6 Big Reasons You Should Freelance on Upwork in 2021

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Hi, I'm Chris and I'm super glad you're here. 7 years ago I taught my self-web design and freelancing. Now, I do my best to teach others what I've learned so they don't have to struggle as much as I did.

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There are a lot of people who will tell you you should freelance on Upwork. And at the same time, a lot of people will tell you not to waste your time.

There are not many things as hotly debated amongst freelancers as Upwork.

On the one hand, the naysayers say there’s no real money to be made. In fact, Upwork is only for clients looking to pay rock bottom prices. If you have any sense of self-worth, steer cleer.

Then you’ve got folks like myself who have had great success on Upwork or Morgan Overholt who’s made $500k in 4 years on the platform who would encourage you to go create an account right now.

So which is it?

Morgan Overholt's Upwork profile to show you why you should freelance on Upwork

The Truth About Freelancing On Upwork

The truth is freelancing on Upwork isn’t all cupcakes and puppy dogs. I myself have had some pretty rough experiences working with tough clients through the platform.

BUT, the same could be true of doing any kind of freelancing ANYWHERE…heck the same could be true of just about any type of work there is.

Do you want to know the key factor in whether or not Upwork is a good experience?


Read that again. ☝🏼

Your experience on Upwork will either be good or bad based on how you approach it.

There are plenty of opportunities to work for some pretty bad clients and get paid next to nothing.

But, there are also A LOT of opportunities to work for some really great clients who are more than willing to pay freelancers what they are worth.

The same is true no matter where you’re trying to find freelance clients.

So, if you want Upwork to be a great experience like it has for myself and many others then that is 100% possible if you approach it with intentionality and a healthy mindset.

If You’re Not Freelancing On Upwork You’re Missing Out

I believe platforms like Upwork are only going to continue to get bigger with greater and greater opportunities for freelancers.

So, in this article, I’m going to talk about 6 reasons why you should be freelancing on Upwork in 2021.

The good news is all of this is coming from personal experience. I’ve been freelancing on Upwork since 2015, and I’ve personally seen the platform improve more and more over time.

When I started I had hardly any experience in the skills I was freelancing with. Upwork gave me the opportunity to grow my skills AND get paid while I was doing it.

Then I went on to start earning $4k to $6k on projects as a web designer.

Image of feedback from $6k project on Upwork to illustrate why you should freelance on Upwork

And, this doesn’t have to be a unique scenario. There’s nothing special about me as a freelancer. In fact, I was pretty horrible at first.

So, if you’re asking me, you SHOULD freelance on Upwork, and here’s why.

1. It’s the Biggest Freelancing Platform in the World

Here are a few crazy stats about Upwork

  • It has 145,000 core clients (clients who have spent $5k or more in the past 12 months)
  • It processed $2.52 billion worth of payments from clients to freelancers in 2020
  • Of all it’s clients 30% are fortune 500 companies
  • Businesses like Microsoft, GE, Dropbox, AirBNB and many others use the platform


So, what does that mean for you?

It means there is a ton of opportunity for you as a freelancer to find really good projects and you definitely should freelance on Upwork.

And, that opportunity is only getting bigger. In 2015, McKinsey reported that online freelance platforms like Upwork could add $2.5 trillion to total GDP.

And, we’re not just talking about clients that you do a project for and never hear from again.

I’ve had clients that have stuck with me for years from the projects I’ve gotten on Upwork. Some of them keep me on a monthly retainer others come directly back to me when they have a new project.

AND, I’ve had spinoff clients from those clients meaning a client I got from Upwork referred me to another client who wasn’t on Upwork.

Don’t get me wrong other platforms like Fiver and Freelancer are great. But, their numbers don’t even really come close to Upwork.

So, if you’re wondering which freelancing platform will give you the most bang for your buck you better believe it’s Upwork.

2. Nothing But Warm Leads

You know the difference between a warm and a cold lead right?

Cold leads are potential clients that don’t really know you and weren’t actively searching to hire someone do the kind of work you do as a freelancer.

These types of clients are pretty tough to win over.

Have you ever tried? I have. It was not fun.

You basically have to reach out to strangers who look at you as the equivalent of a telemarketer interrupting their family’s evening meal. On the off chance that someone gives you the time of day, you’re not done yet.

You have to follow up again and again. Giving away free advice and potentially never seeing anything come of it for years.

Upwork on the other hand has nothing but WARM LEADS.

Every day there are more and more projects from clients who are basically saying, “This is what I’m looking for. Now pitch to me.”

Upwork has taken out the process of turning a cold lead into a warm lead.

You don’t have to spend months or even years building relationships that you hope one day turns into an opportunity. The opportunity is there for you instantly!

Now don’t get me wrong. There is something very important about building relationships as a freelancer and having a network that can be a source of referrals.

BUT, why can’t you build that network of people while getting paid through the projects you win on Upwork?

That’s what I did.

Whether or not your clients on Upwork become one and done depends entirely upon you. If you develop a relationship outside of the project and follow up with them consistently after the contract is over you better believe you’re building a network.

It all depends on you as a freelancer.

Upwork is just giving you a platform to do just that while you’re getting pad with warm leads.

3. Clients Come to You

Since starting Self-Made Web Designer I’ve not freelanced a ton. In fact, I gave away one of the highest paying projects I would have ever had to a friend of mine because I was too busy 🤦🏼‍♂️ Where did it come from? Upwork.

Definitely second-guessing that one.

But, despite the fact that I’m not actively freelancing on Upwork I am still getting invitations to interview for projects almost weekly sometimes multiple TIMES a week.

When you first get started on Upwork you’ve got to be the one going out to find clients. They don’t necessarily come to you. But, after a while (in my case a very short time), when you build your reputation as a freelancer you won’t have to work very hard to find clients. They reach out to you directly.

When a client fills out a job posting Upwork suggests a few freelancers to invite directly to apply. And, if a client likes what they see they send that job posting directly to whichever freelancer they chose.

Imagine having qualified leads, who know how much you charge and the kind of work you do show up in your inbox every week.

That’s the exact scenario that can happen for you as a freelancer on Upwork.

Does it take some time to build a reputation? Sure.

But, it’s probably not as bad as you think.

I had my first direct invitation to interview on Upwork 1 month after I signed up. Then at 6 months of freelancing on the platform, I started consistently getting multiple invitations to interview every single week.

So, don’t a little bit of effort deter you from what could be a consistent source of projects for the rest of your career as a freelancer.

4. Upwork is Actively Marketing to Tons of Business Owners

What’s your marketing budget as a freelancer?

Well, whatever it is, Upwork’s is $96 million.

That means if you ever thought the word Upwork in your head, not even out loud, some algorithm somewhere picked up on it and sent you an ad online.

Okay, I’m going a little overboard here.

But, suffice it to say, Upwork puts a lot of effort and cold hard cash toward getting out there in front of business owners.

Yes, you have to pay Upwork fees out of the money you make from the projects you get. A lot of people will tell you not to work on Upwork because of the fees they take out. But, if I can be a bit controversial here, that might be one of the strongest reasons why YOU SHOULD freelance on Upwork.

Upwork takes a good portion of that money and puts it to work for you through things like marketing. AND, they have a vested interest in seeing the platform succeed. And, Upwork succeeds when freelancers succeed.

That means that both of your interests align! This is the exact thing Adam Smith was talking about in Wealth of Nations.

In my opinion, the fees you pay are well worth the price you pay for doing business with clients on their platform.

I’ve worked with people from all over the world. I wouldn’t have had the opportunity to connect with as many clients from as many parts of the globe as I have if it weren’t for Upwork.

You’re able to get in front of the type of clients you never dreamed of having access to all because Upwork is actively marketing to tons of business owners.

5. The Upwork System Provides A Lot of Security for Freelancers

There is no system that is 100% hassle-free when it comes to getting money from clients.

There are a lot of things you can do to put some guard rails to make sure you don’t get taken advantage of. Things like:

  • Good contracts
  • Good communication
  • Setting expectations at the beginning

But, when it comes down to it if a client decides to screw you over, it’s going to be tough for you. You can take them to court but trust me it’s a long and arduous process.

Upwork has some things in place that really help to ward off some of the troublesome scenarios you might face as a freelancer working with clients.

For instance, if you work on an hourly contract Upwork will have the client’s credit card on file with their permission to charge them for the work you do.

On fixed-price projects, they have something called milestones where you and a client determine at what point you’ll get paid during the project.

When the client funds the milestone that money gets taken out of the client’s bank and put into an escrow account for safekeeping. In other words, they don’t have access to it and neither do you.

You don’t just do the work in blind faith hoping they’ll pay you someday. You can see that the funds are there.

I had a friend who finished the work a client had asked him to do and then the client became unresponsive.

He was still able to get his money because it was in escrow. He requested it and 14 days later it was in his bank account.

If for some reason a client disputes your request it doesn’t just go away automatically. There’s a mediation process.

In other words, there are a lot of safeguards for you as a freelancer when it comes to doing work and getting paid.

Can you get screwed over? Sure.

But, there are more safety nets available to you than there would be if you were freelancing on your own.

6. The Job Market is Changing

It’s pretty easy to see the shift that is happening in the workplace today.

More and more workers are looking for flexibility in their schedules and autonomy over their careers.

At the same time, companies are increasingly engaging outside consultants and contractors to help them build their businesses.

Look at the Upwork’s numbers alone. In 2019 they brought in $2.09 billion from money paid to freelancers. In 2020 they brought in $2.52 billion that’s a 24% increase.

An image of the increase in Upwork's managed services revenue to illustrate why you should freelance on Upwork

That shows a trend of companies seeing the value of hiring freelancers to work on projects and using platforms like Upwork to do it.

You couple all of that with the fact that it has become so important to have a diversified stream of income and a very strong case can be made that you should freelance on Upwork.

I’ve known so many people who have lost jobs or had their income drastically decrease because of covid.

And, while the worst of it is likely behind us it’s not hard to think of something in the future that could potentially disrupt the job market in a big way like covid did.

That’s why I feel like freelancer platforms like Upwork are going to be a mainstay.

I’m not trying to paint a doom and gloom picture here. I want to do the opposite.

I want to show you just how much opportunity there is for you to freelance on platforms like Upwork.

There’s never been a better time for you to create a free account on Upwork and start bidding on jobs.

This puts you ahead of the curve and the change that is happening with the way we work and the way companies do business.

You Should Freelance on Upwork

The bottom line is you should freelance on Upwork.

Most of the people that I have found have negative things to say about Upwork haven’t really made a solid effort to become successful on the platform.

Are there things that suck about it? Sure.

But, there’s a reason why there are so many memes about Mondays. It takes work to enjoy work.

So, your experience of Upwork will be what you make of it. But, it won’t be because the platform itself isn’t any good.

After all, it’s the biggest platform in the world, and their constantly marketing to more and more people to make it even bigger. They go a long way to make it a safe place for you to earn money from clients AND if you do it right you will one day have clients coming to you without having to go find them.

But, more than anything, you have nothing to lose.

You could sit in the background without ever really trying wondering if you could be the next Upwork success story.

Or you could just go for it.

And, I think you should.

Happy man on computer to symbolize why you should freelance on Upwork


Hi, I'm Chris and I'm super glad you're here. 7 years ago I taught my self-web design and freelancing. Now, I do my best to teach others what I've learned so they don't have to struggle as much as I did.

Every week, I write an article and release a podcast episode. Sign up if you want to get notified when that happens.



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