Alvah Simpson's journals contain almost daily entries of his activities. Some of the journals provided a full page for each day, while others left room for two days on a page. All of the journals were pre-printed and frequently contained useful tips on the first twenty or last twenty pages of the volume, including legal holidays, population of major American cities, the time of sunrise and sunset, calendars, postage information, weather signs, lists of poisons and antidotes, lists of foreign nations and their capitals, business laws, and rules for calculating interest. There was often space provided in some of the journals for personal information and the 1905 volume provides Simpson's weight and height, as well as his hat, glove, collar, shoe, and shirt size.

Simpson frequently listed the various towns and cities he visited to sell products. Occasionally he noted the name of the hotel where he stayed and the cost of his stay. Simpson commented on unusual weather, such as severe storms, snow, ice, or especially beautiful weather. He noted illnesses, both his own and those of Jennie and James. Special events are recorded, such as weddings, births, and deaths, and more routine activities such as church attendance and visits with his family. Simpson also mentioned noteworthy leisure activities including the Barnum & Bailey Circus, movies, and visits to historical sites. There are some major gaps in Simpson's journals. Simpson occasionally went a month or two without writing a single entry. The first few years and last few years of his journals are especially sparse. The only entry regarding Jennie's death is a newspaper clipping pasted into the journal and there are virtually no entries in the months prior to and following her death. Simpson also rarely explicitly noted job changes or moves, though a reader can detect when these events occurred.

The items removed from the journals were originally placed between the flyleaves and covers of the volumes and consist mainly of business cards, newspaper clippings, receipts, scraps of paper with notes and arithmetic, blotters, car registrations, and hotel stationery. There are occasional references within the journals to events represented by these loose items. For example, there is a pamphlet for the floating museum the convict ship Success, which transported English debtors to Australia during the 19th century. A corresponding entry in Simpson's journal on July 18, 1928, mentions that he and James visited the boat.

Simpson's expense accounts are written in pre-printed volumes. Many of the volumes have printed information similar to that found in the journals. Several of the volumes are labeled as "Salesman's Data Books" and have advice for salesmen regarding the sale of products and dealing with customers. Most of the volumes contain several world maps in the middle. Simpson's accounts list wholesale and retail sales, and expenses for each week. Expenses include stamps, gas, oil, hotels, alcohol, and trolley fares. Many entries note the amount of cash Simpson had on hand and how much money he gave to Jennie or his niece Dorothy. It is difficult to determine Simpson's income from these accounts as there is no indication of his base salary or commission.

The items removed from expense accounts include newspaper clippings, business cards, receipts, scrap paper with notes, and other miscellaneous items.

Simpson's address book contains both personal and professional addresses. There are no dates in the volume and several addresses are crossed out and replaced with new ones, suggesting that Simpson used the volume for many years and updated it as needed.

The papers contain a variety of items relating to Simpson and the family that are not connected to any volume in particular. There are many fliers, advertisements, and letters that relate to the various companies Simpson worked for as well as an ad for the grocery story he owned in Denver. Also included are photocopies of newspaper articles that relate to Simpson's work, his raccoon "Dimples," or other family members mentioned in the media. Three certificates for membership in fraternal orders are part of this series but placed in flat file storage to accommodate their size. Various legal documents, including deeds to land, death certificates, and wills are also part of the series. James Simpson's correspondence regarding funeral arrangements after the death of his father is here. Miscellaneous items include a photograph of a truck, blank postcards, and a pogo stick ad.

This series also includes four artifacts: a glass syringe, a free sample of Allen's Foot-Ease, and two cases Simpson used while working for O. F. Woodward.