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Wilbur was unable to complete his courses and graduate. Hoping to attend Yale and become a teacher, he enrolled in several college preparatory souses at Central High School in Dayton.

Wilbur was self confident controlled and of steady demeanor never tattled in thought or temper as his father described him. Highly intelligent he was a voracious reader, a talented writer, and a gifted speaker. Outgoing when circumstances required he could also isolate himself and shout out the world when he chose.

Wilbur's bright future suddenly changed when he was injured plain an ice hockey type of game during the winter of 1885-86. The damage to his face and teeth healed, but he suffered lingering heart and digestive complications. He became depressed and withdrew from the world. The confident robust Yong Wilbur faded. Uncertain of his health and future, Wilbur dropped his plans to attend yale and descended into a self imposed isolation of reading and contemplation.

By the time of Wilbur's accident, Susan Wright was already ill with tuberculosis and in need of constant care. Struggling with finding a new direction in his own life, Wilbur devoted himself to nursing his mother until she died in 1889.