The purpose of this study was to critically analyze the entrepreneurial orientation (EO) and trait emotional intelligence (EI) of pharmacists to develop an understanding of how these traits are exhibited in different practicing settings and practice roles. In addition, the relationship between trait EI and EO was explored to determine if trait EI is positively associated with EO in pharmacists. Finally, entrepreneurial services offered by pharmacists were evaluated for type and frequency. Critically analyzing the EO of pharmacists in different settings and in different roles and evaluating the entrepreneurial services they offer will produce a better understanding of the need for entrepreneurship training for students in colleges and schools of pharmacy. Participants were practicing pharmacists in Upper Midwest states. Data was collected using an online survey. Item analysis, descriptive statistics, one-way ANOVA, Tukey’s test, Pearson correlation coefficients, and an independent-samples t-test were used to analyze the data. Pharmacists practicing in different settings exhibited no differences in EO; however, significant differences were found when evaluating the EO of pharmacists by practice role. This study found that North Dakota pharmacists had overall higher mean scores for the EO construct of autonomy and are more likely to provide discharge consultation and med to bed services than pharmacists in other Upper Midwest states. Pharmacists who owned a pharmacy had higher mean EO for the constructs risk-taking, innovativeness, proactiveness, and autonomy. No significant differences were found between pharmacists in Upper Midwest states for global trait EI or its constructs. A positive correlation was found between global trait EI and all constructs of EO suggesting that global trait EI could be used to predict EO in individuals. These findings suggest that educators consider evaluating the global trait EI of students to predict their EO. As it has been shown that students with a high EO are more likely to own their own pharmacy, additional entrepreneurship training may be of value to these students.