Author’s Note: This article was originally written in September 2017 and updated in December of 2017. The updates are at the end of the article.

At the end of July of 2017 I began looking at new ways to make some money. I love to write and ultimately want to publish some books. I began to wonder if I shouldn’t try to get some freelance writing jobs. About that time, my cousin suggested a site called UpWork. For those of you not familiar with UpWork, it was created after the merger of two other freelance connection sites – Elance and oDesk. UpWork, like its predecessors, works to link together clients with freelancers. The catch – they take a whole 20% of the total billed amount. Yes, this is a large percentage. That is the biggest downside to UpWork.

Let me give you a little background on my experience with the site as of right now.

Opening an Account

I was confused as all get out at first. I have never been a freelancer and I had no idea what to do on the site. Here are some steps you need to make BEFORE you start to submit proposals for jobs. Take a look at my profile here before you read on so you at least have a visual understanding of what I am talking about.

  • Ensure you complete your profile – There will be a meter telling you how much of your profile is complete. No client will bother with any freelancer who does not have a complete profile.
  • Photograph – You need to find a professional looking photo, preferably of you in business attire. You need to look friendly in the photo, as studies have shown that a simple smile can get you more jobs. I don’t know what program UpWork uses to ensure profile photos are good ones, but it is hard to get one approved (at least it was for me).
  • Profile Information – Go browse successful freelancers on UpWork and see what they put in their profile. Try to make yours look like theirs, just with your information. You need a good and to the point section to tell clients about you. I have changed mine regularly as I learn better ways to describe myself and my skills. You will have sections for your education, certifications, work history, and other experiences. Fill it out as much as you can but DO NOT LIE. If you lie and get caught up with work you can’t handle, it will be evident pretty quickly. (UPDATE ON PROFILE INFORMATION AT END OF THIS POST)
  • Payment Verified – When you browse UpWork clients and freelances, you will see a little mark signaling whether or not payment for that user has been verified. This is very important, as most people simply do not bother dealing with anyone unless they see the payment is verified. I don’t even look at clients who can’t verify how they will pay me and I don’t expect them to deal with me if I don’t verify mine. This is just another way to signal you are a real and serious freelancer.
  • Tests – UpWork offers hundreds of tests for you to prove your skills. These range from language skills, management skills, to programming skills. Take the ones that are relevant to the field you will be in. If you do well, they will say you scored in the top 10% or something similar and note that in your profile. You don’t have to have these tests visible on your profile if you don’t want, so don’t worry about taking one and failing it. Just know that you have to wait 3 months before you can take the same tests again. Why are the tests important? To show clients you really do know your stuff.
  • Portfolio – If you have some good samples of your work, you need to put them in your portfolio for clients to see. I lost my jump drive with all my old work, so I had to piecemeal mine together. As I continue to work, I add in new items that I think show my multiple skill sets.

UpWork Feedback

You won’t have any feedback when you start, which is the hardest thing to deal with. The main thing clients look at is a freelancer’s feedback history, just as it is the main thing you need to look at before deciding whether or not to work for a client. Since you have no feedback, the first job will be the hardest. How do you get feedback? Get some jobs and knock them out of the park like I did.

It will take the completion of about 5-10 jobs before you get a Job Success Score (JSS). You will notice when you start that most clients are looking for freelancers with a JSS of 90% or better. See my update about my JSS score at the end of the article.

Submitting Proposals on UpWork

Now what? It is time to browse and start submitting proposals. Search for jobs in your desired field. One trick I quickly learned – when searching, take OFF the filter that shows you jobs only in the US. All of the jobs I have gotten so far have come from overseas. As soon as you take the filter off, the number of available jobs usually triples.

You are given 60 CONNECTS each month with the basic free account. This will allow you to apply for 30 jobs, as each job usually requires 2 connects to apply. Once you use your connects, you can’t apply for any more jobs until your connects refresh the next month. I ran out the first month, but have learned to pace them. DO use them all, as they do not carry over.

When you find a job you might be interested in, just know that there is an art to submitting proposals. Remember this – there are foreigners who apply to every single job that pops up and they all use the same generic proposal cover letter.

  • Submit to each one with a new cover letter, not just a copy and paste generic letter. You need to show the client that you really read their job description (some have ways to verify this anyway). Here is a typical letter that I write (of course, I tailor it to each posting).


I am interested in helping proofread and edit your statement of purpose. I have attached my resume so you can view my education and experience. I have a bachelor’s degree in political science and a master’s degree in teaching. I worked as a research assistant in graduate school. I spent much of my time in this job editing and proofreading scholarly peer-reviewed journal articles. I then went on to teach high school.

I am a native English speaker. I will use Track Changes in Microsoft Word so you can see what I change and make comments on.

I hope you find the right person for your job. Please feel free to ask me any questions necessary.

Allen W.

There are a few things to this. I offer my resume because it says more than I need to say in a cover letter and I am lucky to have an extensive one with great experience. I also offer the resume because I am still new on UpWork without a whole lot of feedback.

It is important to mention that you are a native English speaker. Most clients are looking for this, not a foreigner who says they know English. I have nothing against them, but their English skills will never quite grasp the language’s nuances needed for some jobs.

Notice how I mentioned specific things from the job posting and then I asked questions. It shows that I read their post and am interested, but not overly interested. Remember, you want jobs that are good fits for you and the clients, so don’t beg.

How Has UpWork Worked For Me?

On August 1st I got my first UpWork job. This was writing five articles about the United Nations for a Model UN website. It was for $50, of which I would receive $40. The articles needed to be about 1000 words each. I got lucky – I’ve created Model UN teams as two high schools. I nailed the articles well ahead of the deadline and submitted them. The client loved them and immediately offered more.


Every client I’ve had so far has used me again immediately after I submitted the first job. Good, fast work leads to recurring clients.

On August 7th I got an entirely different job with an advertising firm. I was to take 60 sentences and rewrite each one three times without changing the meaning – $40 charge. They would then choose the one that works the best for ads. Well, this is nothing like anything I’ve ever done, but I wanted to try. I love writing and I’m good with words. Turns out, I did it in a few hours. I made about $20 an hour with this job. When I turned it in the client was so impressed that they immediately gave me another set. They also left great feedback.

On September 4th I saw a job that involved taking photographs of certain rooms in a house, giving the photo a title, and writing a one sentence description about them. The job offered $20 for 100 descriptions. I bid on it, but I didn’t bid at $20. I bid at $25. Why? Because I know my value and that is what I would do it for. I was actually surprised when the client contacted me the next morning, asked for a few samples, and hired me at the higher price. I finished the job in two days and they offered unlimited work for me. Another recurring client.

So, that is my experience so far. I am certainly not making mega dollars, but I am able to do this work from anywhere with an internet connection. As my feedback increases, I expect to get better work. I have upped my hourly charge once and will do so again once I get a few more jobs under my belt. I always look at profiles of successful freelancer on UpWork to see if I can make my profile better.

I will continue to update this post about once a month. I will let you know whether or not this is something I will stick with. Only time will tell. Again, take a look at my page for some ideas of how to set yours up.

December 2017 Update

Since my last post, I have done better on UpWork, though I have not made it to the level I want yet. I began using UpWork in August of 2017. In September I doubled my money from August. In October I doubled September. November was about the same.

I’ve learned a few things from these last few months on the platform.

One is this – it takes time to get a reputation built. Though I managed to get some pretty good jobs, I’ve been hampered by one piece of feedback. To be honest, it wasn’t that bad, but it hurt. It was from an editing test job I took for $12, hoping to secure long-term work for them. Well, one I started, I realized the article was written in English by someone who had such a poor grasp of the language they might as well have been speaking toddler. I cleaned it up the best I could and sent it back. Overall, my feedback score for that job was 4.6 out of 5. Not bad, but because I didn’t have much feedback yet, it bumped my overall Job Success Score (JSS) down to an 80%. That is important because most clients want freelancers with a 90% or better JSS. So, I’ve spend time trying to build that back up. Look at my page now and you will see I’ve gotten it up to 86% and when the next update comes, I should be well above the 90% mark (It updates every 2 weeks).

I’ve also learned that there will be slow weeks. November was depressing until the end when I got absolutely slammed with work. All I had for three weeks was one of my long-term clients until the fourth week of the month. Suddenly, I had five jobs going at once.

One thing I did do was change my profile. I asked one of the highest paid freelancers on the platform to look at my profile and tell me what they thought about it. They did, and they basically told me it sucked. They said it was like every other profile on the site. Nothing on it was catchy. If you look now, I decided to go the humorous route. The profile I have now is different and had gotten more views since I published it.

I raised my rate as well. As I have now shown that I’m capable of quality work, I’m now at $50 an hour. I think that is a good rate to show I mean business. It’s not too low or too high.

I’m going to keep it up. I enjoy being able to work from wherever I can get an internet connection. You are just as likely to find me at home in my pajamas as you are at Starbucks or Panera Bread. I just want to get it to a sustainable income level.

Succeeding takes patience and the ability to do good, quality work. Without either, you will find UpWork a waste of your time.

If you have any questions, feel free to ask them in the comments or contact me through email or social media.

The UpWork social media team sent me an UpWork t-shirt and notebook!