How to make money with Upwork

How to make money on UpWork ($50K) in six months

If you’re reading this article, then you are curious about how to make money on UpWork. My goal here is to share with you everything you need to know to make significant money, all on the side. I’ll include the exact messaging templates I use and the tricks I found to win me clients. These days, I also hire on UpWork. I’ll do my best to share what I look for when I’m hiring as well.

Overall, I think UpWork is the single best strategy to begin your online money-making adventure. Many other “make money online” tactics, like Amazon KDP, dropshipping, or Amazon Affiliate marketing, can take years of work to get to a consistent income. UpWork is not only much faster, but it will teach you the skills you need to scale and have a more consistent income. This leads directly to our first point, about the length of time it takes to start earning.

How long does it take to start making money on UpWork?

You can get your first deposit from UpWork in exactly a week. I made $3,828 in my first month on UpWork, and all on the side. I actually want back through my UpWork history and found that my first payment was $30 that I received on June 26th, 2019. That last week of June 2019, I made $694.87 total

I was pumped when this happened as it was the first few dollars that came into my bank account outside of my day job.

The best thing about UpWork is that literally thousands of jobs on UpWork due to the thousands of clients are online and posting jobs each day. You don’t need to convince all of them to hire you. If you can prove to just one client, out of thousands, that you can deliver exactly what they are looking for, then you can secure your first job in less than 24 hours. Since UpWork pays weekly, you’ll get your first deposit just a few days after that.

Getting set up on UpWork

Signing up with UpWork is actually pretty easy. You need an email address and photo ID. Be warned, this approval process can take a while if your picture of your ID/driver’s license is blurry. Make sure your photo is easy to read. Mine accidentally wasn’t, and it led to a huge pain where I had to prove that it wasn’t photoshopped and do a video chat with the team there as well.

Once you are set up, the most important thing to keep in mind though is your Upwork profile. At it’s core, UpWork is a search engine. You need your profile to be optimized for exactly what someone could be searching for.

For example, let’s say I want to find someone who is an expert at Xero to manage my bookkeeping for me. As a client, I’d search for “Xero accountant” in the search bar.

In this case, Heather shows up immediately because her profile one-liner explicitly says Xero in it. Since I, as a client, can see she has a 100% review score and is an expert in Xero, I might just hire her directly instead of putting an open post out to everyone.

The other reason why your profile really matters if it’s actually the first thing your prospective client will read. You are required to write a “cover letter” when you pitch on work. However, the client will actually see the profile first BEFORE the cover letter.

In other words, you might have a perfect pitch but if your profile has typos in it, then you won’t get that job.

A profile is relatively easy to fill out so take the time here to put some thought into describing who you are and the type of work that you do.

How do you get your first job on UpWork?

This is an often-cited issue for new freelancers on UpWork, but there is a huge trick here.

When you apply for a job on UpWork without experience or a review score, it’s extremely obvious that you don’t have any reviews. That is risky as hell for a hiring manager. Most UpWork jobs I’ve hired for have received a dozen or more applications. It doesn’t make sense for me to hire someone with no review scores when I have a dozen other people to choose from that do have review scores.

This problem leads to many individuals who just started running into a ton of difficulty getting that first gig. Apply for a job on UpWork takes “Connects”, which actually cost money. I believe they are $0.15 each. If you apply for a 100 jobs and don’t get any, you could blow through $15 and not even get a single interview.

So here’s the trick I found: apply for jobs that need to be filled immediately.

Go to UpWork and search for terms like “Immediate”, “ASAP”, “Today”, “Tonight.”

You’ll find posts like this one.

Whoever is behind the post about filing their taxes needs someone ASAP. They don’t care as much that you don’t have experience on UpWork. They need someone to help them.

I figured this trick out after a few days of not hearing back on dozens of different applications. Once I did this trick, I got five or six jobs immediately, even though I didn’t have any review scores.

I wrote a whole piece on this strategy of getting work without any experience on UpWork.

Lose your pride and take any job for any price

There will be plenty of people online that will tell you not to work for low prices on UpWork. This advice is wrong.

What matters most to you, in the beginning, is taking any job to get review scores. Once you have a JSS (Job Satisfaction Score, or UpWork’s review system), then you can increase your prices. A JSS typically takes 5-10 completed jobs to get.

So lose your pride and get your JSS. I graduated with honors from the top business school in the world and worked for BCG advising Fortun 500 CEOs at 22 for $1,000 an hour.

I took $7 projects on UpWork to get started. My first project was helping a small business owner write a customer service response to a pissed customer.

Lose your pride and get the JSS, then increase your prices. You won’t get first time gigs, even with my immediate trick, if your price is ridiculous.

How can I earn money from UpWork?

There are a couple of different ways that you can use to create an income stream. In short, you’ll make all of your money from delivering projects to clients. However, there are a couple of different variables you should keep in mind to maximize your ability to make money on UpWork.

Hourly vs Fixed Contracts

There are two different ways you can make money. The first is an hourly contract. For example, you could work as a virtual assistant for someone at $15 an hour.

The second is to use a fixed price contract. In this example, you can deliver a fixed output like a completed PowerPoint deck, in exchange for $150.

Both strategies have their pros and cons. Clients tend to prefer fixed-price contracts because they know exactly how much they’ll pay. I prefer a fixed price as well because I tend to work extremely quickly. As a result, I make more money if I do a fixed price because I always finish quality work in faster than expected.

However, fixed-price contracts are often susceptible to “scope creep” where the client begins to ask for more and more work from him. You need to be willing to put your foot down here and say no. This is difficult to do because you want to maintain your sanity, but also still get paid.

I recommend fixed price contracts only for when the work is more than $1,000. At that price point, the clients tend to be sophisticated enough to not destroy you with scope creep.

What types of jobs should I work?

The reality is that there is all manner of jobs on UpWork so you should do projects that are aligned with your skill sets.

For example, what kind of tasks did you do in your last full time job? What was your college degree in?

If you did a lot of graphic design, then market yourself as an artist. Web design? There you go! Really good with Xero software? You’re now a Xero expert. Web development pro? Done deal.

The trick is to go with what you are already pretty good at and then expand from there as you begin your freelancing career. For example, I did business strategy for Fortune 500’s at BCG. I ended up doing lots of financing modeling, PowerPoint presentation building, and strategy development on UpWork because it fit into my past experience really nicely.

Scaling UpWork from 1 to 38 clients

Thus far, we’ve talked about setting up on UpWork, how to get your first jobs, how to make money, and how to position yourself in a way that’s aligned to your interest.

It’s now time to talk about scaling up from there. In my first year, I ended up completing 44 different projects for 38 different clients.

The goal of this section is to show you how to do the same and scale up from those first few clients you ended up scoring. Remember, you swallowed your pride and were taking any projects at any price point just to get started. Now, it’s time to really start earning.

Use personal applications that are client-focused

When I hire, this is by far the biggest problem. If I get 20 applications, probably 15 screw this up and I junk all of their apps. Let me highlight the two biggest problems I see, and then I’ll share the exact application I use.

First, do not simply copy and paste the exact same application for everyone. It’s extremely obvious when this happens because everything is generic fluff and it’s not tied, at all, to my specific posting. Using a generic post is not going to get you any clients. The ramification of a generic post is that it’s 100% about the freelancer. Since clients are different every time, the only way to use a generic post is to make it self-centered on yourself.

That leads to mistake #2: Do not focus the application on yourself!

When I first got started on UpWork, all of my applications were incredibly self-focused. I talked about how I graduated Wharton and had done big consulting for an MBB firm. My success rate was extremely low.

The reality is that most clients do not give a shit about you. They focused on themselves.

It’s now really apparent when hiring. I’ll get applications that say:

  • “I am the number one freelancer”
  • “All of my clients love working with me”
  • “I work full time freelancing on UpWork”

None of those are very convincing as to why that person should be hired. I hire people who send me applications like the one below. My success rate of getting work on UpWork also increased dramatically once I started using phrases like this. It’s focused on the client.

The actual application I use when applying to get work on UpWork

“Hi (Client Name),

Sounds like you are looking for (specific thing mentioned in the client’s job description). Preferably, you need something that will (describe what that specific thing will be used for).

I specialize in this type of (specific thing). My three most recent projects for (specific thing) helped the clients to do (what the clients used my last specific work for)

Can you tell me what would a fantastic result of this project look like to you?

When you work with me, you get transparency and communication daily through the process. For example, I insist on sending you a daily update email on what was accomplished.

If any of this is what you need, please don’t hesitate to contact me. I love to do an introductory call with clients to understand exactly what you are looking for and answer any questions you may have.



PS: Regardless of who you chose, keep my info in case you need someone later. I’m standing by to help”

This is super client-focused, which hopefully should help you score projects at a much higher clip than before.

How to interview clients to save yourself from future headaches

If you spend enough time on UpWork, you’ll note that the best freelancers all insist on talking with phone with clients before they sign on for a specific project. This often has the appearance of the client interviewing the freelancer to make sure they are the right fit for each other.

It’s actually the other way around. In most cases, this is the freelancer interviewing the client to make sure they want to work with this person! A bad client can make your life hell, want to quit freelancing, and can destroy both your earnings and your job success score. You want to get paid, not to quit freelancing.

Good freelancers don’t struggle to get work and there’s always another client who can pop up and hire you. Therefore, get on the phone with the potential client to “feel them out.” If you get the impression this person could be difficult to work for in any way, then politely decline the project.

Here are some tell-tale signs I’ve found that means you should walk away:

  • The client is unclear of exactly what they want from you
  • The client likes to hear themselves talk, and talk for an hour when 30 minutes would do
  • The client is condescending to you in any way.
  • The client has ridiculous ROI expectations that show a lack of intelligence. (One client asked to pay me $100 but I had to deliver $1,000,000 in sales for him. That’s 10,000% ROI, and shows he was a moron. Hard pass)

Increasing your hourly rate to attract the best types of clients

Earlier, I said to swallow your pride and get good review scores. Now that you have those scores, it’s time to time to increase your rates.

You might be surprised to know how high you can push them and still get clients. For example, I started off by charging $45 an hour. I had too much work, so I raised them to $75. I raised again to $125. Then $150. Now, they’re at $250 comfortably and it doesn’t impact the rate at which I secured clients.

Not only does this help you make money on Upwork, but it also helps you ensure better clients. I’ve consistently found that the best clients are the most sophisticated clients who pay the highest amounts.

Don’t be desperate

This is a pet peeve of mine, so I had to mention it.

One guy I hired a while back (I was desperate for some specific help so I hired anyone) had applied to a job posting where I put “immediate” in the title.

He did an OK job, and that was that.

Over the past six months, he has messaged me at least 100 times, begging to be hired for another job.

While I feel for him, begging for a job is not going to get you hired. To get hired, you need to position yourself as coming from a position of strength as an expert. If you position yourself as anything less, then you are not going to get hired.

Don’t waste time begging old clients to hire you. Instead, focus on other projects instead.

How does UpWork make money?

In exchange for connecting you and the hiring manager together, UpWork will take a percentage of your income as payment.

The important thing to note here is that the fees UpWork assigns is directly correlated to how much you get paid by the client. If it’s under $500 total, they charge you 20% of income. Above that threshold, it’s 10%.

For that reason, repeat business is incredibly important to maximize cash flow. If you work online full time, then you can hopefully get significant repeat business and as many projects as possible to 10% fee structure.

Is working for UpWork worth it?

Absolutely, 100%, no doubt about it.

When someone asks me “what is Upwork”, I typically respond with something along the lines of “If someone put a gun to my head and told me I needed to make $1,000 in a week, then UpWork would be a key part of my strategy to make that money.”

I firmly believe you need to learn how to make $1 before you can make $10, then $1,000, then $10,000, then $100,000, then $1M.

UpWork allowed me to figure out how to make the first couple rungs of that list. It allowed me to pay off my debt and build up a skill set.

Once you have figured out this amount, then you can begin to look to other strategies and platforms like Eden McCallum or Catalant or others that will allow you to scale from $10,000 a month to $100,000 per month.

Or, you can put your $10,000 a month into real estate and scale that way!

Tips for managing UpWork and a full-time job

All of my work has been on the side during a full-time job, which can lead most people to go absolutely crazy.

There have been a lot of UpWork tips in this article, but the most important ones are here.

  • Make sure you only take calls at night, not during the day when you are working your day job
  • Give clients reasonable deadlines for when work will be done, but don’t allow them to push you to deliver something immediately
  • If a project is going poorly, walk away from it and move on to a different one ASAP

It’s more important to maintain your sanity and to keep working on UpWork than it is to try to do too much to quickly, and then quit because you did just too much.

Starting your career online with UpWork is a great idea, but it’s okay to look somewhere else later

I firmly believe everyone should try to start the entrepreneur journey on UpWork. Building up a freelancing business is maybe one of the easiest businesses you can imagine, which gives you plenty of business experience in itself. You can develop overall skillsets like setting up an LLC, business bank account, and more. You’ll learn in your freelancing experience how to deal with unhappy clients and how to write proposals.

Ohh, and you’ll get money along the way!

What you won’t get on UpWork is a million dollars. You will also never be able to develop “passive income” that makes you money even while you are asleep. You will have to consistently work in order to develop and maintain that financial level.

Don’t let that discourage you from starting though. UpWork is a tool for you to develop important business skills and earn income to invest in future business endeavors. It was my first successful foray into an online income and I firmly believe it’s one that everyone should look to aim to follow as well.

Let me know about your experience on UpWorrk within the comments: I’d love to hear how it has gone for you and what you think about the platform moving forward!

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