Sorting it all out

I would like to believe that I have the ability to sort it all out. Even physical things such as what to rid myself of gets complicated at times; recently downsizing my life has helped when I moved to a smaller place but I still found myself finding places to put things in more creative areas such as the attic or under a bed.
As the years pass by attachments become stuck to me like velcro; I keep pulling at it but it does not release.
Do you have difficulty with letting go as I do with other things in life that need to detach?