Lake moved to a suburb of Chicago, Harvey, in 1890, where he worked as a roofer and construction worker before returning to his hometown in 1896. According to Lake, he became an industrious businessman and started two newspapers, the "Harvey Citizen" in Harvey, Illinois and the "Soo Times" in Sault Ste. Marie, Michigan, before beginning a successful career in real estate, and later, becoming a millionaire in life insurance dealings. Historian Barry Morton found no evidence that Lake ever owned the two newspapers, citing sources which indicate the "Harvey Citizen" was founded by the Harvey township, and the "Soo Times" was started by George A. Ferris and owned by Ferris & Scott Publishers. Morton further alleges that Lake exaggerated his business career, and that "clear evidence" shows Lake instead worked as a small-scale contractor, roofer and "house-flipper". In the 1900 Census, Lake's occupation is listed as "carpenter".