How to Make Money on Upwork

Over the weekend, I received my “Happy Anniversary!” email from Upwork. The anniversary email celebrates that seven years ago this past Saturday (January 2, 2021) was the first time I made money on Upwork.

And I was so fucking proud of that first payment. I know a thing or two about how to make money on Upwork. Granted, I also believe that success means different things to different people. Getting back to that first payment…it was a whopping $15. To be fair, like most people trying to figure out how to make money on Upwork, I had an outside job (just one…I had already stopped teaching).

Within a few months of that first $15 payment, I was saying no to so many potential clients from Upwork that Bull and I knew that it was time for me to turn in my notice to my part-time paralegal job and focus on building my writing and editing business. And, yes, there was a learning curve involved and some slow times involved…but over the last seven years, my writing business grew into a writing and editing business. Then, that grew into writing, editing, and social media. Then, that grew into writing, editing, social media, and SEO. Then, that grew into writing, editing, social media, SEO, instructional design (including textbooks), and consulting. I have clients both on and off Upwork.

So, let’s just get down to it.

First, a quick disclaimer. I am not affiliated with Upwork. At all. They do not pay me to write about them. I am just a freelancer who uses their platform. I’ve had good experiences and not so good ones. For the not so good ones, I’ve reached out to their Support and their mediation team (the mediation took place probably six years ago). I am just a woman living in Oklahoma who runs a business. I am a special needs mom and working from home works for me. This goal of this blog, other than to showcase the good, the bad, and the ugly of working from home, is to hopefully help show you how you can make working from home work for you regardless of how you choose to go about doing it. I hope I’ve made myself abundantly clear. I’m just an individual with zero connection to Upwork other than being a registered freelancer on their platform. Again, I get NOTHING for writing this.

Some of these tips about how to make money on Upwork may seem obvious, but you would be surprised about the questions I am often asked online as well as through email…as well as the comments that clients often send to me through Upwork’s messenger about why they choose me (aside from the fact that I am Top Rated; sure, being Top Rated can certainly get some invitations, but it guarantees absolutely nothing.).

Complete Your Upwork Profile

Yes, I know…

I told you…I was not joking about some painfully obvious tips. The ability to make money on Upwork (or, rather, the ability to make money in business) honesty starts with your ability to put yourself in your potential client’s shoes.

Think about it…we always tell our kids about stranger danger…of course, we generally have the concept all wrong since there is no just one look for a creepy person in a van.

You want potential clients to trust you? Fill out your profile. Besides, you can’t get approved on Upwork unless you go through their process, anyway…but the more complete your profile is, the more likely it is that a potential client will be interested in you.

Start Out Sticking to Your Strengths

My very first paid project on Upwork was updating the styling of a demand letter for a Canadian attorney who wanted to use it here in the US. They wanted to update the letter to American English spelling and make a few other stylistic changes. Other “firsts” for me included writing for an agency who contracted for American law firms, medical clinics (fairly natural when you’ve worked in personal injury and taught trial prep and when you were once a LOMA certified life insurance underwriter many moons ago, ha! If nothing else, I am an excellent researcher!), ghostwriting both fiction and nonfiction short books, and basic editing. Note that you don’t see anything about SQL or HTML. I am fairly skilled in both (although it’s been a good 15 years since I’ve put SQL to work professionally; I worked for OCU Law last time I used that…and my now 22 year old sons and 20 year old sons were 6 and 4 years old). HTML is fun, but I would be terrified to use it professionally, especially given the amount of CSS and other languages now involved. I was quite a whiz when Geocities was a thing (yes, I realized I’m dating myself…and yes, I know there are great places I can re-learn those skills).

I stuck to my initial strengths without veering too much into my paralegal skills because I wanted a break. And, yes, there is a market for remote paralegals / virtual paralegals, whether you want to work for attorneys or the public (but if you are brand new, you do not want to get slapped with UPL. Some states do allow for licensed legal technicians, though. Do your due diligence.) As a paralegal, I did not want to answer phones or make phone calls (overall, I hate being on the phone). I love research and writing so I decided to use those skills.

Start where you are strongest and market those skills first because that’s where you can get your best reviews.

It’s Okay to Start Small (If You Want!)

Keep in mind that when I started on Upwork, I still had a job. I didn’t need to burn the ship so to speak (although I knew I would ultimately need to do that…to learn more, please read this.) And, yes, there’s more than one school of thought. You can charge what you are worth just starting out. And that is okay to do!

I had a job and little confidence starting out (believe it or not). So, since I had a job that could pay the bills, I set my hourly rate as $10 an hour on Upwork. (I’ve come a very long way.)

So, why start small? Looking back, I believe it made it more likely that not only my first $15 client would give me a chance but also the first agency that hired me would give me a chance. From there, I raised my rates. Yes, I know there are people who will disagree and say that you get what you pay for as well.

Ultimately, it is a decision you make for yourself. I saw starting lower as an opportunity not to necessarily undercut others. I saw it as an opportunity to get my first review. Once you are able to get that first review, it is much easier to gain traction. To be clear, at this stage, I am much more interested in long-term relationships with my clients than constantly looking for new clients.

Talk to Potential Clients in Your Profile, Not at Them

This is something I harp on a lot when I talk to new freelancers. If you go and read my profile, you will notice that I use a lot of “you” language. I want potential clients to recognize that they are the center of my attention…because they are. They are the reason I am on Upwork. They are the reason I am successful or not. I want to talk to them. I do not want to talk at them. Frankly, this is the same thing I say to attorneys and other high-level professionals (but attorneys, especially…because law school changes most people).

Do you know why paralegals and legal assistants are so necessary? Because the general public are terrified of attorneys. It isn’t just that we are less expensive when it comes to billing. It isn’t “grunt work.” It is that we know how to make clients take a deep breath and calm TF down…at least, if we are good at our jobs. We talk to clients and potential clients (without giving legal advice, because that’s illegal) and not at them. Clients and potential clients are afraid lawyers will talk at them (good lawyers don’t…and most paralegals and legal assistants eventually train their lawyers to not do that…at least, in smaller law offices).

Just because you are the professional on Upwork does not mean that you should throw professional jargon at the potential client in your profile. Sure, poke their pain points. Like it or not, that is how you make money on Upwork. No, I don’t care if you think it’s smarmy. As a freelancer, you need to get on Team You and sell yourself. No one else will do it for you. There’s no client fairy (sorry). But…talk to them and not at them. Think about how even you like to buy things you enjoy but you do not like to be sold. So, what do you like? What are your favorite things to buy? If you could go shop tomorrow for anything without any sort of repercussions because everything else was paid, what would you buy if there was no salesperson? Think about your favorite commercials…we all have them. Why do you like them? My son has autism and loves the Charmin bears and Bounty commercials because they’re catchy.

Be Picky When Choosing Upwork Jobs

Even before I became Top Rated on Upwork, I was picky on what I’d apply for on Upwork. Part of that was time constraints. I had three minor children at the time and a job. Part of it was I wanted to make sure I was really happy with what I’m doing. A gilded cage is still a fucking cage.

First, you don’t want to waste all of your connects. Yes, Upwork has again changed their connects. If you get invited to a job, it’s free to apply. You may even be awarded with some free connects…but that still doesn’t mean the gig may be right for you.

Second, each Upwork job costs a specific number of connects. So, even if you buy connects (they’re cheap…and frankly, if you’re not willing to invest $10 in your business to buy connects…which, by the way, much cheaper than Thumbtack!), you need to be mindful of how you use them. You want to pick and choose.

I read the proposal. I look at the budget (although I will often bid outside of the budget constraints because budget is often a placeholder). I will read previous reviews left for and by other freelancers. If they have a history of not leaving reviews, why would I want to work with them? If they have glowing reviews and have nothing nice to say about anyone, why would I want to work with them?

Don’t Use a Copy / Pasted Upwork Proposal

I know it’s tempting to just copy and paste an Upwork proposal. Look, back in the day, I did it. I worked in Career Services at a law school and then at a state university. We encouraged students to write a generic cover letter and then to change it up. I followed that for a while. It’s a meh idea, at best. I’ve written at length here about how to write an Upwork proposal that clients can’t turn down. So I’ll keep this brief. I keep my proposals short, to the point, and I end with a question because a question encourages engagement. Think of a question even if you do not have one. And no I am not talking about:

I mean something related to the project.

Be Cordial in Messenger

When I say be cordial in messenger, I mean be friendly yet professional. Do not be demanding. Do not beg. Do not name call (yes, really). Now, if you do run into issues with a potential or actual client (it’s happened, even to me), that’s why we have Upwork Support. You should always keep your files and your messages. There is a reason why Upwork discourages freelancers from taking conversations off of the platform and provides us with Zoom within the app. It makes it much easier for Upwork to help protect us as freelancers who have agreed to their Terms of Service.

If you act in ways that are less than professional, you will do less than your financial best on Upwork.

Be Reliable

One of the best ways to make money on Upwork is to be reliable. The reason why I am Top Rated Plus (which is a relatively new ranking…but I’ve been Top Rated since it was rolled out several years ago) is because I am reliable. Most of my clients both on and off of Upwork are long-term clients. That isn’t to say that I am not open to one-time projects. I am definitely open to that. I’ve met some amazing people from one-time and short-term projects. I’ve worked on documentation for nuclear reactor software. I’ve worked with architects. I received a request from what appeared to be a member of the mafia to help squash down negative news (I politely turned down that job….). I’ve written for Lawyerist. I’ve written for law schools. I’ve written textbooks. I’ve made my Aunt G so proud I thought she’d burst. But…none of it would have been possible if I hadn’t been reliable.

So, what is reliability? It meant that I worked when I had the flu (between flu naps a couple of years ago). I worked when both Uriel and I had strep. I worked from Las Vegas when Bull was competing in IBJJF. I worked on days when I had panic attacks before going to get my VPO against the ex renewed. I worked when I didn’t feel like it. I found wi-fi hot spots when a tornado tore through our neighborhood and demolished our neighborhood and Uriel’s school a few years ago (that was before we bought the home we live in now). I mean, if anything should get you a break from not working, it should be a tornado curb-stomping your neighborhood…and it probably could have. But…I have a bit of a personal theory when it comes to reliability. My clients shouldn’t need to feel the pinch of my personal life when it is possible. Of course, 2020 sort of seemed to test that…at least, the October ice storm. I couldn’t take Uriel out in an ice storm during a pandemic searching for free internet. There were a few churches around but I couldn’t, in good conscience, possibly put him at risk.

Now, how I run my business does not have to be how you run your business…but when it comes to making money on Upwork, reliability as a professional is key. I’m not making that up. But, you know, as you can see from my list above, I clearly could have come up with any reason I wanted to not work. I could have “done it later.” The problem is that “later” doesn’t often come for any of us. To make a habit stick, it’s important to fight through when it is hard to build the habit of reliability. Reliability is where the money is found.