This is an unusual and important longitudinal study of the complexities of getting things done in large corporations. It is based on interviews with Swedish industrial leaders, interviewed in 1990, and thirty years later in 2020. These industrialists and business leaders reached their top positions in major corporations through a series of learning events, mapping their approach to complexities today. The experiential background typically is internationalized business-to-business (including SKF, Scania, Atlas Copco, Stora Enso), other industries are represented as well, including banks (Handelsbanken), shipping (Stena Line), airlines (SAS), finance, and consumer goods (Volvo Cars). About 675 such learning events were analyzed. The main finding is that they deal with “surprising” situations; being “thrown” into an unfamiliar context. Many of the events analysed focus on periods when uncertainty was at maximum, and the executives needed to construct a credible explanation to why expectations were not met. At that point, what should be done? And how best to persuade others of the merits of the proposed actions? Going into action in these “surprising situations”, means accepting an unknown risk of failure.