The Good, The Bad, and The Ugly of Upwork Freelancing

When I first got on Upwork, I wasn’t looking for a side hustle or some extra cash. I had just moved to San Antonio in 2020 and needed a solid way to generate leads. My wife actually came up with the idea of trying Upwork, and it turned out to be one of the best decisions I’ve made for my business.

It wasn’t easy at first, but over time I figured out what works, what doesn’t, and how to avoid the worst parts of the platform. Here’s what I’ve learned.

Getting Started on Upwork

Landing that first client was a struggle. I even had one client interview me and then tell me he went with someone else because I didn’t have enough history on Upwork. He told me flat-out that he only hires people with good Upwork history. That’s the catch-22 of the platform. Getting those first few reviews is the hardest part.

My first client was a real estate agent who needed a simple fix to his Twilio configuration. It was a fixed-price project for $250. The second was a meme SMS bot. The client paid the first milestone and then ghosted me. Again, it was a low-budget project, but I needed the reviews.

I learned quickly that good customer service and clear communication set me apart. I didn’t treat clients like a source of income. They already knew they had a problem and were looking for help. No need for a sales pitch, just a straightforward proposal explaining how I could fix their issue.

What Makes a Good Proposal

I’ve read a lot of bad proposals on Upwork. They’re usually way too long, full of fluff, and don’t address the client’s actual problem. Here’s my approach:

1. Do a little research. Check the client’s past jobs, reviews, and if possible, find their first name.
2. Get to the point. Tell them how you’re going to solve their problem right away. The proposal is not for selling yourself. It’s to show them potential solutions.
3. Keep it short. If they want a full breakdown, they’ll ask.
4. Ask open-ended questions. This gives the client an easy way to respond and keeps the conversation going.

The goal is to show that you understand their problem, present a solution, and get them talking. That’s it.

The Red Flags to Watch For

Not every job on Upwork is worth taking. Here are some major red flags I’ve learned to spot:

1. The “I know how long this should take” client. If they already know exactly how long a “good” freelancer should take, why are they hiring someone else? This is usually a sign they want fast and cheap, not good and fast.
2. Low hire rate, bad reviews, low average hourly rate. These are all warning signs, but the low hourly rate has actually worked in my favor before. A lot of good clients get burned by cheap freelancers and eventually realize they need someone serious. Those can turn into great long-term clients.

The Best Clients I’ve Worked With

Some of my best projects on Upwork have come from small businesses that needed serious help modernizing their operations. We’ve built full custom CRM software for manufacturing companies that were previously managing everything in messy Google Sheets. We’ve helped a home remodeling company transition from 20+ years of paper-based records to a fully digital system that improved their efficiency and customer satisfaction. These projects have been rewarding, both financially and in terms of impact.

The Nightmare Clients

I’ve been lucky to avoid most bad clients, but there was one that stands out. A guy hired me to build a financial analysis library. He said he wanted simple methods that he could drop into his codebase. I found an existing library that did exactly what he wanted, wrote a wrapper around it, and delivered the project. He was furious. Turns out, he was a developer trying to outsource his own work and wanted a fully custom implementation. I refunded him and told him he’d need the money more than me.

Upwork as a Long-Term Strategy

Upwork isn’t just a short-term gig for me. The goal is to find great clients for the long run and eventually take them off the platform. After two years, Upwork allows you to work with a client directly without paying their fees. We’ve done that with quite a few clients now, and it has helped build lasting business relationships.

Final Advice for New Freelancers

Upwork is hard, and you won’t succeed by underpricing your services. If you try to compete with the thousands of people racing to the bottom, you’ll never stand out. Instead, focus on quality clients, price yourself fairly, and deliver excellent work. That’s how you build a real business on Upwork.