"Good judgement comes from experience, experience comes from experience comes from bad judgement" is a truism.
Fortunately it doesn't need to be YOUR bad judgement.
Hidden Treasures is a collection of mini-biographies of folks that would have been "famous" in late 19th century. The author asks the "why some succeed" while others fail question.
Unless you are a student of 19th Century American history a lot of the names in Hidden Treasures will be unfamiliar, but they all serve as examples of experience gained from "good" and/or "bad" judgement.