For nearly 15 years, Olcott travelled throughout the Pacific Northwest, mostly in order to prospect for gold. Often this interrupted pursuits of other occupations, mostly in the field of banking. His trips would take him to Southern Oregon (1892-93 accompanied by Oswald West), back to Salem to become a bank teller (1893-1895), Northern Washington and British Columbia (1895-1897), and then back to Illinois for a career as a bank cashier.