Starting Upwork and Getting to $10,000

Starting Upwork and Getting to $10,000 Earned in Eight Months

In around eight months I took a freelancer account that had been dormant for years, with a lifetime earnings of $20, and made $10,000. Here’s how I did it and the things I’ve learned along the way.

My Upwork Background

Years ago I opened an account when Upwork was still oDesk, and did nothing with the account. In 2020, I was working a full-time job at a greenhouse and wanted to make some extra money, so I sent out proposals for writing jobs and got a reply, for $20 to write chatbot dialogue.

The client asked me to rush the work overnight, and gave some comment about being too busy to officially start the contract, which is a bad sign. But I was excited to get this far and went along with it. I stayed up late and turned in the work, and didn’t hear anything back. Several weeks later, after some prompting, he did end up paying me. This all seemed like a lot of hassle for not very much money, so I put Upwork aside. As an “essential worker,” I was busy throughout the COVID quarantine period and didn’t want to spend my personal time on Upwork.

Around the beginning of 2023 I left a full-time factory job, and decided to look again at Upwork as a source of income that could give me more freedom.

Given my interests, writing made the most sense, so I started sending out proposals to various writing-related jobs.

It took several weeks to get a client, and then several more weeks to get a repeat client. When I had a couple of steady clients, I slowed down the pace of sending out proposals, and focused on client work. When I entered a period with less work, I sent out more proposals.

I have now done enough work for all of my clients that I’ve passed the $10,000 mark on Upwork.

You can start Upwork at zero and be successful with it relatively quickly. I am not saying you can start with no marketable skill and be successful quickly.

I’ve been writing in various forms for years before doing anything with Upwork. I brought over a developed skill, but it’s not like I had an established business. I just was better at a particular skill than the client was.

If you’re already knowledgeable about voice acting, building WordPress websites, or graphic design—but don’t have Upwork experience—I’m talking to you. It’s easy to think that no one will be interested in paying you for what you can do, but thinking that way is probably short-changing yourself. Some people hate to do the very thing that you find easy. Those are your potential clients.

Filling Out Your Profile

I’ve spent a good amount of time working on my freelancer profile. It’s really important, right?

Well, that’s what I thought, until it came time for me to hire people and see things from the client’s perspective. Out of a hundred applicants, I think I looked at one person’s profile. And that was after making my decision on whom to hire!

My current view of the profile is that it’s like a picture background: people notice if it’s missing or if something is way out of whack, but it isn’t the focus. In this case, the focus is your proposal for the job, and your work samples.

Spend time to write a well-thought-out profile, free of typos and talking about your skills and services, with a good picture of yourself. Don’t agonize over it like it’s going to be a hugely important factor in getting you hired. And don’t get hung up on making it “100% Complete” according to Upwork.

Setting Your Price

How much should you charge for your services?

There are three types of clients when it comes to price:

1. Price-conscious people using their own money.

2. People using a business bank account. They still might have a budget, but won’t feel the money leaving the same way as the first group. This type of client is most likely to care that you can do the job, and not that you are the lowest bidder.

3. The extreme cheapskates. They want an expert to write a “flawless, SEO-optimized, 2,000 word article” for $5.

If you’re American, you will never be able to compete on price, so don’t bother.

Still, when you’re just starting out, I would advise picking the lowest price you can tolerate. This lessens the perceived risk of hiring you. You’ll still be too expensive for the extreme cheapskates, but will look better for the price-conscious people. Clients who don’t use their own money will not care.

For flat-rate jobs, it’s possible to bid higher or lower than the suggested rate set by the client. Unless you can offer something really extraordinarily amazing, don’t bother to bid higher. If the flat rate is reasonable, just bid what is asked. If the client wants to spend $200, for example, and there are 15 other freelancers who will work for that, asking for more just makes you more likely to be rejected without consideration.

Searching for Jobs

You can enter various search terms to find jobs. I’ve experimented with being specific and searching for things like, “product description writer,” “native English proofreader,” or “creative writing.”

I thought this would save me time by only showing jobs I’m interested in. I’ve discovered that it rarely leads to relevant results.

What seems to work best is to put in the broadest possible term. In my case, that’s “writing.” Then I narrow the jobs shown by excluding everything that is below a certain price range, or it has too many proposals already, or costs too many connects.

I search this way the majority of the time, and only occasionally check out the more specific terms, for the slight possibility they will show something interesting.

US vs. Worldwide

Clients can geo-restrict their jobs to only appear in certain regions. Many more jobs are posted worldwide, with more competition and price variation than jobs posted to a particular region. The majority of my clients have been American, but I still will check worldwide jobs and bid on whatever looks good.


These are the currency used on Upwork to bid on jobs and to promote your proposal to the top of the stack, if you pay extra. I haven’t done a deep dive into why some jobs cost 2 connects and some cost 12, so I won’t get into that here.

When you open your freelancer account you’ll get some free connects, and you also get 10 free connects every month. Currently they roll over, so if you don’t use your account for months, you might have a lot saved up.

If you run out of connects, you have to buy more to continue bidding on jobs, or wait for new free ones.

Is it worth bidding on high-connect jobs?
I have not done a scientific split test to see if it’s easier to be hired for high-connect jobs, but personally I don’t bid on anything that costs more than six connects. This is already a decent investment. Why spend eight connects on something when there are many other jobs that cost fewer connects. Also, high-connect jobs get a lot of proposals, so it isn’t even like I’m going to stand out. Because sending a high number of proposals is so important to your success, it’s better to bid on multiple jobs that don’t take as many connects.

Is it worth buying connects?
Yes. As of this writing, you can buy 100 connects for $16. Or you can sign up for Freelancer Plus, which gives your account some extra features, and comes with 70 connects for $15 per month. Even getting one client will pay for the connects. I’m not saying you need to spend money on this all the time, but if you’re sending out proposals regularly, it’s worth paying a little money to keep your momentum going.

Should you spend connects to boost your proposals?
“Boosting” your proposal sends you to the top of the stack in the client dashboard. It might be worth experimenting with, but overall I would say it’s not worth it. It can quickly become costly and from my perspective as an employer, it generally will not be the deciding factor on whether you are hired.

Receiving Invitations

Even when you’re just starting out, you will occasionally get invitations to bid on a job. These happen because when clients set up a job, Upwork presents them with a list of freelancers to notify. Not a lot of thought goes into this list, so you may be invited to apply for something you aren’t qualified to do, or have no interest in.

I advise you to not ignore these invitations. Upwork tracks your response rate and time, and incorporates that information into your profile. It’s not clearly visible to others, but the computer knows it. To keep your profile as appealing as possible, you want to respond to every invitation, preferably within 24 hours. Instead of letting invitations pile up, it’s worth interacting with them—even to decline them—so your profile doesn’t get a reputation for being unresponsive.

Waist-Deep Muck

Looking at the job feed can suck the life out of you, especially early on. There are so many repetitive, badly written, cheap, or just plain crazy-sounding job posts. It’s easy to become discouraged.

You must wade waist-deep through muck to get what you want. However, I can say with complete certainty that there are good clients out there. After a while it becomes easier to tune out the bad stuff. Until then, keep wading through, and don’t give up.

Assessing Potential Clients

I don’t care if a client is unverified or has just opened a new account, if the individual job post looks good. I’ve had a couple of clients who were completely new to Upwork, and they were great. Even so, the scams tend to be new and unverified accounts.

The one thing that does make me cautious is if the client has a bad feedback rating. On a platform like Upwork, both clients and freelancers have a lot at stake when it comes to ratings, so people tend to rate each other generously. For something to have gone so wrong multiple times that the client account has a poor rating—that is a good reason to be cautious.

Spotting Scams

Anyone can post something on Upwork after opening an account. The post might be up for a while before being reported and taken down, so there is always the possibility of encountering a scam of some kind. This is just a fact of life, and it shouldn’t discourage you from using the platform, or responding to a lot of jobs.

Here are some things to keep in mind so you don’t become victim to a scam:

If you see the same job posting listed ten times every day, it’s fishy.

Most new and unverified accounts are not scams, but most scams are new and unverified accounts. I trust an account that has spent a million dollars much more than one that has spent zero.

If you see the same language used in multiple accounts, this is suspicious. For example, I often see a post for editing a romance novel that ends with something like, “I know getting this done professionally is expensive, but I only have $50 for this as I’m just starting out. Can you help me?” This might not be an outright scam, but I’ve seen a variation of this post so many times that it’s clearly not a regular person just starting out.

If they say to contact an email address to get started, and list it in the initial job posting, that’s a bad sign.

It may happen that a client didn’t do any of these things, made a very regular job post, and turns out to be a scam. How can you tell?

They will often respond to your proposal and then say something to the effect of, “In order to get started, contact our hiring coordinator at [email address].” If you don’t contact them within a few hours, the client’s message thread will disappear in your dashboard. I have never had a legitimate client evaporate after a few hours like this, so it is a pretty good sign that something is up.

What happens if you do write to them? When I have done this, I was sent an email that talked about different writing jobs I could do with their company. They had good payouts. The catch? I was supposed to pay them money up front, and if they liked my work, they would give my money back along with payment!

Although this sounds ridiculous in retrospect, it sounded less ridiculous in the email and I have no doubt some people would go for it.

There are thousands of potential clients. If someone pressures you or asks for something out of the ordinary, don’t hesitate to move on.

Bidding and Proposals

Upwork is extremely competitive. In the writing category, most jobs have 15-20 applicants within a day or two. There is a decent chance that when you send a proposal, the potential client will not even read it or open it.

It’s important to still put thought and effort into your proposal, and I’ll go over some lessons I’ve learned about writing them later. But for now, the important point to keep in mind is it’s a numbers game: You must get statistics on your side by sending out a lot of proposals. I’m not saying to go crazy and write 50 a day, but pick a number you can sustain and keep doing it. It might take a hundred proposals to get a client.

Here’s something I wish I knew earlier. For a long time I would only send out proposals during what I considered to be “normal hours.” I didn’t want clients to see that I sent them a proposal at 4:36 AM on Sunday and think I’m weird. Eventually I had reason to use the client interface on Upwork to hire some people, and I realized something: I couldn’t see the time or date anywhere on their proposal! All I saw was a stack of proposals. So don’t feel like you need to wait for a “good” time to send something. Right now is the best time.

That brings me to the next point: Don’t hesitate. Jobs fill up quickly. If you see something that looks worth a proposal, don’t save the job with the intention of proposing three days from now. Jump on it, write your proposal, and move on to the next thing.

Writing the Proposals

When I wanted to improve my proposals, I did online research for advice. One of the points I read was about how it’s good to introduce yourself, to establish yourself as a person and not a spammer. In my case, such an introduction could look like this:

My name is Tom Rozek and I’m a writer living in Rhode Island. I can edit your blog about cat-themed biodegradable ponchos, and help you convey your message in a crisp and clear way….

Although this isn’t terrible, I’ve learned that the introduction is actually a waste of very valuable real estate. In the client’s dashboard of proposals, before clicking on anything, the client only sees the first two lines of whatever you write. The client already sees your name next to the proposal. The client does not care what your name is, or where you’re from, unless there are very special requirements for the job, which is rare.

Say “Hello” and include the client’s name if you can find it, but beyond that, hit the ground running:

Hello Frank,
I can edit your blog about cat-themed biodegradable ponchos and help you convey your message in a crisp and clear way. I have done similar work for three previous clients….

Proposal Length

There’s no formula for the exact best length of a proposal. It depends on a lot of factors, but here are some things to consider:

Keep the proposal as short as possible, while still covering whatever points are important. The average client has just read many other proposals. A big wall of text, even if it’s great stuff, is likely to be ignored as too much work to read.

Have your samples do as much work as possible. Instead of explaining why you’re good for the job, the samples should show why you’re good.

Extra Wordy Proposals

I’m coming at this from the perspective of getting hired for writing jobs. A longer proposal may make sense because of the nature of the job, and articulating what you can do.

If you’re freelancing in a field where you can directly demonstrate a skill, that is by far the most important, beyond anything you write in the proposal.

Real-Life Example
I needed to hire voice actors. I did not care what they said in the proposals. Some people would send a whole page of text. That didn’t matter one bit for who got the job. Nor did it matter if this would be someone’s first-ever job or if the freelancer was an Upwork veteran. I did not care about the person’s education. The only thing that mattered was the audio file that demonstrated the actor’s voice. Actors who had the most specific and relevant voice files got preference over the ones who sent general examples. I didn’t spend any time on people who sent no samples at all.

Work Samples

Providing relevant work samples is extremely important. Your potential client is probably going through 15 or more proposals. It’s likely that the freelancer with the most relevant sample, that is easiest to understand and read, will get the job.

At one point, I thought that having lots of samples would make me seem more experienced, so I created a Google Doc that linked to many other Google Docs with work samples. I would then send a link to that document in my proposals.

Although this isn’t horrible, it’s vague and requires the client to do extra work by searching through my document for the relevant information. I now just send one to three PDFs, with the most relevant samples I have for that particular job.

Making Work Samples

“But Tom,” you say, “I’m just starting out. I don’t have any work samples!”

You can make samples before you get your first client. Many people on Upwork post documents. You can download these and work on them as if the client hired you. For example, let’s say you want to be a short-story fiction editor. Download some stories, edit them, and then use this as a sample for your next proposal.

For responding to some job posts, if the client provides a document, it can make sense to do some work on that document and send it back with your proposal. This is really showing the client what you can do and taking away any need to have imagination. It by no means guarantees you will be hired, but it can be good practice, and it also generates sample material you can use next time.

No-Cost Test Work

I don’t do this every time, but if the job looks right, I will offer to do test work at no cost to the client.

I’ll say something like, “I’m happy to do a sample rewrite of this story at no up-front cost to you. That way, you get to see how I work, and I get to stand out from the many people you could hire, so it’s a win-win. Only if you’re happy with my work would we then move on to the rest of the story.”

This also does not guarantee that I’ll be hired, or even get a response. But it does make it easier to hire me, by separating me from the pack. And if I do a little work and they don’t hire me? I’ll use the before-and-after as a sample for future proposals.

It’s easy to think, “Oh no, if I start offering free work, I’ll be instantly inundated with people taking advantage of me! Better not!” In my experience, there is very little risk of being inundated.

Extra Requirements

Some job posts have extra requirements for the freelancer. These are things like being in a certain time zone or having a good job-success rate.

You can bid on a job even if you don’t meet the requirements, but is this worth it?

It can be, but it depends on the requirement. Something like having a 90% job completion rate is very specific. You probably won’t convince this client to hire you if you don’t meet it. Something like the time zone, on the other hand, might be a preference but not a deal breaker.

In your proposal you can acknowledge that you don’t meet the requirement, and then say how you’re interested in the job and felt compelled to bid on it. I’ve done this successfully.

Doing Work Before You Start the Contract

Does it ever make sense to do work before officially starting your contract? Sometimes, but it depends on the context.

When it makes sense:
You’re messaging the client and things are obviously progressing in a positive direction. Instead of hitting the brakes to ask the client to start the contract right then, you begin work and follow up later about the contract.

It’s a small job that you could always use as a sample later.

You’ll be able to sleep at night even if the client doesn’t pay you.

When it doesn’t make sense:
The client says, “Oh I’m too busy right now to start the contract; can you work on this immediately?” This is what my $20 guy who was a pain in the neck said. It hardly takes any time to start a contract, so there’s just no excuse.

It’s a bigger job and the client is treating you like a worker, but still hasn’t paid you anything.

Even with my worst experience I still got my money in the end. You gain more by trusting people a little and being easy to work with, than by insisting they start the contract before you’ll do any work.

Manual Time vs. Time Tracker

You can be paid by the hour in two ways.

Manual Time is the honor system. You keep track of the time you work for your client, and manually enter it into the “Work Diary” section of your dashboard, along with notes on what you did during that time. It’s important to remember that you can only enter in time you have done within the last two or three days, so it’s best to keep on top of this. Clients can more easily dispute payment when it’s entered through manual time. I’ve never had a problem with this, though.

Time Tracker is a surveillance app you download. When you turn it on, it takes a screenshot of your desktop every ten minutes, and it tracks your keystrokes and mouse movements. This makes it much harder for the client to dispute your hours, and makes it harder for cheaters.

I’ve used both. Overall I like manual time most because I know I’m being honest and I don’t need something monitoring me. However it adds the extra step of needing to enter time into the work diary.

Time Tracker automatically enters all the time you’ve worked. One of my best clients wanted to use Time Tracker. Eventually I got used to it looking over my shoulder. It may not be your first choice, but I wouldn’t turn down a job because the client wants to use Time Tracker.

Because it takes pictures of your desktop, it’s a good idea to remove or rename any files or icons that you consider to be private.

Showing Your Face/Voice

Depending on what you’re selling, you may need to talk to your client on the phone or over a video call. It’s worth thinking about a place where you can do this with an acceptable background and with not a lot of noise. It also makes sense to test your webcam and microphone and learn how to do Google Meet and Zoom.

These aren’t things you need to do on day one, because it’ll take some time before you get a client who wants this, but it’s good to be prepared. If you aren’t willing to video call, talk on the phone, or show your face, you’ll make less money.

Closing Out Jobs

Here’s something that I scratched my head about for months before learning the answer: Sometimes when I finished a job, the client would pay me and quickly give me a review. Other times, the client would pay me, but there would be no review, and the job would be listed as “in progress” on my dashboard, even though I had completed the work. What’s going on?

Once you’ve started an Upwork contract, it has two components: payment for the deliverable, and officially ending the contract. When you deliver your work, the client will click something like “Review and Pay” and release the money to you. However, the job is still technically ongoing. In order to end it, the client has to click into a drop-down menu, officially end the contract, and leave you feedback.

Because the Upwork interface is confusing, many people don’t know about this two-step process, and it’s less work for clients to just not click more buttons.

Having open contracts means you’ll have less feedback and fewer “completed jobs” on your profile. But it also makes you look busier, like you have more ongoing clients, so it isn’t necessarily a bad thing.

If you really want to close the contract, though, you can either ask the client, or close it from your end.

Turning Down Work

I understand the internal pressure to not turn down any work. Still, it’s important to have some boundaries and know when to walk away.

Here are some situations when I may turn down work:

Just too little money, with no secondary benefit to make it worth doing—like experience, or working on a really cool project.

The deadline is too tight. Some deadlines aren’t worth the money.

Not interested in the job at all. One reason I’m doing Upwork is to do more work that I enjoy on some level. To take a job I need to have some interest in it, or at least not find it actively repellent.

If I’m reasonably confident I couldn’t do the job effectively. I have a broad skill set and will take a crack at a lot of things, but I’m not all things to all people, and there are types of work I just don’t do.

Client seems unreasonable or too much of a hassle.

Real-Life Example
I saw a job that looked interesting, and in the post, the client asked for answers to six questions in the proposal. I answered them, and then the client sent this:

I’ve got a few more questions for you:
1. Who were your last 2 employers and how do you think they will rate you when we ask them?
2. Are you able to adapt to any situation, being able to coordinate things?
3. How good are you at managing people? Do you have any experience managing people? This role requires that you work with a couple of people that you’ll be in charge of and make sure they get stuff done on time.
4. Have you ever taken the DISC personality test? If so, what personality type are you?
5. Glad to hear that you’re willing to take an assessment test. Here’s the link to: [Link]

Note that you will not be paid for it, nor will your assessment work be used for any public, commercial, publishing, or personal usage. If you do get hired, you will get paid for the hour you’ve spent taking this test.

Please complete this test within 3 days.

WHAT WE’RE LOOKING FOR: We’re seeking an exceptional editor who goes beyond editing and proofreading content. We need someone who can collaborate with our writer to ensure the excellence of our output. This entails identifying weaknesses in articles, providing constructive feedback, and suggesting improvements to elevate the quality of our content.

Too much for what he was willing to pay! I’m not applying to medical school.

It can feel like the client has a lot of power because jobs can be hard to get, but remember—there are thousands of other clients.

Steady Clients

I have found that steady clients are by far the most efficient way to work on Upwork. When you have built a relationship with a client and are being hired again and again, this removes the prospecting, uncertainty, and time spent writing proposals. You can focus on actually working and making money. It also benefits the client, who’s found a good worker. Unless your steady client is doing something really outrageous to you, treat this person like gold!

Become a Factotum

I’ve made the most money through Upwork by being hired for one thing, doing a good job on it, and then being given unrelated and more complicated work. If I said, “Oh no, I will only do my specialty,” I would have missed out on a lot of earnings, and many opportunities to learn and expand my skill set. You will progress much faster if you’re open to many types of tasks.

Can I Make Money While Also Working a Full-Time Job?

Yes, but it will be much harder to make significant money. This is because you’re competing against people who do this for a living, who can answer messages at 4:00 AM, and who won’t eat if they don’t get hired. They’re motivated.

In your freelance work, you might need to talk at odd hours or during normal working hours in a way that would be very difficult to do while having a regular full-time job.

I’m not saying you should quit your job to do Upwork. You certainly can be hired for some tasks while having a full-time job. But to compete most successfully and be able to accept certain jobs, you’ll need to have the flexibility that comes from self-employment or a part-time job.

Closing Thoughts

Making money on Upwork takes time, effort, persistence, and luck. It isn’t easy money, but as a former greenhouse algae scraper (I am not making this up), I can tell you it’s a lot better than some jobs out there.

This document has a lot of advice—things that I’ve learned on my journey and wish I knew at the beginning. But it’s important to remember that I made my journey without first knowing half of this stuff! And I’m constantly learning new things.

It is much better to go out, do things, experiment, and make iterative improvements, than it is to wait for any sort of perfection.

Do you have questions or comments? Have you used Upwork already and discovered a useful lesson? Let me know!