His work was recognized with many awards during his lifetime and was called the "Dean of Advertising Men" and "arguably the single most important figure in early twentieth century graphic design."

After high school, his father secured him a position in a local printshop as a Printer's devil, and he worked 12 hours a day for six months for no pay.

He learned from the hardware store owner of a contest offering $USD50 (or about $1,696 in today's dollars) to the winner who designed the best ad for a Bissell carpet sweeper as a Christmas present.

One of the three judges for the Bissell carpet sweeper advertising contest was Charles Austin Bates, an important early copywriter and New York ad agency founder and owner.

He found work writing copy for a small print shop for a while, but returned home after less than a year, unsuccessful.

He moved back into his parents' home where he worked various jobs as a printer, reporter, columnist, advertising man, and publisher.

Unable to make a living, he finally secured a job as an advertising manager in a department store in Peoria, Illinois for $USD19.50 (or about $687 today), per week.

[11]: 138 [4] In 1908, George P. Rowell asked him to write a column for the same periodical he had gleaned ideas from some years before, Printers' Ink.

He said ad agencies should hire illustrators like James Montgomery Flagg and Edward Penfield, who created editorial content for periodicals.

[12]: 308 After visiting Europe, he became an advocate for Modernism which he thought "offered the opportunity of expressing the inexpressible, of suggesting not so much a motor car as speed, not so much a gown as style, not so much a compact but beauty.

Newspapers had their own in-house typographers, but Calkins wanted to improve the overall product-related advertising and marketing effort.

[13] Calkins wanted to make advertising akin to fine art, and elevate billboards into “the poor man’s picture gallery”.

[18][19][20]: 9  The advertising campaign, based on a live model, using impressionistic techniques and a fictional character, was one of the first of its kind.

R&G had relied on the then-traditional method of "drummers" who curried local retailers with sales talk, display stands, posters, booklets and promotional items to encourage them to carry the company's products.

Bates persuaded the firm to devote almost its entire promotional budget to occasional, full-page, back-cover ads in Ladies' Home Journal which cost the astronomical sum of $4000 (or about $146,496 today).

[5] In 1925, Calkins was the first recipient of Harvard University's Edward Bok Gold Medal for distinguished personal service in advertising.

One of his theories featured in the book of the same name was that of “consumer engineering,”[25] or the artificial demand creation for a product using design and advertising.

[26] Roy Sheldon and Egmont Arens, both in Calkins' employ, wrote the 1932 book, Consumer Engineering: A New Technique for Prosperity (Harper & Row, NY).

they wrote: Goods fall into two classes: those that we use, such as motor cars or safety razors, and those that we use up, such as toothpaste or soda biscuits.

Still vigorous at age 64, he wrote extensively and contributed many pieces to magazines and newspapers including the Atlantic Monthly and The New York Times among others.