The Judgment Gap

When I was a trainee lawyer, I asked a partner what it took to become great. “Paranoia,” he said.

I remember thinking, Great - now I know why lawyers get called anxious overachievers.

So I did what any good junior does - I became paranoid.
Checked everything. Then checked it again.
Not just typos or cross-references - I mean envelope trays. Most nights, I’d take my laptop home at 11pm.
Not because anyone asked. Just… in case.

Maybe early on paranoia builds precision. 

But left unchecked, paranoia becomes paralysis.

You see it all the time.

Due diligence reports meant to flag exceptions only somehow stretch long enough to send to the bookbinders.

Memos - internal or external - that analyse every angle but dodge owning a recommendation.

One mental model that helps build judgment is what lawyer-turned-investor Charlie Munger called inversion thinking.

He tells a story from his time in the US Air Corps. He was a weather forecaster -  working alone through the night, charting storm systems, calling pilots. His job: don’t get them killed.

Here’s how he thought about it:

“I asked myself, ‘How can I kill these pilots?’ Now that’s not the question most people would ask. But I want to know the easiest way to kill them would be so I could avoid it … There were only two real hazards, and I became fanatic about avoiding them.”

That’s inversion.
Start with how things fail - and work backwards.

Early in my career, I thought good work meant being exhaustive.

But the lawyers clients trust most?
They say, “Ignore that. Focus here.”

That’s not reckless. That’s what matters.

✍️ Note to self:

Precision keeps you safe. Judgment moves you forward.