How To Earn Money On Upwork: Long or Short Proposals?

by Michael de la Guerra in , ,

This collection of Upwork proposal examples for content writers or copywriters is from the beginning of my career. These are the jobs that helped me start to generate $1-2K a month from freelance writing gigs on the side while working full-time. I never published this blog post, but it's packed with very valuable tips and some of my best early Upwork proposals you can use as templates.

Freelancing online via sites like UpWork can be a dream—if you do it well.

While there is no “right” way to do things, there are best practices that you can take from the world of business from before UpWork and were even around.

Today we’re going to talk about the length of your client pitch/proposal. 

The UpWork pitch is a different beast than say, the cold email pitch.

The client has already expressed interest in finding someone to solve their problem, and is expecting a flurry of responses (depending on the job).

This is where some people get confused about whether the post should be long, or short and to the point.

And the answer is that neither one is better, because what matters is quality, not length.

How To Get Your Prospective Client To Read Your Every Word

The more you have to offer, and the more you understand the prospect’s problems, the more they’ll read.


See, if people are looking for a freelancer to help them with something, the more you prove you understand what they’re going through, and connect yourself to their thoughts, the more they’ll warm up to you.

Think about it: if you were looking for someone to do a job for you, yeah sure, you might be ok with the generic person who has proven reliability in lots of those types of jobs.

But someone who understands your perspective and experience as a human being, you’d be much more inclined to listen to them, even if they have less experience.

For example, let’s say you’re a dentist who needs a website created so you can show higher on Google and generate new leads for your business. 

You post a job on UpWork stating what you’re looking for and you get dozens of responses.

Most are spammy, repetitive pitches that are clearly sent out en masse, others are from credible freelancers who have a nice body of work, but then you get one from someone that stands out…

They mention that they’ve done work for their own dentist before, going into a story about how their dentist couldn’t find a reliable web designer.

He was so frustrated at how hard it was to find someone to commit, and communicate properly with.

Not only that, he was worried about what best way portray his credibility online, and what his buddies at the local dental club were going to think (some of them already had beautifully designed websites, and rather than asking for a referral he wanted to find a designer on his own).

Now this story is engaging, speaks to some of the core fears the dentist actually might have, and connects to you—the job poster—on an emotional level.

You’re now more likely to check out this freelancer’s body of work. 

Not only that, your brain already carries with it the warm sense of appreciation that comes from dealing with someone who truly understands what you’re going through.  

So don’t get worried about your pitch being too lengthy—if it’s relevant to their decision making process, the job poster won’t skip over it.

But there are a lot of caveats here, and how do you know what information is relevant to the prospect?

A good rule of thumb that I follow is gathering as much intel from their UpWork posting as possible, and then repeating it back to them (to show you understand and heard their every word).

By doing that, you then take their expressed needs and frame what you have to offer around them.

Upwork Proposal Example #1

Here’s an example of a client I recently pitched. Take a look at the similarities in the language I used in my message:

My response:

Notice that I mimicked the exact same term they used for what they were looking for and what the job they wanted done was in the first sentence.

Then, I used the third paragraph space to let them know that I looked at their attachment (meaning I’m paying attention), and echoed another statement from their job posting about creating a ”lead magnet for high value clients.”

Only after I let them know that I understood what they were trying to accomplish and making sure that they felt heard, did I go into qualifying myself.

Upwork Proposal Example #2

Another example:

My response:

The first difference you’ll notice is the greeting.

With the client being in Australia, I thought it would be an easy way to build rapport by using their common greeting rather than one we use here in the US.

Again, after repeating the problem in a way which shows you understand, then you qualify yourself.

This time I elaborated a bit more, and provided a ton of value upfront.

When you clearly show that you understand the pain that the prospect is going through like this, you give yourself an incredible boost in value, just look at their response:

The saying that you only have a few seconds to grab your prospect’s attention is so true, so don’t waste any time with extraneous details about yourself. 

Focus on them.

Then, after they know you understand their problem, know how to solve it, and actually want to help them, then you can go on and talk about relevant accomplishments.

These, too, must be framed in a certain way so you can show that your expertise lends itself well to the prospect’s problem. 

One of the Best Upwork Proposal Tricks: Talk About Yourself Like A Pro

One really important tip that I learned from Danny Margulies over at was to not just do a simple copy and paste of the link containing my work, but to get the reader excited about it.

This is a trick that’s used in sales copy a lot, and this is a good time to remind you that your proposal is—in effect—your sales letter.

You want to use all the firepower you can get.

The idea behind this tactic is that you want to load up the positive imagery and value leading up to link, CTA, or whatever it is you’re hoping to showcase.

In effect, in a sales letter you want to show so much value that when you get to the price, they’ve already made the decision in their minds that it’s worth it. 

Don’t limit this to any one section of your proposal, remember to build anticipation and get them excited about each part, in any way you can. 

In the examples above you can see that the whole point of my introduction is to get them excited (by showing that I understand them and am capable of helping alleviate their problem) enough to read on and take a look at my work. 

Some people have different ways of presenting examples while getting the prospect interested.

If you have a testimonial, this gives you a huge advantage. But don’t worry, even if you don’t have a testimonial, you can still get them excited without it.

In fact I use a mix of both cosigned and non-cosigned examples when pitching my experience, take a look:

Upwork Proposal Example #3

In this example the client was looking for “creative content.”

This piece of work that I’m talking about in this particular proposal was a piece that I use to showcase my work in other instances, however, for this client’s post, I tweaked the language a bit to again let them know that I read and understood their needs, by repeating what they said. 

I followed up with a quote from the client, and made sure to point out that it was easily viewable from my profile, to give even more of a boost in social proof.

Another example:

Upwork Proposal Example #4

In this example I qualified the piece much more before I presented it.

The job post called for the copywriter to be able to understand different markets, some of which they weren’t familiar with.

In the copy, I played up that the topic was seemingly unknown to me, but I was able to grasp it.

Immediately after qualifying, I went into the testimonial, and then I provided the link to the work.

This is a a great way to play up an already solid piece of work, and get the job poster excited to read.

Another example:

Upwork Proposal Example #5

This is a short and to the point example.

I wanted to get the poster onto the website right away, but needed to do a tiny bit of qualifying.

In this case I had already presented several pieces of work, so the copy wasn’t very long.

No testimonial, but this is a solid piece of work that I wanted to get them to view ASAP.

Is That All There Is To It?

If you’ve done your due diligence and gotten your prospective client to this point in your pitch, you’ve done a wonderful job. 

I use this portion of the proposal to further drive home that I understand them.

Usually, a casual nod at how I understand what the job they’re looking to complete is intended for.

Here are two examples:

But What About Short Posts?

Think about what a client really wants from you.

Of course they want high quality work, but they also want it done in a timely manner. They want to know that you’re competent and understand their needs and the scope of their project.

If you can get them to see, understand, and feel this on an emotional and logical level, it doesn’t matter how short or long your pitch is—they’ll read and respond no matter what.

So, if you can get all the information necessary across to them in a short amount of text, then perfect! 

There are several things that play a role in this though, too.

A freelancer with a higher amount of work completed and superstar ratings, who’s confined to a specific niche (think graphic design for nutrition companies), will have a better chance of succeeding with a short post versus a longer one.

Once you get to a point where you’re a trusted source, less will need to be said as your reputation speaks for you.

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