How I Made My First $1,000 On Upwork With Ease

 How I Made My First $1,000 On Upwork With Ease 

There are nearly 57 million freelancers in the U.S. right now. Upwork had an unconfirmed 145,000+ core clients in 2020. 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). I understand that doesn’t sound great (it might even sound discouraging), but I think it’s important for people to see real growth timelines. Everyone’s journey is different.

I was scared to leap into freelancing. When I was doing my initial research, I was willing to look at success stories and stories of failure. There are lessons in both. So here’s mine:

Table of Contents

· My Timeline

∘ March

∘ April

∘ May & June

∘ July

· Here’s How I Did It

· What I didn’t do:

∘ Propose for Jobs I Wasn’t Interested in

∘ Copy and Paste Job Proposals (Use a Template)

∘ I Didn’t Niche Down

· What I did:

∘ Vetted Each Client and Used Search Filters

∘ Personalized proposals

∘ Ask Questions in Your Proposal

· Communicate Communicate Communicate

∘ Treated My Time as an Asset

· Community and Growth

My Timeline

First, let me establish my timeline. I launched my Upwork profile in March of 2022. I’m publishing this in August of the same year. Let’s walk through my timeline month by month.

March

This 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.

In March, I made a total of $385.

You can see in the breakdown below that this total came from 3 milestones. If you’re unfamiliar with Upwork, a milestone is just a project. As a content writer, a milestone for me is usually 1 blog post for a client. You usually apply for one project at first, and if the client likes your work, they can add milestones (additional projects) after.

My first project was a small sample project, and the next two were full-sized projects. Admittedly, I wasn’t writing blog posts or SEO content like I do now, but I was still writing and analyzing text, so I was happy with the opportunity to earn extra money and get a review.

April

I started to lose motivation in April. The client I had in March didn’t need me anymore, and all of the people I looked up to in the freelance world strongly recommended against working on Upwork. Hearing these messages while looking for new clients encouraged me to make Upwork less of a priority.

In April, 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 project was a simple survey task that took about 10 minutes. It was an uneventful month, but May and June got even worse.

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 graveyard shift to working the dinner shift, 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 my time, so I chose to focus on methods like cold emailing to try and bring in clients. That’s why I didn’t have a single project in May. I just wasn’t putting in the time or effort.

I moved to a new city and left my full-time job in June. I took on freelance content writing full-time about halfway through June.

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 bringing in $30 of revenue for the month. I got sick the last week of June, which meant I had about one productive week for the whole month. June was a bust.

If I had 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 picked up in July.

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 total.

You’ll notice that the two columns on the bottom are gray. That’s because I’m writing this on July 28th. I’ll finish the projects within three days, but I haven’t officially invoiced for them yet. 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 the first week of July sick. I couldn’t 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 $X on Upwork, but everyone’s journey is unique. Some of you are like me, and 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.

When you learn throughout your freelance career, you’ll likely learn from a range of lessons. I learn more from my mistakes than simply doing it right. Failure is easier to remember. It leaves a mark. So, let’s first start with what I didn’t do to make 1k on Upwork.

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. I didn’t sign up for projects on topics I hated.

Instead, I sent proposals for projects that I felt I could do well and had a reasonable pay rate.

Isn’t that a slower path to success? That’s also a yes. Reviews and ratings are a huge (if not the largest) factor in your success on any freelancing project. Clients want to see that you’ve worked with people, and it turned out great.

People 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 low ratings 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, doing it will help you see faster success. But you don’t have to or don’t want to, 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. It feels 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.

Creating a template that you can copy and paste is a for-sure way to save time on your proposals. Or is it?

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, I always customize my proposals 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 scientific 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, it probably won’t help at all.

Pick the most critical parts of your expertise and skill and highlight them in your cover letter. Leave the irrelevant details behind. 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.

That could actually mean you have to submit more proposals in the long run. So while it might feel like you’re saving time with a template proposal, it might cost you more time in the end.

I Didn’t Niche Down

This is actually a partial truth. In the beginning, I tried to niche down and focus on science-based content. I liked sustainability, science, climate, and things like that. I now know that I wasn’t niching down properly (but that’s a story for another time).

What did I do? I threw it all away. I changed my profile information, changed how I described myself, and even changed my portfolio site.

The freelancing course I took absolutely, 100%, hands down recommended you niche down. Most other leaders in freelance say the same thing. So I did it. And it didn’t work for me. Now, I’m writing about whatever I can get. I am writing about pets one day and SaaS the next.

Juggling different topics is certainly harder than having a super specific niche, but I’m finding that I really enjoy lots of other things. Initially, I wrote SaaS content off as too techy and boring. Now that I’ve had $800+ in (non-Upwork) projects, I’m finding that I might actually love Saas.

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 thrilled with where I’m at right now.

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 the $1,000 mark.

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 filters I’m likely to use.

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 piss poor pay. I can weed out some of those cheapskates by setting my pricing filters at or above $25/hour and $100 per project.

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.

I identify as an entry-level professional, but I still apply for jobs listed under intermediate. Why? Because sometimes the clients are open to a range of writers and I might fit their needs. You shouldn’t solely rely on this when you’re bidding on projects, but definitely take it into consideration.

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.

I know several people who still apply to jobs with 50+ proposals. In reality, many proposals will be spammy or just poorly constructed. Ultimately, find out what works best for you.

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 this 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.”

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.

Job posters (potential clients) can only see about 2 lines of text when they’re sifting through proposals. To see more, they have to click on your proposal. You want to make sure you're giving them a reason to click.

Ask Questions in Your Proposal

Just like any good 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 to see if we’d be a great fit working together!

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 posted 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 high-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 when I submitted the project: “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 relationship with your client. 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 in your article.

Treated My Time as an Asset

Last on my 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’ for any career. So I choose to pursue projects that will compensate me fairly. If I work for clients with low budgets, 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 accomplished everything they asked for.

But Andrew, how is that valuing your time? I applied for that project because I knew I’d be a shoo-in and I knew it’d get me a review on my profile. It would also give me the confidence to work with other clients.

Sometimes I value my time by setting a limit on the amount of time I spend 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 promises regular gigs. If you’re struggling to keep or find long-term gigs, this could boost 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.

But regardless of what I’m getting from the project, I always deliver excellent content and great service.

Community and Growth

The last thing I did 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 me, and there will always be others that know more than I do. Find those people and connect with them. Follow them on Twitter, Reddit, Facebook, and LinkedIn.

Freelancing can be a lonely job. You can grow in it alone, or grow in a community. I choose community.

If you want to connect with people like you, feel free to add me on social media. You can find me on Twitter and LinkedIn right now. Share your tips and your journey with me! I want to hear about all the things you’ve accomplished too. See you there!