Abstract This special article is an essay version of the European Society of Regional Anaesthesia and Pain Therapy 2011 Carl Koller Award lecture. Historically, evaluations of a trainee’s regional anesthesia learning focused on caseload numbers. The deficiency of this unidimensional approach is that case numbers alone say little about the resident’s mastery of the nontechnical aspects of regional anesthesiology. Simulation can refine technical skills, but also expands the teaching paradigm to include management of rare complications. Teachers are further challenged by requirements to incorporate systems-based practice topics, including the optimization of operating room efficiency and patient safety. Journals play an important role in regional anesthesia education for both trainees and mature anesthesiologists. Editorial boards build valuable educational foundations by providing critical analysis of new technologies and sponsoring practice advisories. Subspecialty societies such as European Society of Regional Anaesthesia and Pain Therapy and the American Society of Regional Anesthesia and Pain Medicine foster regional anesthesia education through their efforts to define curricula, produce guidelines, and promote international collaboration.