Your judgment is good. This is not in question.
It has been tested in real conditions, against real stakes, over a sustained period, and it has been right more often than not in the ways that matter. The track record is genuine. The confidence it generates is warranted.
And it is now, in specific domains, the primary source of your most consequential errors.
Not because the judgment has declined. Because it has been so consistently confirmed that the conditions under which it is wrong have become invisible. The mind that has been right about a particular class of decision for twenty years no longer fully considers the possibility of being wrong about that class of decision. It pattern-matches to the established framework before the full evidence has been assembled. It experiences the doubt that good judgment requires as unnecessary — a sign of insufficient confidence rather than appropriate epistemic caution.
The Yoga Sutras call this Pramana — valid knowledge — and make a distinction that most successful people find uncomfortable: the validity of past knowledge does not guarantee the validity of present perception. The Vritti — the mental modification — that produces confident judgment is the same mechanism that produces confident misperception. The confidence itself is not reliable as a signal of accuracy.
Daniel Kahneman's research on expert intuition identifies the specific conditions under which expert judgment is reliable and the conditions under which it fails catastrophically. Expertise produces accurate intuition when the environment is regular, feedback is rapid, and the conditions are sufficiently similar to the training conditions. It fails when the environment has changed, when feedback is delayed or absent, or when the situation contains important novel elements that the pattern-matching system treats as familiar. The leader who built their judgment in a particular competitive environment and is now operating in a significantly changed environment is, in Kahneman's framework, applying expertise in conditions that no longer validate it — while experiencing the full subjective confidence that the expertise once warranted.
The Stoic practice of Epoché — the suspension of judgment, the deliberate pause before the confident conclusion — is not a practice for people who lack confidence. It is a practice for people who have too much of it in domains where the confidence is no longer warranted by current conditions.
The question is not whether your judgment is good. It is: in which specific domains has the confidence in your judgment outrun the current evidence for its accuracy? And who around you — if anyone — is in a position to tell you?