Upwork proposal tips: When freelance projects fall down from the sky

Upwork proposal tips: When freelance projects fall down from the sky

Before we dive into the four Upwork proposal tips, I’d like to show you something first.

I normally don’t check emails in bed.

But this one morning I forgot to turn off the notifications and in came this…

I had to pinch myself to make sure I wasn’t dreaming. Having a project fall down from the sky is nice but that wasn’t why this was a big deal.

The sender was. 

This was someone I had been wanting to work with for a long time. I had been following their work and I knew that I could learn from them.

And there it was… their project in my inbox, staring me right in the face. Out of the blue.

It just fell into my lab.

I didn’t show any previous work or sent a proposal. And THAT made it confusing! Compared to my experience on Upwork, this was amazingly simple.

But let’s pause and zoom out for a second.

This is a real-world example we often see used by experts. But things are left out. For example, how the two parties knew each other in advance. Maybe it’s casually mentioned as an afterthought — if at all — but it deserves more attention.

The trust that they already have with each other is what makes the difference and that takes time to build between two parties.

This story is no different and today, I want to peel back the curtain and show you what we normally don’t get to see: how this REALLY happened and what we can take away as Upwork proposal tips for ourselves.

Let’s dive in!

When a freelance project falls down from the sky: the part you missed

Getting that email you saw was the final step in the process.

Three months earlier they offered me a similar project but due to technical payment challenges, we couldn’t move forward. In an attempt to impress the client, I offered to do the entire project for free but they declined.

Before that, I had been casually emailing this person every 1-2 months sharing interesting things I thought they might like. Usually, I would not get a reply or if I did, it would be a simple “thanks”.

That didn’t discourage me because I knew that they were busy and I didn’t expect a response.

That is all… except, that I did that for twelve months. I know that as you are reading this it might feel like there was something left out but there were no secret meetings or phone calls. 

In fact, we never had any communication except for those emails. One of the few clients that prefer to do it that way.

This has happened many times before. Even years after. 

Upwork proposal tips - response from a client

The other day, I was on a call with a reader and they shared how they hadn’t been speaking with this one client for a year but suddenly that business sent them a project worth at least $500-$1,000. All the reader had to do was jump on a call with them and draft a proposal afterwards. 

Why this works

This is the value of a relationship, the by-product of focusing on others first and being a trusted advisor.

It starts with offering a great service that helps the client solve their problem. Otherwise, they are hiring us from desperation and we will be replaced whenever they get a chance. Like when we go to a restaurant we don’t care about but that day, everything else was closed. We know we are not coming back unless we have to.

That service might be driving sales if you work in marketing, delivering mouth-watering images if you are a photo editor or building a website to spec if you are a developer.

Next, we add another layer: just like when we buy juice at the supermarket, we want to buy the one that looks attractive over the one that isn’t. That layer is great packaging.

Packaging can be seen as the overall experience and it might be helping busy clients do everything that we can for them, so their life is a little easier. For example by offering something as simple as three different call times in their specific time zone, so they don’t have to think about it and can simply answer with the one they prefer. 

Another example might be offering advice that benefits that client over our own business. Often the client doesn’t realize that what they are asking for might not be the best solution to what they are trying to achieve.

If we would earn more by helping them with what they are asking for, we can help them more by suggesting a better solution we know of, even if it turns out that we earn less (e.g. by using an automated tool instead of having us do a task manually).

Then, finally, the tip of the iceberg is great marketing with the emails you saw earlier.

We live in a world where everyone wants something from us, especially if you have a successful business. Think about the emails you got in just the thirty days. Whether they were newsletters from a store or someone from work, how many of them wanted something from you?

In a sea full of “me, me, me”, those who consistently focus on others, for example, by sending a thoughtful message and adding value without asking for anything, stand out like a sore thumb. Simply because no one else bothers to do it.

Strangers even do it to me and I like it. It isn’t some hacky trick. This has worked for years because it is genuine, thoughtful, human interaction. You know, like we used to do before the internet.

I’m guessing that the reason no one else does it is that we don’t see immediate results. We love to know that when we do A, we get B. At the same time, we tend to feel that the time is wasted if we don’t get a specific outcome.

Proposal tips for Upwork and both new and existing clients

As I’m working on an upcoming experiment, I’m reminded why I found Upwork so annoying the first time around.

I spend excessive time searching for the right projects. Not only are 80% of the relevant-looking projects actually not great, it is challenging to find truly good projects and clients for freelancers outside the US.

Of the remaining 20% of the projects that seem decent, the majority of the clients are hobbyists or tiny businesses. That means they have no money to pay us and many don’t hire for the majority of their projects. 

Here’s an example response I got on an Upwork proposal recently.

Upwork proposal tips

And another example

Upwork proposal tips
another example

That leaves few projects for us to help with if we are looking to take this freelancing thing seriously. 

From research, it appears to be due to the landscape on Upwork right now. They appear to focus the bigger companies on vetted freelancers and the rest of us have to work our way up from shitty projects with small clients to earn the right to work with real businesses.

This makes perfect sense from Upwork’s perspective but doesn’t help us. The interesting thing is that we tend to believe that that is how it is supposed to be because that’s what everyone says. So how could we even know that it could be different?

Let me show you another that works well with existing clients but tends to leave a GREAT first impression when you send new proposals on Upwork or elsewhere.

Imagine you are a freelance client. It’s Saturday morning. The sun is shining and you are having breakfast with steaming hot coffee.


Your phone beeps and an email ticks in.. You pull it up. The email is from your freelancer.

“Good morning, I wanted to give you a quick status update on the marketing project.


As part of building a growth engine, the search ads are stable and our avg. sale is $50 with a cost per sale of about $25 (2x return). 

This week, we had 100 sales, with the Buzz Lightyear-toy being the most popular (63% of sales). The Facebook campaigns are live as of this morning and the SEO campaign will go live tomorrow.

Here’s what I’ll do next…

  • Prepare the email campaign (deadline: Friday)
  • Interview freelancers for the outreach program (one Tuesday, one Wednesday and one Friday)
  • Research if Pinterest would be a relevant channel for us to use for scaling (deadline: Wednesday)

Attached is a detailed report for the week.

If you are interested in more details, I have attached a detailed analysis. Unless you have any questions or comments, no reply needed.

– Chris”

What’s going on here?

If you’re a client, getting a simple (timely) update feels relieving. The summary works because we know that our client is busy and depending on how much time they have available, they can choose the executive summary or the detailed update. It shows that we thought about them.

The detailed analysis serves to build trust while making sure that we as freelancers communicate everything necessary so that there are no surprises and the client doesn’t come back later and say “you didn’t tell me that”. 

Take a look at what my old clients have said:

Upwork proposal tips response

Another example

Most clients have never worked with someone at the top of their game

When we work to get dream clients that love us, there are two aspects:

  1. A client that is reasonable and a good fit
  2. A freelancer that is professional

Getting reasonable clients is more out of our control than us being professional. While we can’t control that entirely, we can look for specific traits in clients before we take them on. 

Often, the biggest difference we can make for ourselves consists of three things:

  1. Picking the right market
  2. Vetting clients and making sure they are a good fit
  3. Not being desperate (saying no when necessary)

Picking the right market is about finding clients who can and want to pay for us going above and beyond.

Some clients are price-sensitive and prefer a transactional relationship whereas others are more focused on results or convenience such as saving time. The simple way to figure out what our prospect prefers is to ask them. That’s why I like to get on a phone call to talk about their project before starting.

Vetting the client to make sure we have the same expectations is critical in getting clients that will love us.

It is important not to be desperate for the money because it will lead us to take on projects that are going to fail, and potentially send us into a downward spiral.

We have more control over the second part: ourselves.

One of the most surprising things I’ve noticed is that most clients have never worked with a really great freelancer.

That means they don’t know what ‘great’ looks like, why they need it and most importantly why it’s worth paying more for.

It is challenging to understand upfront but as soon as clients see it for themselves, they love it. You and I will dive deeper into showing instead of telling in the next chapter of this article.

But first…

Why would we even want to be someone at the top of our game?

In short, it builds trust with our clients. That means less micromanagement, more room to be creative (if that’s your thing), and when there is a challenge we tend to get the benefit of the doubt because we’ve been trustworthy in the past.

Trust goes so much deeper than simply delivering results.

But most importantly it means we can negotiate more money for ourselves because we are not only doing tasks better but also taking more responsibility. That translates to less headache for clients.

Every client wants to trust us and wants to be able to trust our work. It is the most powerful thing for them because it means they can be hands off or focus on solving other problems.

They might not be aware of it but let’s think about it. Why would someone hire us if they wouldn’t want to trust us working on their business? It makes no sense.

The challenge clients often have are previous scams, that they had shitty work done before by another freelancer, or they may not be self-aware enough to realize that their instructions to their freelancers aren’t good.

Upwork proposal tips to impress clients with your service packaging

Let’s take a deeper look at what we can do to make our clients love us right from when they meet us. If you recall from earlier, we had three different elements: the service, the packaging and the marketing. These four examples are a part of the packaging.

1. Don’t put unnecessary pressure on yourself

I notice many new freelancers pressuring themselves to be good at something they haven’t done before (whether intentionally or unintentionally). By doing that we put ourselves in a situation where we feel the need to deliver something we have no idea how to do.

I’ve found that clients often are happy if we help them with extra projects besides what we were hired for, even if we are new to the topic as long as we are upfront about it.

There is a fine line between that and taking on small projects that are slightly above your level. It often makes sense, especially if you are comfortable giving your client a few extra hours for free to learn and level up.

I like to approach it by drafting a fair time estimate for each part of the project that I don’t feel sure about, and how long it will likely take me to learn. If you don’t know, go look for guides on how to do that task or ask a friend who has the experience.

Rather than putting pressure on ourselves to perform at something we’ve never done before, we instead enter with the mindset that this is something we need to learn step by step and to do that, each step requires practice. Multiple times. That is the same premise for everyone.

2. Are you and your client thinking big enough?

Most freelancers are crowding a tiny space (e.g. talking about conversions in online marketing) instead of the bigger picture.

What happens when clients get the conversions they dream about? What’s next? Do they want to stabilize the sales? Change to organic marketing channels? Scale? Build a team? Figure that out and see if you can help them with the whole thing or a bigger portion instead of just the first step. To figure it out, ask them.

If you are a freelance copywriter: how about learning the strategy behind the articles you are paid to write, so you can help your client figure out what’s next?

Deeply understanding the field our client is playing in is a service to them because we can help propose solutions for their business they didn’t even know existed.

3. Having service standards will impress them

One of the simplest things we can do to make clients love working with us is to bring good etiquette to the relationship. 

Freelancers are notorious for disappearing mid-project and many are terrible at communicating effectively with their clients. 

It gives the client a headache, not to mention the extra work, and they will replace them for another freelancer as soon as they can.

Freelancers are sometimes brought on to a project because they worked well with another freelancer in the past. Often clients will ask their freelancers if they can recommend other freelancers with a specific set of skills they need, but if we are not good at collaborating, we won’t be referred.

The way to make others love working with us is to make life easier for everyone we work with. For example, when we send emails, don’t make them look for links or other things we referred to in the project. Instead, spend an extra 30 seconds to include it right there so it is easy for them to find!

No one likes surprises, keeping relevant people in the loop frequently is a good “trick” as well. 

If something fucks up — and it will at some point because no one is perfect — it will be tempting to hide it. Instead, we need to share the situation with the team as early as possible if it affects the deadlines, recommend a new deadline and explain what we are already doing to fix it. They’ll trust us more if we do.

My personal favorite is if we say we’ll do something, do it!

When meeting clients, tell them you’ll take notes and update them via email immediately after. Then do it. By setting artificial deadlines and sticking to them, we show clients that they can trust that we are reliable and there when they need us.

Employees tend to bring problems to their boss without solutions. Don’t. Instead, be the hired gun that suggests solutions and work to solve problems instead of just pointing them out. If not, eventually we’ll be seen as the person who brings problems to the client. If there is a challenge in the project, brainstorm a few different solutions and suggest a recommendation.

The client will feel a huge difference if they have to think up the best solution for us compared to us coming to check in with them if we can move forward with our recommended solution.

Showing them that we can think on our feet and make good decisions will give us extra points. After working together for a while, they might even want us to simply execute without asking them because we’ve built trust with them.

Especially if we are a new freelancer billing hourly, doing these things simply means we can earn more money (but be fair when billing them).

4. Ask for feedback and update your client regularly

This one might feel uncomfortable which is why so many people don’t do it: Ask for regular feedback. Weekly is probably a good start.

That way you make sure there are no big surprises and you know you are heading in the right direction, working on the things that matter the most to your client. 

As a rule of thumb, keep them updated about their business often and make their decisions easy. That’s how the decision to pay us more and give us more work becomes easy too!

Applying Upwork proposal tips in the real world: behind-the-scenes

In the email newsletter update that came with this article, I’ve attached a behind-the-scenes video that is only available for a few days.

You’ll get Upwork proposal tips and follow the process of deciding on a good Upwork project, what I look for and how I wrote a proposal that got the client to respond.


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