How Upwork works: a client & freelancers’ perspective

How Upwork works: a client & freelancers’ perspective

After working at several outsourcing companies and trying my luck freelancing on different websites, it’s time to show you how Upwork works from both the client’s and freelancer’s perspectives.

I’ll show you step by step how I posted a project as a client, evaluated the proposals and ultimately who I picked to work on my project. 

I’ll also show you the same process from a freelancer’s perspective along with case studies with winning proposals.

If you are new to freelancing and considering Upwork, seeing how clients hire will be useful for you. I usually recommend putting up a project for hire — even if you are a freelancer — to get a feeling for what it is like to be a client. The first section of this short guide shows what happened when I did just that.

How Upwork works if you are a client

First, we’ll briefly look at how Upwork works if you are a client with an overview of the hiring process followed by a step by step walkthrough.

An overview


  1. Sign up for an account
  2. Post your project
  3. Look at freelancer proposals
  4. Pick your favorite and agree on terms
  5. Get your project done and pay
  6. (Leave a testimonial)
  7. Repeat and get on with your life

Upwork does have other products for businesses looking to hire freelancers such as their project catalog, managed services for enterprises, etc. 

Since the standard product of hiring a freelancer seems to be the most popular, I’ll show you how it works step by step below by posting a job and documenting every step of the way along with looking at proposals from freelancers.

Watch me post a project and hire a freelancer step by step

After creating my client account on, I click Jobs > post a job.

The first thing we need to do is decide on the job title and category.

cover letter upwork - setting up a project

Next, let’s click update and write what we think is a good and descriptive project description. 

Let’s select a one-time project and click next.

There are many different skills we can pick between but I’ve found that it doesn’t make that big of a difference since we have the text to explain as well. Let’s pick quantitative research and get on with our lives.

We also need to pick the experience level that the freelancer should have. It’s difficult to know, so I’ll pick the one in the middle.

Next, we have to select if we only want to invite a specific freelancer or make it public, and how many freelancers we need. One freelancer will be fine for this project. 

Let’s keep it open and get some bids so the freelancers can show us what they got, shall we?

Next, we have to enter the budget. A fixed price seems like the right choice but I don’t know how much this should cost. Especially, since we don’t yet know how many leads are out there and we want to pay what’s fair without getting ripped off.

Let’s say $1 per lead and add $200.

A quick review of everything and we are ready to publish the project.

The project is live! We are taken to this page to invite freelancers but since we don’t know any, we’ll let the freelancers come to us.

Fast forward two days… we got 20 proposals! This is what it looks like when we browse through the proposals:

Somehow Upwork has decided for us that 14 out of the 20 options are the “best match”. I have blurred out personal details out of respect for each freelancers’ privacy.

cover letter upwork example - template

Let’s look at the other proposals…

cover letter upwork

This is a long proposal.. Interesting.

This next proposal is long, so I had to bite it up into two screenshots.

Besides the fact that this is very long and a good chunk of it feels like rewording of the project description, this isn’t too bad either.

This next one has attached an example from a similar project. For privacy of the people in the doc, I’ll not add it here but the formatting looks like what you and I are looking for. The proposal is nice, short and not bad at all.

The rest of the proposals are quite similar… except for these two:

winning cover letter upwork example

Nice! Look at this doc:

The freelancer showed a sample of what our project would look like. There were only one other candidate that did the same thing:

winning cover letter upwork example

The proposal itself doesn’t feel that relevant to the project but based on the sample below it feels as if the freelancer understands what we are looking for. Right?

There are plenty more, similar, proposals. Since you are busy and don’t have all day to look at this, let’s leave it with those highlights. I decided to go with the freelancer who sent the last proposal we looked at based on the sample.

Next, let’s look at how Upwork works from a freelancers’ perspective.

How Upwork works if you are a freelancer

First, we’ll look at an overview of the process from creating a profile to getting paid and spending your money (I hope you don’t need help with that last bit), followed by a case study showing how a reader landed a project on Upwork. 

We’ll also discuss common pitfalls to consider as a freelancer using Upwork and if it is a good choice for freelancers.

An overview of how Upwork works if you are a freelancer


  1. Create a profile
  2. Get approved
  3. Find relevant projects
  4. Send a proposal
  5. Agree on terms with the client
  6. Complete the project
  7. Get paid and withdraw the money
  8. Buy cool shit with the money you earn

Case study of a freelancer landing a project – example 1

Let’s look at a few examples from readers who landed real projects on Upwork.

Project description:

upwork proposal sample - project description for digital marketing project

The cover letter:

upwork proposal sample - digital marketing cover letter example

He landed the gig at $35 an hour.

Case study of a freelancer landing a project – example 2

Here’s another example. The project description:

upwork proposal sample - freelance copywriting remote job

And the proposal:

upwork proposal sample - copywriting job proposal

The reader won the project at a $250 flat rate.

Is Upwork a good choice for freelancers?

To figure out if Upwork is a good choice for freelancers, let’s first look at common pitfalls that are difficult to anticipate before starting.

Common pitfalls that cause problems for freelancers

The first and most obvious one is that we might not get your Upwork profile approved in the first place. 

There are things we can do to help the process but there is no guarantee to get the profile approved but without it we can’t apply for jobs at all. Some freelancers end up trying to get approved over and over again with no luck and get stuck there.

The thing is that the reasoning is often vague and polite, so the one we are given might not be the whole truth (there is no way to know), so if you are interested in Upwork my best recommendation is to give it a try once or twice and if you don’t get approved move on to other options so you don’t get stuck.

This might come across as trashing Upwork, which is definitely not my intention. It’s a great website to get started working small freelance projects but it is easy to get distracted by their “gamification”.

By that, I mean all the arbitrary metrics we as freelancers have to adhere to such as the Job Success Score (JSS), top-rated badgers, etc. They are meant to separate the quality freelancers from the scammers and make it easier for clients to find the right fit.

In theory, it’s great since these metrics *should* help us show how good we are and clients would hire us based on that but the reality is quite different. It’s difficult to accurately determine how these metrics should be calculated, which now leads to situations like if a lazy client doesn’t leave a review it can lower the JSS quite significantly even if the project was completed successfully and the client was happy.

I figure it is difficult to calculate accurately but either way, that tends to lead us freelancers to focus on those metrics more than finding and helping clients. In short, it is a major distraction from earning money — kinda like how inbox zero is meant as a good productivity tool but in reality, it makes us feel busy instead of impacting the important results such as how much we earn.

Another thing worth considering is that it is very likely that you’ll feel frustrated sending proposal after proposal and not hearing back from clients until you learn what works. I’ve noticed that more than half of the projects I’ve sent proposals for never hire anyone and I’m unfortunately not alone with that experience. 

This happens everywhere else too, so it is not Upwork’s fault but perhaps the difference is that clients appear like they are ready to hire on Upwork since they post projects with help they need and it only requires a few clicks to apply.

Another thing I’ve noticed when speaking to Upwork freelancers is that it is easy to look at competing freelancers with more experience, better case studies and feel overwhelmed and wonder how we can ever win projects when competing with those freelancers unless we offer a dirt cheap rate.

And looking the other way, how can we ever compete with freelancers offering a dirt cheap rate and turn that into a living and, for example, quit our job.

People talk about Upwork’s holy grail being the project invites we can get from clients. It often sounds like clients will send us projects left and right. In reality, we might get a few invites but usually they are generic mass invites sent to lots of freelancers at once which is pretty much the same as not getting one (that is not to say that it is impossible).

When is Upwork a good choice for freelancers?

There is lots of negativity about Upwork online especially when we look at reviews. I want to emphasize that Upwork is not a bad place to take the first step towards earning money on the side and quitting your job. After lowering my living cost, I quit my job using Upwork!

If you can overcome the obstacles above, it can be a good choice and if you are in a country like the US that is important to Upwork (with many clients looking specifically for freelancers from the same country), you might even be able to clear $100k a year or more.

Upwork is tricky in that the market inside and outside the US appears to be totally different. Basically, we can divide it up into two different types of clients: those looking for international freelancers and those looking for high-end expertise in the States.

The latter appears to be USA-focused since Upwork is putting its efforts into getting big companies there and helping them find the right clients

Those looking for international freelancers tend to want someone with strong expertise but without having to pay several hundred dollars per hour. In fact, many are looking for freelancers charging $50/h or less in my experience. 

It’s not that it is impossible to find high-paying, great clients, looking for international freelancers but rather that it requires us to go through A LOT of projects to find them. It is truly like looking for a needle in a haystack in my experience.


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