We examined the role of desired, feared, and expected possible future identity structures in the restructuring of identity after two life transitions. A longitudinal study was conducted on 86 young adults during the transition from school to university and 143 adults during the transition to parenthood. In both samples, pre-transition desires and expectations about the restructuring of identity predicted post-transition actual identity structures. Post-transition emotional well-being was higher among those whose post-transition identity structures more closely matched their initial desires and less closely matched their initial fears, and among those who reported a greater magnitude of identity change. We propose that possible future identity structures play an important role in the identity accommodation process during life-transitions, and that they have significant implications for well-being. Copyright © 2009 John Wiley & Sons, Ltd.