How I made over $1,000 on Upwork in my first week

Last week I signed up on Upwork to try to earn a little money writing. Upwork is a website that links freelance writers, web designers and other creative professionals with people seeking those services. They call themselves “an online workplace for the world — connecting clients with top freelance professionals.” It gets a bad rap sometimes due to the large number of low-paying jobs and freelancers willing to do the work for next to nothing. However, I’ve discovered that it is possible to get paid well there. Here’s the process I used, which led to booking over $1,000 in work in my first week on the site.

The research

First, I read a few articles about other people’s experiences with freelance websites like Upwork. I started with one I found on LinkedIn called Writing for Content Mills: How to Avoid Getting Scammed, which was pretty much a lesson in what not to do. Then I came across Hacking Elance — the step by step breakdown/guide to how I made $23,700 in 4 weeks. The author, Daniel DiPiazza, runs a website called Rich 20 Something that offers a mix of free and paid advice for freelancers. The approach he took to eLance (now Upwork) was pretty brilliant.

He posted a fake job listing in his own field so he could see what the proposals were like. Then he set out to make his own pitches stand out from the rest. Some of his ideas are not for me (like video proposals) but I did try some of his advice, and I found it did generally work.

The plan

I took what I thought was the best advice from DiPiazza’s article and made my own plan of attack. The advice I followed:

  • Choose the right clients — I’m only pitching jobs that have reasonable budget, and I prefer fixed rate over hourly jobs. Because of this, I’ve only pitched for four jobs in my 11 days on the site.
  • Do the research — I check out the client’s history on Upwork — have they hired a few people, do they have a history of paying fairly, do they have good reviews and a verified payment method? For clients who give their company name up front, I check out their web sites and see what I can learn about them.
  • Prepare — when I write the pitch, I try to use the phrases the client used in the job description. I make it very clear that I read their requirements and understand them, and I show them why I’m the best person for the job.
  • Get in early — while it’s not always something I can control, getting in within the first few hours that a job has been posted means I’ll be closer to the top of the list of proposals that the client sees. I try to check the site daily in hopes of catching the right job at the right time.

The proposals

As I mentioned, I have pitched for four jobs so far (the rates listed are what I pitched based on their budgets.) By the way, it’s really hard to find information about what reasonable rates for freelance work are — I chose my hourly rate based on what I thought was a fair, full-time annual salary, with Upwork’s 10% fee built in. I have already raised my hourly rate since booking some work — we’ll see if this pays off. At any rate, here’s what I pitched:

  • Job A: $50 fixed rate for writing two documents
  • Job B: $20 fixed rate per week to write 3 social media posts for a company
  • Job C: $27/hour or $54/1000 words for travel blog posts (posted as hourly but requested rate per 1000 words)
  • Job D: $27/hour or $0.02/word for proofreading and editing a wide variety of content (posted as hourly but requested rate per word)

The results

Within a couple days, I received a message from Job A and they were interested. They asked when I could start and how long I’d need, and after a few messages back and forth clarifying exactly what he was looking for, I got the job. I completed it in two days, earned $50, and was then invited to pitch what I would charge to write a full version of the project. I pitched the full project at $995 and was offered the job — if I could do it in 10 days. I know the subject really well, and I write fast — it’s a push but I can do it. I accepted, and I’m more than halfway through this project, with three of the five ‘milestones’ submitted. Milestones are deliverables that allow you to claim a partial payment — this project is split into five equal chunks of $199. That’s just over $1,000 in work booked from that one initial pitch — my first.

Just after I accepted the big project with the tight deadline, I heard back from Job B. They requested a couple samples of my work on topics they provided, which I managed to create and return that same day. They’ve said they will be in touch in a few days with their response, which is great — I’ll hear from them just as my current project is coming to a close.

I haven’t heard from Job C or D. I can see that they have both interviewed several candidates, so it’s not looking good. I suspected that because they were hourly jobs, they’d be after candidates with lower hourly rates. I thought I’d give it a try to see how it worked out — I’m tracking all my proposals and results for comparison. They haven’t hired anyone yet, so there’s still a small chance I could be contacted.


Going forward, I’ll definitely look for fixed rate jobs first. By paying attention to the details, being prepared, and writing custom proposals for every job, I plan to set myself apart from people who use generic proposals for everything. I provide quality writing and editing and believe that people who are looking for quality are willing to pay what’s fair. As for the rest of Upwork, I don’t want to write 1,000 word articles for $5 — that’s not a living wage, and I would rather spend my time focused on projects that either pay fairly or provide value to my career and my website. This leads me to question whether I’ll be able to sustain the good luck of my first week on Upwork — only time will tell.

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