Money could not buy everything Jack wanted. Having the undivided attention of his mother was one of his greatest desires. His sister Rosemary was intellectually disabled and needed special care, so Rose paid particular attention to her. Rose was at times overburdened by the needs of her nine children. Joe's work often took him away from home, so it was Rose who carried the burden of childrearing. To counteract the effects of her burdensome life, Rose found comfort in traveling. She traveled extensively throughout the United States and Europe. Sightseeing and shopping were relaxing for her, and it was not uncommon for her to remain away from home for several weeks at a time. While Rose traveled the world, the Kennedy children were under the care of the family maids and nurses.

Jack dreaded his mother's lengthy absences. When he was six years old, a sarcastic Jack told Rose that she was a “great mother” for leaving them all alone. In time, Jack grew to quietly accept his mother's departures, but he never liked them. When his mother was home he became the rebel of the family. He broke the rules, was often late to dinner, dressed improperly, and irritated her with inopportune questions during religious instruction. Rose saw Jack's defiance as an indication of his independence and his desire to do things as he wished.

Jack rarely experienced the warmth, affection, and love he expected from his mother. Rose Kennedy was a strict disciplinarian who required that the children adhere to schedules. As a religious woman, she took great pains to ensure the children received proper religious instruction. Rose took motherhood seriously and viewed it as a profession that required her to take on the challenge with a commitment to fulfill her duty to the best of her ability.