Developing A Winning Strategy for Freelance Platforms Like Fivver and Upwork
The Freelance Platform Reality Check You Didn’t Know You Needed

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That’s it. It’s go time and you’re not wasting another minute feeling crippled by doubts or imposter syndrome. You know you have what it takes to make it as a freelancer, but you’re just not exactly sure where to start. You’ve heard of people gaining success from freelance platforms like Fiverr and Upwork, but you’ve also heard some mythic horror stories. Desperate for your first client, you create an account on every freelance platform known to humanity. But three months later, you're drowning in low-paying gigs, fighting for jobs that barely cover your coffee budget, wondering if you've made a terrible mistake.
Been there? You’re not alone. The bad news is no matter which platform you choose, they will all have their fair share of headaches. The good news is there are quality gigs out there and once you develop a winning strategy, you’ll wonder how you made it so long settling for the low-hanging fruit.
The Freelance Platform Reality Check You Didn’t Know You Needed
Freelance platforms are like those all-you-can-eat buffets. You know? Highly tempting, easily accessible, but rarely satisfying in the long run. You’re promised a feast of opportunities but often receive nothing more than cold, leftover career opportunities.
Here's the brutal truth. Freelance platforms are not your career salvation. They're a tool—one tool among many—and treating them as your entire business strategy isn’t sustainable as your sole option. However, they aren’t the worst thing to consider—especially when you’re just getting started.
The Pros: Why Freelance Platforms Aren't Completely Terrible
Let's give credit where it's due. These platforms do offer some legitimate benefits and a lot of freelancers have made a good chunk of revenue, grown their network, and established themselves through these avenues. Here are just a few of the pros to utilizing sites like Fivver and Upwork:
- They have a low barrier to entry. This easy access removes the intimidating first step of finding clients. There are no networking events, no cold emails—just you, your skills, and potential work making it a great place to start.
- There is immediate access to jobs unlike traditional job hunting. You can start bidding on projects within hours of creating a profile and potentially land your first gig within 24 hours.
- Newcomers can easily build their portfolios because these platforms provide a structured environment to gain initial experience.
- Gain market rate understanding. By browsing projects, you'll quickly learn what clients are wanting/willing to pay and what skills are in demand.
The Cons: The Ugly Truth Nobody Wants to Discuss
Here's where things get spicy. For every pro, there's a compelling con, and by becoming aware of these fallbacks, you can set yourself up for success in the long run.
- The race to the bottom begins here. These platforms have a tendency to create an environment where freelancers compete primarily on price. $5 logos? $10 website designs? $15 blog posts? Know your worth.
- Platform fees eat your profits because most platforms take a significant cut. That $500 project? Congratulations. You might only see $400 after fees.
- Algorithmic changes might limit your visibility. One day you’re featured, the next you’re invisible.
- Client relationships can be limited since these platforms often restrict direct communication, preventing you from building meaningful, long-term connections.
The Bottom Line: A Hybrid Approach Between Platform and Direct Work
Sustainable freelancing requires a balanced strategy. If you’re adding platforms like Fivver and Upwork to the mix, then remember to approach bids, proposals, and projects with a strategy. Most importantly, don’t put all of your eggs in one basket. Dedicate approximately 30% of your time to platform work, using it as a supplementary income stream. Invest the remaining 70% in direct outreach, networking, and building your personal brand. Continue to develop your skills to remain competitive and create multiple income streams that provide financial stability and professional growth. It may seem like a lot at first, but this is just the beginning of an exciting and successful career ahead.