In September 1972, Jobs enrolled at Reed College in Portland, Oregon. He insisted on applying only to Reed, although it was an expensive school that Paul and Clara could ill afford. Jobs soon befriended Robert Friedland, who was Reed's student body president at that time. Brennan remained involved with Jobs while he was at Reed. He later asked her to come and live with him in a house he rented near the Reed campus, but she refused.

After just one semester, Jobs dropped out of Reed College without telling his parents. Jobs later explained this was because he did not want to spend his parents' money on an education that seemed meaningless to him. He continued to attend by auditing his classes, including a course on calligraphy that was taught by Robert Palladino. In a 2005 commencement speech at Stanford University, Jobs stated that during this period, he slept on the floor in friends' dorm rooms, returned Coke bottles for food money, and got weekly free meals at the local Hare Krishna temple. In that same speech, Jobs said: "If I had never dropped in on that single calligraphy course in college, the Mac would have never had multiple typefaces or proportionally spaced fonts".