The Best Work Happens When You Stop Caring
Less approval, more truth
Most founders think their best decisions come from deep analysis. Research. Frameworks. Weighing every angle.
They donât.
The best decisions happen when someone stops caring enough to think clearly. Stops asking âwhat will they say?â
Caring is a trap
When you care too much about how something will land, you stop thinking about the problem. You start thinking about the audience. The reaction. The judgment.
What will the board say? What will X say? What will the investors think?
Every move is public now. Every opinion is measurable. Every decision gets a like count. The cost of being wrong is no longer private. Itâs screenshots and threads and hot takes from people whoâve never built anything.
So many play it safe. Approval first, truth second.
And they end up building things nobody hates.
And nobody cares.
AI makes this worse
AI makes everything look right. Sound right. Feel polished and professional. But all these models are built on existing patterns. It gives you the average of whatâs already been done. A very convincing average, but still the average.
If youâre using AI as your strategic compass, youâre aiming for the existing. The place where every pitch deck, brand voice, and product positioning blurs together. And when youâre indistinguishable, you start competing on price.
The companies pulling away right now are the ones where a human made a call that no model would have suggested. AI gives you consensus, never conviction.
Design by consensus kills companies
This goes beyond logos and colour palettes. Design by consensus is what happens when every strategic decision gets filtered through too many opinions. Pricing. Positioning. Product direction. Go-to-market.
A creative presents a bold direction. The room is excited. Then a few days pass. Legal has concerns. The advisory board suggests toning it down. Three people on X say it looks weird.
Slowly, the edge gets sanded off. Everyone is comfortable. Nobody is excited.
The market rewards the brave
Some of the most successful founders Iâve been lucky to work with had this insane conviction in themselves that borders with insanity. From the outside it looked reckless. From the inside it was a risky move theyâre willing to take.
Itâs one of the reasons so many YC founders are that young. Youâve seen less. Youâve been told no less. So youâre less likely to listen. And thatâs the edge.
Look at crypto. The entire industry was built by people who didnât care what traditional finance thought.
Solana was declared dead after FTX collapsed. âGhost chain.â The founders who stayed and kept building? One of the biggest ecosystem comebacks in crypto history.
Tether has faced regulatory pressure, transparency concerns, and constant FUD for years. Still the dominant stablecoin by a massive margin.
Every major crypto cycle produces the same pattern - the projects that ship during bear markets, when everyone says itâs over, dominate the next cycle. Building when the crowd says stop.
Disagreement is attention
When people criticise your brand, your positioning, your decisions, it means youâve said something specific enough to provoke a reaction.
The alternative is silence. And silence in a crowded market is just burning money.
Brand equity, community loyalty, pricing power.
None of that comes from being fine.
How to care less (without being careless)
Caring too much costs you.
Every week spent second-guessing a positioning decision is a week your others ship. Every round of âletâs get more feedbackâ dilutes the thing that made the idea worth pursuing.
Before any major decision, ask whether the hesitation comes from the problem or from the audience. Are you solving for whatâs right, or for whatâs comfortable?
Care less about approval.
Care less about being polished.
Care less about whatâs safe.
Safe is how you lose the one position nobody else could have taken.
If youâre a founder looking for positioning only you can claim, thatâs the work we do at Pony. More about our strategy sprints at uncomparison.com.