An individual's insights into success during an academic career are enhanced by observing successful long-term career academics and staff members within our colleges/schools of pharmacy and across the academy. What were the reasons for the success of these individuals? Based on these observations, we propose 5 simple insights that can aid in navigating organizational sub-cultures and cultures. These insights include knowing their WHY, utilizing the 24 to 48-Hour Rule to maintain resilience, demonstrating basic courtesy and politeness in interpersonal interactions, recognizing the impact of words in written communication, and optimizing the use of communication methods beyond email and text messages.