Life and Early Career
Born in Bellefontaine, Ohio, Flora attended the Art Academy of Cincinnati from 1935 to 1939. In 1938, he met writer Robert Lowry, then a student at the University of Cincinnati, and the two launched The Little Man Press, a letterpress series of limited edition publications, for which Flora supplied illustrations, design, and layout. They collaborated on Little Man Press until 1942. (Lowry, a volatile and self-destructive literary turbine, later self-published many works under a revived Little Man imprint without Flora's involvement.)
In 1941, he married his college sweetheart, artist Jane Sinnicksen. Following a brief, struggling period as a commercial artist in Cincinnati, Flora was hired at $55 a week by Columbia Records in 1942, at which time the Floras moved to Westport, Connecticut, since Columbia was then based in Bridgeport. (In 1945, the couple relocated to Rowayton, Connecticut, where they lived the remainder of their lives. They had five children.)
Beginning work in the art department under Alex Steinweiss, inventor of the illustrated album cover, Flora illustrated ads, new release bulletins, and retail and trade literature. In 1943, when Steinweiss entered the navy, Flora was promoted to Art Director. That year, he launched Columbia's monthly new release booklet, Coda, which he continued illustrating and designing through 1945, when he was promoted to advertising manager. His replacement as art director was Robert. M. Jones, who later became art director for RCA Victor (where he twice won the Grammy Award for Best Album Cover - Classical; Flora and Jones remained lifelong friends, their careers sporadically interwining). Flora's artwork began appearing on Columbia 78 rpm album covers in 1947 (not earlier, as some accounts allege).
Flora worked as advertising manager and sales promotion manager at Columbia, but felt ill-suited for bureaucracy and grew frustrated because he was working a desk job while doing little art. Finally reaching his endurance of what he called "endless meetings, endless memos, and wrestling with budgets," Flora resigned in 1950. "Bitten by the bug of wanderlust," he drove to Mexico with his family in a Hudson sedan. They remained south of the border for 15 months, during which time Jim and Jane painted, created woodcuts and lived as bohemian gringos in Taxco.
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