How to write Upwork proposals when everyone is better than you
An underdog strategy for beginners (that won't take forever)

Written By Steven Alexander Young
Published on April 14, 2022

The strategy I'm about to teach is a total game changer for anyone who thinks Upwork is too hard when you're new.

And even if you're not a beginner, you'll still want to see this – I still use it today, despite now charging $999/hour:

Obligatory proof that clients actually pay that high

Why other Upwork proposal advice sucks

Most advice for writing Upwork proposals falls into one of two terrible extremes:

  1. More VOLUME: Upwork is a numbers game, so just send more proposals – Google “best cover letter template”, copy/paste 100x, and pray 🙏
  2. More DEPTH: Higher effort = higher chances, so write 10k words minimum – or better yet, record a custom video proposal for each client 😫

The first never works, and Upwork might even ban you. The second is super hard and takes so much time that it's never profitable.

Finding a good middle ground is tough. Most who try end up with "Frankenstein proposals" where they lazily personalize a copy/pasted template (the worst of both worlds).

My approach to proposals is entirely different. And by the end of this post, it’ll be part of your freelance arsenal too.

Keep reading to see:

  • How other Upwork bloggers ruin this strategy
  • An example of how I rewrite a real Upwork proposal
  • Proof this strategy helps even if the client doesn't hire you

...and tons more. Let’s get started:

How Upwork is as unfair as baseball

One of my coaching students started calling this type of proposal a "Moneyball Proposal" and the name kinda stuck.

Yeah, I know how it sounds... But “Moneyball” isn’t some pyramid scheme hype word I made up!

It’s inspired by one of my favorite underdog stories, told in the bestselling book "Moneyball: The art of winning an unfair game" (also a great movie).

I'm not a sports person at all, but I was gripped right from the title.

Professional baseball isn't called “unfair” because the rules are rigged, but because each team has a very different budget.

Naturally, the wealthiest teams snap up all the best players while the poorer ones are left with the scraps.

Upwork is similarly an unfair game – freelancers may get "equal" opportunity to send proposals, but some applicants just have way more credentials and work history.

The reality is: If everyone writes the same kind of proposal, the most experienced freelancers will ALWAYS win.

To level the playing field, you need a more strategic approach...

Breaking down the “Moneyball Strategy”

Moneyball tells the true story of how one unsuccessful baseball team – the Oakland A's – found a way to start winning despite having one of the smallest budgets in the league.

20 years ago, baseball teams scouted players based on various criteria like running, throwing, hitting, etc.

Then they combined that with less objective things like “Does their form look good?” or even “Does their girlfriend look ugly?” (which supposedly signaled a lack of confidence 🙄).

The way the Oakland A’s built a winning team was simple, but genius:

First, they identified good players by laser-focusing on the #1 thing that was most directly tied to winning games:

“How often do they get on base?”

Then, they purposely hired the players who looked the WORST according to everyone else's "proper" standards.

This meant all their players had proven stats where it actually mattered – while saving a TON of money because of their "flaws" in meaningless areas (like how their girlfriends looked).

To everyone’s surprise…

This team of dirt-cheap misfits was able to beat wealthier teams filled with “traditionally-good” players.

And despite their tiny budget, the Oakland A's achieved a record-breaking 20-game win streak!

Writing "Moneyball" Upwork Proposals: The #1 thing that really matters

To write an effective Moneyball proposal, you want to double down on the one thing that truly matters for winning a job – and make sure you don’t waste your "effort budget” on anything else.

It’s as simple as that… but most freelancers never correctly identify the right goal.

When I look at proposals from my coaching students, almost all of them fall into the same mental trap:

They assume the point of a proposal is to instantly get them hired.

In the worst cases, freelancers might fill their proposals with all sorts of bloat:

  • Info on their background, years in business, and life story
  • A description of how they’ll do the job
  • Their proposed pricing terms
  • When they can get started
  • A suggested deadline
  • Maybe even more, like cancellation terms or number of revisions included

This is a TON of weight for one message to carry. Not to mention, a ton of extra work to put together, making each proposal feel like a slog to write.

On the other hand, there are freelancers who try to fill their proposals with “persuasion tactics” like faking how busy and in-demand they are (which clients can see right through).

With your Moneyball proposals, you’re going to slash all of that dead weight and focus on a very different goal:

Getting a reply.

I’ll say it again:

The only job of your proposal should be to GET A REPLY.

Let me explain…

Your Upwork mantra: Apply fast, Sell slow

Getting a reply doesn’t guarantee that you’ll actually win the job. But it leads to several valuable upsides that are unavailable when you try to get hired instantly.

For starters, chatting with a client lets you:

  1. Show more personality and build rapport
  2. Get behind-the-scenes info about what they really care about
  3. Clarify requirements to help you price better
  4. Educate the client on what they should really be looking for
  5. Address all of the client’s actual objections, as they come up
  6. And much more, depending on where the conversation goes! (Plus, stay tuned for even more surprising benefits)

All of these are real, tangible advantages which help you sell yourself better – meanwhile, your competitors only have whatever info is in the public job description to work with.

That's why a good Moneyball proposal deliberately sacrifices all the salesy talk in exchange for a higher chance of starting a back-and-forth conversation.

Not having to write a whole sales spiel also means shorter, leaner proposals – letting you apply to many more jobs, much faster without sacrificing any personalization.

Then, you’ll only put in the effort to sell when you:

  1. Have an information advantage over your competitors, and
  2. Are confident that the client is ready to be sold.

Time is money for freelancers, and this saves you TONS of it.

How to get more clients to reply to your Upwork Proposals

Ok, so how do you actually get those replies?

My favorite way is to end my proposal’s cover letter with a simple question about the job details.

This gives the client a specific action step, making it easier for them to follow through.

It takes much less brainpower to respond to a direct question than to formulate a reply to typical closing lines like “Hope to hear back soon”, “Let me know if you have any questions”, or worst of all: “I look forward to working with you”.

The concept of asking a question isn’t anything groundbreaking, and other blogs have tried to give this advice before.

The problem is, the way they execute is always a little “off” because they don’t understand the full psychology behind it.

For best results, there are a few simple rules you want to keep in mind:

1) Do NOT ask too many questions

Even if there are a dozen questions you want the answers to, don’t try to cram them all in your proposal. The goal is to make responding as EASY as humanly possible. Asking a question every other sentence or linking to a long survey will make replying to you feel like a chore. You can always ask additional follow up questions later, so try to stick to just one in your initial proposal.

2) Do NOT ask questions that are too tough

You don’t want your one question to be too daunting to answer either. For example: One blog post I saw tells freelancers to ask a question like “I have a couple more ideas I could share as well. When is the best time for us to connect this week?” This may seem innocuous, but replying requires the client to check their calendar and commit to scheduling something. That’s way more effort for them than if you asked something factual about the job that they could answer off the top of their head. Ask for the call later.

3) DO make your question the last thing

If you ask your question at the very beginning of the proposal, clients are going to forget it’s there. They most likely are sifting through dozens of proposals. Make their lives easy and put your question at the very end so they can immediately answer it without having to scroll back up and dig for it.

Example of an actual Moneyball Proposal

The following is a real proposal I found on another blog that only gets halfway there. That blog post does suggest asking a question to get replies, but the result isn’t as effective as it could be:

Original:

Hello ___ 

Thanks for the job invite. It's a pleasure to meet you. Can you please tell me more about your cloud based products and services? Also, can you send me a link to your site? What web platform are you using for your site? Do you have a monthly budget in mind for PPC advertising?

I am google adwords search certified. I have done adwords work for clients from all over the world in a variety of industries including the following: hospitality, marketing, real estate, retail, and tech. 

Best regards,

____

They use this as an example of a well-written proposal since the freelancer won the job, but that doesn’t mean that it can’t be improved (and them winning the job probably had more to do with the fact that they got an invite from the client).

You’ll see that this proposal breaks all 3 of the rules I gave above:

First, they ask four different questions. Sending a reply to this freelancer requires the client to complete the equivalent of a small survey. Too much work!

Second, the questions aren’t too easy to answer either. The first one in particular is extremely open-ended and presumably would require a several-sentence response.

Finally, the questions are all asked at the beginning of the proposal rather than at the end. Now, I doubt any client will think “Ugh I’m too lazy to look at the last paragraph to see what those questions were… guess I just won’t hire this person!”. But this DOES add unnecessary friction, and every little bit adds up.

Here’s how I might have edited this proposal with the following limitations:

  • I don’t know what the actual job post said, so I’m going to assume it was super vague.
  • I don’t know the freelancer’s skills and background, so I’m not going to add anything that might not have been true.
  • I’m going to stay as close to the original proposal as possible, since I want to focus on composition rather than writing style.
  • For example purposes, I'm going to rewrite this as if it were for a public job posting instead of an invite since that's more common.

Here it is:

Edited:

Hello ___

Whatever type of business you have, I’m confident I can help – I’m google adwords search certified and have done adwords work for clients from all over the world across industries like hospitality, marketing, real estate, retail, tech, and more.

One quick question so I can better understand where you're at and what you need: Do you have a monthly budget in mind for PPC advertising, or are you looking for suggestions on that?

Best regards,

___

The content stays true to the original, but the few tweaks make it MUCH easier for a client to reply to.

Just imagine this proposal hits them when they’re sitting in an Uber ride that’s ending soon, or when they’re sitting in a conference call where their attention is split. Chances are now much higher that they can reply right away instead of putting it off for later.

Note that I used only one of the four questions and made it even easier to answer by giving an “out”. If the client has no idea what their monthly ad spend should be, they can still reply with something like “I’m not sure, what do you suggest?”.

Only asking one question doesn't mean you'll always get a short response either:

If the client does have the time, they might not wait for you to ask and will reply to your single question with a giant essay containing the story of their life and all the minute details of their business.

And even if they don’t, their one single answer opens the door for a bigger conversation. In the next message, this freelancer can use this “exclusive info” (that other freelancers won’t see in the job description) to better sell themselves, or just ask the remainder of their questions if they need more info. Either way, it moves them closer to a sale.

A real sample of one of my own Upwork proposals

The section after this is where things get really good. I'm going to show you 3 more “Secret Benefits” from Moneyball Proposals that have nothing to do with what I've explained above.

But before we can move on, I need to quickly address what I know is going to be the #1 request:

"Can you share an example of how you write your own Upwork proposals?"

Now, this would definitely be the perfect place to show that.

But…

That kind of thing is too juicy to just throw into this already-long post, so I'm going to write a separate one later on.

If you want to get notified when that drops, make sure to sign up for my email newsletter. It’s free to join!

You’ll not only be the first to know when I publish new stuff, you’ll also get access to the things I want to keep a little more exclusive (like examples of my own proposals).

Just sign up here:

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3 More “Secret Benefits” from writing Moneyball Proposals

Ok, so we’ve already gone over how starting a 2-way conversation helps you get “secret” intel your competitors don’t have, making it much easier to sell yourself.

But there are other, less-obvious benefits to writing Moneyball proposals that make them even more effective:

1) “Interviews” scare away your competition

When a client replies to your proposal, you are now considered to be in the “Interviewing” stage.

This happens to be one of the things Upwork displays on job postings. Here’s how it looks:

Even if all the client did was answer your clarifying question, their reply will update the job posting to show all other freelancers that there’s at least one person being “interviewed”.

This has a HUGE demoralizing effect on other freelancers.

When your competition sees that the client is already “interviewing” someone (and maybe multiple people), they may wonder if they’re too late to have a shot. If they’re trying to budget their time, they’ll probably decide to just move on and find a less contested job to apply to.

A drop in new applicants also speeds up the hiring process – a steady stream of new proposals will make clients wait and see what else they get, but a sudden drop will push them to just decide on someone already.

You really shouldn’t obsess over how many competitors you have, but less competition obviously means higher chances of winning the job!

And that’s not all:

The Moneyball strategy has benefits even if you DON’T win the job…

2) Upwork pays you for each reply

For anyone who hasn’t sent their first proposal yet, “Connects” are the tickets you need to apply to jobs. It’s basically a system to stop freelancers from mass spamming copy/paste proposals to every job they see.

Each job costs between 1-6 Connects, and you can bid a higher amount to boost your proposal's visibility – but you only get a limited number of free ones each month before you have to pay money to buy more.

But there’s another way to get more Connects for free…

Every time you get to the “Interview” stage, Upwork will reward you with 10 Connects!

With a high enough response rate, you can hypothetically send an infinite number of proposals without ever running out.

Yes, even if the client replies with “I hate this proposal and would never hire you”, you still win Connects to apply to more jobs.

This client scoffed at my quote… but I still got the Connects!

… just make sure that’s not the only thing you’re hearing 😅

Finally, what’s arguably the most valuable benefit of all:

3) Upwork’s algorithms turn replies into invites

Getting more interviews boost your interview stats (which Upwork not only tracks, but openly displays on your “My Stats” page).

Here’s how that looks:

With a higher-than-average interview rate, their algorithm will consider you to be more potentially hirable (even if other stats like your hire rate aren’t quite there yet).

That leads to showing your profile in more searches and suggestions, which means more clients will send you job invitations.

Needless to say, you have a much higher chance of winning a job if the client is inviting you to apply.

Most new freelancers won’t have enough of a work history for Upwork to suggest their profile very often. But getting a lot of responses will really help get the ball rolling.

“But what if everyone on Upwork starts using Moneyball Proposals?”

After the Oakland A’s won their 20-game win streak back in 2002, all the other teams started copying their strategy.

The Red Sox actually tried to hire the Oakland A’s manager, offering the highest ever manager salary of the time – and they won the World Series just 2 years later (even though he declined).

Once everyone knew this “secret” winning strategy, it ceased to be an advantage and just became the new way of playing.

But lucky for you, Upwork is a different story.

I can see whenever I post jobs as a client. The vast majority of proposals I get are absolutely terrible.

Just publishing this free blog post won’t change that. For years I wrote about Upwork strategies (ghostwritten for other peoples’ blogs and courses), but only a small fraction of people put in the effort to read, and even fewer actually implement anything.

Just having read this article means you have a huge advantage over everyone else.

And this is just the tip of the iceberg. If you want even more of an advantage, make sure to subscribe to my newsletter for first access to new content and material I don’t release on the blog.

If you liked this blog post, things only get better on the inside.

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Special thanks to Daniel Throssell for heavily editing an early version of this post. Any issues with the current post are from me not listening to his advice.