We are interested in the origins of phenotypic diversity, and work at the intersection of phylogenetics, ecology, and organismal biology to reconstruct the natural history of adaptation. Questions that motivate us include: why have certain traits evolved multiple times in certain lineages but not in others? What are the initial steps in the evolution of a complex trait, and how do those initial steps influence subsequent evolutionary possibilities? In this talk I'll focus on our recent work in two areas. First, we will look critically at the evolutionary dynamics of 'leaf economic spectrum' traits within a closely related group of deciduous woody plants; second, we'll focus on understanding the partially shared evolutionary trajectories of two alternative and important adaptive syndromes in plants, C4 and CAM photosynthesis.