Tired of sending Upwork proposals and not hearing back? This is for you

Tired of sending Upwork proposals and not hearing back? This is for you

Look at all this contradictory advice on why someone’s Upwork proposals aren’t landing clients.

The first response points out that we should not work for free.

quora upwork proposal recommendations
I had to cut the entire response short because it was too long for one screenshot

Next, someone says to do pro bono work.

One answer is saying “don’t do any free work” and the next is saying “do pro bono work” (free work). How are we supposed to know what to believe?

The best part is that there is no background info to the question, so it is challenging to offer advice that is actually helpful.

Granted, a place like Quora is not the best place to ask a question like that since it’s mostly an opportunity for marketers to sell their product these days.

But there is a deeper point behind all of this. Sometimes we feel so desperate for help that we’ll ask anyone for help — even those that we shouldn’t listen to because they have no experience.

We have to be careful who our heroes are and who we listen to advice from (that includes this blog). Allow me to show you why through a little story. 

working on the beach dream

For the longest time, I had this dream of wanting to work on the beach. I’m sure you’ve seen the videos of people hanging out on tropical islands with an amazing pool.. It looks like a dream, right?

As a naive kid from the countryside, I discovered the internet and all the ideas and promises that come with it.

Many of the promises sounded too good to be true but with no other way to learn, I had no choice.

So I bought a program and went to work.

Things went okay at first and I earned some money. So I bought another program and repeated that process over and over for years.

Things were going okay but not great. As I began to go to offline networking events and meeting with people on a similar path, I discovered one thing that almost all of the programs had in common.

It wasn’t as much about what was in the programs but more so what was NOT being said. The more I learned the more I noticed that often important details were being left out.

For example, showcasing someone with an overnight success of how they landed a client and bagged $5,000 in a week with little experience.

..but forgot to mention that they already knew that client as a friend and that it took a month or two to deliver the project after it was landed, so the money wasn’t earned until that happened.

During that journey, I asked for advice but I listened to the wrong people because I didn’t know any better and I didn’t have anyone else to ask.

That took me on many side-quests and things took way longer than they should have. Of course, that is my fault for doing it in the first place — not the creators’. 

The point is to be careful of who you listen to for advice. I’ve found that wanting the same outcome as that person you are listening to is a good place to start. 

Now, when I listen to two competing arguments around the same topic, I assume both are true for the time being and the stop to think about who I’d rather be like for that topic specifically.

How to self-assess your Upwork proposal

There can be a number of reasons why we are not landing any Upwork projects so there is no one size fits all answer. Instead, I’ll show you a framework you can use to find the problem and solve it. 

We can look at Upwork as a marketing funnel with different steps throughout.

upwork proposal - upwork is a marketing funnel for freelancers

By breaking it up that way, we can assess where things go wrong and fix each specific step in our funnel.

The first step is to send out enough proposals, so we have some data to look at. 20-30 proposals is a good place to start at (the more the better). 

Have you sent out more than 30 proposals? If not, it’s too early. Did 10-14 days pass by? If not give clients a chance to hire.

Done that? Good. The next thing we do is track our proposals to see what happens the most when we send out proposals. That way we can thoroughly understand the problem before we look for a solution.

Are people not hiring anyone? Are they hiring someone else? Why? That’s what we’ll figure out in this step. 

If we skip this step and continue with the rest we might not be solving the right problem, or one that will actually make a difference for us. Instead, we’ll be spending a lot of time on work without making any real progress or earning money.

Here’s how. First, create a copy of this template by clicking FILE > make a copy. Then open Upwork and fill it out with your proposals by going to find work > proposals > archived.

upwork proposal - finding your archived proposals

By now you should have the sheet filled out with at least twenty proposals that have been sent and details about if the client hired anyone and who.

The next step is to calculate the number of times someone didn’t hire compared to the number of times someone else was hired. Use the second tap in the sheet to tabulate it easily.

tracking an upwork proposal

Whichever option has the highest percentage is our biggest challenge right now and what we should focus on improving since that is our biggest win.

If there is an overwhelming number of times that someone else was hired, look up who was hired for those projects and compare their profile with the job description and your proposal to guesstimate what might have made them more attractive for that particular project. 

Sometimes it is simply because they were cheaper but that isn’t as often as you think. I’ve seen several times where the client seemed to be looking for someone who had more specialized expertise and was charging more for the project.

Here is a basic (not perfect) approach to finding the solution and forward with your new-found data.

If no one was hired at all

If no one was hired at all for most of the Upwork projects you applied for = the client is not serious or couldn’t find a relevant freelancer.

When that happens the most, the next step is to practice finding projects with serious clients. This is challenging but you can build your intuition over time following the approach of bidding and tracking the outcome. 

One example is to guesstimate how long it took the client to write the job description? If it is long and detailed, it probably took them a while so they are likely more serious. Looking at their hiring rate is another way.

If someone else was hired

If someone else was hired = we are not a good fit or the proposal sucked.

If the clients are mostly hiring for the projects you apply for but it is someone else than you, it is likely because they were looking for someone more relevant than us or because we sent an unattractive proposal. 

We might solve that by comparing the winning freelance profile to our own. See if you can spot differences and guesstimate if it was because the client was looking for something different than what we offered. If the winner’s profile and yours appear similar, it is likely because the client got a better proposal from another freelancer.

Did you spend enough time to write the best cover letter you could?

If you realize that it is because the proposal might not have been good enough, consider if you spent enough time writing each one. I suggest one hour per proposal until you have mastered it and feel confident in landing clients at your command.

Do you get a lot of visits to your profile? 

You can check that by clicking my find work > stats in Upwork and then scroll down to the bottom of the page and find marketing effectiveness. 

Compare the number of visits to your profile with the number of proposals you sent to get an idea of how many potential clients actually visited your profile from the proposal. You might be surprised how few it is.

If you have lots of profile visits but no writebacks, clients might have gotten curious but something they saw isn’t attractive.

In this example, a reader sent out 98 proposals but had only 13 visits to their profile, and of those three were from discovery (from search or clicking around – not proposals).

That means only about 10% of the client proposals looked at the profile. Even if we focused on optimizing the profile text, it would only affect 10% of the clients and it wouldn’t be relevant for the remaining 90%.

That is common and exactly why I suggest looking into exactly what is going on before looking for advice on how to make your profile better. Spend LESS time on the profile and MORE time on the proposal.

Do you get many writebacks but things don’t go any further?

In this case, your proposal seems to have worked well enough to get a writeback. It could either be due to unserious clients or something we responded with to the writeback. 

Most often I see that freelancers send the busy clients lots of questions, which can feel overwhelming and there are other freelancers doing the same.

Suddenly it becomes a whole big thing to reply to them and the client might delay and “do it later” which usually becomes never. 

When there is one freelancer (usually there is NONE) who stands out and caters to busy clients by making their life easy, they win! 

We can do that by researching the project thoroughly, so as not to ask questions that could be googled or read in the job description. We can also make it easy for the client to say yes by asking one question at a time and offer suggestions instead of letting the client do all the work in writing out the ideas.

For example, instead of asking what they are looking for, we might suggest three options so they can simply reply with the choice they prefer. It could look something like this: 

“Hey NAME, I’d love to better understand what you are looking for. Based on the job description I have three ideas for directions you might be interested in:

A) Idea A

B) Idea B

C) Idea C

(Add whatever else is relevant)”

Do you get on calls with clients to discuss the project and don’t hear back? 

If so, clients are likely not that serious or aren’t convinced we are the right person for the job.

As shitty as it sounds, it might be that the client just wanted free advice but was never serious about hiring anyone in the first place. That happens sometimes and the only thing to do is move forward to the next project.

Alternatively, it might be that we said something that was off putting or the client simply found a better match among other freelancers. Here the challenge is that we often won’t know why and clients usually don’t feel like telling us because it is uncomfortable and requires extra energy. 

There is nothing to do about it except working to guesstimate what we might have done that didn’t work and how we can tweak it the next time.

Next, let’s zoom out. This self-assessment is the easy stuff and only 20% of the work. The real work, the 80%, is that we don’t give up and continue to tweak until things are working.

[convertkit form=2588400]

The counterintuitive skill needed to create an amazing Upwork proposal

When I began sending Upwork proposals, guess what? They sucked!

The uncomfortable truth is that only working hard and consistently makes a meaningful difference. 

I know that might sound intangible and “woowoo”-like. I don’t believe in hoping for the best and “manifesting” things, and all that mindset voodoo. 

In my experience we get better by practicing again and again.. especially, if we are not great at first. 

When things aren’t working, we often tend to think that we are missing some secret piece of the puzzle. That one thing that will change everything.

Usually, it doesn’t exist and when we’ve sent out many proposals without getting a client, it feels like we’ve wasted our time. That’s the hard part. It’s the “secret” if you are looking for one. People are not emphasizing that enough and that’s why I’m spending energy on it in this article. 

Anyway, this is not meant as a moral crusade. The point is that the skill of committing to seeing it through is more challenging to learn than the skills needed to send proposals that land clients. It’s more important too.

The best approach I’ve found is to build the commitment by creating a habit out of playing around with the proposals every day. Even if it is just 15 mins at first, we can always spend more time once that becomes a habit.

Often, we try something new because we got curious. But switching from “just trying it out and seeing how it goes” to taking it seriously, is a whole other game. 

We only tend to do that once we have a particular reason to. Such as if we know that we want to buy a specific pair of shoes or surprise our significant other with a beach holiday or a trip to their favorite restaurant. 

This is Simon Sinek’s story of the why all over again. The short version is that if we don’t have a particular reason to, it is hard to motivate ourselves on the days when we feel a little tired and lazy.

Motivating ourselves and thinking of why we are doing it is a personal choice that I can’t help with.

How are you reacting to what you learn? 

The most common reaction to ideas like these is “this is great! See ya!” 99% of people move on with their life and never do anything with the ideas they read about.

You’ve probably been sending out proposals and not hearing back, now you’ve read this article and you can do one of two things.

One is to tell yourself “I’ll figure this out later” or you can do the exercise right now or schedule a time in your calendar to complete it (feel free to email me your results or comment below).

“It can’t hurt, right?”

Recently, my friends and I were comparing our upbringing and their pros and cons. I’ve never been forced to practice something for a long time and push through the struggles to get really good. If I wanted to switch from one sport to another, learn a different instrument or something, my parents were all for it.

Yet, I have many friends and family members that got pushed to continue whatever they were interested in and over the years they got really good at it.

That means they experienced what happens when we push through the difficult times until we get really good at something. A skill that we can use to learn other new skills such as sending Upwork proposals that wins clients.

If we’ve never pushed ourselves to continue working when something is challenging, we’ve never experienced how amazing it feels on the other end.

In fact, starting a bunch of projects and leaving them unfinished helps us tell a story about ourselves that we are someone who doesn’t finish projects. Contrary to popular belief, that is not something we are born with or even a character trait but rather a skill that we can learn and get better at.

It challenges our confidence since that is built on past experiences.

This can feel confusing because on the surface, it has nothing to do with the proposal we send for a client project yet it affects it indirectly.

That’s one of the real differences between those we see having an “overnight success” compared to others that struggle for a long time before giving up or eventually figuring it out. 

The tangible skills are often the easiest to learn. The point is that some people have learned this through the environment they grew up in, without realizing it, while others have not.

An example is someone with parents that are well connected and might have been hanging out with top professionals like CEOs all the time. 

They might feel totally comfortable talking with them about business problems and have a much better understanding of the challenges, and why they don’t want to learn how to solve their problem but rather just want to pay someone else to do it for them.

Compare that to someone growing up learning from their environment not to piss off the boss and the only way to earn more is to work more hours. It’s like two different worlds as described in the book “Rich Dad, Poor Dad”. An extreme example to prove a point.

In order to figure out that that isn’t true, one has to power through the challenging times until they figure out that the reality is different.

Mark Manson argues that we tend to have two responses to challenges: distracting ourselves from them or working on a solution.

Far too many of us distract ourselves and run away from the challenge if things aren’t going well. That leads to a lovely little circle where we think of that as a failure and then trust ourselves a little bit less.

That in turn makes us prone to distract ourselves and run away the next time something challenging isn’t going well. And the circle continues. That’s why there is a cost to “just trying something because it can’t hurt”. 

We end up with a suitcase full of things we’ve tried that didn’t work and it builds up this idea in our heads about ourselves that we are someone that fails at stuff.

So if you decide that you want to earn money freelancing, I strongly recommend that you either commit to it until you reach your goal or don’t do it at all. Half assing it is the worst option.


  1. Shahid

    BY BY Upwork,
    After an hard struggle no one order I could catch so leaving Upwork.
    Seemed Upwork discourage new freelancers, its connect policy, why any one will waist 4 connects for $3 work, some buyers post for test. But waist connects of freelancers. Doesn’t show how much proposal a buyer had also received.
    A buyer hired one but post is still showing.
    Usually computer expert having weak English while Upwork focus on English.

    • Smith

      Comunication is important thoght.
      They’re people who succeed with basic English out there on Upwork.
      Don’t worry.

  2. Gurmeet Singh

    Hello Chris,

    Thanks for sharing the great tips and encouragement.

    I overcome from making many mistake and discovered many tricks behind of apply bids to find serious employers.

    But, I’m losing in one situation which is getting bid placed in 5 to 10 for Dev jobs especially for WP & Shopify. There is huge competition and i don’t understand how other freelancers place the bids in just few seconds and get response. What they are write in that time?

    If you can give any solution for that would be appreciated.

    Excited to hear from you.


    • Chris

      Hi Gurmeet, great to hear that you are moving forward in the process. I don’t know about those dev jobs but I imagine they might be using a bot or a template proposal asking a question or something to get a quick response from the client. I guess you could try that and then follow it up with an amazing proposal since you’ll then be able to message them directly. In general, I wouldn’t worry about it and just focus on sending them the best proposal they’ve ever gotten.

      Another thing you could do is to set up your own, similar, project and wait for them to bid to see what it says.

      Out of curiosity, do you happen to know that those who respond first wins the project? It hasn’t been the case in my experience 🙂

  3. Joanne Taylor

    Thanks, Chris, I have been freelancing on Upwork for a few months now, and this is the first article I have read to offer really useful advice on using archived proposals and ‘My Stats’. It confirmed my suspicions that I need to return to spending as much time on my proposals as I did at the beginning!

    • Chris

      Hey Joanne, thanks for reading. I’m glad you liked the article 🙂

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