The author is now 30 years old. For more than a decade, she has been paid to facilitate an array of outdoor-based programming with varying groups of participants. With such breadth of experience, she frequently feels like she is a valuable asset to the organizations for which she works. However, at recent staff training and trip preparation days, where she has been surrounded by other outdoor professionals working in a similar role, she has begun to get inklings of feeling "old." Is there an expiry date for frontline outdoor professionals? How valuable is the experience of an outdoor professional over age 30? Is it worth adapting current organizational practices to retain these individuals for more than one or two seasons? To answer these questions, the author refers to her personal experience and the available literature in order to share a few insights about longevity on the frontline as an outdoor professional.