The summers of his school years, he worked for the New York Central System Railroad on construction jobs, going up the scale from axman, rodman and topographer to bridge-building inspector.

His first position after leaving Harvard was a nonsalaried spot with the law firm of Kline, Tolles & Goff, attorneys for the Standard Oil interest in the central states.

Under his leadership the company pioneered in establishing pre-fabricated enameled steel and glass service stations which replaced their less-appealing predecessors.

Sales soared as he went to work on every phase of the business, establishing training schools for station attendants and following one of his chief ideas that the key to management was the industrial relations department.

Promotions were made from within the company, causing the famous quotation "when the President retires, we hire a new office boy".

[citation needed] Nellie B. Stiers was Holliday's first wife and bore him 3 children: Samuel Trevor, James R., and Margaret Louise.

[11] In 1947 he wrote a long article, entitled "Our Number One Job: World Peace,"[12] which in January 1948 was privately published in a booklet.

He was a member of Delta Upsilon fraternity and belonged to the Rowfant Union, Cleveland Athletic and Chagrin Valley Hunt Clubs.

In 1943 he became president of the Cleveland Chamber of Commerce,[5] in which he had served for years on such committees as manufacturers, public finance and taxation, and aviation.

In 1945, he joined other community leaders to incorporate the Air Foundation,[16] a nonprofit organization making grants and scholarships for space and aviation-related purposes.