My beloved has a 5-year rule: If you haven’t used or worn or read something in 5 years, you probably don’t need it.

It’s the “probably” and “need” that catch me off guard every time.

One of my daughters died 20 years ago. (I can’t believe I’m even writing that sentence). I have a dress and a sweater of hers I’ve never worn even though they fit me. I don’t “need” them physically, but I “need” them emotionally. I predict that “need” will never have an expiration date.

You might begin by making a catalogue of some things, perhaps putting them in categories of physical and emotional need, with sub categories based on the age of the object and emotional association.

It’s a process. You’ve already begun. Be gentle with yourself. Take your time. There’s no right or wrong way to do this. Your family will love you no matter what.