The term 'TIME TO RETIRE?' can be answered by the following crossword solutions: NIGHT (5 letters), EVENING (7 letters), and PITSTOP (7 letters). NIGHT and EVENING both refer to the time of day when most people are winding down and preparing for rest. A pitstop is a brief pause in a journey, usually for refueling or restocking supplies. Taken together, these three words suggest that it is time to take a break from a long journey and retire for the NIGHT.