Anderson Cooper, a journalist and news anchor for CNN, and his mother, Gloria Vanderbilt, an extremely wealthy artist, writer, and designer, emailed each other continuously for about a year in an effort to get to know each other better. Cooper's father, Wyatt Emory Cooper, abruptly died during open heart surgery when he was ten. Cooper had repeatedly said that he longed to discover a letter written to him by his father, talking about himself and teaching Anderson about life. Shortly before Vanderbilt's 91st birthday, she developed a severe respiratory infection, and came near death for the first time in her long life. This incident caused Cooper to start a conversation with his mother that he never had the incentive to begin before. Realizing that his mother could soon be taken from him like his father had been, Cooper reached out to her, so when she did pass away, nothing would be left unsaid.
The book is a series of emails written between Cooper and Vanderbilt in which the latter writes about her life experiences and obstacles she has faced. Cooper replies with questions and comments regarding the stories she tells, and he compares and contrasts himself to her. One major similarity between Cooper and Vanderbilt, is that Vanderbilt's father also died when she was very young. She was left in the care of her mother, Gloria Morgan Vanderbilt, her grandmother, Naney, and her governess, Dodo. Vanderbilt's mother was never there for her, and was always away with her twin sister, Thelma. Naney and Dodo conspired against Vanderbilt's mother, which resulted in a custody battle between Gloria Morgan Vanderbilt, and her sister-in-law, Gertrude Vanderbilt Whitney. Along with the custody battle, Vanderbilt's multiple marriages and independent experiences contributed to her accumulated strength and wisdom of life, which she passes on to Cooper via the emails discussed previously.Other than her wisdom, she also passed on her excellent drive. In the book, she comments to Anderson, "I understand and know too well that no matter what one achieves, it is never enough."