Developing A Winning Strategy for Freelance Platforms Like Fivver and Upwork

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:

1. 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.
2. 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. 
3. Newcomers can easily build their portfolios because these platforms provide a structured environment to gain initial experience. 
4. 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.

1. 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.
2. Platform fees eat your profits because most platforms take a significant cut. That $500 project? Congratulations. You might only see $400 after fees.
3. Algorithmic changes might limit your visibility. One day you’re featured, the next you’re invisible. 
4. Client relationships can be limited since these platforms often restrict direct communication, preventing you from building meaningful, long-term connections.

‍

Strategic Platform Navigation is Your Key to Freelance Success

Okay, if platforms aren't the enemy or the end all be all, then what are they? They're just a starting point. They’re a place for you to land some gigs while you build your business. They’re also a place you can return to while you manage external work. The one thing to remember is not to put all of your eggs in one basket by solely relying on freelance platforms. If you want to be successful in your endeavors, you’ll need to use these platforms strategically. Here are a few ways to set yourself up for a promising start—no matter your skill level.

‍

Setting Up a Profile That Converts

Your profile needs to shine bright to attract the right clients and stand out from the crowd. Whether a client searches for you or they visit your profile after reading your proposal, you’ll want to give them a reason to stick around.

Aside from having a quality headshot, an achievement-oriented description, and using strategic keywords, you can also include a pre-recorded Loom video introducing yourself and expressing why you are the perfect fit.

Remember, people buy from people. Your skills are important, yes, and so is your personability. This is especially true when you are roaming in a sea of other talented professionals. Make every pixel of your profile count and convert.

‍

Crafting A Stand Out Proposal

If you want to waste your time, send out a bunch of generic proposals.

Generic proposals are the fastest route to being ignored in the already crowded freelance marketplace. However, if you want to supercharge your success, then you have to personalize your proposals per gig application. 

I know you might feel exhausted applying to post after post, but this is where quality trumps quantity. This means setting goals and standards for the gigs you will and won’t go after. With these boundaries, you can better direct your time and focus to crafting proposals that don’t just get read, but get you the gig.

Read the entire project description with laser-focused attention, demonstrating that you've truly understood the client's needs. Most times, these descriptions will contain secret code words that you must add to your proposal to demonstrate you’ve read through everything.

Once you’ve read the description, start with an engaging hook to stand out from the crowd before you get into the specifics. Make sure your proposal is conversational and engaging and showcases your expertise to demonstrate why you are their go-to problem solver. 

When you position yourself as the expert with solutions, instead of just another freelancer, you position yourself to stand out amongst the competition.

‍

Set Your Rates Like a Boss

Let's talk money—and not in that awkward, sweaty-palmed way most freelancers do. Pricing isn't about racing to the bottom or being the cheapest kid on the block. It's about knowing your worth and communicating it like a pro.

You're not just selling a service; you're selling an experience, a solution, a transformation. Your pricing should scream, "I'm not just another freelancer—I'm the expert you've been searching for."

How do you do this? By being brutally honest about what you bring to the table. Your expertise isn't just a bullet point—it's years of hustle, learning, and problem-solving. The project's complexity? That's not just work—that's a challenge you're perfectly equipped to crush. Your time investment? That's precision, not just hours.

When you set your rates, you're telling a story. A story that says, "I'm professional, I'm confident, and the quality of my work is worth every single penny." So price yourself not just as a service, but as a solution.

‍

Building Your Freelance Empire

Platforms are your starting line, not your finish line. Think of them like training wheels—useful for getting started, but definitely not how you're going to win the race.

Your real magic happens outside these digital marketplaces. Start collecting testimonials like they're precious gems. Every satisfied client is a walking, talking billboard for your awesomeness. Use your platform work to build a portfolio that doesn't just show what you can do—it proves why you're the only one who can do it quite like you.

Don't just sit back and wait for clients to come to you. Reach out. Create relationships. Network like your professional life depends on it—because, spoiler alert, it does. And when a client loves your work? Ask for that referral. Shamelessly. Satisfied clients are your most powerful marketing tool, and they're usually dying to sing your praises.

Remember, you're not just building a freelance career. You're building an ecosystem where your talent, reputation, and network grow together. Now go out there and make some noise.

‍

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.