South Africa celebrated 20 years of democracy in 2014. In 1994, life satisfaction among all South Africans peaked following the first open non-racial elections. Since that time, only some 45–55 % of the total population, on average, state that they are satisfied. Drawing on Alex Michalos’ classic Multiple Discrepancy Theory (MDT), this chapter explores the needs, expectations, aspirations and perceptions of progress among black South Africans, who were promised a better life under democracy by the new government they voted for in 1994. Findings suggest that expectations raised by the new government in the early years of democracy, coupled with a strong sense of entitlement to state services and welfare in later years, are among the stronges...