Upwork tips: the good, the bad, and the ugly (& the ONE tip for success)

Upwork tips: the good, the bad, and the ugly (& the ONE tip for success)

The best Upwork tips I’ve ever gotten was when my friend gave me specific feedback on my proposals.

At the time, I was getting projects randomly here and there, and his advice helped me to be able to land projects week in and week out, month after month. It allowed me to predict exactly how many proposals I had to create in order to land a client.

The key points he shared with me were to write a better proposal hook, not to ask questions right at the beginning of the proposal, and that the goal of a proposal is to get the client to reply.

That last point is key, the goal of a proposal on Upwork is NOT to get the business to hire us right away but to get a reply. The rest will come through a phone call or further messages.

In this article, you and I will debunk some of the shitty and hilarious tips I’ve found around the internet, and look at some counterintuitive tips to land more freelance projects on Upwork.

Hilarious Upwork tips (follow with caution)

Let’s start out by looking at the funny side of things first. I’ve collected some well-meaning advice and Upwork tips that feels good to read but doesn’t do any good if you are serious about landing more freelance projects.

Lower your rate to get projects in the beginning

If we don’t have a profile full of case studies, why would anyone ever hire us?

The idea is that by lowering our rate perhaps we can strike a deal and get something to show off on our Upwork profile.

The reality is that clients pick who they work with for many reasons. You wouldn’t believe the number of times I’ve landed a client without showing ANY past work.


Years ago, I had the same conversation with a friend who is more experienced than me and runs an agency. He told me the exact same thing and even pointed our how rare it was for him to actually show anything like testimonials and case studies. 

At the time I didn’t understand how that was even possible, yet now I share the same point of view. I guess this only changes with experience.

Do free work now for exposure later

This is a common one as well and someone once phrased this really well: Good clients never want free work. 

If you surprise them with something cool, they’ll love it but they will never engage you trying to get free work. The quality is more valuable than the money it costs, and by paying for our time they are reserving it so we can focus on delivering something good.

If we are building a portfolio or wanting exposure from someone, imagine working full-time with them to do something amazing.

Then the question becomes do we really want to spend that much time doing an amazing job for someone who can’t afford to pay us?

If they can’t afford to pay us, despite what they might say, it is unlikely that they are doing well and thus what we would be learning from them wouldn’t be worth much.

Only shitty clients will ask for that with a meaningless promise about exposure after. Every time I’ve worked with a shitty client and every time I’ve worked with a great client this has been proven to be true.

Follow with caution.

Get more experience or certificates

This follows the same advice as above. In some rare cases, it makes sense to get more certificates if it is related to something ultra specific or if we work with high-end clients like Fortune 100 clients.

But in most other cases, it is something that is nice to have but doesn’t really make that much of a difference.

If we don’t have any experience, getting more is probably a good thing but often even experienced people feel this way. It tend to come from a lack of confidence or from a fear of selling rather than not actually being able to do a good job.

For many freelance projects, if worst comes to worst we could simply put in some extra free hours to make sure we do a good job or offer the client their money back – but it rarely comes to that.

The way we know that we are procrastinating is if we can’t pinpoint specifically when we have enough experience.

If the answer is when we have done a particular project, we can simply do that to gain the experience.

If it is a certain certificate, what happens when we get it? Why is there a change? Have we felt this way before and then gotten the certificate only to want another one?

If you disagree, simply get the certificate (or complete the project) right now and see how you feel.

Take the Upwork skills tests

I’ve never taken any tests except for the one that is mandatory when we sign up for the platform.

It’s one of those things that make us feel like we are making progress when it really makes no difference – similar to certificates.

Make sure your profile is perfect

Before even bothering with this, here’s the main question to ask ourselves: when is it perfect? What makes it perfect?

Most of the time, this is another way to procrastinate and avoid diving into the uncomfortable meat of it: sending proposals and pitching clients.

So many clients never checked out my freelance profile when they hired me or contacted me from a proposal. How do I know? 

Because in the “my stats” section on Upwork, we can see how many profile visitors we have. If say, I send out 20 proposal per week, ten respond but I only have two new visitors to my profile, that means that at least eight didn’t look at my profile.

Proven Upwork tips to get more clients

Next, let’s look at some specific field-tested tips that I have experimented with and used successfully.

Send fewer proposals and spend more time on each one

Go deep on a few proposals rather than mass-sending things until you find a way that works well for you (then you can figure out how to make it more effective).

Write proposals the way you’d like to receive them if you were a client. You might even send the proposal to yourself via email and act like you are the client reading it. Would you hire you?

Be a “try hard”

Being a “try hard” (showing that we are working hard) is usually not seen as cool but business owners will often appreciate it because they are among the few who know that it is necessary. We’ll often get a lot of points just for trying hard.

Work to accept the hard fact that even if we have the right skills, the client might just not recognize it because they are busy.

Instead, focus more on building trust with the client and accept that they might not hire a stranger that they don’t know, even if we have the right skills.

We can build trust with them by over-communicating and showing them that we are organized.

Point out the elephant in the room

If you are not able to land projects in the beginning, here’s another approach than to lower your rate or do free work: point out the elephant in the room, in your proposal. Point out why your profile is empty.

For example by saying “I’ve been freelancing for X years and recently decided to try Upwork, that’s why my profile is empty. I’ve attached testimonials from former clients outside of the platform.”

Or if you haven’t been freelancing before, you might attach testimonials or case studies from personal projects or work, and ignore talking about your experience freelancing since most people don’t care at all anyway.

They care more about your experience within the project you are doing, but really they only care about that because it appears as a good indicator for if we can do their job well. Another great approach is to focus in detail on how you’d do the project itself by outlining the process for them.

If you don’t feel confident yet, you could do a trial run of the project so you know the steps. Preparing is one of the secrets of successful people.

Use a friendly profile picture and why going to a studio doesn’t make a difference

On the surface, this sounds obvious and may even seem like a dumb, useless, tip but the harsh reality — whether we like it or not — is that it is human nature to make a quick snap judgment based on our photo. 

The counterintuitive part is that what makes a good photo is not that it is done in a studio but rather that we appear friendly and easy to work with.

The best way to appear that way is with a smile. Using your phone is perfectly fine and Danny over at freelancingtowin.com has a great tip of using photofeeler.com to take the “temperature” of how approachable the photo is.

upwork tips - good profile photo example

Basically, you upload your photo there anonymously and people will rate it for things like likeability. I see some freelancers remove the background of their image and replace with e.g. an all white or blue background that is clearly photoshopped. 

The idea is good but in my experience, if it is clearly photoshopped it makes clients feel that it isn’t real and so they can use it to trust us since it isn’t an accurate representation of what we look like.

That is often a mismatch between eastern and western values and there no right or wrong, only how the client reacts.

If I pick just ONE tip for Upwork

The reality is that many of these tips are writing for your entertainment. Not because I don’t believe in them but because I know from experience, that realistically we can’t do that many new things at once and make sure they stick.

If there was just one thing for you to take away from this article — to get the biggest bang for your buck in terms if the time you spend vs the results you’ll get — it is one of these two things:

  • Send VERY personalized proposals and spend at least an hour on each one
  • Practice getting better at finding Upwork jobs with serious clients that actually hire

The second one seems a bit unusual but as you’ll see in my case study on freelance digital marketing, I tracked my proposals and for more than 50% of the projects, the client never hired anyone. It’s difficult to land a client if half the ones you spend time on never want to hire.


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