Research on the structural features of people’s most enduring regrets has focused on whether they result from having acted or having failed to act. Here we focus on a different structural feature, their connection to a person’s self-concept. In 6 studies, we predict and find that people’s most enduring regrets stem more often from discrepancies between their actual and ideal selves than their actual and ought selves. We also provide evidence that this asymmetry is at least partly due to differences in how people cope with regret. People are quicker to take steps to cope with failures to live up to their duties and responsibilities (ought-related regrets) than their failures to live up to their goals and aspirations (ideal-related regrets). As a consequence, ideal-related regrets are more likely to remain unresolved, leaving people more likely to regret not being all they could have been more than all they should have been.