A Newbie’s Guide To Navigating Upwork

Brandon Summers-Miller reports on how copywriters who have joined the self-proclaimed “largest network of independent professionals” try to get better rates and gigs.

by | February 7, 2023

When Amy Suto, a former TV writer, began her career as a full-time freelancer six years ago, she turned to Upwork because she was between shows and needing new paid opportunities. Initially, she was drawn to the flexibility and expansiveness the platform brought her. Six years later, she is still an avid enthusiast.

“Right now I travel the world — I’m a digital nomad,” Suto said. “I find a good chunk of my clients through Upwork.”

Suto is one of many freelancers who have turned to Upwork to make a living. Upwork has existed in several iterations since it was originally founded as Elance in 1999. The site merged with oDesk — founded in 2003 — in 2013, and became “Elance-oDesk,” before finally launching in its current state as Upwork in 2015. According to Upwork, they are the largest freelancing platform on the market, based on gross services volume.

Over the years, the site has connected writers like Suto with companies turning to the gig economy for labor. According to internal data provided by the company to Study Hall, freelancers collectively earned over $3.5 billion on the platform in 2021.

Potential clients on the site range from B2B and B2C, as well as across industries including fashion, design, and tech — just to name a few. Connecting the writer to the client continues to be a challenge, and an especially daunting one for new freelance writers. Upwork aims to bridge this gap and facilitate writer-client relationships. Though some writers, like Suto, have undoubtedly found success on Upwork, navigating the platform can be perplexing.

While it may connect you with more potential opportunities, Upwork doesn’t necessarily offer an alternative to the hypercompetitive, exploitative dynamics that freelancers often face and as a business, has found various ways to monetize it. Study Hall spoke with experienced Upwork copywriters to get insight on how they set rates, pitch clients, and try to stand out from a sea of other writers.


Like other freelancers on the platform, Avery, who is going by a pseudonym due to their concern of how their clients may perceive their business practices, started on Upwork focused on their hourly rate. Avery said that what they’ve liked most of all about Upwork is the site’s ability to match them with clients.

They started on Upwork with an hourly rate of $45 to account for the chunk of change the site takes in each transaction. Since then, they’ve doubled their rate and have moved to charging on a project basis.

“It can feel like a little bit of a race to the bottom in the beginning,” Avery told Study Hall when explaining how they set rates while bidding for initial projects.

To account for not having a company provide benefits like health insurance, PTO, and 401k plans, freelancers must set rates higher than many salaried positions’ hourly earnings. Due to intense competition, writers may feel like there’s an incentive to set their prices lower to make themselves more appealing. However, writers also need to consider how much research each specific project takes and that they will likely be juggling multiple clients at once.

Avery believes that project rates benefit both the freelancer and the client because it encourages the freelancer to do the best and most efficient job while the client gets a better understanding of what the total cost should look like by the project’s end.

“In the beginning it was very difficult because I didn’t know how to price my services. I was just like, ‘Oh, $15! I can do this in 20 minutes!’” Suto said. “Rather than actually thinking about things like burn-out, or overstretching myself, or how to manage clients, or how to build systems.”

She noted the quality of clients has improved since she’s increased her rates.

“I do think that the clients get better when you become more expensive,” Suto said. “When clients are trying to make their decision on who to hire, especially if those clients are looking for experts and want to pay for the best, they’re going to look for those markers.”


The appeal of Upwork is that you get access to a database of gig opportunities and can get paid in a relatively efficient manner. That being said, a glaring drawback is that you’re facing endless competition.

According to Avery and Suto, there’s one accreditation that can make a huge difference: the Top Rated badge. Freelancers receive this accreditation after meeting a set of criteria the platform imposes on freelancers, which can take months depending on how long certain projects last.

Avery and Suto both said that after receiving Top Rated badges, they started getting invitations to apply to jobs that aren’t publicly listed. Suto added that these opportunities are often better than the ones that can be found by scrolling through pages of other jobs.

In the case of both writers, Upwork’s badge system incentivized them to take lower-paying gigs in the beginning to accrue positive reviews.

Welcome to freelancer FarmVille where you will be harvesting Google Docs, not digital corn. In addition to badges, Upwork has created its own form of currency — “connects” — for bidding for jobs. To land a gig,  freelancers need to submit a proposal to clients detailing why they’re specifically the best fit for the job. Users are only given a certain number of connects to bid for these jobs; each bid costs at least one connect and sometimes more. For 15 cents a pop, users also have the option to purchase more connects. Connects are currently sold in sets of 10, 20, 40, 60, and 80. Free accounts on the site begin with 40 connects as a new member perk, but beyond that, unpaid memberships are only replenished with 10 connects a month which means that users can’t pitch that many clients at all.

For a $14.99 per month “Freelancer Plus” membership, Upwork freelancers that pay-to-play get topped off with 70 connects each month plus the standard 10 replenished connects. Costing 1 connect per day, freelancers get an “availability badge” which keeps their profile publicly listed for clients to solicit work.

Any writer can tell you about that harrowing feeling of sending out one more pitch after countless rejections just in case things pan out differently this time. In a similar vein, but with clearer financial implications, a freelancer who runs out of connects may believe that it’s worth paying money upfront to make more money down the line.

Suto characterized these business practices as undemocratic, though she admitted it has made job hunting less competitive for her.

“It’s kind of classist in a way, in terms of preferencing people who have the money to spend to apply to all these jobs,” Suto said. “I still think that the platform has gotten worse in the fact that it hasn’t been prioritizing the freelancers themselves and is kind of hurting freelancers from applying to the jobs that they want to work for.”

According to Suto, writers who have tons of experience, in media and B2C and B2B industries, can join the site and potentially command high rates without the Top Rated badge.


Upwork presents challenges for hopeful freelancers looking to secure their first contract or expand their client roster. Even for vetted freelance writers on the site, finding clients who pay well and agree to reasonable terms can be challenging.

“So many clients don’t really know what they’re looking for,” Avery said. “There’s a lot of confusion and sort of arguing about what freelancers deserve.”

Although freelancers can secure work on the site fairly quickly, both Avery and Suto stressed that early opportunities don’t always pay well. Suto told Study Hall that writers who are successful on Upwork play the long game. And arguably, it never really ends — there’s always the promise of landing something bigger and better. She’s currently trying to earn an “Expert Vetted” badge that would open her up to a more lucrative pool of corporate clients.

With its tokens, hierarchy of badges, and need for strategic thinking, the self-dubbed “largest network of independent professionals” has essentially gamified freelancing. The allure of Upwork is that it can offer quality opportunities for writers who are patient and dedicated and have enough time to learn how to navigate an often opaque system. But like with any game, winning is far from a guarantee.

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