This series documents a majority of Totman's formal educational experiences. From his first year at high shool to later scholarly research, Totman was constantly accumulating information. The materials relating to his high school, Arms Academy, show not only a general curriculum, familiar to almost any contemporary American high school student, but also the roots of Totman's future professional writing career. Examples of early writings include reports for classes such as English I through IV, U.S. History, and French; and notes for classes such as Biology, Chemistry and Plane Geometry. While his pursuit of a baccalaureate degree at the University of Massachusetts at Amherst started with a concentration in Horticulture, it ended with a degree in history. The primary catalyst for this switch was a United States Armed Forces Institute (USAFI) course entitled "Survey of the Far East," taken by Totman while in the U.S. Army from 1953-1956. Two essays written during the 1956-1957 school year back at UMass show further development in writing style, as well as a firm commitment to the study of history as a profession. His writing further improved at Harvard University, as evidenced by two seminar papers, as well as the culmination of his pre-professional education: his Ph.D. thesis. Totman's research for his Ph.D. thesis brought him to Shinkoganei, Japan. Materials from his first (Shinkoganei) and subsequent (Tanashi-shi, Kichijoji, and Mitaka-shi) scholarly research trips to Japan showcase the trials and tribulations of a professional scholar. Also included are documents relating to his decades-long research into Forestry.

The bulk of this series constitutes Totman's teaching career. Documents relating to his major teaching posts at the University of California at Santa Barbara, Northwestern University, and Yale University cover a wealth of information, most notably with individual class lecture notes and test materials on topics about Japan, ranging from the general to the specific. These are mostly organized by class number. Where the class number is inconsistent, the course title is used. Totman's guest teaching posts at the University of Chicago, the Kyoto Center for Japanese Studies and Stanford University are organized in the same manner and offer further insight into his teaching methods and topics. In addition to teaching, Totman served his profession in an administrative role. The Association for Asian Studies (AAS), in addition to other professional groups, was assisted by Totman in an administrative capacity. These materials, which include minutes of meetings, correspondence with other members, and collective proposals, show the scope and diversity of the scholars of Asian Studies, as well as indications as to which scholars specialize in what specific area. Guest lectures were another important part of Totman's career. These materials, organized by subject, may or may not include physically substantive information, but they will, at the very least, indicate who is (or was) conducting research on these topics.

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A prolific writer born into a family of prolific writers, Totman seemingly never put down the pen. This series is comprised of a majority of Totman's written works, and is divided into published and unpublished sections. The bulk of the published works are the documents relating to Totman's major books. This section relates virtually to every stage of publishing a book, from working drafts, to evaluations by his peers, to correspondence with publishers, and even to royalty and sales statements. Other published works include reviews of other scholars' books, encyclopedia entries, journal articles, book chapters, and newspaper articles. The highlight of the unpublished section is the collection of letters, original and transcribed, the bulk of which were penned by Totman during his military service in Korea and Japan. The letters from Korea show a unique glimpse of reconstruction efforts, as Totman reached the peninsula less than a year after an armistice ended the Korean War. The letters from Japan are restricted until 2015, however, recollections of that time period can be found in the unpublished section as well, in a work entitled Kathy's Story - For Laurel, which summarizes the childhoods and lives of both Conrad and Michiko Totman and their family. Another work, dubbed Farm Life in Conway Mass. in the 1940's, explores aspects of Totman's childhood in further detail. Other unpublished works include essays, abandoned projects, and unused fragments of his Ph.D. thesis. Early scholarly writings, such as term papers and reports, can be found in Series 1: Education.

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The majority of this series' contents are genealogical materials. These materials were researched and collected over the course of many decades by Conrad Totman's cousin, Alice Totman Hawks. In 1936, Alice started a family newsletter, which would be eventually known as Tot-Kin. In each installment, Alice presented her family research, along with substantial and diverse contributions from other members of the family from all over the United States. Tot-Kin featured letters, written to Alice for publication, which let the entire clan know what was going on in their neck of the woods. These letters, while they initially served as current news, are now a historical record, documenting such events as the Great Hurricane of 1938 or Lt. Clayton Totman's experiences with the U.S. Marines in Shanghai in 1937, during the Japanese invasion of China. Always having family history on her mind, Alice prompted family members to submit their own recollections of their childhoods, which many members did, including J. Monroe Totman, who in his own words describes many aspects of his life in Massachusetts and South Dakota, which began in 1850 in the former and would last until 1945 in the latter. In addition to personal anecdotes, Totman clan members were encouraged to submit historic letters, or transcriptions thereof, which might be in their possession, in order to share via Tot-Kin. Some of these letters include Rev. Harvey Totman's Diaries from 1833 to 1868, and Eli Totman's Letters home from 1862 to 1863. Harvey was a traveling priest in New York State, and Eli was in the 25th Wisconsin Regiment and was witness to parts of the Dakota War (a.k.a. Sioux Uprising) of 1862 in Minnesota. The Tot-Kin was discontinued in 1942, but was resurrected by Betty Jo (Totman) Jensen in 1971. These later issues, which have similar content to the earlier ones, are also included. The remainder of the genealogical materials constitute Alice Totman Hawks' notes, drafts, subject and alphabetical files. In addition, Conrad Totman's transcription of the letters and diaries of his paternal grandparents, his wife Michiko's letters to Totman family members, and Joshua Totman's Economics notebook from circa 1800, are also significant parts of this series.