To take full advantage of their experiences, people must be able to transfer old learning to new situations. Abstract representations, such as symbols and formal equations, efficiently capture structural commonalities across widely dissimilar contexts. However, novice learners often have difficulty learning abstractions because they seem largely arbitrary. Contextualization helps learners understand deep principles and apply them naturally. However, novice learners have difficulty transferring richly contextualized knowledge. The dilemma is this: in order to get learners to understand structure, they need meaningful contexts; to transfer to dissimilar situations, their initial learning must be decontextualized. Five series of experiments with preschool children and undergraduate participants examine combinations of contextualization and decontextualization to foster learning that transfers. In particular these experiments examine the role of symbols as decontextualizing elements as well as the role of language as a hybrid between symbols and rich experience. Across the series of experiments, words were implemented as decontextualizing elements for rich contexts; they were used as a source of interpretive contexts for idealized graphics; and they were placed in similar and dissimilar contexts, all to examine the conditions under which relational meanings are learned and transferred. The final series of experiments examined other methods of contextualizing learning such as hands-on experience and narrative perspective. Typically symbols are thought to enhance generalization, and experiential contexts are thought to enhance learning. The results of these experiments suggest that combining the influences of stable symbol-like entities with diverse experiences can enable better learning and encourage generalization by influencing future interpretations.