How I Got My First $800 Freelancing Remotely (And The Stupid Mistakes I Made)

So, this is not one of those “quit my job, now I make 10k/month” stories. Honestly, I almost gave up after my third rejection on Upwork. I remember closing the tab and opening Netflix out of frustration. But two weeks later, something shifted…

The First Real Gig (And How I Landed It)

I started on Upwork. My profile was bland. No reviews. No ratings. Just a picture of me looking confused and a bio that read like a college essay.

Then I rewrote it. I spoke directly: “Hey, I’m not a 10-year pro. But I’ll work harder than most, and I reply fast.” Boom. That little tweak got me my first invite—a $35 blog rewrite. I said yes before I even read the full brief.

Fiverr Was a Whole Different World

I also set up a few gigs on Fiverr. Nothing moved for days. But one morning, I woke up to “You’ve Got an Order!”—it felt like Christmas. It was a $20 voiceover script editing job. The client tipped me $10 extra just for being fast.

My Workflow (And Why It Was a Mess at First)

• Used Google Docs to draft and share
• Relied on Grammarly to catch silly grammar issues
• Tracked payments manually on Notion (terrible idea, I missed $40)

I now use AND.CO to track income, invoices, and time. Life-saver.

The Stupid Stuff I Did

1. Charged way too little because I didn’t believe in my value.
2. Said yes to everything—even things I didn’t know how to do. (YouTube thumbnails? Why did I say yes??)
3. Forgot to send invoices on time. Rookie mistake.

The Real Turning Point

After about four small jobs, one of my clients asked, “Do you do content planning too?” I lied. I said yes. I watched 4 hours of YouTube tutorials that night and built a Trello board. The next morning, I delivered a full monthly plan. She loved it—and hired me for $400/month part-time. That’s when I knew: freelancing isn’t just about skills. It’s about adapting.

Would I Recommend It? 100% Yes. But…

If you're someone who likes predictability and hates writing awkward intro messages, freelancing might drive you nuts. But if you're curious, adaptable, and okay with a little chaos—it might just be the most freeing way to earn money online.

Still curious? Check out this guide on making money online — it pairs perfectly with this post.

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