There are nearly 57 million freelancers in the U.S. right now. Upwork had an unconfirmed 145,000+ core clients in 2020. So it’s no surprise that freelancers like you and I turn to platforms like Upwork for freelancing gigs.
It took me about 3-5 months to reach $1,000 in total revenue on Upwork (depending on how you count my time). 5 months to make 1k? I know, it sounds bad. But, my journey to that milestone was a bit different than some of the other stories you’ll find online.
And as a freelancer that started without any knowledge about freelancing, I read everything I could about others’ experiences. I was willing to look at success stories and stories of failure. There are lessons in both.
This article is really divided into two sections. First, I’m going to walk you through, month-by-month, my Upwork journey to $1,000. I’ll include detailed breakdowns of how many gigs I had, how much I made, and more.
Then, I’ll tell you exactly what I did and didn’t do. Let’s get started.
Table of Contents
My Timeline
I launched my Upwork profile in March of 2022 so we’ll start there.
Freelancing on Upwork in March
This is the month I jumped into freelance content writing as a baby freelancer. I took a freelancing course, built a website, and signed up for Upwork all at the same time.
Here’s what I made this month on Upwork:
You can see in the breakdown below that this total came from 3 milestones. If you’re not familiar with Upwork, a milestone is basically a project.
As a content writer, a milestone for me is usually 1 blog post for a client. If you’re, say, a web developer, a milestone could be something like a website sketchup or completing a page.
Typically, you apply for one project at first, and if the client likes your work, then they can add milestones (additional projects) after.
Freelancing on Upwork in April
I started to lose motivation in April. The client I had in March didn’t need me anymore and I was seeing a lot of experienced freelancers recommend avoiding Upwork. These things combined let to a deprioritization of Upwork. I was beginning to put my energy elsewhere.
So this month I made a total of $274 from 3 projects. The first and the last project were from the same client I had in March. The $25 dollar project was a simple survey task that took about 10 minutes. It was an uneventful month, but May and June got even worse.
My Upwork Journey in May & June…?
Like many new freelancers, I was still working a full-time job at this point. May brought a change in work shifts; I went from working the nights to working dinner, and the time I could devote to freelancing was cut in half. So in addition to feeling like Upwork would never lead to success, I also had even less time to give freelancing.
I had to prioritize my tasks and make the most of the time I did have, so I chose to focus on methods like cold emailing. As a result, I didn’t have a single project in May.
In June I left my full-time job and moved to a new city. After a few weeks of well-deserved time off, I took on freelance content writing full-time.
While I still devoted 90% of my time to non-Upwork tasks, I was beginning to submit more and more proposals. I had a single project that brought in $30 of revenue for the whole month. Then I got sick the last week of June, which meant I had about one productive week for the whole month. June was kind of a bust.
Had I devoted more time to building my presence on Upwork, I’m confident I would have reached 1K much quicker. But with my new energy and available time, things began to pick up in July.
Freelancing on Upwork in July
All of my earnings in July came from two clients. One client paid $75 per project and the other paid $150 per project. Altogether, I invoiced for $900 dollars total.
You’ll notice the last two rows are missing a date. That’s because these projects haven’t been completed just yet. I’m writing this on July 28th, but they’ll be done before the end of the month. They’re still factored into my totals though.
While I barely fell shy of earning $1,000 in one month, I spent the last week of June and first week of July sick. I wasn’t able to get any significant momentum until the second week of July. I have no doubt this month would have been a 4-figure month had I not gotten sick.
Here's How I Did It
Everyone has tips for how you can make money on Upwork, but everyone’s journey is unique. Some of you are like me, you won’t have 40 hours a week to devote to Upwork. You might get sick, your child could get the flu, work might be extra busy, or your in-laws come and visit. Whatever it is, shit happens.
Regardless of what life throws at you, there are several things I’ve learned over the past few months that helped me cross the $1,000 mark on Upwork. If I had to do it all over again, these things would help me get there in half the time.
What I Didn't Do:
Propose for jobs I wasn’t interested in
You’ll hear people saying things like, “Apply for anything and everything you can do. Even if you don’t want to do it, apply.” I didn’t do that. And I wouldn’t recommend you do that either.
Yes, not every project was what I dreamed of or wanted to do long-term. But I took care to avoid projects that had low pay and high expectations. And I definitely didn’t sign up for projects on topics I hated. Instead, I proposed for projects that I felt I could do well and had a reasonable pay rate.
Isn’t that a slower path to success?
Yes. Reviews and ratings are a huge (if not the largest) factor in your success on any freelancing platform. Clients want to see that you’ve worked with people and it worked out great. So influencers tell you to apply for anything and everything, even when it’s dirt-cheap, because it helps get you reviews. I just wasn’t interested in that route. Partly because I had a full-time job and didn’t need to grind like that, partly because I just wasn’t interested in working for pennies.
There are plenty of people on the platform that recognize this need for reviews though. Some clients will hold you hostage and make difficult requests while threatening to leave a poor review if you don’t comply. Others will offer rates like $0.007/per word in exchange for a good review. (Yes, I’ve actually seen rates for less than a penny per word.)
If you have the financial means or the time to work that hard for less pay, then doing it will absolutely help you see faster success. Just know that I didn’t.
Copy and Paste Job Proposals (Use a Template)
If you’re unfamiliar with Upwork, clients post jobs and freelancers can bid on them. You create a “proposal,” which includes a cover letter (a few sentences) and a rate, and submit it to the client. Then the client picks the freelancer they want.
Proposing on Upwork can feel exhausting, repetitive, and it gets old quickly. It can be really tempting to try and get the most bang for your buck, or in this case your minute, so people often look at templates as a solution.
For a short time, I had a template of sorts. Half of my proposal was the same while the rest was customized to the job posting. I abandoned that process once I started taking Upwork seriously in June. Now, my proposals are almost always customized to the project. I don’t copy and paste any more.
Your clients only care about one thing, how you can help them. So make sure the info you include about yourself is relevant to the job.
If I’m trying to land a job for a science blog, it will definitely help if I flex my B.S. in Biology. But if someone is looking to hire a content writer for their B2B marketing blog, my biology degree probably won’t help at all. Copy and pasting templates throws it all in there every time, and it will likely mean no client feels you’re the perfect fit for them.
If your potential clients are struggling to see that you’re a good fit, it could mean you actually end up submitting more proposals in the long run, which is the opposite of saving you time.
Instead, pick the most important parts about your expertise and highlight them in your cover letter, leaving the irrelevant parts behind. Creating a new cover letter from scratch, every time, will help you do just that.
I Didn’t Niche Down
At first, I tried to position myself as a science writer, focusing on climate, sustainability, and science in general. Almost every freelancer out there will recommend picking a niche at the start of your career. But I was struggling to find postings on Upwork that I was actually qualified for.
So, I threw it all away. I redid my profile and even my entire portfolio site to match my new generalist approach. Juggling different topics is certainly harder than having a specific niche but I found that I enjoyed writing about pets one day and online learning the next.
Becoming a generalist has helped me understand freelancing and better understand what I’m capable of. It’s true that you can charge more for specialization, but I’m very happy with where I’m at right now.
Update: (January 2023) After half a year of freelancing, I have chosen to niche down. I’ve now landed on SEO blog posts for SaaS companies. But everything I’ve said remains true. And I will likely still take on the occasional project outside of my niche just to mix things up.
What I did:
Now that I’ve exposed the rule-breaking rebellious things I didn’t do, let’s look at things I did do to help me reach $1,000 on Upwork.
Vetted Each Client and Used Search Filters
You’ve probably heard the horror stories. You sign on for a project and the client doesn’t give you enough details to do a good job. They inevitably complain about the final product. Or, you get into the relationship with the client and it turns out they nitpick every little detail and ask for revision after revision.
I don’t want that. You don’t want that. And I don’t want that for you.
So when I’m looking for projects on Upwork, I always use filters. Here’s a screenshot of the Upwork search filters I use most often.
Pay
First, I filter out the jobs that are paying $5/10/15. Some of those clients know they’re paying for low-quality content. Others expect high-quality writing for pisspoor pay. I can weed out some of those cheapskates by setting my pricing filters at or above $25/hour and $100 per project. leo.
Experience
I also look for jobs that fit my expertise. Every job will have an experience level listed. This can help you understand what level of experience the client is looking for in a freelancer.
Be honest with yourself. Are you truly an expert? Or are you more of an intermediate professional?
Here’s how Upwork defines the categories.
Proposals
I rarely propose for projects with more than 20 proposals. Once the project reaches 21 proposals, it’s in a new bracket of 21-50 proposals. That’s way too many proposals for one person to look at, and I find it unlikely they’ll even see mine. So I don’t waste my time.
I stick to tasks with less than 20 proposals. If you find a project with only 5 or 10, then I recommend sending a proposal in immediately. Getting back to it even an hour or two later can sometimes mean the client has received 50+ proposals already. Most projects get 50+ proposals in their first 8 hours.
Still, if you feel like you’re the right person for the job and the client NEEDS you, then apply. Best case scenario, you get it (yay)! Worst case scenario, you don’t.
Reviews
At the end of every relationship between a client and a freelancer is the opportunity to give and receive a review. That means you rate and review your client just as they rate and review you.
When you’re looking at a project posting, you can see the client’s reviews. You can see how much money they’ve spent, what freelancers rate them, and how highly freelancers speak of them.
I look for reviews like, “Avery was so responsive and always clear about what she wanted in her blog posts. I loved working with her.” If the info next to that review has a high dollar amount, then I know the freelancer also worked with the client for a long time. These are green lights.
If I see a review like, “Jamie ghosted me after 2 days and didn’t give me any info on the project. When I submitted an article with the info they did provide, they trashed it and terminated the contract. Later I found the exact article I wrote published on their site.” As the saying goes, I wouldn’t touch that client with a 10-foot pole. Runaway.
Personalized proposals
Speaking of reviews, freelancers will often leave the client’s name in their reviews. For example, “Working with Andrew is always a pleasure. He’s quick to respond and clear with what he wants.”
Upwork won’t put the client’s name in the project listing but they don’t block it out in freelancer reviews. Looking at the reviews can help you personalize your proposal/cover letter greeting with their first name. “Hey Andrew” is much better than, “Hello” or To whom it may concern.”
I also start my proposal by mentioning something about them. For example, “I’ve read your project details and it sounds like you have some really exciting content for dog owners coming up!” Or, “I’ve looked at your site and you have some fascinating content!”
This tells them I’ve actually read their details and I’m already invested in them. That will encourage them to keep reading past the introduction.
Ask Questions in Your Proposal
As with any quality content, you should always include a call-to-action (CTA). The end of your proposal should always ask the reader to do something.
I’m not a natural salesperson and I wasn’t a marketer before so I struggled with asking a stranger to do something for me. It got much easier with practice.
Here’s an example of a weak CTA: I look forward to hearing more about this project and seeing if we’d be a great fit!
Imagine you’re on a date and your date says, “I look forward to seeing if we’re a good couple,” as they leave your front door. Would you feel urged to follow up? To call them back? Did they even ask you a question? (The answer is no.)
Here’s an example of a CTA I frequently use: “Would you be willing to send a link to the website these blog posts will be published on? I’d love to learn more about your target audience, style, and tone.”
Do you see how that compels them to act?
The weak CTA assumes they’re going to respond. They likely won’t. My CTA explicitly asks them to send me something. But it even goes one step further and demonstrates that I’m already ready to work on delivering quality content catered to their target and brand.
Communicate Communicate Communicate
When I get an opportunity to work with someone, I communicate communicate communicate. If you’ve ever worked in customer service then you need to turn those skills on. Here’s an example of my communication with a client.
“[Name], that sounds perfect. A week from today is July 12th and my workload this week is pretty light so I can begin working on this tomorrow.
I’ll review the example you sent over more thoroughly then. I’ll be in touch if I have any questions.”
The very next day I had two questions and I sent them over.
That same client later sent me this, “Hey Andrew, I think this was really great! You mimicked our style wonderfully. Thank you so much! I’m in the process of testing out a few candidates, but you’re top of my list currently!
Spoiler alert, they chose me. Later that day I had a new milestone (blog post) from the client and have invoiced for hundreds of dollars since.
Communication is an essential part of your client relationship. Of course your product/service is important, but clients also want someone they enjoy working with. Asking questions when you have them isn’t a sign of weakness or ignorance, it’s a sign of strength and loyalty to the client. I promise you, they’d rather you ask a seemingly stupid question than have to fix a simple error 10 times.
Treated My Time as an Asset
Last on my “things I did” list is how I treated my time. I touched on this earlier, but I treated my time as a highly valuable asset. Because it is.
There’s a popular freelancer out there that says, ‘young people don’t want to pay their dues. They want to be paid these high rates before they’ve put in the work.’ I have to disagree.
I don’t think exploitation wages should be considered ‘dues’ in any career. So I choose to pursue projects that will compensate me fairly. If I work for clients with low budgets, then I make sure I can budget my time accordingly or I make sure it’s going to pay off in other ways.
You may have noticed I accepted a $30 job in May. I delivered a 750-word article to a client and I accomplished everything they asked for.
But Andrew, how is that valuing your time? First, I was able to complete the project in two hours, so I didn’t lose much money. Sometimes I value my time by setting a limit on the amount of time I spent on the project. I wrote that article in about one hour. I won’t take a job for less than $25 an hour, so it only makes sense that I don’t take an article that will work out to less than $25/hour.
But as with every rule, there are exceptions. And everyone values their time differently. For example, maybe the project is paying less than you’d like but it promises regular gigs. If you’re struggling to keep or find long-term gigs, this could be a real boost to your mood and your profile. Taking a job for a little less than your normal rate doesn’t mean you don’t value your time, it might just mean you have to sacrifice money in exchange for reviews, ratings, experience, or something else.
Community and Growth
The last thing I did to make one thousand dollars on upwork was lean on my community. If I had a question about how much to charge or what to do in a certain scenario, I put it on a forum, a subreddit, or a facebook group. There will always be freelancers out there that have done this longer than you and I. Find those people and connect with them.
If you’re looking to connect with people like you, feel free to add me on social media. You can find me on Twitter and LinkedIn right now. And if you’re interested in reading more posts like this, sign up for my newsletter. You’ll get access to new articles, videos, podcast episodes, and other resources.