Side Hustle Lessons: How I Failed My First Skill Challenge
One failed side business, too much pride, and what it taught me about real self growth
No one ever bought a single thing from my first side hustle.
I spent six months building it - late nights, skipped weekends, ignored calls from friends. I was convinced I had the next big idea. I called it “SkillCrate” - a subscription box for people who wanted to learn creative skills each month. Origami, watercolor, brush lettering, beginner’s coding - it had variety, it had branding, and it had exactly zero customers.
Worse than the failure itself was what came after: silence.
No feedback. No trolls. Just… nothing.
The Side Hustle That Never Took Off
I had read dozens of success stories on Medium. You know the type:
“How I made $3,000 in my first month freelancing.”
“How I built a six-figure side business while working full-time.”
So I thought I could just reverse engineer it.
I brainstormed, bought a domain, mocked up the logo in Canva, spent hours on Shopify, and filled my apartment with supplies I couldn’t afford. The boxes looked great - really great. But I never validated the idea. Never spoke to a single potential customer.
I just assumed if I thought it was good, others would too.
That’s how I learned one of the hardest truths about side hustle jobs: the market doesn’t care how hard you worked. It only cares if what you built solves a real problem.
What Really Hurt
After two months of trying to sell the box, I quietly let the site expire.
No announcement, no “final launch.” Just… shut it down.
I told myself I was too busy at work. That the timing wasn’t right.
But the truth? I was embarrassed. Ashamed that my brilliant idea had tanked.
Everyone around me seemed to be thriving in their own side business. Meanwhile, I felt like a fake.
That experience forced me to confront a part of myself I didn’t want to see:
I didn’t fail because I wasn’t smart enough.
I failed because I wasn’t listening. Not to the market, not to people, not even to myself.
The Self Growth I Didn’t Expect
After I stopped licking my wounds, I started reading again - but not the “10X your productivity” stuff. I read about failure. About ego. About starting small.
One article in particular - "Learning a New Skill Changed My Life" - hit me hard. It made me realize I had jumped to monetizing without mastering anything first. I wanted the result of a successful side hustle without earning it through growth, feedback, and grit.
So I slowed down.
I picked one skill - copywriting - and just practiced.
No funnel, no website. Just rewrote emails, headlines, and ads for fun.
Then I offered to write for a small local business for free.
They said yes.
That “yes” felt better than all the imaginary dollars I had hoped for with SkillCrate. Because this time, it was real.
A Quieter Kind of Success
It’s been over a year now.
I don’t make six figures. I still have a day job.
But I write copy for a few clients on the side. It’s consistent, it’s fulfilling, and most importantly - it’s real.
The journey gave me more than income. It gave me clarity.
It taught me how to listen, how to test small, and how to separate self-worth from side hustle performance.
If you're starting your own side hustle journey, here’s what I’d tell you:
Don’t chase noise. Follow what quietly sticks.
Whether it’s a single subscriber or one stranger saying, “This helped me” - that’s your signal.
Build from there. And let the self grow with it.
