In this episode, Loretta McGregor (Arkansas State University) and Randy Smith (retired) chat with Dave about knowning when it's time to retire or to make a career change, based on what we personally find rewarding. We reflect on technology-related changes in teaching, especially with regard to writing (ever wonder where "cut and paste" came from?). Randy and Loretta also offer some practical suggestions for earlier career faculty about setting themselves up for a successful late career and retirement.