Data from the Academy reveal that non-tenure track (NTT) faculty are less likely to advance through academic ranks compared with tenured or tenure-track (T/TT) faculty. Multiple factors likely contribute to this disparity, including insufficient guidance, lack of purpose, and limited access to resources. Although there are various paths to achieve success in academia, it is valuable to learn from those who have navigated the journey before. This Commentary, aimed at new and mid-career NTT faculty, highlights the five key lessons I learned while progressing to the rank of clinical professor. These lessons emphasize the significance of humility and service to others, setting clear goals while advocating for the necessary time to achieve them, working strategically rather than solely working harder, actively contributing to the advancement of the profession, and ensuring work-life balance through time off and flexible work arrangements.