Why Am I Not Getting Jobs on Upwork: 5 Mistakes Most Freelancers Make


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A couple of years ago, I found myself in need of a little extra help around the ‘virtual office’ and decided to begin searching for a new “intermediate-level” freelance graphic designer.

Read Also: Can you make good money on Upwork? How I made $600,000 in 5 years

I had a lot of expectations about what the hiring process might be like.

We expected applicants to be competitive.

We expected to be inundated with quality portfolios.

What we didn’t expect was that our search for a new designer would turn into a case study on what not to do when applying for a job.

In fact, over the course of about 24 hours, and 203 applications, only a single candidate stood out above the crowd.

Think about that – 1 out of 203.

So what did he do so differently? Read on young padawan, read on. 

In this article, I’ve summarized five of the biggest real-life mistakes that applicants made when applying for our job posting that you might be making right now and not even know it.

And while the following article is geared toward designers and graphic artists, I believe many of these mistakes are common throughout a variety of industries, and that valuable insight can be derived for all.

Without further ado, here are a few reasons why I believe freelancers aren’t getting hired on Upwork.

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5. Their portfolio samples were awful

Admittedly this is a subjective one – and I realize I asked for an “intermediate” designer.

And to be clear, we are not talking about “underwhelming” portfolio examples in this statistic.

I’m talking about truly inexcusably amateur portfolios with neon color schemes, squished photos, bad cutouts, difficult-to-decipher typography and more.

Designers who expect to work in exchange for payment in a professional setting are expected to understand basic design concepts like contrast, balance and legibility.

Clients are usually looking for professionals on platforms like Upwork, not interns.

This leads us to the next biggest mistake …

4. They had no experience

This one baffled me. A surprising 15 out of 203 candidates had no experience in graphic design.

None. Nunca. Zip.

Again, you need to know the basics – even if you’re applying for an entry-level position in graphic design,

When I was a young newbie designer, I spent my free time going through tutorials online, making Geocities websites (it was the late 1990s, no judging) and working on my high school’s yearbook staff – all easy ways to gain valuable experience.

And with so many free tutorials and courses available online nowadays there’s really no excuse not to familiarize yourself. (Pro tip: For newbie designers, the big 3 programs you really need to focus on are Photoshop, InDesign and Illustrator.)

3. Their cover letter was riddled with typos

Talk about a quick way to find yourself in the discard pile. 

This one is easy and yet many people fail to take the extra steps necessary to carefully review and proof their cover letters before applying for the job.

Multiple typos indicate to the client that you either aren’t paying attention or worse, are an error-prone individual.

Who wants to trust their project to someone who can’t even be bothered to make a great first impression with a professionally written cover letter?

Read Also: How to write an Upwork proposal: 11 proven tips with samples

If you don’t feel comfortable proofing your own cover letter – say for instance English isn’t your first language – ask a friend, peer, or colleague to do so for you.

2. They did not provide a portfolio

A shocking 55 out of 203 candidates provided no sample work or a portfolio of any kind. 

I realize if you’re new to graphic design, building that first portfolio can be a daunting task, but it is absolutely necessary. 

Keep in mind, your portfolio doesn’t have to feature real client work. Your portfolio simply needs to demonstrate your ability to do the work.

If you currently have no clients, challenge yourself to create mock-ups for the made-up brand XYZ or offer a bit of free work to your family and friends if needed. (Fake it til ya make it baby!)

With that said, notice I said to only use made-up brands – don’t slap Coca-Cola’s logo on a flyer and pretend like you were commissioned for some important campaign if you weren’t.

Always be truthful and transparent when asked.

1. They provided no indication they actually read the job post

And finally, the biggest mistake that over 80% of candidates made – they failed to actually reference something specific to our job post in their cover letters.

In fact, most proposals were so generic that it left us wondering if they even read the post at all.

And yes, I get that applying for jobs can be a time-consuming task – heck, I use a template all the time when I’m applying for work.

But I also customize that template and tweak it for every client.

Applicants should always strive to include a personal note in their cover letters or at least express an interest in the type of work mentioned in the listing.

Make the hiring company or client feel special, and prove you actually took the time to read the listing all the way through. 

The freelancer we hired

As Upwork freelancers, we often worry too much about our “competition”. We assume that the client will simply pick the cheapest freelancer and that Upwork is just a “race to the bottom”.

But that belief couldn’t be further from the truth.

Clients want to hire the right professional for the job.

It’s important that we freelancers learn to quit worrying so much about our competition, and instead learn to improve ourselves.

Standing out in a crowd isn’t as hard as you might think.

In the end, there was only one freelancer who expressed genuine interest in the work described, had the right experience, had a solid portfolio and provided a professionally constructed cover letter.

Even better, after our interview, he included a thoughtful follow-up thank you note.

And of course, that’s who we ultimately hired.

I hope you found at least one of these insights helpful. What are some of the biggest mistakes you’ve made when it comes to applying for jobs? Share your stories in the comments and don’t forget to connect with me on social using the links below.

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