Upwork success stories: a case study and what really works

Upwork success stories: a case study and what really works

People like to share random recommendations for how to win with freelancing and become Upwork success stories. Like: 

  • “Fill in all the details on your Upwork profile”
  • “Complete Upwork tests” 

Or my personal favorite “find your why”. 

Most of the advice is technically correct but doesn’t really help you. You don’t need to be a rocket scientist to know that filling out the details of your profile can help you get work. Duh.

You’ve probably seen the success stories from some freelancers earning $100,000 or more on Upwork and for many of us, it feels like a dream. 

But when we get down to business, the story becomes something else. First, we feel that spark of motivation for a while.

But all of a sudden, that feeling “what if I can’t do it?” creeps up on us and the voice in our head yells “who are you to do that? You have never earned that kind of money before! You don’t even have [insert credentials]…”

And you know what? Maybe you don’t have the credentials or whatever you tell yourself it might take to earn that much. That doesn’t mean you can’t start freelancing and become that.

Why can’t you discover the crazy amazing feeling of earning money completely without depending on being having to be at the office every day?

Most of us didn’t have that when we started. That’s why we began.

In fact, clients, as well as traditional employers, often hire for attitude rather than skillset arguing that the right attitude is more difficult to learn. You can take advantage of that as well.

I got started with little knowledge but I really wanted to figure it out for myself. If you feel the same, I bet that there is nothing stopping you from taking that first step except your own thoughts.

There are ways to get started with little experience and without faking your skills and feeling like a fraud. Here’s a guide that shows an approach that works well.

In this article, we’ll look at a success story of a reader that made it work for himself and we’ll look deeper at the counterintuitive things he did.

Case study: from a frustrating job to earning 2.5x his salary with freelancing

After graduating, he got his first job as an analyst at a major market research firm.

It was exciting to get into the real world and he was ready to prove himself and make a difference.

That lasted for a while until things began to feel predictable. It took forever to get anything done and obvious solutions constantly had to go up and down through the bureaucracy for weeks only to fizzle out.

Often that meant long hours and meaningless meetings across town. He felt frustrated. 

And then there was the pay.

It wasn’t great. In fact, as he describes it, it was enough to survive in a shared apartment with a bit for fun and barely anything left to save up.

Hrishi felt like the brand name would be good for his career and figured he could stick it out, rise up the ranks, and surely things would get better.

He suggested different ideas to improve things at the office but the same thing happened over and over again. It got lost in the bureaucracy and fizzled out after a while.

He felt that maybe this corporate culture wasn’t the best fit for him, which made his performance drop and made him feel like he didn’t really care for market research anymore.

Eventually, he had enough. He wanted to quit but he needed the money.

As he was thinking about other options, he realized that he might be able to earn some money helping students with their applications for universities in the US.

He got his first client pretty quickly. And then another. It wasn’t great money but it was a start. It felt like there was something there.

Until one day, where everything suddenly dried up… 

The semester had started and no one could enroll until next year. That meant he wouldn’t get any clients until then.

He was back to square one. Stuck.

We met up one day, over what turned out to be shitty chicken burgers, and the topic came up. I was freelancing on Upwork at the time and suggested he look for inspiration there.

After getting past the first few client calls, he earned his first couple of hundred dollars within a month.

Then he managed to double that the month after and reached about $450 working with freelance clients on Upwork.

The following month, he earned about the same from freelancing on the side as he did from his monthly salary and decided it was time to quit his job.

He turned that into $30,000 in his first year of freelancing.

An analysis of what happened

upwork success stories
Photo by Franck V. on Unsplash

What happened? Why did it work?

The reality that I wish more people would bring up is that most of the tactics you see on other articles work but they don’t really make a meaningful difference. 

Sure, you might see a little boost here and there. And when you experiment, you’ll eventually discover tactics and tricks that work well for you – and they might not work for others.

But most of us aren’t looking for small tactics. We want life-changing stuff. That’s why we always ask famous and successful people “what was the one thing that led to your success?”. We didn’t ask “what were the 100 things that you did to earn more money?”

Rather, the reason it worked for the hero in our story is that he kept reiterating his ideas. He could have given up after his first idea didn’t pan out. He probably even felt like giving up and maybe he even took some time to think about what to do next before trying something else.

Another important aspect was that he created stability in life. He planned out his week and even though he fell off the wagon here and there (we all do, we are only human), he kept working to get used to his schedule. 

He would work weekends and spend time after his day job. At first, motivation was up and down like a rollercoaster but soon enough things became a habit and it became easier to stick to.

We can see it in his earnings. It was slow going at first and then step by step he increased his earnings as he got comfortable with the process until he earned the same on the side as from his full-time job. 

And I bet that if you ask him, he will tell you that on top of that, it felt too good to be true and he wondered why clients would pay good money to work with him. Many of us feel like that and it doesn’t matter how much money we are used to earning.

Another thing that I’ve noticed is when we work to earn more, it’s funny how the people closest to often don’t understand what we are doing and say things like “can’t you just get a stable job? I’m worried about you”. 

What’s really happening, is that they feel bad because if you succeed they have to confront themselves and why they didn’t do it as well. And for some, it’s just easier to tear you down instead even if they don’t mean to.

I’m sure that if you ask him, he’ll tell you that he began hanging out with friends that wanted something more instead of those that would question if he should try.

For many of us, outside factors like being able to have a stable week and that we are in control of the way we feel are a bigger deal than we would like to admit. 


  • Tactics are easy and will help but they can’t rescue you in the long run. Stability, control over the way we feel and continuing to reiterate on our ideas will take us much further than we can imagine
  • If you want tactics, follow this guide to earn your first $1,000 freelancing on Upwork


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