10 Lessons I Have Learned Freelancing On Upwork

It's Freelancing Month on Amanda Cross Blog and I am SO excited. All throughout September I will be sharing awesome content that will help you become a better freelance writer. Check out this month's road map:

  1. 10 Lessons I Have Learned Freelancing On Upwork (this post)
  2. Should You Take Hourly or Fixed Price Jobs When Freelancing
  3. How To Advertise Your Freelance Career
  4. 10+ Freelancers Share Their Best Secrets To Getting The Job

I hope that you get a lot out of this series. Let's chat about today's topic though.


Now I have been on Upwork since the tail end of last year, but I just recently started taking it seriously. Since then I have earned just under $1,000 from the platform, although it doesn't feel like it necessarily.

I do love Upwork, although even I get frustrated by some of the lower paying jobs sometimes. Today I am going to offer my best tips for getting jobs that don't feel like a complete waste of your time and energy.

Here are 10 lessons I have learned since freelancing on Upwork!

10 Lessons I Have Learned Freelancing On Upwork | Upwork is a popular freelancing site that I have been using to connect and work with clients. Click here to learn the ten lessons that I have learned while freelancing on Upwork. I have earned nearly $1,000 on Upwork, and  I am sharing what I wish I knew when I began.

1. Under Promise, Over Deliver

On Upwork, you need to create some great reviews on your profile, because it will really help your profile stand out. So, in order to do that, I love to use the old under promise, over deliver trick.

I do this for a couple of reason. Sometimes, I genuinely need the extra time. Even though writing an article may only take me a couple of hours, I don't spend all day writing for my freelance clients. Often I am writing for this blog or The Happy Arkansan because I do make money from those through sponsored content and affiliate links. So, my days are not completely focused on freelancing. I have come really close to being late a couple of times just because of random life issues, and if I had given myself a later deadline, I wouldn't have been able to reach it.

I also use the under promise, over deliver trick because it creates a great connection between you and the client.

For example, in a recent post I did with Aventr I ended up offering 10 tips for them to use instead of 7 they asked for in their post on engagement statistics found here. I really love how this article turned out and so did the client. Now obviously you can't do this for every single freelance thing you do, but don't skimp. Produce great content and you will get consistent work.

2. Create a Great Client Experience

Second, you need to create a great client experience.

Be prompt with responding to messages.

Create great content in alignment with what the client needs.

Be open to feedback and changing things as necessary.

Be patient when it comes to getting content reviewed.

Just be a general pleasure to work with. Don't be rude or obnoxious to clients. Follow instructions.

It's not rocket science to create a great client experience, just treat your clients like you would want to be treated.

3. Try To Branch Out When You Can

I have created two pieces for Aventr, but the first time I created content I didn't really think career content would be in my wheelhouse. I create content about college, blogging, marketing, social media, and stuff like that. I mean, I had published a few pieces of career content here and there on The Happy Arkansan, but I wouldn't have put career down as a niche that I would volunteer to write.

Aventr wanted a piece about how the desire for open office extended beyond desks and floor layouts. I didn't have a ton of super relevant pieces for them to look at, but I had some of my personal writing and I had an idea for how to execute the post. Luckily, Aventr said yes, and I was able to write this piece. Turns out it was exactly what they were looking for.

So, if you can branch out from your usual niche every blue moon, you can create some great content. I feel that Upwork is great for breaking out of your niche because there are so many different types of jobs. You can explore jobs in all the genres and then pick ones that you actually love.

15 Frequently Asked Questions About Freelancing


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4. Understand The Pricing Structure On Upwork

Next week we are going to be talking generally about what pricing structure you should think about, but we are going to chat specifically about Upwork's pricing today.

Hourly Versus Fixed Price On Upwork

Okay, just going to be honest, I HATE doing hourly work on Upwork. I am a fixed price girl all the way.

Upwork's hourly system is clunky, uninformed about the variety of work that freelancers do, and also distracting. When I did hourly work on Upwork, it took screenshots of me every 10 or so minutes. Not only that, it logged all my keystrokes, mouse clicks, etc. The worst part? If it wasn't what it deemed active enough, it wouldn't count your hours at all.

Depending on the work you are doing, you may not move much. I know that when I was editing, I didn't move much because I was reading over a piece. I might have a few mouse clicks in a 20 minute time span because I am just reading, not writing. Or when I am researching to write a piece, my mouse may not click much, because I am doing research.

With fixed price work I am free to type as much or as little as I want and to get the article or whatever I am working on done at my own pace as long as it is finished before the deadline. This helps me focus, and it helps me because I am able to take breaks when I want to while creating content.

Upwork Fees

Upwork fees are kinda ridiculous, not going to lie. Upwork takes 20% of your money, which sucks. Upwork fees do go down the more money you work with a company though, which is nice, but you really have to create some long-term working relationships with companies in order for that to happen. I believe the first milestone is at $500 made with one company. At that point, Upwork fees go down to 10%.

There are other places to get freelance work that won't take those fees from you, but I don't mind Upwork fees in a way. The fees are a safety net of sorts. When you are working with a company individually you aren't sure if they will pay. With Upwork there are a lot of protections in place to make sure that if you do the work, you get paid for that work which is nice. Upwork wants to get paid as much as you do, and they have a system in place to make sure they can protect you.

5. Know Your Worth, Then Add Tax

Okay, Upwork is notorious for people who try to undercut your worth. A lot of Upworkers are looking for the cheapest way to get things done, but a lot of them are also looking for the best way to get things done.

I have had experience with people trying to undercut my worth and initially I fell for it, hard. Don't let the sight of a potential job undercut the value that you bring to the position. Know your worth then add some tax on top of that, y'all.

You need to stick firm with your pay because if they are willing to undercut you on that, who knows what they would be willing to undercut you on.

6. Fill Your Profile Out As Much As possible

Your profile should be as complete as you can make it. The better your profile, the more invitations you will receive to apply for jobs, and the more you will stand out as a potential candidate.

Things to include in your profile:

  • A nice picture of your face
  • An overview that talks about your experience and what you can offer
  • Portfolio items that people can look at
  • Test results from the tests section of the site
  • Employment, education, and any certificates you have they may be interested in

Work History & Feedback

Your work history and feedback can be really helpful to you getting more work and clients. If I were you, I would try to find a couple of really great clients, and specifically I would focus on quick, fixed price work. It doesn't have to be cheap, fixed price work though. One of my first reviews is from a quick, fixed price job that paid $90 for an article. Start building up your feedback so that other people can check it out and want to hire you because of it.

A Video

The great thing about Upwork is that you can include a short video introducing yourself and giving your potential clients a moving face to a name. I created a quick minute long video for my Upwork profile, and I encourage you to do the same. I didn't create the video the same week I joined Upwork, I just created it about a month ago, actually. I like that it gives my profile a little something extra though. There are many types of videos you can share, it doesn't have to be an introduction video. For example:

  • If you are a graphic designer, share a video of some of your graphic designs.
  • If you are a website developer, share a video of some of your websites or you creating a website.
  • If you do voiceovers, share a video of you creating your voice overs.

Be aware that you CANNOT place ads on your Upwork video. You have to demonetize whatever video you decide to add to your profile.

Here is my video:

7. Respond To Interview Requests (Even If You Say No)

One thing I did not know about when I first started was the importance of responding to all the interview requests you get. Now that I have built up my profile a bit, I get quite a few interview requests every week. Many of them are not in my wheelhouse or they are not the price I would like to be paid for my work. Even though that may be the case, I cannot just let them go.

Your response to interview requests effects your response time. You don't have a response time right away, it happens over time. The more interviews you respond to (and within 24 hours) the better your response rate will be. This can really impact your future interview request if someone is looking for workers who can turn things back to them quickly.

Now, you don't have to respond to every request as soon as you get it. It's okay to have a life. Some requests that I get I have to think about longer than other requests. You should strive to reply to every request in a timely manner though.

15 Frequently Asked Questions About Freelancing


Subscribe to get all of your frequently asked questions about freelancing answered like who hires freelancers, what you need to get started with freelancing, and taxes as a freelancer.

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8. Filter Your Job Searches

I filter as much as possible when I am looking for jobs. My go-to filters are:

  • Article & Blog Writing
  • Client Info: Payment Verified
  • Client Location: United States (sometimes Canada too)
  • Job Type: Fixed Price

I feel like this is the best way to stop myself from getting scammed. Once I did get out of my comfort zone and someone tried to put some sort of virus on my computer through an attachment.

Not everyone on Upwork is good. Just like there are shady people in other areas of the internet, there are shady people on Upwork. So, get a virus checker. Send all attachments through that virus checker unless you trust the company you are working with.

Many Upwork clients won't use attachments like PDFs, and instead they will use a Google Drive document or something cloud based which is helpful for you. Overall, don't open anything with a weird file extension. If it's not .PDF or .Doc/.Docx you probably don't need to open it if you are writing articles. If you are doing something else like editing a video or Photoshop file, you will have other file types to worry about though.

9. Be organized With Your Content Creation

Once you start taking on multiple clients things can get kinda hectic. As you may know by now, I am a fan of a good organized spreadsheet. I have a huge spreadsheet where I keep a lot of blog information and one of those tabs is dedicated to freelance articles I have been working on. 

Organization is key. Finding a way to be as organized as possible whether that means you are creating a spreadsheet or using the layout that Upwork gives you is crucial. Find whatever floats your boat and keeps you accountable to your clients.

10. Be Okay With Transparency

Transparency is a huge thing on Upwork, and it may not work for everyone. Everyone can see exactly how much you made from each post, how much you have made on Upwork in general, and all your public feedback. That's just the tip of the iceberg, unfortunately.

There are different transparency options for free accounts, but they are rather one-size fits all, and they don't really get at the core of what is wrong with how transparent the Upwork profiles are. There is a way to hide your earnings if you get the Plus plan which cost $10 a month.


There you have it folks. These are the 10 lessons that I have learned since I started freelancing on Upwork. There are other potential sites for freelancing success, but I really do like the simplicity and protection of Upwork.

What did you learn about Upwork today?