The $100 Challenge That Changed My Life

The Story

I was sitting at my kitchen table on a rainy Saturday morning, staring at my bank app, when I realized something had to change.

My salary was fine on paper. I wasn’t in debt, but I also wasn’t getting ahead. No matter how carefully I budgeted, I ended each month with a little less than I’d planned.

That morning, over lukewarm coffee, I made myself a deal:

I’d find a way to make $100 in one weekend.

Not a life-changing sum — but enough to prove I could earn extra money outside my 9-to-5.

Day One: The Search

I started with the obvious.

Online surveys? Too slow.

Freelance design gigs? Possible, but competitive.

Selling old clothes? I’d done that before, but I wanted something faster.

Scrolling through a local community board, I spotted a post:

“Need help organizing garage. Will pay $50 for two hours.”

I messaged instantly. Ten minutes later, I had my first gig lined up for Sunday morning.

Day Two: The Unexpected Hustle

That afternoon, I remembered a box in my closet — a dusty stack of vintage records I’d inherited from my uncle. I’d been meaning to donate them, but curiosity got the better of me.

I posted a few photos in a neighborhood buy-and-sell group. Within an hour, I had three offers. One collector offered $60 for five of them, cash, if I could meet him that evening.

Just like that, my $100 weekend goal was already within reach.

Day Three: The Garage Job

Sunday morning, I showed up to the garage gig in jeans and gloves. The owner, a cheerful woman named Linda, had boxes stacked to the ceiling. My job was simple — sort items into “keep,” “donate,” and “trash” piles.

Two hours later, she handed me $50 and offered me a plate of homemade cookies.

It was physically tiring but oddly satisfying. I realized I’d spent more time outdoors and moving around than I had in months.

The Total

By Sunday afternoon, I was $110 richer.

$60 from selling vintage records.

$50 from the garage organizing gig.

It wasn’t about the exact amount — it was the proof. If I could make $100 in two days without much planning, what could I do with more strategy?

Turning It Into a Real Side Hustle

Over the next few weekends, I tested different ways to replicate that success.

Selling unwanted items: Books, old electronics, kitchen gadgets.

Offering small services: Lawn mowing, dog walking, helping with moves.

Quick freelance work: Writing short blog posts for small businesses.

I tracked every dollar in a simple spreadsheet. Within three months, my “weekend money” added up to $1,275 — which I used to build my emergency fund.

The Big Lesson

The $100 Challenge taught me three things that completely changed my mindset:

Small wins build momentum. Waiting for a “perfect” business idea can stall you. Doing something — anything — gets you moving.

Money is everywhere if you look. Skills you think are basic (organizing, cleaning, creating a quick graphic) are valuable to someone.

It’s easier than you think to start. You don’t need a website, a brand, or a massive plan. You need to take the first step.

Six Months Later

Now, my side hustle brings in around $400 to $600 a month — not bad for something that started with a weekend experiment.

I still do the occasional organizing job, but I’ve leaned more into buying and reselling items. Thrift store finds, clearance rack steals, and the occasional lucky online flip have all added to my monthly total.

That extra income covers my car insurance and adds to my travel fund. More importantly, it’s given me a sense of control I didn’t have before.

If You Want to Try It

Here’s my quick-start $100 Challenge plan:

Step 1: Look around your home for 5–10 items you can sell. List them online today.

Step 2: Check local boards for short-term gigs (moving help, cleaning, pet sitting).

Step 3: Commit to a 48-hour time limit. It creates urgency and makes you think creatively.

Step 4: Track your earnings — seeing progress in numbers is addictive.

I started out thinking $100 in a weekend would be a one-off win. Now, it’s my proof that I can create income whenever I need to.

And the best part? Every time it rains on a Saturday morning, I make another coffee, open my laptop, and think, Alright… let’s see where the next $100 comes from.