Whether you're moving to a smaller home or clearing out a longtime family house, downsizing asks you to make hundreds of decisions in a row. That's exhausting, so plan for it.
Start with the easy categories, like duplicates, expired items, and things that are broken, and save sentimental items for last. Each easy decision builds momentum for the harder ones.
Measure the new space before you decide on furniture. If it won't fit, it's not a decision; it's a fact. For keepsakes, choose a container size and keep what fits, rather than trying to justify each item.
Finally, know where things are going. Items given to family, donated, or sold are much easier to let go of than items headed to the trash. We coordinate the drop-offs so nothing lingers.