I do have regrets over some items I have given or thrown away. Not many, mind you, but a couple come to mind. One was a portable manual typewriter. Logically, it was a good thing to give away as soon, finding ink ribbons would have been impossible. It's just such a novelty for kids nowadays, I 'might' have enjoyed showing it.
The other thing is a scrapbook of photos from my student teaching/college days. I practice taught in a 1st grade classroom and my supervising teacher surprised me with a scrapbook on my last day in her class. Other than the fact I was a lot heavier and had ugly clothing (it's not easy to jump from college student into the professional world), those pictures were fun. Let's see, those kids would now be 32 or 33 years old.
Worrying about what you will regret clearing out is dangerous because you run the risk of never getting rid of anything! However, if it makes you feel any better, my two regrets surface maybe once every three or four years, only briefly. Most of the time I feel lots better seeing my home uncluttered!
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