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 definitely going to be more personal and try to get a conversation going instead of just trying to “force myself” on this job.
Hey, Danny.
You write high-quality content. This will certainly help me. Many thanks to you.
I am new in Upwork. Thank you for the tips.
I’m excited to take your courses. I don’t have any experience in copywriting, but I write a lot. I want to work from home and get paid well. Copywriting fits that description lol. I appreciate your website too! Its changed my approach to copywriting. If I didn’t come across your info, I’d be one of the freelancers that make you throw your laptop off the balcony. You know exactly what you’re talking about. This article highlighted several mistakes I would have made. Simply because I didn’t know any better. I look forward to learning this high value skill.. I’m guilty… Read more »
Thank you so much for all these tips. I have been interested in freelancing for a while and due to the COVID-19 situation was essentially thrust into it and I am finding so much value from your articles. I’ve had a bit of luck so far just being myself in a cover letter but the additional tips your providing are fantastic. I’m glad to hear you’re able to be a fulltime freelancer on this platform, and I’m excited to put your suggestions towards my own efforts.
Hello Danny,
They’re exactly the best way to write a cover letter for Upwork Proposal.I was copywriting the same cover letter, form now I Use your tips and write a new cover letter.
Thanks for your Tips
I am just too excited to have learnt this so early in my journey in freelancing.
I am new in freelancing thanks for all the tips
Hello Danny,
I just finished going through your tips. They’re exactly what I was looking to find. You made me realize that the best way forward is to be real. another thing is this, prior to reading your article, I had no clue about what copy writing is. While reading through, however, it gradually came back to me that a number of years ago, I used to prepare a ‘magazine’ for a local church’s annual convention and all the content for the magazine came from sitting down, thinking and writing from scratch. My gosh! I was a copywriter all along!!
Hello, thank you for the great tips, I found them very useful and can’t wait to try them out! For my next proposal I’ll just be me, and won’t try to offer a better deal than the clients budget just to offer a better deal.. thanks again!!
I’d say that it really boils down to one thing: cutting out the BS. We often forget that we’re talking to people, not robots. I think a lot of it has to do with what we’re taught when we were younger about the ‘formality’ that surrounds the professional world, which is why ‘corporate droll’ is so many people’s default. Thanks so much for bringing these issues to light, Danny!
Hello Everyone
Congratulations on all of your success!
The information you have shared excites me and inspires me to join Upwork and begin working immediately!
I appreciate the various tips & insights that you took of your time to share with us.
I can’t wait to implement them into my proposals😁
I’m so happy I found this. Thanks for helping out!
Since I’ve been reading different kind of blog posts, yours is spectacular. The article is very educative and straightforward with more cogent information.
Feel like I struck gold with this article! Thank you so much!
Me too
Amazing post! Thank You very much. After reading I checked my profile photo on Photfeeler and my rates are amazing. That made me more confident.
Hello Danny,
Congratulations on all of your success! The information you have shared excites me and inspires me to join Upwork and begin working immediately! I appreciate the various tips & insights that you took of your time to share with us. I can’t wait to implement them into my proposals😁
Great post, great blog. Thank you.
Hi Danny, Your content really push me and give me some instinct about upwork proposal but I will appreciate it ,if you can allow one-one conversation either through email or whatsapp.
Thanks
I’m excited to hear from you as soon as possible
after spending 2 months on upwork , and not winning jobs your suggestions are the best Medicine to prevent mistakes. As many people says “Precaution is better than cure’ your instructions will definitely help me to take precaution before submitting a proposal . it really going to help me because i have done all the 8 mistakes in my proposal.
thanks a lot man
Thanks for sharing. Hope that I will reduce the mistakes.
I absolutely default to the boring corporate clone when it comes to marketing, especially in the written form. Glad to have this gentle reminder that there are benefits to pursuing a more relaxed and natural approach when it comes to engaging with clients!
Hello, I’ve recently decided to actually give freelancing a go. I have had one job on upwork but since then I haven’t heard back from anyone. I’ve been looking for tips online to do better proposals but instead of getting better i think they’ve been getting worse! I’ve tried following examples from other people’s cover letters and after reading this article I realised that maybe they weren’t the best examples to look at… I’ve made many of the mistakes above recently, convinced that it was a good idea! Then I also realised that although seeing other examples is helpful, you… Read more »
I’ll just keep my proposals simple while focusing on how to add value to the client’s life.
Also, I would like it if someone shows me, love, and pays attention to my needs; this I will do to clients.
I’ll give them the best of value without forcing a sale or even hire on them.
Edit: I’m new in freelancing. I’m a web developer. I look forward to having success after reading your blog, Danny.
Thanks for the great article.
Could you please send me an email on the steps to writing a great cover letter?
I’ll appreciate you do.
Till then,
Leonard L.O
This article is why i got my first Upwork Job 1 year ago! Eye opening! Really appreciate!
One thing I am going to implement is putting a reference in my proposal like the third example. How do you create a proposal for a position where I may not have ‘a lot’ of or any work experience just training in a particular area? Are there examples like that in the course that I’m signed up for? Thanks, again.:)
Thanks, Danny for putting all of this together. I just signed up for your class, and since I’ve been reading a few of your emails, I’ve already learned 4 key things to improve upon. I look forward to your class and getting better on UpWork.:)
Best article
..
Thank you so much
Thank you the article..best article
Worst mistake ever: making proposals too long. Why? Been there, done that, nobody wants to read the professional ASOIAF-lenght equivalent in a proposal. Nobody wants to read that. Not even your grandmother. She would definitely smack you in the head with a knitting neddle if you try to make her read that. Ever thought of her tired sight? You inconsiderate freelancer, tut tut. Long proposals are many things: tiring, annoying and most of the times, is incredibly boring. Cut to the chase, ask the right questions and show genuine interest and skills in selling your experience to work together. Showing… Read more »
Thank you for sharing,this is my first upwork proposal which is a good tip
Awesome article, by far the best material I have read about the subject. I know that landing the first gigs is hard, but it’s not impossible. I have landed my first gig last week, it was a $25 dollars blog article for a test. It was before I read this article, and the fun thing is that upon checking the proposal of that gig, it had many elements resonating with you article. The other proposals that I made after I landed the job got flunked. I thought I just got luck, but upon reading your article I understood. I was… Read more »
I’m definitely going to continue to keep this mind. I’ve come back to sites like Upwork time and time again when I want to take on some extra work for myself. From my experience, it can take a few days to hear back from the proposals I send, but it’s good to know that you still have this article up for future reference, Danny! Thanks so much for all your incredible insights on this topic. I’ve also noticed that having a profile picture and the way it looks also does make a difference on the way people perceive you. I… Read more »
These are really great tips. I’m still waiting to get my first job on Upwork and I need to rewrite my profiles. I intend to read the samples and craft better proposals by focusing on the clients needs. Maybe even provide suggestions they could implement that I might be able to help with.
Quick question: Do you have articles that deal with how much to pay for more connects?
Thank you, Danny. Although I am an experienced writer, I must confess your post is an eye-opener. I know in real life, nobody cares how much you know until you show them how much you care. Now, I will shift the attention away from my experience, skills, and expertise, and focus on my client needs. By the way, I would love to connect with you on LinkedIn. You can look me up with http://www.linkedin.com/in/sheisawriter.
Thanks!
This is a great eye opener. After going through this piece I realized I have been writing ‘rumors’ instead of winning proposals.
Thank you for sharing these beautiful insights Danny.
This is an amazing piece…. it’s gonna help alot of us Danny.
Thanks for opening my eyes Danny!
I just wrote my first Upwork proposals and now I realize they are so bad to be taken seriously.
Now I will get better everytime and thanks to your writing.
Thanks for your help, Danny! I’m very brand-new on freelancing but a girl from Twitter (@elivolpicelli) advice me to read about your blog and advices and it is really helping me on this journey.
The insight this article gave me it’s a great way to start making changes and apply them to my proposals on upwork.
Hope to write you in a future comment about how benefical was this for me! Greetings from Venezuela 😀
New to creating a simple eye catching proposals. Definitely have over complicated this process in the past so I’m glad to have a fresh start with new insight. I just created a profile on upwork and I like the advice for treating your client like a human. Makes sense!
This is really helpful. I am new into online freelance job, from this tips I learned what mistakes to be avoided in writing proposals. I hope I can win clients and help them by giving quality work to build their trust.
I enjoy your site. I am a newbie and have made some of the mistakes already. I know now that I will be writing proposals on a more human approach
This site is very helpful. Thanks a lot for sharing your ideas. Your advise will help us a lot in getting hired.
This post is really helpful. I just got an insight on creating an online portfolio, where I can easily direct buyers to. Also asking clients for a Skype call, is that right according to upwork TOS?
I appreciate you for writing this article sir, what i will do that i feel others dont do and if any only a few does is:
1. Trying to attack the fear of the Client, for example a Client trying to write a B.sc. thesis is focusing on having an A and how to defend the project. So if one adds the information that shows concern for this needs, you just bursted the brain of the Client.
Thank you, once again for writing this article, more blessing.
hi please, can i get private tutoring about upwork from you plzzzzzzzzzzzzzz
Since Last few weeks i didn’t get any job by proposal submission.Finally i got this article and its totally change my way of thinking about writing the Proposal i will use your Tricks and will try to avoid above mentioned mistakes. I hope i will succeed.
I came directly to this post because my profile got rejected on UpWork the first time and after reading your article about making a winning profile it was immediately approved! I am so happy, so as I am preparing to find the job that fits perfectly in my niche and make the proposal, I decided to do some case study first and come here. I am amazed by how much I have learned with your post, thank you very much! In my field (That being Architecture) many times we fail at asking the right questions instead of just showing all… Read more »
Wow, I’m looking to launch a freelance career, after 20+ years of working for a company, I wanted to branch beyond working for someone else and try working for myself. I figured I try upwork. I needed help understanding how to write proposals. My search led me here. The pointers are fantastic. Thank you very much for putting this together.
Good luck
Hey Danny
It’s great to see some good, specific advice for freelancers getting started on Upwork or for any other place hiring freelancers. I must admit that it only recently dawned on me that my proposals should be the very place where I use my most persuasive and relatable content, kind of like a portfolio sample! Thanks for helping drive this home for me. I will personalize one of your sample proposals and send it to a prospective client today.