How do we tell caution from a worry loop that never ends?

You tell each other it's due diligence. You run the numbers again. You list what could go wrong, again. Someone asks 'but what if' one more time in the meeting. Somewhere along the way this stopped being work and became a habit. No one marked the moment it happened. The thinking itself has become the danger. You are not weighing risk anymore — you are performing the weighing of risk, for each other, as proof that you care enough, that you're responsible enough. It feels like diligence. It works like paralysis. You cannot control whether the plan fails. You can control whether your team spends this week deciding or spends it circling. That is the whole question in front of you. Everything else is a story you are telling each other to avoid answering it.