When is the best time to start thinking about downsizing and moving to a smaller house or a retirement community? The answer is … well before you need to do so. Downsizing is often a stressful process. Start slowly and give yourself plenty of time to make it seem less overwhelming. Take photos of cherished items to remember them by. Research and look at the various options for retirement living before you need to make a move. It will take the fear and stress away knowing that you have done your homework and have started the downsizing process.