How I Win High-Paying Clients on UpWork

Tessa Palmer
Feb 14, 2018 · 5 min read
The start of next week’s to do list. I couldn’t share the current week’s unfortunately, as it was crammed full of sensitive information about my clients!

I won’t beat around the bush: most of my current income comes from clients I’ve found through UpWork, not from my new business. But finding and winning projects on this growing platform can be a real you-know-what show. In this article I’ve put together below my top tips on how I find and win clients.

I love the clients that I’m working with at the moment, the wide-ranging projects that I’m working on and, most of all, I love being able to create my own schedule.

Whatever your reasons for going freelance, if you’ve already given it a go then you know it can be tough to find good quality and high-paying gigs.

So how do I find high-paying clients? Most of them have come from the global freelancing platform, UpWork.

As someone who’s had a lot of success from the platform, here’s how I’ve found quality and enjoyable income through UpWork:

Get 5 star ratings and positive feedback

This is the most important factor if you are just starting out. Even if this means taking a few low paying jobs to begin with, make it your mission to get several 5 star reviews on your profile. These will go a long way to give you traction to get more clients, and to start charging higher rates. Just like when I look up reviews on Amazon — if there aren’t any reviews, I’m a bit hesitant. Your potential clients feel the same way.

When you’re new, max out your proposal connects

I believe you get 60 connects when you first sign up, that refresh once a month. In the beginning I quickly ran out but over time these don’t matter nearly as much since clients will start reaching out to you directly.


If you’re not sure what to apply to, UpWork is a great opportunity to try new things. Pick one or two examples of quality work you’ve done (and enjoyed doing!) and can show as an example to a client. Use these examples to find similar projects that require similar skills. Upload these examples onto your UpWork portfolio.

Be quick

UpWork is a time-sensitive platform and there are many other qualified freelancers on it that are all vying to win the same proposals that you are. If a client messages you, try to get back to them ASAP. Quite often jobs are won because you’re the first person who got back to them. Get the app to stay on top of messages.

Speed also goes for applying to proposals. Stale projects that have been posted for several days if not weeks are unlikely to garner much of a response. Sort active proposals by time posted and apply to the most recent ones first. Again, you may just be the first credible person who got back to them.

Ignore some of the stats

I don’t pay any attention to how many people have applied for the project and I don’t think this should put you off applying, especially if the job is fresh and highly correlated with your specialist skill set.

Pay attention to the budget, but take it with a grain of salt

Instead of focusing on the client’s budget, I tend to pay attention to the type of freelancer they’re looking for:

  • experienced
  • mixed
  • cheapest rates

I don’t apply for clients looking for candidates with the cheapest rates, because they often have laughably high expectations for very little pay.

For the budget, clients often don’t know what to put so if something takes your fancy but the budget seems a bit off, go a head and apply. If you showcase yourself well and impress the client, they may be willing to compromise and meet you in the middle.

Don’t waffle with long, wordy cover letters

My cover letters usually go something like this:


I saw your proposal and I believe I am a great candidate for you.

I have x years experience / a background in / have done a similar project before [1–2 sentence of skills specific to job]. Here are some links to my previous work / portfolio / see attached relevant examples.

[One or two genuine questions about the proposal]

I would love to connect with you to find out more about how I can help. Do you have some time this week to chat?”

Short, sweet and to the point. I like to ask some thoughtful questions for two reasons: 1) to engage with the client to encourage them to respond and 2) to make sure the job is actually the right fit for you.

Think about the type of work-streams you want

There are many arguments over the benefits of hourly work vs. project-based work. Project work takes some knowledge on how to price your time correctly. It’s easy to underestimate the total time you’ll spend on a project which can be stressful and result in low paying work. Project-based work can also often lead into project scope. BUT clients are sometimes more hesitant to pay hourly and you can sometimes lock in a bad rate which is awkward to change later (you should always re-negotiate your rate though, if you need to!)

Be friendly and open to calls

If you’re not yet overwhelmed, don’t forget to be friendly and to try to engage with potential clients! I like to jump on a quick call to cut down on wasted time spent sending messages back and forth. It can put your mind at ease too, to know whether it’s a red or green light. It’s also a good opportunity to show them that you’re a friendly, intelligent candidate and can connect over any shared interests. Or likewise, if they sound a bit creepy and a nightmare to work with, calling will let you find out that information early on so that you can run far, far away!

All this being said, I’ve certainly done a lot of trial and error and made quite a few mistakes along the way. The great thing about UpWork is that it’s quite forgiving, so don’t be afraid to experiment a little. Hopefully the above tips are helpful, whatever stage you’re at on your freelance journey!

Finally, please don’t despair!

I’ve been there. Keep ploughing through and remember it usually only takes one great client to turn around your situation. Be consistent, be aggressive and keep trying. You will find something!

Summary of my tips:

  • Get 5 star ratings and positive feedback
  • When you’re new, max out your proposal connects
  • Experiment
  • Be quick
  • Ignore some of the stats
  • Pay attention to the budget but take it with a grain of salt
  • Don’t waffle with long, wordy cover letters
  • Think about the type of work-streams you want
  • Be friendly and open to calls
  • Don’t despair!

Tessa Palmer

Written by

Life after quitting the rat-race.

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