How to use Upwork: a craftsman’s approach to landing clients on Upwork

How to use Upwork: a craftsman’s approach to landing clients on Upwork

Do you know who this is?

This man is in his 90s and still works around the clock doing what he loves… and it shows. 

He is widely regarded as the best sushi chef in the world. His restaurant was the first to receive the famous Michelin star and it got three of them EVERY year since the guide began including restaurants in Japan. 

They lost them all when the restaurant closed for the public and now only caters to guests with ‘special connections’ — world leaders and superstars.

Apparently, there are constantly five hundred people on the waiting list while the restaurant only seats ten people.

His food is so famous that Japan made him a national treasure and Netflix made a popular documentary about his work.

His name is Jiro.

One of his sons is helping him in the restaurant but Jiro doesn’t allow his son to cut the fish until after 10 years of practicing preparing the rice. 


Imagine just how good you and I would be at preparing rice after ten years of practice.

In fact, a bachelor degree and a master degree is five years. Imagine taking both of those in the topic of making sushi rice.


What is your first reaction? How can THAT take 10 years to learn? Glad you are not forced to follow in their family’s footsteps?

Sure, we can insult people and wonder what they are up to but the worlds’ best is the best for a reason. They are not dumb. In fact, it seems as if they figured out something that the rest of us haven’t.

The two secret benefits of a craftsman

I’m fascinated by the best craftsmen in the world. It takes something unique to be among the world’s best and it is exciting to see masters at the top of their game.

There are many books and podcasts that work to distill what got them there so the rest of us can learn from it.

The insights are often a balance of hard truths and sexy slogans like “work hard” or “don’t be afraid to fail” but there are many subtle things that are kept off the books.

In the world of Formula 1, motor racing with the most technologically advanced cars on earth, the competition is parabolic. Each race driver is a top athlete with an entire team of specialist coaches around them. So to win, every little detail counts.

Yet, when Lewis Hamilton, one of the most winning drivers of all time, switched to a vegan diet for better athletic performance, fans barely heard about it even though he won all three world titles since making the change.

We are often told that if we become good at what we do, the rest will come and it is insinuated that we will get what we want.

As comedian and actor Joey Diaz explained in an interview, he starred in the popular football movie The Longest Yard with Adam Sandler and was sure he would get his career breakthrough after that.

He just had to wait for the phone to ring…

…But it never rang. 

He discovered that he had to go out there and promote himself.

When we learn what it really takes, most of us don’t want to be the best. We don’t want to do the work it takes even though our wildest dreams would become real.

But we are lucky.

With freelancing we don’t have to be the best in order to land clients on Upwork. Who wants to be the best freelancer anyway? What does it even mean to be the best freelancer?

Instead of trying to be the best, we can make one simple tweak to double the responses to our proposals.

Many of us have somehow gotten into our heads that quantity is better than quality. That more shitty Upwork proposals are better than a few good ones.

It feels like more work because we tend to value the number of proposals we send out as if the quality was the same. 

But when I’ve worked with readers on their proposals, I’ve noticed better results by prioritizing quality first. 

So, why do we machine-gun shitty proposals?

…I actually tried looking it up with no luck.

The best I could find was the argument that we might have been exposed to it through our school systems, since the number of grades and extracurricular activities sometimes win over the quality of our assignments. Although, on the other hand, we still need some level of quality in our assignments to get good grades.

It could also be that we’ve heard the sentence “it’s a numbers game” and assume that it is black and white rather than grey — that there is no middle ground.

Either way, because most freelancers on Upwork aren’t proactive, they send proposals that appear the same to the clients and that makes it difficult to tell them apart. 

In comparison, the vast majority of freelancers I’ve seen appear to work from the goal of doing as little work as possible while still landing clients.

The hidden side effect is that we send ourselves a signal that we aren’t taking it seriously. Combine that with the fact that it is much harder for us to land clients and earn money, and we quickly start thinking of it as a failed project that we want to escape from. 

Not a productive way to learn something new…

Instead, approaching freelancing as a craftsman means we can leverage that our society rewards specialists with deep expertise — not just with the service we provide but also the way we provide it and talk about it to clients. 

Freelancing isn’t a great career choice for life because we trade time for money (imagine being a 90-year-old freelancer) but being a freelance craftsman helps us:

a) Start something that can give us total freedom AND where we earn money quickly instead of waiting years to see any return 

b) Craftsmanship has another side effect that most of us overlook: it is a good way for us to teach ourselves that we can do a hell of a lot more than we think we can

It serves as a great purpose for us to show ourselves that we don’t have to have a traditional job unless we want to, that we don’t have to be tied down to a particular city unless we want to, and most importantly, that we can achieve a challenging goal if we put our minds to it.

Basically, by doing a little more we reap disproportionate results.

The craftsman’s approach to landing clients on Upwork

This blog focuses specifically on landing clients online. It’s a little different to work with people online than what we tend to be used to from our jobs. 

Online, everyone has access to more information, more clients, more freelancers. More everything! 

how to use upwork

That means clients get more freelance proposals. Before the internet, the challenge was finding a freelancer that could help with the problems a client wanted solved — any relevant freelancer would get a chance.

Now, it is no longer a problem to find a freelancer with experience in the right tasks but instead, finding the RIGHT freelancer. This is a terrific opportunity but it also means that we as freelancers need to stand out more. 

Lucky for us, that isn’t too difficult since the biggest supply of freelancers is in the group of untrained, unprofessional, freelancers. 

A concrete example is an Upwork job with 20+ proposals. It might feel like an overwhelming amount of competition but in reality, at least half of the proposals are so bad that they don’t even count. Try creating an Upwork project and see for yourself.

At a high level, there are four Upwork proposals categories: 

1) generic copy-paste proposals that are not relevant for most projects

2) those that are (almost) custom written for each project but only talks about the freelancers’ experience or background 

3) the one that focuses on the client’s challenges and what success looks like for each specific project along with why this freelancer is a good choice to solve the particular problem

4) the perfect proposal. This one fits each project description well, focuses on client challenges, only shares relevant background info as it relates to the project and is based on extreme research

The first category wins projects if the client is desperate enough and there are no other freelancers that seem better right then and there.

Generally, the second category wins projects when competing with the first proposal category, for example, by giving away a free sample of the project before starting or through sheer luck.

In the grand scheme of things, the third proposal category is the best category for many Upwork freelancers. Where the fourth category takes a lot more time to complete, the third proposal is the sweet spot where our proposal is much better than most but without spending an insane amount of time. 

It usually won’t be the winner if competing with a rare, amazing proposal from the fourth category but if you move up from category one or two, you’ll experience a lot more interest from potential clients.

Starting out in the first group is nothing to be ashamed of — I did it too! It’s not like we are taught how to write good freelance proposals at school anyway. The essence here is that in a sea of untrained, or even mediocre, freelancers we will stand out like day and night by being a little better. 

Instead of approaching landing clients from the perspective of “how little can I work and still land clients”, we are taking the craftsman’s approach of “what can I do so I am sure that I will land the client?”

In other words, we move the focus from ourselves and what we want onto the client and their needs.

Most freelancers focus on being better at the skill they offer clients but at some point, everyone is good enough to solve the client’s problem. At that point, we can earn a lot more by focusing on the packaging of our service and the experience the client has.

We do it by working with fewer clients at once and impress them by going above and beyond right from the beginning, even before the project starts.

Imagine a nice present. It’s great in itself but it becomes extra exciting when it is wrapped and delivered nicely.

That extra wrapping might be your communication style with the client and the way you present the information and project you deliver to the client. 

For example, by offering comprehensive documentation if the project includes a technical setup of some sort, so if the team is working on it in the future they can easily understand what’s what without having to contact us.

Another example is sending frequent updates in an easy to digest-format if you know the client is busy and rarely has time to respond or do longer phone calls.


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