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.
“Hot Dog Eating Contest 2010” by Space Pirate Queen is licensed under CC BY-NC-ND 2.0
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!
This was definitely helpful! I’m guilty of telling the client about my previous experience. I’ve landed good jobs on UpWork this way, but I can see where others would’ve been turned away. Thanks for the info!
Sincerely speaking this is an eye opener to me .am a beginner and was almost giving up but now am motivated to give it a shot.thank you so much
Nice work, Danny! Your article is thoughtful and easy to read. Points are clearly explained and tips are doable. I hope to learn more from you as I take a leap of faith in freelance writing.
Your articles are truly an eye-opener Danny. Thanks for sharing such a wonderful tips
Inspiring piece of work.
Thanks for the sharing. This is so inspiring. Authentic and true.
A wise man once told me “A candle never loses anything by lighting other candles, it has only produced more lights” Thanks for sharing these. This is very inspiring of you, natural and selfless. A piece from a grateful heart.
I am a new freelancer and all your tips are very helpful I am going to focus more on the client.
Thanks a lot!. Am yet to write my first proposal. I will get it done soon, by following your steps. Any means I can chat you personally
Hey Danny. I decided to become a freelancer just a few weeks ago, and I thought I should probably get a heads up on what to expect before jumping in. That’s how I found you, and man am I glad I did.
Because of you and all of your advice, I’m confident I’ll get started the right way and avoid costly mistakes that would definitely have impeded my success.
Thanks for taking the time to write such great articles.
As a new freelancer this information is beneficial. I will definitely look at things from the client perspective.
Hi DANNY MARGULIES,
i really appreciate your working and analysis of proposal. you just clean sweep all the wrong ethics for profile / proposal writing in my mind, after the reading and applying these natural tricks, i’m dam sure to get my first job ASAP.
thanks for all of this.
This is awesome. Am a new freelancer and am really inspired by your tips. Basically, is just trying to put yourself into the shoes of a client,and reverse the reaction.
Hi Danny
Its so much helpful and as a new freelancer, I am grateful for these tips. I want to be more human in my proposals. I want to apply this tips for bids
can you please share and cover letter with additional questions .
Wow! Thanks alot for giving tips on how to be a good freelancer, I really appreciate.
As a new freelancer, I am grateful for these tips. I want to be more human in my proposals. I want to connect with the client…
Being new to freelancing, the tips you give here what I needed, as I was not sure on how to go about writing good proposals. Thanks a million.
wow! this is really timely. It came just before I made too much errors and become frustrated at not being hired.
Thank so much for sharing.
Thanks, for showing me the mirror in which I see my mistakes. I am new to Upwork, I have applied to 10 jobs for which I am over qualified but still I didn’t get hired. Now I can see what mistakes I am making. I don’t know why people make such mistakes but my reason is being desperate to be hired. The more I get rejected the more likely it becomes to make above mentioned mistakes.
Thanks Danny for the tips. I’m a new freelancer. I have written lots of proposals, up to no avail. But your tips will go a long way helping me get a job.
Thanks alot!
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.