How I Landed My First Client on Upwork in 3 days (Story Time!)

When I realized I was finally stepping away from my 9–5, I knew one thing for sure: I had to find my first client. That moment hit in December 2024—festive vibes everywhere, but there I was, deep in hustle mode, setting the stage for my next chapter.

My plan? Start with Upwork. It’s a safe and legit space for freelancers, and it opens the door to working with clients from literally all over the world.

Now, I had heard all the horror stories—“It’s so hard to get clients on Upwork,” “You need 100 proposals before one reply”—but honestly? That didn’t scare me. I was determined. Focused. I’ve danced with entrepreneurship before and knew the ride wasn’t going to be smooth. But I was ready.

A friend told me, “Make sure your portfolio is solid.” So I rolled up my sleeves and got to work. The hard part? Positioning myself. I had a whole buffet of skills, but didn’t know which one to lead with.

See, I have a background in Finance, and I’ve done the accounting thing. I could’ve branded myself as a bookkeeper. But let’s be real—I don’t enjoy repetitive tasks (read: Finance gave me the ick 😅). So that was a nope.

Then there’s the virtual assistant side of me—two years of supporting different clients with inboxes, calendars, travel, expenses… You name it. I’m actually great at it. But again, it didn’t light me up. And I’d made a promise to myself: if I was going to return to entrepreneurship, it had to be in a space that made me excited to show up.

So I looked at what I genuinely enjoy—Social Media & Digital Marketing. It just made sense. I’d already been doing it for my own brand (YouTube + Instagram) and a few big brands in Kenya. It was fun, creative, and gave me real job satisfaction. So that’s what I leaned into.

I crafted a portfolio that told the full story:

✔️ Social Media Manager & Digital Marketer (my main focus)

✔️ Bookkeeping and Admin VA (because, hey, these are still useful skills)

Once my profile was ready, I hit Upwork and started bidding. I won’t lie—I expected a long wait, but guess what?

On Day 3, I landed my first client. 🎉

I was over the moon! Not just because of the win, but because it validated everything. I had made the right choice. I was on the right path.

Now… do you want to know what happened with that first client? 👀 Let’s just say, it wasn’t a walk in the park. There’s drama. There are lessons. There’s tea.

Before we got started, we had a quick interview. He was looking for a Social Media Manager with experience in AI. I had used AI before, but not at the level this role required.

I didn’t pretend to know everything. I was honest with him, told him where I stood, and promised to level up fast. And that’s exactly what I did.

I enrolled in a free “masterclass” on YouTube and binge-learned prompt engineering.

Let me tell you—this cracked open a whole new world. I saw how powerful AI can be, especially in marketing. From idea generation to content planning to writing captions—it’s now part of my daily toolbox.

📌 Pro Tips for New Freelancers (from someone who just started):

✨ Believe in your skills—even when you’re still learning

✨ Be honest, but also ready to learn and adapt fast

✨ Stay curious. The online world changes fast—AI today, something else tomorrow

✨ Be proactive—don’t wait for instructions, anticipate needs

✨ Build your own resource bank: YouTube, ChatGPT, Notion, Canva, etc.

✨ Communicate clearly, confidently, and consistently

✨ Tech-savviness isn’t optional anymore—it’s a superpower

That’s how it all started. From quitting my job to learning AI overnight, to landing a client I enjoyed working with—it’s been one wild ride already.

If you’re thinking of jumping into freelancing, let this be your sign. Start before you feel “ready.” The clarity comes as you move.

📣 I’d love to hear from you—what skill are you turning into a business?