Things I've failed at
And why they didn't matter
In 2022, I was trying to figure out how to make money as a writer.
So I started this service — it was called “The Emergency Editor."
My idea was to position myself as an editor who could help businesses get their copy ready for print in an instant. I’d be available 24/7. Need something done in an hour? I got you. After all, I had nothing else to do.
I printed off fliers. I mailed them to local businesses. I spammed cold emails.
I never got a single client from it.
In 2023, I started an event rentals business.
Built a website. Created Google Ads. Bought a truck, a trailer, hundreds of chairs, and dozens of tables.
I set up two grad parties before deciding it wasn’t worth giving up my weekends to make a few hundred bucks.
So I sold everything and closed the business down.
In 2024, I started another blog that got no traction. I launched a writing account on X that flopped. I designed an online product that no one bought.
And between the failure of The Emergency Editor, the failure of my event rentals business, and the failure of all my aborted launches in 2024, you know which of those failures actually had a lasting negative impact on my life?
Not a single one.
A universal truth:
Failure is irrelevant unless it’s catastrophic. And almost nothing you do has enough leverage or importance to truly be catastrophic.
Ever heard of asymmetric risk?
In venture capital, they talk about it all the time. You invest in 10 companies. Nine of them fail. You lose your investment. The 10th one returns 100x, and suddenly you're driving the same car as LeBron.
The worst-case scenario for almost anything you try is "Well, that didn't work."
But the best-case scenario for most ventures is uncapped.
Think about it. What's the worst that happens if you:
Start a side hustle? You lose some evenings and weekends.
Learn a new skill? It doesn't immediately translate to value.
Ask for a promotion? You get turned down.
Write a book? No one reads it.
When I started freelance writing, my downside was a year of financial uncertainty. My upside was looking back in 40 years and thinking, “Man, I could’ve done a lot more with my life.”
Asymmetric risk.
Most people confuse catastrophic failure with regular failure.
Catastrophic failure means you:
Damage key relationships beyond repair.
Put yourself in insurmountable debt.
Risk your physical safety.
Regular failure means you:
Felt some embarrassment.
Wasted some resources.
Learned a lesson.
I'd bet 95% of what you're afraid of falls into the "regular failure" category. And regular failure is just a transaction cost of living a meaningful life.
So go ahead. Print those fliers. Buy that trailer. Write that blog.
There's an easy path back to where you are now if it doesn't work out.
But if it does?
There’s no telling what will happen.
Asymmetric risk.