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Upon reaching Cleveland, Harry quickly entered the maritime industry, initially seeking work aboard ships on the Great Lakes. Facing rejection due to lack of experience, he didn't give up. Instead, he took on manual labor jobs, such as pushing wheelbarrows for construction firms, and attended night school to learn new skills like typing and stenography. These efforts paid off when, by 1886, at only 21, he landed a job as a stenographer at Pickands Mather & Company, a leading firm in shipping, iron ore, and steel.