Objective: To identify differences between generations of orthodontists in the U.S. and Canada and to evaluate the perspective of each generation on widely debated topics in orthodontics. Materials and Methods: A 22-item IRB approved survey was distributed to orthodontists in the U.S. and Canada. Participants were asked questions about the use of technology, future of clear aligner therapy (CAT), orthodontic education, student debt, marketing, and corporate orthodontics among other topics. Results: Significant increase in female orthodontists over generations and a decrease in orthodontic educators was found (P<0.001). Among generations, differences were found in regard to their amount of student debt, use of specific diagnostic tools, marketing preferences, and their opinion on the future of CAT. Conclusions: Clear distinctions exist between different generations of orthodontists. Issues such as increasing student debt load and a decrease in orthodontic educators over generations should be addressed to preserve the future of the orthodontic profession.