Hacking Upwork: How to score the high-paying gigs


Jackie Lam

Jackie Lam

Blog author Jackie Lam

Jackie Lam is a money writer and educator. She helps artists and freelancers get creative with their money at Hey Freelancer.

Published|4 min read

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If you’re a freelancer, you may have been told to avoid freelancing platforms such as Scripted, Upwork and Freelancer. They have a bad rap of being loaded with low-paying gigs, and you’ll have to compete with eager freelancers who’ll charge a fraction of your rates.

I had a bad experience with these platforms a few years ago when I took an assignment to write product descriptions for an online Halloween costume store. After six hours I was only $40 richer. My spirit was crushed, and I vowed never to take another gig on one of those platforms again.

But when my freelancer pal Chad recently told me how he’s managed to land high-earning gigs on Upwork, I was interested. Surprisingly, there are freelancers who tout earning up to six figures on Upwork.

Curious to learn how, I reached out to a few freelancers who have earned a lot on Upwork for their top tactics to hack the platform and land high-paying gigs.

Establish a niche

Find a specialty, said Carissa Lintao, a 21-year-old app strategist who earns 90% of her income from Upwork. For instance, instead of promoting yourself as a “social media strategist,” a heavily saturated role, figure out which industry you specialize in, said Lintao. Through trial and error and taking on projects in different areas, Lintao learned app marketing and content was her niche.

If you don’t want to get too industry-specific, home in on specific skills. For instance, tout the fact that you excel at image curation or initial social media strategy.

Experiment with different job titles

Along the lines of establishing a niche, try out different job titles, said Chad Eschman, Los Angeles ambassador for Upwork and company director for Trap Street. Eschman started with general job titles such as “blogger, designer and copywriter.” Now he's a “brand story specialist.” Because it’s specific and what he’s truly an expert in, companies know to come to him when they’re looking for someone to help develop their brand story.

Go for the smaller projects first

Another tactic to land gigs on the platform is to apply for smaller projects you know you’re overqualified for, then work your way up to larger ones, said Lintao. Remember: Having a high rating is everything.

“A lot of people make the mistake of biting off more than they can chew and get poor reviews and feedback, which looks really bad on your profile when you're just starting,” said Lintao.

Instead, apply to small jobs on which you can overdeliver. As you get more projects and positive feedback, you can up your rates.

Optimize your profile

Besides stuffing your profile with keywords to make it easier for prospective clients to find you, use your profile to showcase your chops. If possible, show, don't tell. For instance, Eschman’s original profile was essentially a list of his abilities written in an overly professional voice. His profile now starts with a story about the time he got set up on a blind date on Yelp.

“It’s made a huge difference to simply show the power of storytelling, rather than explain it, and to do so in my own style,” said Eschman.

Ask for detailed feedback

Politely ask your clients for a detailed and specific review of your performance on a project, said Lintao. It doesn’t have to be long. A short paragraph, as long as it’s detailed and talks about how you contributed and brought value to an assignment, is golden. Lintao suggests asking right after your contract ends.

Create specific proposals

Proposals need to be handcrafted and targeted, said Eschman. You wouldn’t approach a potential employer with an uninspired, generic message, so prepare detailed proposals.

“I’ve learned to talk to clients not like general prospects, but like individuals with unique situations, which they are,” said Eschman. “I’d rather spend a big chunk of time on one proposal than fire off several messages, and that's also improved my results.”

High-paying clients do exist

While there are many gigs on Upwork that don’t pay well, there are also high-paying clients who may not advertise their projects on the platform. Think of this as a secret job bulletin, or a hidden menu of sorts. Eschman discovered this after being on the platform for two years and establishing a reputation.

“By now, most of my offers are private invitations, sent directly by a client when they're looking for someone very specific,” said Eschman.

When Eschman first signed up for an account two years ago, his first assignment was an "About Me" page that paid $25.

“As someone who's freelanced for 10 years, this seemed insane for half a day's work,” said Eschman. “But it got me started on the platform, earned me a glowing review and led to my next assignment, which paid over $2,000.”

Negotiate for higher rates

Clients also usually have room to negotiate. So put your hustling skills to use. For instance, Eschman’s highest-paying client to date had an initial project budget of $750. But after a having a few discussions and getting a better understanding of the project’s scope, the client agreed to a budget of $2,200. Eschman then justified increasing the budget to $3,000. When the project was completed, the client threw in a $100 bonus, so Eschman ultimately made $3,100.

While I’ve never used Upwork, after talking to these folks, I've signed up.

“When people say there are no high-paying jobs on Upwork, I say: Keep looking. They're out there,” said Eschman.

Image: Geber86

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