The idea of economic planning and state ownership of the means of production, which had been central to socialist economic thought for a century and a half, suddenly fell out of favor even among socialists after the fall of the Soviet Union. The three essays of this dissertation are in essence critiques of this 21st century orthodoxy. The first essay addresses the idea of market socialism, as proposed by several academic works in the decades before and after the fall of the USSR. The essay questions whether market socialism would be substantially different from capitalism in practice. It aims to show that any economic system which is based on market relations and atomized ownership of the means of production would feature a type of exploitation very similar to that found under capitalism, meaning that such a system would not be substantially different from a capitalist society with a welfare state. The second essay is a study of a problem that may be faced by all planned economies. Historically, planned economies faced pressure to maintain old industries, old workplaces and old jobs, so as not to cause social disruption. There is a tradeoff between technological progress and job stability. This creates a dilemma: Can socialism keep pace with capitalist innovation while providing full job security? The essay explores this question and answers in the affirmative, with some qualifications. The third essay aims to challenge the notion that socialist economic planning "failed" in the Soviet Union and East-Central Europe. It is an empirical study of the economic performance of the Soviet-type socialist economies under the stagnation conditions of their worst-performing decade, compared with the experiences of the same countries after the transition to capitalism. The findings suggest that although a few countries saw a net benefit from the transition to capitalism, the majority saw a net loss. The region as a whole also saw a net loss, and its current economic trajectory makes it unlikely that this loss would be offset by higher gains in the foreseeable future.