Depending on what the item is, I can be sentimental about it.
I had an old, cloth covered sewing box. It was broken and had been repaired with black stretchy tape. I got the box when my Grandmother died and we were packing up all of her stuff.
15 years later, I have children of my own, and I needed a bigger sewing box, and I was sick of this old broken inefficient sewing box. But... I had a hard time throwing out this box. It felt like I was throwing out one of the last connections to my Grandmother. And then, I had an epiphany.
My Grandmother wouldn't have wanted me to be beholden to a broken box. She wouldn't have wanted me to order my life and my surroundings and my space according to things--especially things that don't serve me. SHE would have thrown out the box at this point! And even if her thinking would have been different, I'm an adult and can decide what things are good for me and useful and needed, and what things are useless and in the way.
A couple of years ago, I transferred all of Grandmother's spools of thread and sewing shears and needles to a new box, and I threw out the old sewing box and didn't think twice about it. My grandmother's not in that box. She's in my father and me and my siblings and my children. She's in paintings and politics and crusty loaves of bread.
What should you throw out or give away? What are you needlessly holding onto? Do you have any broken sewing boxes?