This is the 8454th most frequent Japanese word.
懲り
"懲り" means "learning from experience or failure to avoid repeating mistakes."
The word '懲り' here is used to indicate someone's learning or becoming cautious after experiencing failure.
彼は失敗して懲りた。
He learned from his mistakes.
In this case, '懲り' indicates the opposite, where the subject did not internalize a lesson from prior experiences.
懲りずにまた挑戦した。
He tried again without learning from his previous failure.
Here, '懲り性' describes a characteristic of a person who tends to learn from experiences and applies care in future situations.