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Stephen Hodgetts read the e-mail over and over again and still could hardly believe what he had read. He had just come back from his vacation, well rested and refreshed, and this e-mail had dampened his high enthusiasm. It took time to absorb such bad news and for Hodgetts to get over his incredulity.Yet in the end Hodgetts accepted the truth‐a deep, dark terrible truth that would not go away. Robert Davis, his business partner’s son, had confirmed in an e-mail his worst fears about their newest business partner, David Russ.Many thoughts were running through his mind simultaneously yet each screamed to be heard.“How could he and his partner Richard Davis have been so blind, so trusting?” “How could Russ not have heeded the advice of his business partner, Richard Davis, Russ’s former English professor?” And most important, “What was now going to happen to their new business?” Yet the one thought that continued to echo among them all was surprisingly a quote from Sir Arthur Conan Doyle’s beloved character, Sherlock Holmes: “But there are always some lunatics about. It would be a dull world without them.”

Managers’ work is surrounded by complex environments, from which they need to learn, in order to understand them. However, complexity poses several challenges to managerial learning, for which usually management educational programs have not prepared managers. Thus, the purpose of this paper is to explore such challenges and possible ways to overcome them.

This is a conceptual paper that explores in depth the issue of managerial learning challenges in a complex world. Managers face these challenges during their practice, yet sometimes management education has not prepared them for this.

Three managerial learning challenges due to complexity are identified. First, through cognition and cognitive structures, managers simplify the world around them. Nevertheless, biases, inertia and inaccuracy emerge, as managers’ mental models are not truly capable of capturing complexity. Second, managers look for information to aid them in their learning processes, but the information they gather is sometimes bogus, invalid or unfounded. Third, managers could seek for support from management research to improve their learning. However, given management research intricacies, limitations and particularities, a learning challenge emerges as well, as management research has been rarely capable to capture complexity.

Having explored these managerial learning challenges due to complexity, this paper discusses a carefulness-based management learning ideal, which by being underpinned by the quality of carefulness and the related concepts of critical thinking, negative capability and a deep learning style, suggests a potential new way to approach management learning in light of complexity.