Back in 2009, the online freelancing world looked entirely different. Way before the terms "remote work" and "the gig economy" became tied to the industry, I was taking on ghostwriting work at night on oDesk. At the time, I witnessed oDesk and Elance compete against each other as the biggest freelance marketplaces. I was there when the email about the two giants' merger in 2013 was delivered to our inboxes, and was on the platform until the official rebranding to Upwork in 2015.
I've been on the platform for a while, with 61 jobs, 3,824 hours billed since the merger, and a career built on a combination of corporate work and the freelancing lifestyle. I even joined community groups, talking about the experience, sharing tips to survive the congested market, and offering mentorship to curious ones online because I truly believed Upwork paved the way to give more opportunities to those seeking financial stability in the comfort of their homes.
Landing a long-term job, or even a project-based gig, was already difficult even for me who has once reached the prestigious "Top Rated" status. Lately, the bridge they built to connect freelancers with potential clients is being destroyed by the very platform that built it.
FROM TALENT RECRUITERS TO TECH AUTOMATION
Freelance marketplaces achieved multi-billion dollar valuations on one thing: the skills of freelancers. The platform acted as a middleman that charged transaction fees to connect a business with a skilled professional from anywhere in the world.
And then, Upwork integrated native AI features through its automated work agent, Uma. In essence, Uma was promised to help job bidders reduce the application process by using AI to streamline the proposal drafting aspect and the manual writing of cover letters for every single bid a freelancer submits.
Upwork notifications will tell you to open Uma to chat and encourage you to have it generate the first draft of your proposal.
Little did we know at the time that this automation is also a trap. How? Because thousands of freelancers use the same work agent, the platform became flooded with "AI slop." GigRadar shared that 80–90% of proposals now use identical AI clichés. With this, Upwork's system flags the applications as spam, deprioritizes the applications, and drops the client reply rate to 0%.
GATEKEEPING THE JOBS FROM THE ONES THAT NEED IT
After Upwork rebranded in 2015, they replaced application quotas with what they introduced as "connects." At the time, users had 60 free connects they could use every month, and applications only cost 1–2 connects each. This allowed freelancers to seek opportunities and apply to as many as 30 jobs per month. Later on, they once again changed this into paid subscriptions to purchase additional connects or reward systems to earn free connects, but the reward systems aren't generous for new users.
Ten years later, under the guise of filtering out applications for clients, the entry barrier has increased even more. The required connects have surged to as high as 25 connects per proposal, and that still depends on the job value and market trends. Job application has become a high-stakes move in a pay-to-play ecosystem. Spending became a requirement, only to be filtered out by a machine.
Freelance marketplaces achieved their valuations based on a single resource: the freelancers. For a long time, they gave hope to skilled professionals whose competencies could compete globally. Now, they are adding a layer to gatekeep jobs from the ones who deserve and need them the most. From starting as a platform that took pride in hosting the best talents from all over the world, it is slowly making its way toward killing its talent pool.
THE NEXT BEST MOVE
As a freelancer, how can you navigate this change? Where can you find opportunities?
It is not yet the end of remote work, but a transition is needed from becoming "platform dependents" to "independent systems architects."
Start your own lead-generation funnels: Bypass the middleman and do direct inbound and outbound. Optimize your LinkedIn profile and show off what you can do to the world. You can also start reaching out to small-to-medium businesses and offer your services to address their operational bottlenecks. Show them how you can fix their systems.
It's time to stop seeking financial safety nets in platforms. Seek opportunities from other channels that choose to vet skilled professionals instead of putting them out there in the open marketplace to fend for themselves. Look into community-led job boards—the ones that truly prioritize experience and skills as the selling point. Reach out to local agencies and collectives to find opportunities with niche brands.
Are you a freelancer who has independently built a career off platform? Share your experience and best advice for a newbie freelancer.
✍️ Mianne Cudal
#radarPH #remotework #freelancing