Person matching promotes career exploration and choice by linking persons to persons in occupations based on inventory profile score similarity. We examined the efficacy of the procedure for career specialty choice. Medical students (N=196 women, 224 men) responded to the Sixteen Personality Factor Questionnaire (16PF) in their first year of training. After graduating and selecting a medical residency, members of a reference subgroup (n=62) of the total sample were matched with members of a criterion subgroup (n=358) based on 16PF score equivalencies determined by the D[2] statistic. Person matching predicted medical specialty choice 43-60% of the time. Using broader specialty group categories and adding criterion persons increased the number of specialty matches. Additional refinement and analysis should enhance the efficacy of this idiographic approach as an alternative to nomothetic P-E matching for career exploration. Future research should examine person matching in terms of consequential validity.