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Most of the important lessons about regional anesthesia and acute pain medicine I learned by improvising and getting things wrong. This article recounts those intuitions and mistakes and the patients, students, mentors, and colleagues who helped me turn them into something potentially useful. It begins in 1975, in a field hospital during a secret, forgotten war in Angola, where necessity drove a young, fledgling anesthesiologist to develop what may have been the first continuous peripheral nerve blocks. It traces the journey through decades of clinical practice: epidurals that failed when they shouldn’t have, assumptions that didn’t hold up under scrutiny, and an increasing realization that nerve blocks and regional anesthesia alone are not enough. Along the way, the scope broadens from nerve blocks to the larger question of what acute pain medicine ought to be: a systems-based specialty that collaborates with other specialists and encompasses continuous analgesia, neuromodulation, rehabilitation, opioid reduction, and an expanding understanding of autonomic and inflammatory mechanisms. If there is a single lesson from these 50 years, it is that progress never comes from defending what we think we know but rather from the discomfort of realizing we were wrong and the discipline to adopt, adapt, and improve.