How to make money on Upwork with the Hollywood Superhero-technique

How to make money on Upwork with the Hollywood Superhero-technique

In this article, you and I will look at how to make money on Upwork, so you can earn your first $1,000 even if your profile is new and you feel as if you have no experience.

I still remember my first few clients and how nerve-wracking it was on those phone calls feeling like I had no clue what I was doing.

I later learned that clients typically care less about what our situation and background are as long as we can help them solve their problems.

I earned my first about $10K as part of an experiment some years ago and through experimentation I developed a technique to land clients even if you feel like you have little experience.

The reality is that even though I felt like I had no experience, I still had more than the clients I helped.

Let’s dive in!

Two key elements to land clients on Upwork

There are two key elements that matter when we want to land clients:

  • What problem can we help solve?
  • Are we the right person to solve that problem for the client?

Let’s begin with the first one: what business problem can we solve? 

The tricky part is that clients don’t pay the same for every business challenge. Imagine what they might pay to get their shirt ironed compared to increasing sales.

Since the latter of the two creates more money for the business, they will probably pay more for help with that.

Most of us are able to solve a bunch of different challenges for clients without years of expertise. That might be things like:

  • Researching leads for a client
  • Organizing data
  • Posting to social media or uploading content onto websites

Since these types of tasks don’t require specialized expertise we won’t earn as much as if we have years of specialized expertise but they are a terrific place to begin.

And because they don’t require specialized expertise, that means clients often hire for something else than experience…

That leads us to the second important element of landing clients: if we are the right person to help with their project.

Trust is the currency between freelancer and client. Many clients value trust and reliability almost equally with expertise for less specialized projects, in my experience.

Building a personal connection with the client, so they feel we are the right person to help, is key.

Depending on the project, you can also use other elements of psychology to land the project. Besides trust, that could be: being easy to work with, having good communication, reliability, drive, and attitude.

Trust is the foundation that will make or break our chances, so let’s look at that first. Common examples to display trust are:

  • Testimonials
  • Case studies/portfolio
  • Showing better understanding their problem than other freelancers
  • Go-getter attitude (clients sometimes hire for attitude over skills thinking skills are easier to learn)

Since you might not have all of these weapons available to you, let’s look at how you can leverage some of them to your advantage.

How to earn your first $1,000 on Upwork with the Hollywood Superhero-technique

In a normal situation, we often pitch clients with our experience from similar projects. If you don’t have that luxury, you might opt to show how you’d go about helping them with their project and win based on attitude instead.

One approach to show that is to outwork the competition and do more than the minimum required right from the beginning when you submit your proposal. Your future clients will be pleasantly surprised that you did.

You might do that by giving them examples or a step by step process of how you’ll handle their project.

If it’s a project where you have to gather leads, begin by finding a few leads as an example and add them when submitting the proposal with a nicely formatted spreadsheet. 

It’s an easy way to stand out. By showing that you did something extra upfront, they will be impressed by your attitude because no one else bothers to do it.

I’ve found that it’s great to share a bit about what you did during the process. Not only will it help them get to know you better but you’ll also be able to get feedback that you can use in the proposals you’ll send in the future. 

The tricky part is that if you aren’t careful about how you phrase your explanation, it can come across as douchebag-y rather than helpful.

Here’s a simple framework to begin with: before you submit your proposal, imagine you were in their shoes and needed help with the same project. 

What might they not be saying? What might they not know?

Is someone else on the team bothering them because they haven’t gotten that project done yet? Is it difficult to pick the right freelancer because everyone seems the same?

Are they concerned that a freelancer might collect shitty leads for them so they have to start the process all over with someone else?

You might not get it right all the time but when you hear back from potential clients, you’ll know you did something right. You might even ask them what they liked about your proposal. Over time, you’ll get better and better and thus get more responses.

When you’ve prepared your proposal and your “extras”, you might add comments like: 

“I’ve attached a few examples of leads to make sure I did it in the way that you prefer. You mentioned that you only needed the name and emails but I took the liberty of adding the social media links and number of followers so you can get an idea of their size. Would you be able to take a look and share your feedback?”

What’s going on here?

By sharing your thoughts behind the work, you show that you’ve worked to imagine what the client needed the most even if it might be incorrect.

Consider any popular Hollywood Superhero movie like Superman, Batman, or Wonder Woman. The hero always fails a few times before winning in the end. We don’t like the hero because they are a hero, we like them for trying because we can relate to the struggle.

This is your version of trying and if you get it right the first time, that’s just bonus points to you. I call this the Hollywood Superhero-technique.

You also show that you are comfortable with feedback, which makes them more open to a long-term relationship. It is common for any client and freelancer to have to work out the best way to collaborate in the beginning and most freelancers don’t dare to ask for feedback.

This is really about going above and beyond to impress them. It sends the client a signal that even if we are not the most experienced freelancer on the website, we work hard to do a good job.

That means thinking long-term, to get more projects from them in the future because they like working with you, and it means putting the client before yourself.

It takes a lot less work to get more projects from existing clients than having to find new clients all the time, so it is worth it. Think about what you can do, that no one else is doing to impress them like crazy.

At one point, I worked with a client on an email sales funnel. To make sure they were impressed, I also wrote a sales page to go with the emails and set up the entire thing for them in their system free of charge. I didn’t tell them that upfront but I did it as a nice surprise to them.

If you collect leads, you might give them 25% extra leads or give them extra information they might need about those leads.

If you design logos, you might give them five variations instead of two.

If you have to organize data, organize it in different ways, show them, and ask them to pick the approach they prefer the most.

I’m sure you get the gist.

Another point that I can’t emphasize enough is to focus on being reliable. Most freelancers are flaky as hell and it’s an instant turn-off for clients because you can’t trust that things get done (again, trust is key). 

This is perhaps the number one point and if you do nothing else, focus on being reliable, and do whatever you said you were going to do. You’ll be so far ahead of other freelancers, you won’t believe it.

Read this article if you are looking for a freelance idea.

How to make money on Upwork if your profile is new: go after urgent projects

With freelance clients, you’ll often run into two types: one needs help with certain expertise to solve a problem and doesn’t know how to do it.

How to make money on Upwork

Another knows how to solve the problem and might even be good at it but doesn’t have the time to it. This type of client often has the process mapped out and needs someone to follow it step by step.

If you have a fresh new Upwork profile without projects and case studies, it’s easier to earn money by working with the second type of client.

In exchange for the lack of expertise, you can offer reliability and be easy to work with while learning how to do that type of work from someone good at it. After a while, you can offer it to the first type of client as an expert.

You could also focus specifically on projects that are urgent because the clients might be willing to take a chance on you because of the urgency.

Either way, you’ll have to give them a deal they can’t refuse. You’ll benefit from getting on calls with them to understand how they think about their business and understand their problems better. 

That way, next time you send a proposal you’ll have a better idea of which of the following examples you can use to land the next client.

Some of the ways you can offer them a great deal are:

  • To solve their problem quickly (especially good for urgent projects)
  • Offer a discounted rate
  • Give extras

I’m not a fan of discounting work because you’ll train clients to get used to getting discounts. But in the beginning, you’ll learn more from getting clients with discounts than none at all.

Should you do free work?

A popular question is if you should do free work.

Everyone has their own take on it. Some say it’s OK to do for your dream clients and others say you should never do it. My point of view is to do it for clients that are already paying you.

Don’t tell them about it, just do it for them as a nice surprise. You can always tell them that you wanted to see how XYZ would look, so you tried a few different approaches and wanted to hear what they think.

When you give free work “to get experience” without any payment before, the client isn’t invested and might drop the project at any given moment (e.g. by ghosting you from one day to the next).

That happens often and means neither of you will get anything from a half-completed project.

On the other hand, if they are already paying you, you are doing marketing for your freelance business, and betting that you’ll land more work from those clients instead of having to find new clients (a good bet in my experience).


  • To land freelance projects, there are two key elements: a problem that the client needs help solving and someone they can trust to help them solve it
  • By focusing on attitude and going above and beyond instead of experience and skill, we can win over other, more experienced, freelancers


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