Pursuing his interest in jazz, Eshleman travelled to Los Angeles in the summer of 1954. He parked cars for a living and studied jazz piano with Marty Paitch and Richie Powell, the younger brother of Bud Powell. Returning to Indiana University in the fall, Eshleman changed his major to Business. His academic performance suffered. Put on academic probation for low grades, he was expelled for having too many parking tickets, but able to return to school the following year, this time as a Philosophy major.