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.
Leave a Reply
286 Comments on "8 surprising Upwork proposal mistakes I see every day (and how to avoid them)"
I love what you teach. It’s ironic to see that all of my success on Upwork has come when I’ve done exactly what you’re teaching, but I never consciously thought about it. It also explains why I’ve landed higher pay gigs, even above client budgets.
Early on I decided to make my business about others. When you think of someone else other yourself, you always succeed. When they win, you win. It sounds counterintuitive, but if you need something, give it first. The more generous (giving mindset) you are the more you receive (not just financial). You reap what you sow.
Thank you for sharing your insight with us. While I’m doing these things already, we all need reminders, to be encouraged, and even to find ideas that we haven’t quite done or thought about before. Your words encourage and motivate me to go even further.
You rock!
I will start giving more time to the additional questions. This client-view display was interesting.
Thanks Danny! I’m been with Upwork for years but never applied for jobs because I didn’t know what to do. Thanks for the info and the free gift!!!
So I need to charge more? Something that amazes me is how much some people charge- I don’t charge huge amounts, but I live in the center of the country where it’s cheap to live and my house is paid off.
Thanks for the great, eye-opening content! I’ve learned so much. I have been on Upwork for about three months. I’ve earned over $2000. I can see now that the projects I was rewarded were all the ones that I laid out a plan for the client in how I would complete the project. I will work harder to research the work requested before engaging.
Also, my mind was blown when you showed the screenshot of the questions appearing before the cover letter. WHAT!?!? I will definitely take more time in answering the questions than I have in the past.
I entered my name and email address in the box requesting it and confirmed my subscription from email received in my inbox … and then I never got a second email sending me the 3 successful proposals 🙁
I used the contact Danny button and hopefully he checks his messages and corrects this for me soon
how do i get your proposal.
.then what should be included in the cover letter?
Great and informative piece. Mr Danny, i have been following you.
I so much want to freelancer on upwork, Over-ready for work. Also a professional in my field of librarianship. i wasn’t accepted by upwork.
couldn’t identify where i went wrong. please any pointer please on how to do it
This post was amazing! Great information and hilarious! It was easy to relate to and understand for a beginner like me. I am actually laughing out loud over the video! The website below isn’t quite up yet. Hey! Cut me some slack. I’m NEW! 🙂
Greetings,
Many thanks, I joint Upwork from three years but I didn’t hired yet because of some small things I thought that there are not important, but your article like a light in my dark road.
Many thanks for your time & effort.
Mohamed
Amazing post really
Thanks for sharing this Information.The information you provided is much useful. i really enjoyed your blog article and save your site on bookmarking.
When I graduated high school, I looked for essay-writing jobs. I found jobs writing essays for students. For one of my first projects, I wrote a paper on German history, and I found research conducted by three different types of scholars. As I was a quarter of the way through with writing and researching, I realized scholars from two of those areas used two different sets of jargon in order to discuss distinct features of two, separate sets of phenomena. I realized I needed to go back, and do more research on both of those topics. Such enabled me to understand the topic of the research paper in a better fashion, and, as a result, I now appreciate the concept of learning histories of a variety of ages. Ultimately, I believe this made me appreciate learning even more.
Hello Danny,
I’m just beginning on this world of freelancing and you article was the thing that I was looking for. Really inspiring and giving very useful information. I hope to get my first job sooner. Now I have enthousiasm and information 🙂
Thank you very much, Grazie Mille, Muchisimas Gracias Merci Beacoup, Большое спасибо
Alla Emelianova
Great articles love it
Great tips, Thanks a lot.
Just a little chirp to say thanks Danny for writing this post. I’m just submitting my first proposal and it’s helped a lot.
Anybody whosoever if ever wondered of trying their hand in Upwork Freelancing, this is a must read article for them. It is so very practical and holding an impact, I often refer to this when ever it crosses my way. And yeah surely it has helped me a lot this year especially. Thanks Danny for sharing this explicitly researched data.
Danny changed my freelancing career. Before seeing his webinar I could hardly make 300$/moth on up Work. Now I charge >50$/h and have more job than I can handle. Thank you Danny.
Amazing post ! Thank’s so much Danny
Hello Danny,
Thanks for this wonderful piece… a big thumbs up to all who have shared their experiences.
Remain blessed…:)
Emmanuel from Nigeria!
Great artcle Danny. It came at a point where I was looking for that much needed tip for writing a proposal. Now I feel like I am all ready…
Hi Danny,
I am really pleased whenever I recieve sth on my email from your website. I wiuld like to declare that I have benefited a great deal from them, especially hoe to correctly write my proposal and let the client choose me.
But I would like to say how this worked out with me..
I kept on writing devoted proposals and great words on them for almost 2 months- with no hires at all!
So, once I was so furious and could bear it no more. @ months of working hard and zero achievement!!!
I did a little change to my profile while I was angry, I changed my title to sth (I dont really know where from I got it!) then went on searching for new jobs, fished a job, hit submit a proposal , searched for the client’s name, had a look at his previous hires and started to write:
Hi Jim,
It is Amal here, I did not read your post, and I don’t know you are looking for a Romanian Translator.. Dont hire me, I am not suitable at all for that job. Dont visit my profile, all my experience is a secret, please.
what is that, are you still reading my proposal ?? close it please, I told you I am not a translator………………..
======
This is part of what I have written. but I was amazed to find the next day that I was offered the job!
I can be creative on upwork even though I am there for only 2 months!
regards
I actually LOL so hard :D, sometimes fun is really a big factor.
Funny and it worked!
Hello Danny, I will admit, the greatest trap I had fallen was the “Generic cover letter” one, where I would spend the first 2-3 paragraphs with one of 3 sets I had ready to introduce myself (As if my profile wasn’t supposed to do that job already https://www.upwork.com/o/profiles/users/_~010b801c3d46667ea3/ ), making it too much about me, and then, finish with about 2 paragraphs asking questions about the project and expressing my desire to work for it.
The curious thing though? It wasn’t out of laziness; rather being EXHAUSTED of putting my heart into each one.
My real problem with my cover letters (now that I’ve reflected on the generic and self-centered ones), is that in my work niche (Story/plot writing for videogames; which I tittle Narration designer as I also consider the game design involved in my projects), most proposals lack any real information AT ALL, it’s like they aren’t even trying to attract good workers…
I always find myself at a loss when all the info I get is something along the lines of “We are making a game on X generic and unclearly defined theme, and we need a writer for it”. I end up either just writing the generic cover letters, or some extensive reinterpretation of said theme with gameplay elements to try to show my effort for it; so freaking extensive I was able to create portfolio posts out of them.
Could you give me any advice (or create an article for everyone to enjoy) about how to deal with uninformative job posts?
Hello Roberto,
The goal of proposals is to start a conversation, not to win jobs. So in my experience, many clients who post uninformative job posts don’t have a clear idea of what they want /need , or even what exactly their problem is.
You can send a proposal based in this perception and making them know that you are committed to understand what they really need (here you can use Danny’s best practices and also be creative)
I recommend you to focus your proposals on knowing better what the client wants. If they can feel you know your stuff and is willing to understand their needs, many of them will likely reply to you, so you can start from there. If you realize he/she is a high quality client, you go ahead with your negotiations.
Of course, some of these people are just looking for cheap work or they are “window shopping”, but you can find this in informative job posts as well, so it’d not a big deal.
Success!
Whaat a great post you have delivered, am astonished that you havent checked out the products yet –
Be sure to visit and am utterly grateful for this helpful post.
Great Article. Thank You for sharing knowledge.
Danny you rock
Thanks For Help to the others and increase more confidence!
Great articles , the lessons are exquisite. I read it and applied the lessons and the results have been great.
Thanks
Hi Danny! Great article. I’ve learn so much from this and from the comments. I’m new in online freelancing and I’m glad that I found your blog. I have this question in mind. Is it okay to include in my proposal that “I am a part-time freelancer working for 3 hours and day, 4 days a week.” Because I’m a full time employee and I want the client to know the working hours which I’m available so that they know what to expect. Thank you. 🙂
Thanks for the great article; some solid takeaways in there.
Over time I’ve learned that clients go through the ringer with vendors and freelancers. So many are high-maintenance, need hand holding, or are tough to nail down. While the goal for freelancers is to make clients’ lives easier, they often have the opposite effect.
With that in mind, I gear all of my communication with potential copywriting clients (proposals, emails, phone conversations, etc.) towards illustrating that they will get what they need without drama and might even enjoy the process. Operating a business is a stressful circus act, so I set the expectation that I am a professional, easy-going, and friendly vendor; a vibrant, thinking partner, not a mindless spigot.
This makes the process more enjoyable for the client and for me!
Life is too short to be a thorn in someone’s side.
Excellent article Danny! The big story is being human while communicating with potential clients instead of sending automated mechanical non-human proposals and letters.
This post is very simple to read and appreciate without leaving any details out. Great work! You completed certain reliable points there. I did a search on the subject and found nearly all persons will agree with your blog
Hi Danny,
Your tips are really interesting, definietly throws me into a brainstorming session before everycover letter. While I am waiting the response from potential Clients, I admit that I have changed my approach from indirect one to direct one. It really makes difference for me as a freelancer, I am sure the Clients will react appropriately.
Thanks and keep the good work,
Cheers
This is precisely why many clients choose the wrong candidates and why all of you skilled freelancer have trouble finding a job !
🙂 🙂 🙂
🙂 🙂
🙂
I have made many of the above mistakes. Now I find myself with an ongoing contract to write 5 articles a week for 15 dollars per 1000 words. Plus I have to do all the research on top of it. I would really like to get out of this contract but I’m afraid it will make other clients not want to hire me if they give me a bad review. What should I do?
great… A great pic is something I was missing in upwork.. thanks
These actually makes sense! I haven’t had an experience with Upwork yet but this is definitely an eye opener. Thank you so much, Danny!
Hi Danny,
Every since you told us that the questions come first, it definitely seems that the response to my proposals has improved.
However, since this was written last year, I wanted to check on whether that is still the case. I looked at one of my proposals a couple of days ago, and it shows that cover letter to be first. So my proposal look odd.
Does the client still see the questions first?
I really like this article. Thank you for sharing such actionable insights. I’ve been finding clients through freelance vendor sites for years. This is the first time I’ve learned that I can bid above the client’s posted budget. So that is what I will do differently from now on.
I also want to share my perspective as someone who has also hired and worked with freelancers via sites like Upwork. Of the 70+ proposals received for a project post, usually only 1-3 stand out that I look at more closely.
What makes them stand out?
Their proposal tells me they’ve actually read and responded to the details of my project description and they can tell what I am looking for – and even pinpoint what I am most concerned about re. the project.
When I write a project post, there are certain items I include, because those are important to me. When a freelancer notices this, and responds, I feel like this person not only sees what I am looking for, but also cares about my project.
Ultimately, that’s what I’m looking for – someone who will care about my project. A proposal that addresses the details I have highlighted tells me that freelance professional cares.
Another observation – perhaps the biggest turnoff is the proposal that tells me all the additional services the freelance professional can provide for me.
In my project descriptions, I am clear on what I am looking for. That’s all I want to hear about in response. When a freelancer uses the proposal to upsell me on services I didn’t ask for (and don’t need), not only is this a waste of time, but it also tells me the freelancer isn’t paying attention to what I said I needed, and isn’t completely focused on the project I actually need.
I don’t want to work with someone who is continually trying to upsell me. If I like working with that person on the first project, I will ask them questions about future needs, and then they can respond.
Show me your expertise on my initial project, show me you care, and I’m sure I’ll come back to you with other projects.
On the humble flip side …
I’m sure, as a freelancer, I’ve made these same mistakes.
So: note to self!
Janet
An additional observation that just struck me –
In all my years of posting freelance projects and reading through proposals, I just realized that I’ve never once looked at the freelancer’s proposed rate.
Instead, my sole focus has been to find the right person.
I’ve also never negotiated down someone’s rate. When I found the right person, I paid what they said they were worth and never questioned it.
It’s interesting how, as a freelancer, I so often get stuck on proposing the right fee; while as a client, that’s never been an issue.
Thanks for this great learning opportunity!
Janet
Here is a tactic I often employ to break the ice in an unconventional manner.
I simply tell a joke or express understanding.
This is particularly useful if you are unable to find the clients name to start the proposal with.
Examples:
I can see you’ve had a lot of proposals. It’s tiring filtering out the junk, isn’t it? I know because my inbox gets inundated with the same weak proposal every day.
Here I show I’ve used a little initiative, I’m empathetic, I know how they feel, and I build rappot.
Or I might start the message with:
You want an Upworker to research (topic) AND produce persuasive copy. The monkeys that work for peanuts aren’t going to be able to handle doing 2 things at once.
Here I simply crack a sarcastic joke (be careful with which clients you do this with) and point a finger at below par freelancers that work for $5 an hour.
The trick is to be original. As Danny points out in his freelance course, you want the client to be nodding and agreeing when they read your proposal.
If you can reach out to clients with originality or humor, AND get them saying yes throughout the (short) proposal, you’re doing a better job than the monkeys (no offense to monkeys)
Thanks for writing such a good article. This is a concept that is very effective. I have benefited greatly through you. Read this article, I learned a lot. Thank you so much for letting us know about it.
This is a great school for new freelancers.
I want to learn a lot from you in the future.
Keep up the good work!
Thank you Danny.
why always like this ?
We’ve reviewed your profile and currently our marketplace doesn’t have opportunities for your area of expertise.
If you have more relevant skills or experience to add, you can update and re-submit your profile. You can find more information regarding our decision here.
Love these tips. I have been working on Upwork for a few months now, with spotty results. Reading this I’m connecting some dots.
One thing I have noticed: The longer answers/cover letter are more likely to get a response. It’s just like the rule in direct sales that says longer copy sells more, use it when you have the space. We have the space!
One request? Flip your comments so the most recent ones are on top. I know this post has been out there a while, but it is where I landed when requesting the proposal samples.
Thanks & I’m really glad to have found this! Keep up the good work!
Kat
Excellent, thanks for sharing.
thanks for suggestion. i will follow it. can you give me any example of any proposal.
i am new here so it helps me.
Amazing post Danny. While at first point it looks like validating what i used to do with proposals, deeper it gave lovely insights and learning points. Just a question. Any suggestion for agency profile over Freelancer one? I run a web and mobile development agency with 10 member team on upwork and not sure how can i position ourselves on upwork.
Great post Danny. I have question about portfolio.
I am new to UpWork and not sure how portfolios work around here, so, my question is,
Is OK to use outside portfolios, like Behance or 99designs in my case?
No one is reverting to my bid*
No one is reverting to my big