To promote our theoretical understanding regarding the exploration process during adulthood, the current study focusses on this process as it relates to work and family life roles and the relations between them, during the transition to motherhood. Two instruments assessing vocational and maternal exploration, relating to self and environment dimensions, were developed. Validation was conducted through two independent studies of two groups of Israeli Jewish women during their transition to motherhood: exploratory factor analysis (N = 125) and confirmatory factor analysis (N = 232). Results demonstrated good fit of the model to the data, and reveal statistically significant estimates for each of the measurements. Positive, significant correlations between the two exploration processes were found. The findings support the life-long and holistic approach of career development that exploration is an ongoing process, which occur in different life domains simultaneously. Implications for future research and practice are discussed.