Gordon filled his journals with daily entries of varying lengths. The first was a gift from his mother, and the second a Christmas gift from his father. In the journals, Donald wrote about issues of typical concern to a young boy, including his schoolwork, especially algebra, spelling, latin, and drawing. He attended church regularly, and early in the first journal resolved to "try to be more Christ-like." His days were primarily spent with other Americans living in Japan, though he refered on occasion to the family's cook, Denkichi, a Buddhist monk who visits his father regularly, and other Japanese. The journals occasionally refer to local events, as in the entry for April 13, 1890 in which he wrote "We heard that Mr. Pierce or something like that had been murdered by the Japanese. They cut him to pieces..."

Donald's leisure activities included tennis, playing dominoes and tag with friends, gardening, attending theatrical productions like The Mikado, and reading, especially works about Abraham Lincoln and children's newspapers like Youth Companion. The family lived in Kyoto, but took vacation in various spots around Japan including Tokyo, Yokohama, Tokayama, and many others. While fishing on vacation he caught a poisonous Fugu, or pufferfish. Donald also celebrated American holidays with his family, including the 4th of July, at which he set off firecrackers, ate chocolate ice cream, and went for a boat ride. In addition to written entries, each volume includes clippings, sketches, musical notation, and other ephemera. A fold-out map was pasted inside the back cover of the first volume, on which Donald translated some of the Japanese place names into English.