I Made My First $100 Online While Crying in My Parents' Basement

"I Made My First $100 Online While Crying in My Parents' Basement"

Genre: Memoir / Emotional Survival

I was 27 years old, broke, and living in my parents' basement—the same one I used to play hide and seek in as a kid. But this time, there was no game, no giggles, and nowhere left to hide.

The room had changed over the years. My childhood posters had been replaced with peeling paint and stacked boxes of my parents' old tax files. I slept on a mattress that groaned louder than I did when I woke up, and each morning felt like a cruel reminder of how far I hadn’t come.

College was supposed to lead somewhere. That’s what they all said. But I graduated into a job market that shrugged at my degree in communications, and after a series of unstable jobs and even more unstable roommates, I found myself home again—unemployed, ashamed, and depressed.

I spent most of my days scrolling endlessly. Job boards. Social media. YouTube videos on “How to Make Money Fast.” Every click felt like proof that I wasn’t doing enough, being enough, or becoming enough.

Then one night, after yet another rejection email from a job I had convinced myself was “perfect for me,” I cried. Not a single tear, not a dramatic sob—no, this was the deep kind. The kind where you fold into yourself like a crumpled paper and try to muffle the sound so no one upstairs hears how broken you really are.

That night, I typed into Google, for the hundredth time: “how to make money online with no experience.”

But something small shifted. Maybe it was desperation, or maybe the algorithm finally gave up trying to sell me dropshipping dreams and affiliate scams. One link caught my eye: “Freelance Writing Jobs for Beginners – Get Paid to Write What You Know.”

Writing? I hadn’t thought about writing since college. I used to be decent at it—maybe even good. I wrote little essays, poems, and sometimes rants that felt like therapy. But I never imagined anyone would pay me for it.

Still, I clicked.

That led me down a rabbit hole of blogs, videos, and Reddit threads filled with people sharing their side hustle stories. I stumbled onto a site called Fiverr. It looked basic—like Craigslist met LinkedIn—but people were offering services I knew I could try. Resume writing. Blog posts. “I will write your About page.” That one made me laugh. Could I really get paid for that?

I stayed up all night creating a profile. I wrote and rewrote my bio five times. I uploaded an old headshot, made some gigs, and priced them at $5 each because who was I to charge more?

Then I waited. And waited.

Days went by. I refreshed the page like it was a slot machine. Nothing.

I started to feel stupid. Embarrassed. I deleted the Fiverr app from my phone and told myself to “get real.” But that night, while eating cereal at 2 AM under the dull yellow basement light, I checked my email one last time.

"You’ve received a new order."

My heart stopped. I thought it was a glitch.

The client wanted a 500-word blog post about the benefits of journaling. It was almost funny. I had spent the last six months journaling my pain into a dozen spiral notebooks that no one would ever read.

I took a deep breath, wiped the sleep from my eyes, and wrote the piece in an hour.

He messaged me back: “This is perfect. Thank you.”

He tipped me five dollars.

I cried again. Not from sadness this time, but something else—something quieter and brighter. I had made money. Real money. Doing something that didn’t involve a boss breathing down my neck or a uniform with a name tag.

It was $10 total—two orders followed that week. Then a $25 gig came in. Then a $40 one. By the end of the second week, I had made $102.38.

I remember staring at the screen, numb. Not because it was a lot—but because it meant I wasn’t useless. I wasn’t stuck. I could do something.

My parents didn’t know at first. I didn’t want to say anything until it became “real,” whatever that meant. But a few weeks later, after crossing $300, I told my mom.

She smiled like I had won an award. “You always loved writing,” she said. “Even as a kid. I still have your story about the talking orange cat.”

I laughed. I had forgotten about that one.

Things didn’t magically change overnight. I still battled depression. I still questioned my worth. But that first $100 was more than money. It was proof that something inside me could still grow, even in the dark.

Months later, I would turn that little Fiverr profile into a full-time freelancing business. I’d build a website, learn content marketing, even ghostwrite eBooks. I eventually moved out of the basement, into a tiny apartment with spotty Wi-Fi and leaky pipes—but it was mine.

And every time I get discouraged, I remember that night. The night I hit “publish” on my first gig while wiping tears off a secondhand keyboard. The night a stranger on the internet said “yes” when the world had only said “no.”

The night I made my first $100 online—while crying in my parents' basement.