Lessons I Learned as a Client and Why It Matters for New Freelancers

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“The grass is always greener on the other side,” or so I thought.

Rookie mistake.

Recently, I was presented with an opportunity to lead my own team of writers. Until now, I’d been going at it solo—discussing, negotiating, finalizing, pitching, outlining, drafting, editing, submitting, revising, resubmitting…. You get the point. This was my chance to step up to the plate and not just peek into the other side but live the experience of my clients.

I recall when I despaired every night, pounding my head and questioning why the clients were not responding. Why did they keep rejecting my heartfelt proposals all those years ago when I was just an amateur? At the time, they seemed like an ethereal entity; it was far above their dignity to hire mere freelancers like me. They only wanted the crème de la crème: professionals who had nested on these platforms and made it their home.

I blamed them so much for making me go through this harrowing experience. Sometimes, even when the response did come, the client didn’t continue our discussion. Other times, right before initiating the contract, the client would disappear.

Why? Why? Why? Well, time to find out.

The reality is different from the mangled narrative I brewed in my mind. The client didn’t hate me; in fact, the client wasn’t even acutely aware of me. How would he be when there were hundreds of freelancers waiting to storm their job posts within five minutes of posting? I had to find out how these top 1% freelancers were standing out and landing these clients.

Time would pass and I learned many tricks of the trade. I learned to overcome camera anxiety and send video proposals, professionally handle negotiations, alleviate client concerns during the screening phase, solve problems that arose during projects, and ultimately, I learned how to secure new clients.

Turns out, the fault really was mine; and it became all the more apparent once I stepped into the other side. I don’t want to take up too much of your time with an excruciatingly long post that fails to leave you with any proper insights. Instead, here are a few lessons I learned as a freelancer when I became a client on Upwork:

Don’t waste words. The first two sentences of your proposals need to be succinct, targeted, and must be able to hook readers. If I see openers like “Greetings! I'm excited to express my interest in XYZ work,” I am skimming over you (real example, btw).

Show clients you mean business by directly addressing the points of their project; there will always be something you can pick up from the project description.

Be a problem solver. When I posted my first job description, the first feeling I had was, “Who can solve my problem?” I am not interested in finding out your interests, your hobbies, why you may not be the perfect fit but will learn, etc. I need to know how quickly and efficiently you can take the stress of this project off of my mind.

Even if you feel like you’ll need constant feedback to improve the outcome (which God knows I feel so many times when onboarding new projects), tell the client directly and confidently instead of mincing around with words; present it as an opportunity for growth rather than an absence of experience.

Respond quickly. I had some decent prospects lined up for the job; guess who I chose? The people who responded the fastest. One lady seemed like an excellent match but took a whole day to respond; you can safely assume I didn’t wait around. I need to hire people who can be like “Messaged, project discussed, project delivered.”

Speed matters a lot; this is, after all, a cutthroat market. Why should clients wait around for you? As a new/rookie freelancer, you cannot afford any communication delays. Be stuck to your keyboard once you’ve sent 40 proposals. One of them is bound to respond. Then, it’s just a race against time.

Don’t lead with “How much will you pay me and when will you increase my rates?” Sigh… Just don’t.

And…. that’s it from me. I hope I was able to enlighten you and leave you with food for thought. If you were able to learn something useful, I’d love to read it in the comments. Thank you.