Particularly for sentimental items, consider this strategy I often practice.

Find someone—family or friend—who will value the thing you are giving away. Then, as you present the item to them, tell them the story behind it. Take the memory that gives the item its sentimental value and pass it on to someone else.

I did this once for a special casserole dish I owned. As I gave it to a girl I had mentored, I told her about my Aunt Eva, who had always made a bean casserole in the dish. The container always reminded me of her, and by sharing the story with my friend, I got to pass that memory on.

My friend would remember Aunt Eva when she used the dish, and even if she regifted the dish, telling the story helped me release it.

Many good places exist for donating your no-longer-needed belongings. As you go through the downsizing process, be open to gifting your things to others who want or need them. This will help you accomplish your goal of a simpler life in your new home!