This manuscript focuses on regret as a significant moral experience in surgical professionalization. It distinguishes between constructive regret, which encourages self-reflection and growth, and destructive regret, which can lead to emotional withdrawal and impaired decision-making. This article also offers recommendations for how both colleagues and organizations should respond to each type of regret, especially regret over poor outcomes, to nourish professional formation. Recognizing the tipping point at which regret shifts from a positive driver of improvement to a source of harm is essential.