The Art of Failing, Creatively
Become Anti-Fragile
“I need to create what wants to be created, regardless of anything or anyone.
Sometimes I will perform badly, I’ll write badly, I’ll film badly. But I have a right to do that to get to the other side.”
— Julia Cameron, The Artist Way.
My Future Proof experiment failed.
Notice how I say the experiment failed, not that I failed.
Ego separation is everything.
When an idea dies, we mourn the future it promised. The version of ourselves we’d already started fantasising about.
Our ideas are how we connect with the world. So when they flop, it feels personal.
It feels like proof we were wrong about who we are.
But that’s our ego talking shit.
The stories in our heads are only true if we believe them.
Here’s the reality.
The experiment died. My creative thinking and problem-solving skills are alive and well.
Our experiments succeed or fail. We don’t.
It will sting. But the wounds are not fatal.
Here are the numbers of the experiment.
$150 on Meta ads. 17k impressions. $0.30 CTR (which is impressive, to be fair).
11,000 Substack subscribers with high open rates.
6 people joined the waitlist.
2 of them were me testing it.
As idea flops go, that’s significant. But it’s just information.
It makes pivoting easy.
Listen to the signals, not the noise.
20,000 Gen Alpha parents were interviewed. 93% are scared about preparing their kids for an AI future.
Every Gen Alpha parent I spoke to got triggered by the problem.
They loved the solution.
But they didn’t sign up for the mailing list.
Which means they wouldn’t pay.
Research means nothing in isolation. Get real data.
Better for the experiment to fail now than after months and thousands of trying to force it.
This problem isn’t going away. Someone will solve it at the right time.
Maybe it’ll be me. Maybe it won’t.
That’s what drives every great pivot.
Pivoting is an act of necessity. When our backs are against the wall we have to overcome our fear and pivot.
Most careers will experience it.
Sara Blakely sold fax machines door to door for 7 years before Spanx.
YouTube launched as a dating site. Nobody cared. They pivoted.
Play-Doh was a wallpaper cleaner. When wallpaper went out of fashion, they pivoted into toys and made a fortune.
Mathew McConaughey was the rom-com king. He got bored. Took a risk. Didn’t work for two years until Dallas Buyers Club. He won an Oscar and reinvented himself as a serious actor.
Nintendo made playing cards, love hotels, and taxi services. Pivoted to video games in the 1970s.
David Bowie struggled for 9½ years before reinventing himself as Ziggy Stardust and becoming a creative icon.
We all face reinvention.
A lot of entrepreneurs believe in burning the boats.
But I prefer having a pivot ready before I experiment.
As multi-talented misfits, we can solve lots of problems. We are never short of ideas.
So if you’re in your reinvention era.
If you feel stuck.
Solve your problem. Create your solution. Have a pivot in mind.
Test your idea before going all in.
I’m pivoting.
I’ve already tested and validated a digital product. Now I’m experimenting with the system to turn it into a flywheel.
This is a steep learning curve, but it’s also a high-value skill.
Every creative business needs to earn more money.
The Lessons
Gen Alpha parental AI anxiety is real, but it’s a new category. It requires serious education, time and money.
Now I know what doesn’t work with cold traffic. Which means I know what does.
I started this to help my daughter. She helped me build Future Proof. Now she’s helping me pivot.
She’s learned that every failure contains an opportunity to pivot into something better.
She’s learning that being antifragile in an uncertain future means running lots of creative experiments that will mostly fail, but it only takes one idea to explode.
Have a great Easter break, everyone!






