Have you ever stared at your laptop, eyes blurry and heart heavy, wondering if this was it? If maybe you’re not cut out for this whole freelance dream after all?
I have. More times than I’d like to admit.
Especially in those early days—when money was tight, imposter syndrome filled my lungs heavier than air, and every rejection email felt like another quiet way of the world whispering, “Don’t bother.”
But one night, after yet another overcaffeinated deep dive on Reddit, I stumbled across a freelancing thread where someone casually mentioned they’d used ChatGPT to land writing gigs. I was intrigued. Skeptical. But I’d hit the part of rock-bottom where trying couldn’t hurt more than staying stuck.
So… I did.
And within 48 hours, I’d made $500. No fancy website. No degree. Just a bit of curiosity, a sprinkle of courage, and ChatGPT in my corner.
Let me take you back to how it happened—because if you’re in that stuck place, I want you to know something deep and true:
You can absolutely do this too.
When Self-Doubt Is Loud and Rent Is Louder
The day before I landed my first AI-assisted writing gig, I was sitting cross-legged on the floor, laptop balanced on a pillow, scrolling job boards and feeling… nothing.
Well, not nothing—more like a heavy fog of “what’s the point?”
You ever feel that?
Where every job listing feels out of reach and every pitch you’ve sent vanishes into a black hole and all you’re left with is your unbrushed hair and another cold cup of coffee. Yeah. That feeling.
That night, instead of pushing through more job boards, I opened a blank doc and had a quiet chat with ChatGPT.
“Could you help me write a pitch for a blog post about lifestyle design?” I asked it, almost sarcastically.
It did. And it was good. Really good.
Letting AI Hold Your Hand (Until You Find Your Voice)
I think a lot of us assume everyone else has it all figured out—that we’re the only ones fumbling through the learning curve.
But using AI tools for freelancing isn’t cheating or lazy. For me, it’s like having a gentle mentor on standby—someone to bounce ideas off of when my creative tank hits E.
Here’s the exact way ChatGPT helped me land that $500:
- Writing gig descriptions: I read between the lines of freelance job posts and asked ChatGPT to reframe my skills to fit the vibe they were looking for.
- Blog post outlines: I’d draft basic structure and let the AI expand it. Then I edited it with my own stories and voice—making it mine.
- Testing tone: I’d say, “Write this more casually, like we’re having coffee,” and boom—I had a readable base to work from.
By repurposing and refining its words, I developed my tiny portfolio in a matter of hours—and pitched it that same night.
The next morning, I had a reply. By that evening, I had $250 in PayPal and an agreement to write two more pieces.
Wait, Passive Side Hustle… or Something More?
A lot of folks online call this kind of thing a “passive side hustle” that you can spin up quickly with AI writing gigs.
And while it’s true that the tools make the work lighter, here’s what I’ve found:
The real magic isn’t in ChatGPT. It’s in what you choose to do with it.
Because when you’re drifting in self-doubt, something as simple as one paid gig can crack the door open to everything else waiting for you on the other side of fear.
What if it’s not about becoming the best writer on the internet?
What if it’s just about finally hitting ‘send’?
That’s what ChatGPT did for me. It didn’t write my future. But it helped me believe, just enough, that I could.
Want to Try This Yourself? Here’s a Gentle Start
If your heart is pounding with possibility and panic—take a breath. You don’t have to run at this. Just… walk. Slowly. Kindly.
Start with these little steps:
- Pick one niche that you’re kind of curious about—parenting, travel, self-help, tech—and ask ChatGPT to write a sample article title and a short intro paragraph.
- Edit that intro with your voice. Add a small story only you could tell.
- Save it as your first portfolio piece.
- Search Upwork, Fiverr, or r/HireaWriter for related gigs—and when a post resonates, copy the job description and ask ChatGPT: “Help me write a quick, warm pitch for this.”
Not to fake your way in. Not to be perfect. Just to quiet that panic loop enough to see what’s possible.
The Truth I Never Believed Until I Lived It
You are so much more capable than your fear lets you believe.
Even when you’re tired. Even when you don’t see the results yet. Even if every part of this feels like a slow dance in the dark.
You don’t need endless experience or a polished brand.
You just need one soft moment of trying.
Let this be that moment.
With you every step of the way,
💛
Shara
