoted him a price that was five times as much as what I normally charge. 

I’m not exaggerating when I say I felt kind of sick quoting him that price. Really? Who did I think I was charging that much? Surely he would laugh and never speak to me again.

His response? 

“Sounds great. When do you think you can have the first one finished by?” 

Don’t limit yourself to what you think is possible. If you think that the best you can find on Upwork (or anywhere) is clients that pay $10 per blog post, you may need a different perspective.

And if you can’t summon the belief on your own, you may need to borrow someone else’s. 

Learn how to spot difficult clients

I think most freelancers could save themselves a ton of frustration if they just learned to spot difficult clients from the start.

Every time you interact with a potential client, they give you very clear signals about what they will be like to work with. 

And freelancers on Upwork have a huge advantage. You can really learn everything you want to learn about a client just by reading their job description. Here are a few warning signs I look for:

1. They mention that they need someone “affordable”

You will never have a successful freelancing career by trying to be the most affordable option. And the irony is, these are usually the pickiest clients. 

They will expect limitless revisions and will make you jump through serious hoops trying to earn the scraps they are paying you. Avoid them at all costs.

2. They make a demeaning comment about freelancers

So in all fairness, I get that there are a lot of flaky freelancers out there. And anyone who has hired on Upwork quite a bit has probably been burned by a freelancer at some point.

But I’m not referring to clients who are just looking for someone reliable. I’m talking about someone who makes comments like: 

  • “Do ‘x, y, and z’ so I know that you can actually read and follow directions.”  

  • “I’m not looking for someone who will just write to a word count or plagiarize an entire article.”

Look, I have been burned by clients before. I have had clients that didn’t pay me but that doesn’t mean I assume every client is like that.

So personally, I don’t want to work with someone who goes into the relationship assuming I’m an idiot, do crappy work, or resort to plagiarism.  

3. They ask for free work

Okay, you may be thinking, “Duh, Jamie. I know not to give away free work!” Bear with me because this one can be more nuanced than it sounds.

This will often look like a client asking you to write a “200-word test piece” so they can figure out if they like your writing.

Or asking you to send them a detailed outline of the blog post you plan to write before they decide to hire you.

Or asking you to give them 10 blog post ideas about a particular subject.

And this type of person will always dangle some sort of carrot in front of you to try to tempt you to say yes. 

“We pay up to $250 per blog post!”

“We can give you a lot of ongoing work!”

I have given in to these requests before and I can tell you from personal experience, this type of client never follows through.

So always let them know that you don’t do free work but they are free to check out your portfolio.

4. They consistently give freelancers bad ratings 

Most people like to look at how potential clients have been rated by previous freelancers. While this can be helpful, I find it much more revealing to look at how clients have rated the freelancers they’ve worked with.  

I am always wary of clients who consistently give freelancers poor ratings.

I’m not saying everyone deserves five stars but in my opinion, rarely does anyone deserve a one-star rating either. 

Don’t act out of desperation

Freelance writing jobs on Upwork

When I first started freelancing, I got tons of work right off the bat.

Then I hit my first inevitable slump in my business. 

It started with me losing one or two clients.

That in itself if jarring but then I noticed that nobody was responding to my proposals.

No one was offering me new work.

And I got desperate. I just needed to find something.

So I took a really low-paying job writing a product review about different types of gaming systems. It was better than nothing, right?

No matter how consistent and talented you are, slumps will happen. And it’s easy to get really desperate and worry that you’ll run out of money, be unable to pay your mortgage, and have to move in with your parents.

The problem is, desperation causes most of us to make bad choices. It causes us to choose to work with terrible clients who don’t value our work. And in the long run, it will cause more problems with money. 

The bottom line on Upwork

There are great clients out there, both on and off Upwork. If you can’t find them, other people can help you get the perspective you need. And often, the best way to deal with difficult clients is to spot them and refuse to work with them in the first place.