Most products try to make users succeed immediately.
But the best products do something counterintuitive:
They let users fail on purpose.
Not because they are badly designed.
Because failure is what creates understanding.
And understanding is what creates retention.
We’ve Been Optimizing UX the Wrong Way
For years, product design has been obsessed with one goal:
“Make the user successful as fast as possible.”
That sounds correct.
But it hides a deeper problem:
Fast success often creates shallow understanding.
And shallow understanding leads to drop-off.
If a user doesn’t understand why something worked, they don’t build mental ownership of the product.
They just experience it.
And experiences are forgettable.
Failure Is Not the Opposite of Good UX
It’s part of it.
Think about the best products you actually remember using:
Notion
Figma
Excel
Photoshop
Linear
None of them feel instantly obvious.
You probably failed a few times when you first used them.
But that failure did something important:
It forced you to build a mental model of the system.
That mental model is what creates long-term usage.
The Science Behind Productive Failure
There’s a concept in learning science called productive failure.
It suggests that:
People learn deeper when they struggle before they receive guidance.
In product terms, that means:
If everything is explained upfront → users forget it
If users struggle slightly → they remember it
This is why “too good onboarding” can actually hurt retention.
It removes the cognitive friction that builds understanding.
Every product has a hidden decision:
Do we optimize for immediate success or long-term mastery?
Most startups choose immediate success.
Because it looks better in:
demos
onboarding metrics
activation rates
But long-term winners optimize differently.
They design for:
exploration
small confusion
discovery moments
“aha” learning loops
Because that’s what turns users into power users.
Why AI Makes This Even More Important
AI products are removing friction everywhere.
But friction was never just “bad UX.”
It was also:
feedback
learning
understanding
If AI removes all struggle, users may never understand what the system is actually doing.
And if users don’t understand it, they don’t trust it.
So paradoxically:
A perfectly smooth AI product can feel less trustworthy than a slightly imperfect one.
The Real Goal of Great Product Design
It’s not to eliminate failure.
It’s to design controlled failure.
That means:
users fail safely
users recover instantly
users learn from the failure
and most importantly, users understand the system better after it happens
Good UX doesn’t prevent confusion.
It engineers useful confusion.
The Shift Most Founders Miss
Startups often ask:
“How do we reduce drop-off?”
But a better question is:
“What kind of struggle helps users understand us faster?”
Because understanding is what drives:
retention
habit formation
power users
product loyalty
Not frictionless onboarding.
The Future of Product Design
The next generation of great products won’t be the ones that feel easiest at first.
They’ll be the ones that:
teach the system through interaction
let users explore safely
turn confusion into clarity
and failure into mastery
Because in product design, the goal is not to avoid failure.
It’s to make failure useful.
The Change Is Already Here
If you are designing, building, or shipping products right now, what comes next will matter more than what worked before.
The patterns are already here. How AI products fail. How behavior is replacing interface. How the best founders build. How the next generation of products gets made.
I write about them every Tuesday. Be the first to know.
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