[4][5] The novel follows five days in the life of cultural history professor Moses E. Herzog, who at age 47 is having a midlife crisis and burnout following the divorce from his second unfaithful wife.

Herzog spends much of his time both on intense and often hilarious intellectual reflection and mentally writing letters he never sends.

These letters are aimed at friends, family members, and famous figures, including historical recipients who are dead or whom he never knew.

The plans were a ruse, and shortly after arriving in Chicago, Madeleine throws Herzog out and attempts to have him committed to an asylum.

He subsequently witnesses a series of court hearings, including one in which a woman is charged with beating her three-year-old to death by flinging him against a wall.

He goes to his stepmother's house and picks up his deceased father's antique pistol with two bullets in it, forming a vague plan to kill Madeleine and Valentine and run off with June.

The next day, after taking his daughter to the Museum of Science and the aquarium in Jackson Park, Herzog crashes his car and is charged with possession of a loaded weapon, the antique pistol.

To Will's surprise, Ramona joins them for dinner, and Herzog begins making plans to fix up the house, which, like his life, needs repair but is still structurally sound.

"[8] It is only when he has loosened this bondage and gotten in touch with the "primordial person" who exists outside this ideology that Herzog can "achieve the experience of authentic being.

[13] Both Lamont and Ludwig reviewed Herzog without mentioning the autobiographical elements, with the latter favorably describing it as "a major breakthrough.