Jennings was an artist intent on producing quality work, as is seen in the text of the business cards he handed out in the 1900s:
If you have anything photographic you wish well done, call, write or
Though Jennings focused more on his photography than on the state of his finances, the jobs he held were a key element of his success in photography. He started out as a stenographer, and typed away for Wanamakers department store until he had a chance run-in with Pennsylvania Railroad real estate agent Robert Stiltson. The executive appeared in Wanamakers in urgent need of a typed letter, and Jennings earned his admiration by quickly typing exactly what he dictated. Shortly thereafter Jennings began working as Stiltson's private secretary, and was able to bargain for free railroad passes over the entire rail system. His personal and professional travels allowed him to photograph America, and his collection of scrapbooks and photographs are an invaluable portrait of the 19th and early 20th Century United States.
Jennings took pride in photographing Philadelphia; shown here is one of his aerial shots of the growing city and the notes written on its back, indicating that it was taken from the basket of a hot air balloon.
Please note: The non-darkened version of Jennings' note is authentic, while the darkened version has been manipulated for convenience.