I have a strategy to avoid this. You might find it helpful also.

I go through stuff and set aside in boxes anything that I think might be useful, but I don’t really want or need. This brings that item into my mind, the same way throwing it out does. I label the boxes with the date, and either donate or trash, and put stuff in accordingly.

If a box sits unopened for 6 months, I toss it or donate it without opening it and seeing what’s inside. If I open a box to use something, I put the new date on it and reset the clock.

Then there’s no pain from actually getting rid of stuff. There’s no “man I just threw that out!” regret.