8. Retail Manager
After serving in World War I, Truman opened a haberdashery with military friend Eddie Jacobson. Truman oversaw operations of the store, which was something of a precursor to a department store (which was the precursor to Amazon).
Proving just how difficult owning a small business can be, Truman’s foray into retail management ultimately proved less successfully than his presidency. The haberdashery closed during a recession in the early 1920s, setting Truman on course for a career in politics.