Selected for development in 1998 and launched together with CloudSat in 2006, the Cloud-Aerosol Lidar and Infrared Pathfinder Satellite Observations (CALIPSO) mission terminated science operations in the summer of 2023 after completing 17 years of on-orbit observations. As one of NASA’s Earth System Science Pathfinder missions, CALIPSO was truly a pathfinder. CALIPSO observations have provided a new perspective on clouds and aerosol and have not only met but far exceeded the original objectives of the mission. Many unanticipated findings and data applications have been discovered along the way. Flying with many other remote sensing instruments, as part of the A-train constellation, stimulated the discovery of numerous retrieval synergies between lidar and other sensors. This paper describes how the CALIPSO mission came to be, discusses some of the early choices made by the CALIPSO team that shaped the mission, and some of the challenges facing the team in developing the first-ever global climatologies of aerosol and cloud based on lidar observations.