Reduction in faculty positions in higher education and increased graduate matriculation rates represent a higher education conundrum. Planned happenstance theory (PHT) is a career development model focusing on positive outcomes resulting from unpredictable precareer events. This mixed methods study explores how PHT applies to the career paths of a clinical anatomy (CA) postgraduate cohort. It provides insight into educational practices designed to equip students for labor markets inside and outside academia. Alumni of CA (n = 12; 2014-2018) were interviewed about career-related events transpiring from graduate studies to present, allowing exploration on how PHT contextualizes their shared experiences. Planned happenstance career inventory (PHCI) enumerated planned happenstance skill (PHS) scores. Total PHS was referenced 527 times across 12 interviews. Of the PHS references, curiosity established highest incidence (154 references, 29%), optimism (132 references, 25%), flexibility (101 references, 19%), risk-taking (85 references, 16%), and persistence (55 references, 10%) and 43 distinct happenstance events were documented. In addition, social networking (52 references) arose as an emergent code and was divided into internal networking (28 references, 54%) and external networking (24 references, 46%). Application of the five-point PHCI scale revealed: curiosity (4.4 ± 0.3; mean ± SD), flexibility (3.6 ± 0.7), persistence (4.4 ± 0.3), optimism (4.3 ± 0.4), and risk-taking (4.1 ± 0.5). Curiosity had the strongest association with happenstance event incidence. Social networking was a key substituent of PHT not yet described in the literature. Educational practices incorporating PHT concepts, with emphasis on curiosity, may provide graduates novel metacognitive skills needed to develop novel career paths. Anat Sci Educ 14: 460-470.