Why 90% of Side Hustlers Fail (And How to Join the 10% Who Succeed)
Not a Medium member? You can read this article here
We lost $12,000 on our first side hustle. And that was the best thing that could have happened to us.
Let me explain why that painful (and embarrassing) failure taught me more than any success could have. After interviewing 50+ successful side hustlers and analyzing my own spectacular failure, I discovered a shocking truth: Most people aren’t failing because of bad ideas or lack of effort.
They’re failing because they’re following terrible advice.
The Brutal Math of Side Hustles
Here’s what nobody tells you: 90% of side hustles fail within the first year. But here’s what’s even more interesting — of the 10% that succeed, almost all of them broke the “conventional rules” of side hustling.
I learned this the hard way. I did everything the experts told me:
- Built a perfect business plan
- Created an impressive website
- Spent months perfecting my offer
- Invested in expensive tools and software
Result? Zero paying customers and a maxed-out credit card.
The Counter-Intuitive Success Formula
After my failure, I became obsessed with studying successful side hustlers. What I found challenged everything I thought I knew about building a profitable side business.
Here are the counter-intuitive principles that separate the 10% from everyone else:
1. Start Before You’re Ready
The successful side hustlers I interviewed didn’t wait until everything was perfect. They launched with imperfect products, ugly websites, and incomplete plans. One entrepreneur started her now six-figure consulting business by posting a simple Google Doc as her service offering.
2. Embrace “Expensive” Problems
Most failed side hustlers chase trendy markets. The successful ones? They tackle expensive problems nobody wants to solve. One of my interviewees built a $50K/month business helping dentists manage their Google reviews — boring, but incredibly profitable.
3. The 24-Hour Rule
Here’s the most shocking insight: The top performers all had one rule in common — they would implement any new business idea within 24 hours of conceiving it. No perfectionism. No overthinking. Just rapid execution.
The Psychology of Success
But here’s what fascinated me most: The difference between success and failure wasn’t about strategy — it was about psychology.
Failed side hustlers often say:
“I need to learn more first”
“I’m waiting for the perfect time”
“What if it doesn’t work?”
Successful side hustlers say:
“I’ll figure it out as I go”
“Now is always the perfect time”
“What if it does work?”
The 30-Day Challenge
If you’re ready to join the 10%, here’s my challenge to you: For the next 30 days, implement every business idea within 24 hours of thinking of it. No excuses. No delays.
Will you fail sometimes? Absolutely. But here’s the secret: Small failures lead to big successes. Every “failed” attempt teaches you exactly what doesn’t work, bringing you closer to what does.
The Choice Is Yours
You’re standing at a crossroads right now. Your primitive brain wants you to keep planning, preparing, and perfecting. Your future self is begging you to take action.
Which voice will you listen to?
Remember: The difference between the 90% and the 10% isn’t talent or luck. It’s the courage to start before you’re ready.
