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.
I’m a beginner and looking forward to work with Upwork, I find this a very helpful and a really encouraging piece for me, thanks so much Danny ready to learn more from you.
Really helpful and encouraging.
Thank you Dany, I am new on Upwork and I was asking myself: what am I doing wrong? I have the answer and the solution in one article. thank you. i really liked this page
Thanks Danny, I was indeed focusing on myself and my expertise in my portfolio rather than the client’s needs and it turns out a bit of great advice… thank you very much
Really helpful.
Thanks a lot for providing this helpful material.
Some clients don’t give much information to work with. Especially those looking to hire into their organization. They talk a bit about who they are and say something like “Further details are to be discussed in the interview.”
How do you convince such clients you’re a good fit?
This is helpful.
Thanks Dany,
Here is my One year Upwork Journey
Total Proposals Sent= 1674
Total Responses= 93
Project Won = 42
Response Rate 5.5%
Hiring Rate 2.5%
I have won a few quality projects which are still ongoing. Yet I was bit struggling these days to grab some new opportunities from Upwork.
Things I need to focus while writing my proposal
Hello,
I am new to Upwork, just signed up. The tips you have offered here have been extremely helpful.
It is my goal to present high quality project proposals and cover letters, I thus feel a lot more confident now. You have assisted me in a great way to find my footing. I will always use the tips as great reference material whenever I present my project proposals and cover letters.
Thank you very much.
One way I’ll stand out is by using the client’s expectation as my lowest level of delivery, I mean I’ll deliver way more than their expectation so it would be easy to work with. Thanks for the tips Danny. I’m new to Upwork, I’ll work with the tips, sure it would land me a job faster than I think.
Thanks Danny! Most of the guides have been reading about copywriting have been making it more complicated for me to start but yours has provided a lead for me.
Your definitely right! I’ve been sending the same proposal but failed to get a client. Truth is im worried because there’s a lot of good competitors and before I even send my proposal there’s more than 50 that was already submitted. I’m new as freelancer and always worried about the qualifications that I dont have I may not be skilled but I’m sure that I always give my best to help my employer long story but I have same experience with my past job thaeverytime I give extra time to my customers on the phone my supervisor or team leader… Read more »
Hi. Just before I go to this website and read this, I saw first your video on YouTube on How to Write a Winning Upwork Job Proposal in 2021. That video is very helpful in so many ways. I left my BPO job last Dec 2020 because of family matters and wanted to learn how to start with freelancing job since I want to work remotely. I’ve seen tons of videos before about creating cover letter, making upwork profile and so much more but I’ve never seen so helpful like this that’s why after I watched the video I head… Read more »
Thanks, Danny, this was helpful. I am always scared of bidding above the client’s budget, but now I know it’s better to bid above.
Hello Danny! I am Architect Md Amir from Bangladesh. I have completed a Bachelor of Architecture (BArch) from china in Architecture university. So now I want to know from you, How can write a good proposal and How to win more jobs? Please let me know. Thanks!
I joined one month back and I wrote a mediocre type of proposal which landed me in frustration. Thanks to your guide, hope this will end up with some good outcome.
It’s really hard to get a job on Upwork. Anyways, Danny, thanks for this guide, now I know the do’s and don’t’s of writing good proposals on Upwork.
I am a video editor and animator I send 1200 plus proposals but got just 12 small projects can you please assist me for some little time to talk with you or can you write proposal for me am waiting for your response
Thank You
There are several crucial points that have captured my attention.
1. The client wants to hire a person who is relatable.
2. Your years of experience do not matter at all if you do not have the passion, drive or focus.
3. Pay close attention to the additional questions asked by the client because this is what will speak volumes about you as a person.
4. Let the client know that you have their best interests at heart. Your soft skills such as empathy matter as much as your hard skills.
I was annoyed the whole way through this presentation thinking that I would not get a chance to see examples of winning proposals, but you came through! Thank you. The one thing I am going to do is update my photo to make myself look more professional. You’re doing great work. Thank you.
I’ve never been more shocked to realize I’ve been repeating the same mistake times without number. Thank you Danny💯
Sir, I was just about to give my first Upwork proposal. And surprisingly, I was around to do the mistake you just discussed. The article and video really help me to think again for my first proposal.
Thanks
Greet them and comment what intrigued me to make a proposal. Then, follow up with a brief overview of how I would approach their project
These are great tips I have ever read!
Everything is succinct and effective.
I, therefore, think I am more confident now.
Regards 🙂
Thanks Danny! I am more confident to get the jobs. I will focus on less proposals with good quality.
Thanks Danny! You really make my day. Am very lucky to be part of those that read this mistake corrector guide.
I will make use of your advice right away.
I’ve been wrong all the time and I’ve never been this ashamed! This poked me in a very good way. Now I will go and follow your insights.
Thank you Danny!
I was so surprised to see that I have actually been writing my proposals backwards. I usually put 90% of my effort in the cover letter and 10% in the additional questions. I have to work on that right away
Additional questions are very crucial.
Thank you
Thanks a lot Danny! This is really educating and different. An eye opener to everything I’ve been doing wring.
I’m so excited because i already have a lot of ideas running through my mind on the different approaches to use when writing my proposals now. This was really helpful and insightful.
Do you think that people from the 3rd world have the same opportunities people from europe or US have? For example would a client hire a 3rd worlder whos bidding $30+usd/hr over a none 3rd worlder whos charging around the same?
Thanks a lot Danny! This is really educating and different. An eye opener to everything I’ve been doing wring.
I’m so excited because i already have a lot of ideas running through my mind on the different approaches to use when writing my proposals now. This was really helpful and insightful.
This is kind of a problem. Some clients also mention that they want to hire people From Philippine, India or Bangladesh
I got a job 4 days ago by just following your instructions. It was some thing like this, Hi [name],
I see you’re looking for something.
need to know more about winning proposals
I’ll focus on been myself as I write my proposals and avoid sounding weirdo
I am going to bid a suitable price.
I have learned a lot from your tips. This is so inspiring. Thank you Danny.
Hello,
I am new to Upwork, just signed up. The tips you have offered here have been extremely helpful.
It is my goal to present high quality project proposals and cover letters, I thus feel a lot more confident now. You have assisted me in a great way to find my footing. I will always use the tips as great reference material whenever I present my project proposals and cover letters.
Thank you very much.
Thanks for your effective tips about winning proposal
Hi Danny,
It is really great that you put all this information out there for free. I have done okay on Upwork but your tips have me optimistic that maybe I will follow this at time of applied for job,
Thanks again
I have been bidding on Upwork for more than a year now…my turn out rate is very less. I have always tried to change my writing style and one thing I was very sure from starting that copy-paste won’t work so I did not do it but what mistake I did was I sell the pen, why me? and cheap rate negotiations, forcing them why I’m the best person to hire, I did this. I read hundreds of articles by now to improve my turnaround rate but no one literally no one wrote the points you did. After reading this… Read more »
Very helpful. Thanks alot
Thank you for this post, Danny! Before I read this, I was guilty of mentioning my years of experience and being a sleazy salesperson. I cringed so hard reading this and recalling the last proposal I had sent on upwork. I read this and subscribed for your hacks on sending great proposals. On my next proposal, I applied the knowledge I got….and it got me my second job on upwork. With a much better pay. This after a series of failed proposals. I doubt I would have gotten the job had I submitted a proposal in my old way. Thanks… Read more »
Hello,
This is very insightful. i have gained more tips on how to write a winning proposal.
Thanks Danny, I am new in upwork and your tips on proposal, i know will work. Thanks
Hi Danny,
Love your article, thanks. What are your thoughts on testimonials on your profile? I currently have none and I’m wondering if that’s why my proposals haven’t been going through.
Hi Danny,
It is really helpful for beginner. I will follow these instruction when submit my proposal.
Hi Danny,
Very impressive and eye-catching cover letters…
Really helpful for new Freelancers like me.
Thanks for sharing
Helpful tips, dear!
Thanks Danny for this article, since I am a newbie, I will say getting to understand the job description stated by the client and then play the reverse button putting myself in the position of the client,I think that will help to land jobs.
Hi Danny,
Thanks for the helpful info! I am just starting out with Upwork and love the authenticity and uniqueness of your approach.You come across as a real human being and not a clone. I like being able to be myself rather than pretending.
As a freelance translator I am now going to play with ‘translating’ your approach into my field.
Thanks again,
Petra
Danny, this information is priceless. Your have a generous heart.
This freelancer has been re-energized ! Thanks for changing my paradigm Danny.
Wow! I’m a newbie at freelancing on Upwork (on the verge of opening an account).
Reading this unique article will definitely set me on the right path to success.
Thank you so much!