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This study examined associations between elementary mathematics teaching candidates’ decisions to enter teaching and their individual characteristics and preparation program characteristics. We drew on data from the Teacher Education and Development Study in Mathematics (TEDS-M) to investigate such associations in the United States, Singapore, and Taiwan. In terms of individual characteristics, age and prior work experience were linked to the decision to enter teaching. Further, candidates with strong inherent commitments to teaching and those interested in engaging students in challenging assignments were more likely to enter teaching. Several program characteristics were associated with U.S. candidates’ decisions to enter teaching including program size, percentage of candidates completing the program, percentage of candidates switching from another career, and percentage of part-time faculty.