This article discusses the key issues of macroeconomics and finance, raised in a new book by Alan Greenspan “The Map and the Territory: Risk, Human Nature, and the Future of Forecasting” (2013). Firstly, the role of the state in economy, excessiveness of the government interventions, the need to clarify the Greenspan’s position, taking into account very special “nature” of the emerging economies, sustainable patterns of collective behavior and long regulatory cycles. Secondly, the limitations to forecast the risk overconcentrations, market failures and crises, according to Greenspan, are discussed. Lastly, the role of the rational / irrational behavior in formation of the macroeconomic dynamics, as well as to what extent the monetary authorities could rely on long-term patterns and forecasting when influencing the economic growth and mitigating the financial risks in macro-space.