How to be successful on Upwork

How to be successful on Upwork (meme edition)

Want to make $1,000/week on Upwork? Read the article to discover how to become successful on Upwork. Tested and proven.

There’s a real philosophical debate about what ‘success‘ means, what it entails and how to achieve it in your life. Success can mean so many different things to so many different people based on their personal tastes, affinities, life experiences and uprising that it’s almost undefinable.

While we could debate for hours about this concept, I’d like to cut it short and stay pragmatic. To me, among other things, there are two important factors that define success on Upwork:

  1. Money: The reason why you signed up on Upwork in the first place is usually because you want to make some money. Let’s face it – we are all after it, and making a shitload of money on Upwork would be a good sign of success.
  2. Popularity: Being popular on Upwork has a very specific materialization. When you’re a top-rated Freelancer with a 100% success rate and one of the first search results in your field, one can say that you’re quite popular.

To reach Upwork’s version of King Arthur’s Holy Grail, here are four tips that I would recommend to any newcomer.

Looks matter.

That’s the number #1 tip I give my students whenever they ask me where and how to get started with Upwork.

I have never, ever seen a ‘successful’ freelancer on Upwork that had a half-baked freelancer profile with a shitty profile picture, a boring headline, and a confusing skill set.

If you’ve not read my article on ‘How to write a successful Upwork profile‘, I highly suggest you to go read it. Basically, your profile should be perfect:

  1. It should be 100% complete.
  2. Your headline should be compact and powerful.
  3. Your description should follow the Hook, Achievements, Skills, Call-to-Action pattern.
  4. Your skills should be coherent.
  5. Your portfolio should be written like a story.
  6. Your past experiences should be succinct and coherent.

If you follow all my tips, your profile will look neat and you’ll find interesting gigs even with no Upwork history.

In an upcoming article, I’ll discuss the “Art of Proposing” and tell you exactly how you should talk to clients to get gigs even when you have no Upwork history.

Reviews matter more than money

I’ve been in this situation, and most of my friends as well.

Basically, you’re dealing with a really obnoxious client. This client wants you to do things that were not previously agreed upon, or he wants you to revise things that are perfectly acceptable.

He ends up becoming threatening, saying that if you don’t comply with his petty requests, he will leave you a one-star review, and kill your freelancing career in the egg.

So, what should you do? Comply with the bullying and hope he’ll leave you something at least above a 4-stars, or completely cut your losses?

From my experience, it’s absolutely counter-productive, both psychologically and money-wise, to keep going and work for this client. The petty requests will keep increasing, and it will become an endless vicious circle of fear, bullying and free work.

On Upwork, if you refund a client, his review basically gets removed from the face of the Earth (your profile, here). It may still affect what’s called your “JSS” (Job Success Score), but it will look as if you never worked for this client.

Giving money back to your client even though you did the job. Sounds crazy, right? Wrong! Think again.

By refunding your client small money (let’s say $500), you’re basically making sure that your profile looks neat, and that it looks acceptable to land bigger, juicier gigs.

Imagine a client with a big budget right in your field – he’s got $5,000 to spend. He goes to your profile, and sees this review along with a cute 1-star:

Horrible freelancer. Zero communication. Underperformed. Don’t work with him.

Do you think that this client will choose you over someone who doesn’t have this kind of shitty reviews?

I cannot emphasize it enough, so keep it in mind: reviews and how your profile looks is way more important than money.

Long-term is better than short-term

Upwork is not Tinder.

When you get started with your freelancing career on Upwork, you may not be able to tell the difference between two $50 gigs. After all, they pay the same, right?

It’s totally OK. It’s a skill that takes time to develop, and it will help you figure out whether a gig is worth the time it takes to apply to it or not.

However, there’s really a science behind it, and successful Freelancer know exactly what it’s all about.

Let’s imagine for a moment two different freelancers with two totally different strategies. Basically, short-term vs. long-term:

James – the short-term guy
He likes his gigs short-term (max. 7 days). He rotates clients often and applies to new gigs on a daily basis.
John, the long-term guy
He likes his gigs long-term (at least 2-4 weeks). He’s got a couple of recurrent clients and applies to new gigs once in a while.

OK, so here, we have two guys. One is called James, the other John. Both have two different strategies. James thinks that he can make a living just stacking short-term gigs, and John thinks that only long-term, meaningful relationships with clients are worth the struggle.

Let’s imagine this situation:

  • James gets around 10 short-term gigs per month. These gigs range between $100 and $250.
  • John gets around 2 long-term gigs per month. These gigs range around $250 and $500.

Who do you think is right, James or John?

Anyone looking at these raw numbers would be tempted to say that James is right. Indeed, you made the mental math and you can tell that he’s making more money on average than John. And isn’t it why we are working on Upwork, after all?

The thing that most people overlook is that freelancing involves a lot more than just simple additions. Basically, there are two factors to take into consideration during the whole process:

  1. Time spent looking for a gig: At the beginning of your career on Upwork, it will take you dozens of hours to find good gigs, write compelling proposals and convince clients to hire you. The process will be the same for both ‘good’ and ‘bad’ gigs.
  2. Upwork’s fees: Upwork takes its fair share of your earnings. And the more you make, the less the take. Really.

In other words, as you’re moving forward with your Upwork freelancing career, it will remunerate you better to focus on long-term clients when all things are taken into consideration (including time spent).

I’ll soon write an article describing in detail why long-term is far superior to short-term.

Maintaining rather than changing

You’re guilty. Admit it. I must admit that I’m guilty too.

In today’s world, we are prompted to change stuff all the time, rather than maintain them.

As you grow older, you start to realize that all these changes are more artificial than natural. They’re the way capitalism works. Things need to change in order for the economy to survive. Companies have to sell stuff. You have to buy stuff.

When we get a new car, we want to change it after a couple of years. The same happens with our phones, computers and even partners in some cases! Crazy.

This pattern is so omnipresent and deeply rooted in our weak minds that we automatically apply it to all areas of our lives. And unfortunately, you may be tempted to do the same with your Upwork freelancing career.

You’ll notice that there’s no shortage of “fresh” batches of new clients. So, at the end of the day, why would you bother keeping old, boring clients when you could get new clients? Maybe these new clients have more money, right? Maybe these clients can make you rich when others couldn’t, right?

That couldn’t be more wrong.

There’s something that’s called “trust“. I cannot emphasize it enough. Trust is at the core of any business relationship, and it’s something that takes months or years to develop.

When a client gets on Upwork, he doesn’t particularly trust anyone on the platform – quite the opposite. He has absolutely no reason to trust you more than anyone else, and even less so with his money. This, alone, explains why most clients want you to perform a “test” gig before anything.

Trust is so difficult to obtain in clients that it’s something that should be cherished and maintained. At the moment you start working for a client, the whole trusting process begins. And it gets only better and better.

From my experience, once a client trusts your abilities to deliver, he will give you more stuff to do. Or at least, you’ll be the first person he thinks of when he needs something that you can do.

Now, imagine that you develop this kind of relationship with a dozen clients, all of them regularly rotating long-term. Do you understand where this is going?

That’s the thing. That’s the real key to your freelancing career on Upwork. Maintain good relationships with your clients and you’ll (almost) never have to spend time looking for work ever again.


Being successful on Upwork is really an iceberg that would take a million years to melt. However, I believe that I gave you 4 important keys to kill it on the platform. These keys are a bit unusual and focus more on ‘fundamental’ values rather than tips & tricks:

  1. Make your profile look perfect.
  2. Prefer reviews over money.
  3. Look for long-term gigs.
  4. Maintain good relationships with clients.

I’ll probably write a series of additional articles on the topic, and eventually, make a compilation of all the tips. At least, I hope this helped you on your freelancing journey!