Why your best decisions still feel wrong

There's this moment that happens about six months after a founder makes a big call. The product launched. The hire worked out. The pivot paid off. And they're sitting there thinking: "I got lucky."

Not "I made a good decision." Lucky.

I used to think this was imposter syndrome. Then I started paying attention to what actually happens when founders make decisions. The pattern isn't what you'd expect.

The decisions that feel certain? Those are usually the safe ones. The ones that work out but don't move the needle. Hire someone with the exact right resume. Build the feature customers explicitly requested. Stick to the roadmap you showed investors.

The decisions that change everything? Those feel terrible going in.

Your fourth employee was someone who'd never done the job before, but you couldn't shake the feeling they'd figure it out. You killed a feature half your team loved because something felt off about the usage patterns. You walked away from a partnership that looked perfect on paper.

Six months later, these are the decisions that defined the company. And they still don't feel smart.

Every decision you make contains information you don't have. That's not a bug in your process. That's the actual condition of building something new.

You can't know if your next hire will work out. You can interview them for six hours. You can do reference checks. You can have them meet the whole team. At some point you're still guessing about whether they'll ship when it's 11pm and the demo's broken.

You can't know if the feature will land. You've got user research, you've got data, you've got a prototype half the team is excited about. You still don't know if people will actually use it until it's live.

The uncertainty doesn't go away when you get better at this. You just get better at deciding anyway.

I've watched founders go through their first 50 major calls. Something shifts around decision 30.

Early on, they're trying to eliminate uncertainty. More research. More data. More input. They're searching for the decision that feels obviously right.

By decision 30, they've figured out the pattern. The obviously right decisions are usually the boring ones. The decisions that matter always come with doubt.

So they stop trying to feel certain. They start looking for something else.

They're tracking: What happens when I ignore this feeling? What happens when I follow it even though I can't explain it?

The best founders I know have gotten comfortable making calls that feel 60% right. Not because they're reckless. Because they've learned that 60% is as good as it gets when you're doing something that hasn't been done before.

Here's where it gets useful. Not all uncertainty feels the same.

There's the wrong feeling that comes from incomplete information. You're hiring for a role you've never hired for. You're entering a market you don't fully understand. You're making a technical bet on something that might not work.

This feeling is sharp. Specific. You can name exactly what you don't know.

Then there's the wrong feeling that comes from going against the script. Everyone says you should raise a Series A before shipping. Everyone says you should hire a VP of Engineering before you hit 10 engineers. Everyone says you should build the enterprise version first.

This feeling is fuzzy. Social. You can't quite articulate what's wrong, you just know the standard advice doesn't fit.

The first type of uncertainty gets better with information. Do the research. Run the experiment. Talk to someone who's done it.

The second type gets worse with more input. The more you listen to what you "should" do, the further you get from what actually makes sense for your company.

The founders who move fast have learned to tell these apart.

I watched a founder make a decision last month that looked insane from the outside. They killed a product line that was generating 40% of revenue. Profitable revenue.

They didn't have a replacement ready. They didn't have a grand strategy. They just knew that keeping it meant splitting focus, and splitting focus meant they'd lose the race on the thing that actually mattered.

When I asked them how certain they were, they said: "Maybe 65%."

Then they did it anyway.

That's not recklessness. That's understanding that waiting for 95% certainty means someone else ships first.

The decision felt wrong. Six months later, it was obviously right. But it didn't feel right at the time, and it probably never would have.

They think the goal is to get better at predicting outcomes. More data, better models, smarter analysis.

But the actual skill is getting better at making decisions with the same amount of uncertainty.

You'll never know if your fifth hire will work out. You get better at interviewing, you get better at onboarding, you get better at supporting people through their first 90 days. The uncertainty at the moment of hiring doesn't change.

You'll never know if the product will work before you ship it. You get better at prototyping, you get better at reading early signals, you get better at iterating fast. The uncertainty at the moment of launch doesn't change.

What changes is your tolerance for moving forward anyway.