I’m always convinced I’ll be ready next time.
Before every trip, I tell myself: this time I’ll pack early.
I’ll charge my Airpods. I’ll download podcasts. I. Won’t. Forget. Earplugs.
And yet… there I am.
One hour before the flight, standing in the kitchen, screaming “Where’s my passport??” like I’ve never traveled before.
I knew what would go wrong.
I just didn’t feel the pressure when I had the chance to fix it.
Your users are the same.
They see the limit.
“Only 3 AI runs left.”
They nod. They get it.
But they’re still just exploring.
Tapping around. Trying things.
They haven’t built anything worth protecting yet.
They think they’ll upgrade if they hit the wall.
But most of them don’t get that far.
They drift off way before that.
Because the product never became important enough to hit the wall in the first place.
You thought the cap would create urgency.
But caps only matter when people are actually using the product.
If they never cross that threshold, the upgrade prompt means nothing.
Empathy Gap
People don’t upgrade to avoid a limit.
They upgrade when they feel the loss.
But here’s the catch: when they’re calm — just browsing, trying things —
they can’t imagine how bad “stuck” will feel.
So they shrug it off.
“I’ll deal with that later.”
But later never comes.
Because they don’t use enough.
They never push far enough to feel blocked.
And if they never feel blocked, they never feel the need.
So they drift away. Not because the cap was wrong —
but because it came too soon, before anything mattered.
How we are making it worse by trying to make it better
You think: “If we show the limit early, they’ll remember.”
But early in the journey, there’s nothing to lose.
Nothing to restore. Nothing to protect.
They’re calm. Uncommitted. Still deciding if they care.
And in that state?
No limit feels urgent.
No cap feels painful.
No upgrade feels necessary.
Here’s a move you can steal from Duolingo to make it right
Duolingo doesn’t push “Pro” that much while you’re cruising.
They wait for the drop.
You miss a day. Your streak disappears.
That’s when they hit you:
“Restore your streak — $X.”
And it works.
Because now you feel it.
You built something. You lost it. And you want it back.
They didn’t convert you with features.
They converted you with panic.
3 steps to break this pattern next week
Stop asking people to upgrade before they’ve received any value
Start upsells after they’ve actually used the thing — not before
Frame the upgrade around keeping what they’ve earned: “Keep your streak,” “Keep your messages history,” “Keep access”
If you forget everything, remember this:
No one pays for what they haven’t felt.
They pay to keep what they’d hate to lose.
