9 Common Mistakes Freelancers Make on Upwork When Trying to Win Projects

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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.

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

I’m a coach for my 8 year old’s soccer team. It’s a lot of fun, but it’s also excruciating at the same time.

Me and my daughter at a soccer game to illustrate the mistakes freelancers make on Upwork

During their games I’m forced to stand on the sideline while I watch them make really simple mistakes that are super easy to fix and would end up making a HUGE difference in the number of goals they score.

It takes everything in me not to rush the field and just play for them. But, that would be wrong and I’d get kicked out of the league.

I also see freelancers make really simple mistakes on Upwork that end up costing them projects. But, thankfully, those common mistakes are SUPER EASY to fix and can make a huge difference in actually landing projects.

It doesn’t take some magical touch to win really great projects on Upwork. It doesn’t even take being the best freelancer in your category.

It just takes a degree of intentionality AND taking a step back and asking yourself “Why?”

  • Why am I not winning projects on Upwork like I want to?
  • Why was another freelancer chosen over me?
  • Why are my bids not getting responded to by clients?

If you don’t stop to ask yourself that question you are bound to make the same mistakes on Upwork over and over again until one day you decide to give up all together, and say something ridiculous like “Upwork is just a race to the bottom, anyways.”

I’ve Personally Made a Lot of Mistakes on Upwork

I’m not immune to making mistakes on Upwork. I’ve made a lot of them. We’re talking A LOT. Probably more than your average Upwork freelancer.

I’ve gained and lost the coveted Top-Rated Status multiple times now.

It would have been easy to give up. But, instead, I’ve taken those moments as an opportunity to learn and grow. I asked myself hard questions and slowly but surely grew over time.

So, here are the 10 most common mistakes on Upwork I’ve made as a freelancer AND mistakes I see a lot of other freelancers make when trying to win projects.

1. They Don’t Filter Their Job Feed Enough

The amount of projects on Upwork hovers right around 35,000 at any given time

Screenshot of number of jobs on Upwork for freelancers to show you the mistakes on Upwork freelancers make by not filtering their job feed enough.

If you filter those down to a specific type of freelancer like “Web and Mobile Design” it gets in the thousands or right around 2,000.

BUT, if you want to really win projects on Upwork you’re going to have to get those numbers down more, A LOT MORE.

At most, your search results should be in the hundreds. Even that is a lot. Imagine applying to 100 jobs on Upwork. That alone would take up all your working hours.

So, do everything you can to filter out as many jobs as possible.

To do that you’ve got to start by making a guess about which clients are MOST LIKELY TO HIRE YOU.

You are perfect for a specific type of client out there. Those clients are what I call your match made in heaven clients.

Your job is to figure out who those clients are.

  • What’s their budget?
  • What kind of skills are they looking for?
  • What are their underlying motivations?
  • What kinds of keywords would they use in their project descriptions?

The answers to those questions will help you filter out all of the projects you don’t have any business wasting your time on.

Thankfully, Upwork has some really helpful search and filter tools for you to play around with until you get the “Jobs Found” results down to a number that is actually helpful for you as a freelancer.

2. They Bid on Jobs That Don’t Match Their Skills

So, you’ve filtered your jobs down to less than one hundred. But, you start to notice something. New projects don’t show up quite as often as they once did.

Listen, this is normal! The more restrictions you put on what you see in your job feed, the less frequent new opportunities show up. It’s pretty simple.

The mistake would be to get nervous, lose your patience and start bidding on projects that you aren’t a good fit for just because their there.

That will waiste your time AND the client’s time. And, ultimately, it can leave you feeling discouraged about the actual possibility of winning good projects on Upwork.

It’s much easier to land a project when you’re full of hope about the possibility of actually winning. This isn’t some mind over matter talk. It’s just reality.

You’ll sound more confident. You’ll think more clearly and ultimately you’ll have a better chance of actually winning a project.

So, consider the jobs you bid on carefully.

Is the client actually looking for a freelancer like you?

Are they asking for skills that you know you’re capable of performing?

If yes then feel free to bid. But, if not don’t make this common mistake on Upwork. The right projects will show up!

You just have to be patient.

3. They Bid on Stale Projects

Some projects might be perfect for you BUT they might be stale.

What’s a stale project? I’m glad you asked.

A stale project is one where the client has either lost interest in the project altogether OR it looks like they’ve already found a freelancer they want to hire.

You can determine a projects freshness in 4 areas:

  1. When the project was originally posted
  2. How many proposals it has
  3. When the client last viewed the project and/or looked at freelancers bids
  4. How many people they’re interviewing

All of that can be found on the project description itself.

When the project was originally posted is right up near the top near the project title. AND, everything else can be found a little further down under the “Activity on this job” heading.

a screenshot of an upwork project showing you how to determine if a project is stale

A stale project is one that was posted a while ago hasn’t been looked at by the client recently and has A LOT OF other freelancer proposals.

I tend to stay away from anything that wasn’t posted within a few days of when I’m looking and was last viewed by the client within a few hours.

When it comes to proposals I only like to bid on projects that have max 10 other bids. AND, if they’re interviewing someone else already I don’t even waste my time.

So, do yourself a favor and only bid on the freshest of fresh projects on Upwork. You’ll have way more of a chance at actually winning.

4. They Make it All About Themselves

It’s really easy to think that in order to win a project you need to figure out a way to make yourself look really good to a client.

It’s like how birds try to make themselves look big and beautiful for potential mates. And, just like those birds: it’s silly.

You’ve got to make it all about the client if you want to win projects on Upwork. Don’t overemphasize how many years experience you have OR try and list every single skill you bring to the table.

Instead, take what the client has mentioned in their project description and talk about how you’re committed to their success. Then very gently mention how the skills and experience you have would be a perfect fit for making the project a success.

But, even when you do that, always bring it back to the client. Make it much more about THEM and much less about YOU.

5. They Don’t Mention Their Limitations

Have you ever heard the adage, “If it’s too good to be true, it probably is.”

Of course you have. We all have. In fact, we’ve not only heard it WE SENSE IT on a gut level.

When someone’s trying to sell you something the one question that floats around in your brain throughout the entire pitch is, “What’s the catch?”

Client’s have the same question when they’re looking at your bid on Upwork.

Their thinking, “You’ve done everything you can to make yourself sound perfect. SO, what are you not telling me.”

If you’re not honest about your limitations then clients are going to think something is up OR that you’re trying to keep something from them.

So, put all the cards on the table and tell them what your limitations are. Most of the time, when you do that clients will start coming up with solutions FOR YOU.

BUT, if you hide them a client will likely come up with something that’s worse than the actual truth!

Now, when you do this you want to continue to sound confident. Don’t apologize for your limitations. Everyone has them! Just communicate that you are confident that you’ll be able to deliver exactly what they need despite your limitations.

One CEO I heard of has a slide in his pitch deck called “Why You Shouldn’t Invest In Us,” that he shows when his talking to investors. You’d think that would be the end of it BUT he’s raised $145 million all because he was honest about his companies limitations.

You be honest, too.

6. They Don’t Go All in On the Right Projects

You’ve got to go for it when you find the right project. You do that by bidding more connects on the projects you pitch to.

Connects are Upworks currency for freelancers. You get a certain amount each month AND each bid you make costs a certain amount of connects.

Once you run out of connects you’ve got to buy more if you want to bid on more projects.

Upwork recently changed the way they handle connects on projects. Now, if you want your pitch to show up at the top results for a client you tell them the highest number of connects you’re willing to put toward that project. AND, the freelancers who were willing to part with the most connects will show up at the top.

It’s kind of like a silent auction only you have no clue how many connects the other freelancers are bidding.

This is actually good news for serious freelancers.

That means when you see a project that you really like and feel is a good fit for you as a freelancer GO ALL IN. Bid a lot of your connects.

That way you’re assured the client will actually see your proposal.

You have to be willing to take risks if you wan to find success on Upwork. So, don’t be afraid to bid a high number of connects.

You get new connects every month AND you can always buy more if you really need to. But, hopefully, you’re being really selective about the projects you’re bidding on and never come close to using up all of your connects.

If not, go back to point 1 and 2.

7. They Don’t Ask Their Clients Simple Questions

Don’t keep the “Why” question just to yourself. It’s a good question to ask your clients as well.

When you win a project ask your client, “Why did you chose me over other freelancers?”

Or, if you get an interview with a client and they chose another freelancer ask them why they went with someone else.

the "y tho" meme to illustrate common mistakes on Upwork that freelancers make because they don't ask their clients why

Getting feedback about what made you stand out OR DIDN’T stand out can be really helpful data that will help you not make mistakes on Upwork in the future.

It gives you invaluable insite about what clients are looking for AND what your secret sauce might be as a freelancer.

Now, the next time you bid on a project you can really emphasize the things the client said were the reasons they hired you OR even go on to correct some of the reasons a client might have chosen NOT to hire you.

But, don’t feel like you need to keep everything a guessing game. Have an open conversation with your clients and learn how to improve.

Some mistakes on Upwork are unavoidable BUT this is one of the simplest things you can do to make sure you’re successful on the platform.

8. They Don’t Follow Up After an Interview

Sometimes a client will be slow to follow up with you after an interview. You can’t take that as they’ve gone with someone else or don’t want to hire you. You have to follow up.

Give it a few trys OR wait until it’s a definite no.

A lot of times clients will get busy or they’ll forget about their job posting. You sending them polite messages every once in a while reminding them that you’re still here will sometimes be the nudge they need to actually hire you.

The key is you can’t sound annoyed AND you can’t pester them.

Wait a few days between a follow up AND try to approach it differently every time. If you always say, “I’m just following up,” that gets annoying. So, spice it up a little bit.

But, don’t take silence as an answer. Follow up!

9. They Quit to Soon

On average, it takes about a month from when a freelancer signs up for Upwork to win they win their first project. And, that’s for folks who are consistently bidding.

But, a lot of freelancers give up after the first few bids.

If you want to be successful on Upwork you’ve got to stick with it.

And, listen, I know it gets discouraging. It’s no fun to get rejected. It’s no fun to get passed up. But, I guarantee if you stick with it the opportunities that you find on Upwork will be well worth it.

Upwork was a game changer for me. It’s what I used to double my income as a freelancer and what helped me to go on to change careers completely.

But, if I would have given up when I felt like giving up that would have never been true.

Your next big client might be right around the corner but you’ll never know if you quit to soon.

Don’t Make These Mistakes on Upwork

Don’t make the same mistakes on Upwork many freelancers do. The good news is all of these can be easily avoided with a little bit of effort and some reflection.

Now you’ve got the tools in your hand to be successful. All that’s left is you going out there and doing the work.

So, what are you waiting for?

Go bid on some projects 😉

a broken ice cream on the ground


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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