8 surprising Upwork proposal mistakes I see every day (and how to avoid them)

In 2001, a skinny kid named Takeru Kobayashi devoured fifty hot dogs in 12 minutes — double the previous world record.

The guy weighed a whopping 131 pounds. Yet he took down competitors 3x his size, and changed the sport forever.

How did he do it?

He didn’t just stuff hot dogs into his mouth faster than everyone else. Not even close. His massive success came from thinking strategically, and going beyond the obvious.

• He removed the hot dogs from their buns
• He broke each dog in half, so he could fit the whole thing into his mouth at once
• And he dunked the buns into a cup of water to make them easy to chew and swallow

This is a classic case of working smarter, instead of harder.

You can find top performers behaving this way in every competitive arena. Even freelancing.

For example, the most successful freelancers I know don’t spend a lot of time writing cover letters and answering screening questions. In fact, they usually spend less time putting Upwork proposals together than their less successful competitors!

But when you compare the QUALITY of their proposals, the difference is like night and day. You can see the average group is just focused on sending out as many proposals as possible, as quickly as possible.

The result? Mistakes.

Mistakes that prevent them from having more income, more enjoyable work, and more freedom.

Mistakes that make them work hard without any real payoff.

And most importantly, mistakes that you can easily avoid.

Mistake #1: Thinking you can’t charge higher than the client’s budget

When a client posts a job on Upwork, they have to choose a budget.

Most clients don’t know what that budget should be. So they err on the side of caution, because they’re afraid of overpaying.

Like this job, where the client ended up happily paying double their posted budget:

Or this one, where they paid TRIPLE:

It happens every day.

Say you were able to take advantage of even one opportunity like this each week. You’d make at least $10,000 more per year than someone who automatically bids according to the client’s budget.

Mistake #2: Focusing on years of experience

Many of your competitors will start their Upwork cover letters by talking about their previous experience. But that’s not what clients are interested in. If it were, I never would have been able to make six-figures in my second year as a freelancer.

Think about how you make spending decisions. When you look up a movie on Rotten Tomatoes, you’re not looking for the director’s work history. You just want to know if the movie is good!

The problem with filling up a cover letter with “years of experience” is that it tells clients nothing about the quality of your work, which is all they really care about.

Check out this excerpt from the book Talent Is Overrated by Geoff Colvin:

We all know people like this. They’ve been doing something for years — even decades — yet they’re still not any better at it than a rank beginner.

Keep this in mind if you’re new to Upwork. Don’t let the crusty Old Pros intimidate you. Clients love to hire freelancers who are enthusiastic, dedicated, and intelligent — even if you don’t have years of experience.

Mistake #3: Being a sleazy salesperson

There’s this old trick where a sales manager hands a pen to a job candidate, and says “sell this to me.”

It’s fascinating. Almost everyone reacts by listing out reasons why the manager should buy the pen. A minute later they’re being shown the door, having no idea what went wrong — even though a child could tell you the answer. No one likes to have a product pushed on them!

When you’re hungry to make money on Upwork, it’s natural to want to tell clients why they should hire you. But, like “selling the pen,” it doesn’t work.

I want to share something special with you. It’s a 2-minute segment of an audio interview I did with Chris Davis, a premium Upwork client.

Listen to Chris explain the real reasons why he hired me for $135/hr (hint: it’s not what most people think):

Pay close attention to the types of words Chris uses:

• “Trust”
• “Being a human being”
• “Getting to know you”
• “You weren’t trying to sell me”
• “You respected me”
• “You talked to me like a person”
• “People crave connection”

It wouldn’t even occur to most freelancers to think in these terms. If you want to write proposals that win over clients like Chris, you need to focus on the CLIENT’S goals, not just yours.

Mistake #4: Writing your proposal upside down

34% of Upwork proposals require you to answer one or more “Additional Questions” after you write your Cover Letter. (Yes, I’m a weirdo who tracks stuff like this.) Imagine looking over the shoulder of a freelancer while he writes the proposal above. How do you think he’ll tackle it?

Since the Cover Letter comes first, he’ll put the majority of his effort into making it stand out. Then he’ll treat the Additional Questions as an afterthought.

What if I told you that was a totally backwards approach? To understand why, you need to look at it from the client’s perspective. Check out what they see when they review your proposal:

As you can see in the above screenshot, “Additional Questions” are the first thing clients see when they receive your proposal. That makes them even more important than your Cover Letter. Treating them as an afterthought is Upwork proposal suicide.

Most of your competitors don’t realize any of this. They’ve never seen it from the client’s point of view. That’s how embarrassing situations like this come up:

Oops.

Mistake #5: Using a canned cover letter in your proposal

Every week I get an email from someone who can’t seem to land a job on Upwork.

It’s always the same story: They’re trying to “save time” by sending out the same cover letter in each proposal over and over again. Every time it happens I throw my laptop off the balcony. Do you know how hard it was to write this post with a dented keyboard?

Good clients can spot canned proposals a mile away. Even if you’re the best freelancer on earth, a canned proposal says:

• You’re not that interested in the job
• You’re not a good communicator
• You probably won’t give your best work

The reverse is also true. In one of my earliest jobs, I was the least experienced, most expensive bidder. But the client hired me because she was tired of rolling her eyes through one-size-fits-all proposals. She even went out of her way to mention it in the feedback she left me:

Mistake #6: Not looking the part

There’s more to your proposal than what your write.

I’ll prove it to you.

A few weeks ago, I uploaded 2 pictures of myself to Photofeeler.com, and had impartial strangers vote on how competent I look.

One of them is the profile picture I’ve used to earn hundreds of thousands of dollars on Upwork. The other one is a similar-looking outtake.

First, look at the results from the outtake:

If I’d used this as my Upwork profile photo, my results probably wouldn’t have been very good.

But watch what happens when we shift just a few elements of the picture:

These small changes had a huge impact on my income. It’s worth taking the extra time and effort to make sure clients perceive you as someone who can get the job done.

Btw, here are some of the comments from the group of people who voted me (mostly) incompetent in the first test:

Mistake #7: Bidding too cheap

As an Upwork client myself, I get tons of freelancers offering me “bargain deals” in their proposals.

What’s amazing is that my client profile clearly shows I’m happy to pay an average of $27+ per hour…

Yet the range of bids I get when I post a job still looks like this:

Think about that for a second. I’m offering someone $27+ per hour…and they’re negotiating me DOWN to $11!

This signals all sorts of problems to a good client.

They know that cheap work is one of the most expensive things they can buy. Freelancers who charge too little aren’t motivated to do good work. They cut corners. They’re always rushing to move on to the next job. Then the client is forced to sink more time and money into cleaning up the disaster.

Amateur freelancers think all clients are attracted to low prices. Professionals know that high quality clients want high quality work, and they’re willing to pay you well to do it.

Mistake #8: Coming across like a weirdo

You can follow all of my best instructions for writing great Upwork proposals — yet still come off as a total weirdo if you aren’t careful. Watch the video below to find out how to play it cool so clients are virtually guaranteed to love your proposal.

Take a look at these real winning proposal examples

No matter how many mistakes I show you, there’s nothing quite like seeing what real winning Upwork proposals actually look like.

That’s why I want to show you some, free of charge — my gift to you. These 3 proposals have won over $3,000 on Upwork and are full of surprising insights you can apply to your own proposals today. You can grab them here.

I’ve shared these proposal examples with thousands of my readers, and the responses have been incredible. Like this:

“LOVE THIS! Thanks for creating this resource Danny! It was so eye opening! I’ve read so many articles on writing great Upwork proposals and most of them advise boring, cookie cutter proposals like some boring cover letter you would staple to the front of your CV for doing the job searching rounds around the town.

But this approach is so casual and personal that it really captures the reader. I mean I don’t know why I should be surprised this is the winning formula because it’s the exact tone I’m trying to tell people all the time to use in their marketing copy! I really need to follow my own advice!

It’s so funny to think even though we may tell our clients one thing, when it comes to marketing ourselves as freelancers we default to a boring, corporate clone…the very thing so many of us became freelancers to escape from!”

Get the real winning proposal examples (for free) here.

What are you going to do?

Do you want to write Upwork proposals that stand out and get you hired? I want you to share one thing you’ll do differently from “everyone else” in the comments below.

It’s okay to pick one of the proposal tips off the list I just gave you. But let’s have a conversation about it. Why do you think others don’t do it?

Maybe you’re gearing up to write your first proposal. Or maybe you’ve already written 100 or more. Doesn’t matter. Share one way you’ll stand out going forward in the comments.

This isn’t just for freelancers, either. If you’ve been a client, flip it. Which mistake is a deal breaker for you? What Upwork proposal tips do you have for freelancers?

I’m excited to hear from you.