Options Are Cheap. Conviction Is Rare.
Marco has twelve browser tabs open.
He has been building his app for fourteen months. Shipped it in October. Four hundred users. He has been thinking about the paywall for three weeks, which means he has been not thinking about the paywall, which means he has been producing tabs.
Soft paywall. Hard paywall. Feature gating. Usage gating. Seven-day trial. Fourteen-day trial. Freemium with limits. Freemium without. The $9.99 tier. The $14.99 tier. The “most popular” badge on the middle option.
He has a spreadsheet. It has conversion rate benchmarks. It has twelve rows.
He is not stuck because he lacks information.
He is stuck because he has too much of it.
This is the new problem. Not the blank page. The full one.
AI can generate options. It cannot generate conviction.
Building vs Crafting
Building is making something that works.
Crafting is making something that feels inevitable to the right person.
Building outputs features.
Crafting outputs belief.
And belief is what turns:
a product into a habit
a landing page into a conversion
a tool into “this feels like me”
When building was expensive, scarcity forced decisions. You could not afford twelve options. You picked one and lived with it.
Now the cost of “plausible” has collapsed.
And the discipline of choosing has not kept up.
Taste (Defined Without the Vibes)
Taste has a reputation problem. It gets treated like a personality trait — something you either have or you do not.
But taste is not a mood.
It is not an aesthetic.
It is not “I like this.”
Taste is a set of skills that let you navigate abundance without drowning in it.
Here is a definition that holds up under pressure:
Taste is the ability to consistently choose what matters.
It shows up as:
Signal detection: noticing what is real and what is noise
Coherence: decisions that reinforce a point of view
Editing: removing “almost right” things that dilute the whole
Timing: knowing when “good enough” is actually wrong
Empathy: understanding what the user is trying to become
A punchier frame:
Taste is compression. Direction is selection. Empathy is calibration.
Taste is compression
You take a messy reality and compress it into something simple without being simplistic.
You are not adding clarity. You are removing confusion.
Direction is selection
Direction is the ability to say: “We are doing this, not that.”
Not because you are stubborn.
Because you have a point of view, and you are willing to be misunderstood by the wrong audience to be unforgettable to the right one.
Empathy is calibration
Empathy is not “being nice.”
It is the skill of mapping what people desire, what they fear, and what they will actually do on a Tuesday morning when they are tired and their alarm just went off.
Empathy lets you calibrate craft to the human on the other side.
Why This Matters Now
AI does not just speed you up.
It multiplies the number of plausible paths you could take.
That abundance sounds like freedom.
But it creates a quiet failure mode:
You keep moving.
You keep generating.
You keep shipping.
And you stop committing.
Options become a substitute for decisions.
That is why crafting gets harder.
Not because we lost tools.
Because we gained too many.
Where This Gets Painful: Paywalls
Paywalls are where “options vs conviction” stops being abstract.
The conventional wisdom says: run tests, track conversion, optimize the flow. The data will tell you what works.
This is not wrong. It is incomplete.
Because monetization is not just a pricing tactic.
It is product philosophy.
It teaches users what the product is.
It shapes how safe they feel exploring it.
It decides whether the relationship starts with trust or pressure.
And in the long run, trust compounds harder than conversion rate.
I have run this calculation myself. I was building Clueless Clothing, an AI wardrobe app — a product where the user shows up every morning already tired, already making dozens of small decisions before they even open the app. I had the same spreadsheet Marco has. Every paywall option was technically defensible. None of them felt obviously right. The question that eventually cut through the tabs was not “which one converts best?”
It was: What kind of relationship am I building?
A trust-first answer tends to sound like:
“We will not trick you.”
“We will not punish curiosity.”
“We will not create regret.”
Because the best monetization is not extracting value.
It is aligning value.
It is the user thinking: “I’m paying because this helps me. And it feels fair.”
That feeling cannot be generated by more data.
It requires conviction.
So how do you actually build it? I have been using a five-step framework I call the Conviction Loop for every decision that matters, features, onboarding, positioning, paywalls. It is not a scoring matrix. It is a forcing function. And it comes with a worksheet you can copy into any decision you are staring at right now.
For paid subscribers: the full Conviction Loop framework, the copy-paste worksheet, and a worked example using a real paywall decision below.
