When I work with clients, I notice that the things they no longer like and use anymore have the feeling of an abandoned house. There's an emptiness about what's no longer a part of a person's life. The person's energy isn't in it.
Initially they don't see the emptiness. They still see the things through the eyes of when the thing mattered to them. Their memories give the person an illusory connection to the thing.
That's why I directly ask, "Do you enjoy and use this, or can we let it go?" If it's no longer a part of their life, I want them to see that on some level they have already let it go.
There's a clear realization that they no longer feel present with this thing. It's an empty experience.
I encourage you to go into your clutter busting shining this questioning light. It will give you the clarity to see what you've outlived. When you feel that your heart doesn't live in this thing anymore, it becomes easier to physically let it go.