4 Tips to Win As A Freelancer on Upwork

Being a freelancer definitely has its perks: flexible hours, flexible location, and the freedom to choose which clients you work with.

But freelancing is not easy.

You have to handle insurance, taxes, and accounting all by yourself. You have to develop real discipline for getting shit done without someone telling you what to do. And, you have to constantly persuade new bosses why they should pay you.

Thankfully, Upwork helps make this process a little bit easier.


Upwork is a website that provides freelancers with short-term and long-term projects to work on. While it comes at a cost (20% off your paycheck, ouch) it’s a brilliant place to get started in the world of freelancing if you have no current network of business contacts.

I got started in early 2017 and have since found success getting a constant inflow of new job opportunities almost daily.

If you’re starting out as a freelancer on Upwork, follow these 4 tips and you’ll be getting job offers your way in no time.

1. Write a headline and bio about the benefits the client will receive from working with you.

Always lead with what you will do for the client. People want to know how hiring you will benefit them. So you need to create the picture in their mind for them.

Explain what makes you different — why your life experiences make you such a unique person, the right guy/gal to get the job done. Detail work or related experience you’ve done in the past to show what kind of results you get.

Complete your profile to 100%, meaning 1) list the skills you want to get hired for, 2) adding some samples of your work to your portfolio, and 3) filling out the rest of the background information (certifications, work history, and aptitude tests).

Bonus points if you create a personal video for your profile. I haven’t tested this out myself, but I’m eager to know the success rate of a well-made video.

2. Get a friend to create a client profile and give you a 5-Star ranking.

Yeah, I said it.

It sounds cheap, but if you’re just starting out, you need some type of “recommendation” or rating that gives a signal that you’re a real person and/or dependable. Otherwise people will think you’re spam or too green (which is true but you have to get that first opportunity somehow).

This starts you off on a good foot on Upwork. I don’t know the exact numbers on it, but I believe that after getting that first 5-star rating, the trust factor goes up exponentially higher for freelancers.

3. Make each pitch personal.

We all know we’re not supposed to shotgun a bunch of standardized proposals to everyone (though that’s not stopping some people). It’s so ineffective and no one talks about it, but it’s a HUGE drain on your mental battery. Getting high rejection rates can do that.

Instead, take the time to craft proposals that reference the original job posting, and give them confidence that you’re the right person to handle it, however you see it best to do so. When clients start responding to you, reply within 24 hours, to give them a taste of what it will be like to communicate with you.

The goal of a proposal is not to win it outright. It's to give you a chance to start a dialogue. The goal is to want them to be so impressed with your proposal that they have to respond immediately after seeing it.

One extra thing that worked for me was including a video pitch in the proposal. It was not something that took more than a minute, it was simply a video message that stated “Hi, I’m Evan” (a real person who can speak English), and what I wanted to help them get done. Not necessary, but I attribute the human touch to winning me a couple more replies than I would have.


4. Earn a Rising Talent badge.

This badge program is the accelerant to your success on Upwork. Literally, you will get so many more job offers THROWN TO YOU instead of you having to pursue them yourself. Upwork does the job searching for you and sends you things that you may be interested in (depending on your profile skills).

This is by far the best way to earn more jobs rapidly.

You’ll show up in search near the top way more often for clients who are looking for talent, and you’ll have a shiny badge next to your name that just makes you look so much more credible. Clients will reach out to YOU so that you can interview for their job.

You can get the badge by following Upwork’s guide to becoming a Rising Talent.


I hope that was helpful to all of the new freelancers. It's a fun life and the flexibility is awesome if you're the type of person who wants it!

Who else has had success on Upwork?

Comment below if you have any unique tips of your own!