Most estate cleanout guides give you two piles: keep or toss. That's wrong. Two piles forces a binary decision in 30 seconds, while you're exhausted, before the grief has settled. The result is regret. I see it constantly — families who shredded a box because someone said it was junk mail, then realized later it had a 1962 land grant or an annotated genealogy at the bottom.
The third bucket — DECIDE LATER — is the release valve. Anything you can't decide on in 30 seconds goes there. Box it, label it, store it at one address. Set a calendar reminder for 90 days. Most things end up moving to the toss pile in three months when your head is clearer. But the things that don't — those are the things you would have regretted losing.
This is also why I never schedule cleanouts within four days of a death if I can help it. Four to six weeks is the sweet spot. The decisions are clearer, the family has had a chance to talk, and nothing has been done that can't be undone. For families specifically wondering about the books, my guide on what to do with books after someone dies covers donation, selling, and preservation at the same unhurried pace.