Wilbur was quiet, but sure of himself. He was intellectually motivated, excelled in school, had an extraordinary memory, and was a good athlete. Toward the end of his senior year at Richmond High School in Indiana, the family suddenly returned to Dayton due to Milton’s church responsibilities. Wilbur was unable to complete his courses and graduate. Hoping to attend Yale and become a teacher, he enrolled in several college preparatory courses at Central High School in Dayton.
 
Wilbur was self-confident, controlled, and of steady demeanor—“never rattled 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 shut out the world when he chose.

Wilbur’s bright future suddenly changed when he was injured playing 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 young 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.