The aim of this paper is to examine the process of the unemployment changes in Taiwan in a macro approach. Over a historical view of Taiwan's economic development, there have been seven cyclical phrases since the mid-1960s. It was not until the fifth cyclical phrase during the 1990s that the unemployment problem in Taiwan became more and more serious, with the unemployment rate reaching a record high of 2.99% in 2000. Thereafter, there was no sign of relief within the labor market, indicating that Taiwan's economy started experiencing both the structural and cyclical unemployment. In fact, since the fifth cyclical phrase, Taiwan encountered the structural unemployment as a result of the transformation of the Taiwan's economy in the last century, with a dramatic rise up to 4.57% in 2001 and 5.17% in 2002, then a gradual decrease down to 3.91% in 2007. And then again, the island's unemployment rate climbed sharply from 4.14% in 2008 up to 5.86% in 2009, with the rate eventually reaching an all-time high of 6.13% in August, 2009, that reflected the impact of the financial crisis since 2008. It also seems that Taiwan's economy is suffering from the worse structural unemployment corresponding to the longer-term unemployment.