A few times each year DH and I get a bug to clear out unused stuff from the house. We got pretty agressive about it last year, clearing out a lot things like unneeded furniture (such as extra bedside tables taking up space in the spare room).
Throughout spring and summer of last year donation bags and consignment bags and trash bags and goodie bags for Freecyclers and Craigslisters streamed steadily out the door. By fall we had reached a stopping point, feeling pretty good about the amount of stuff in the house we'd managed to unload.
In my case I've found that it helps to take breaks from endeavors like this. Once you've cleared out stuff to a certain point, the risk of regret in going further it seems to rise.
While it's great to get a jump on a healthy activity like this when you're feeling motivated or especially ready to part with certain items in the house, sometimes it's also good to take a pause from it. This helps balance out some of the emotional stress that can come with aggressive clutter clearing. Most often the breather gives DH and I the time and space to realize that no, we won't feel much sting from the loss of many of the remaining things over which we were hesitating, and spurs us to clear out more. It sometimes also gives us time to rethink things, like when we decided the luxury lounge chair we had up on Craigslist for a few weeks could stay after all.
But, even when I feel like I've reached the point of taking a pause on clutter clearing, my mind is always alert to the question of "what am I ready to part with next?" and it typically doesn't take long for either DH or I to pick a few more things to let go of.
A few years ago it was easy to fill up several bags for donations pickups or the trash pile. It feels encouraging to have reached a point where the amount of clutter taking up space around the house has decreased so much that choosing more things has become more challenging. At the same time it's also become easier, as I've found that the act of clearing out things seems to free up more willpower to keep going on to part with even more things which I had been emotionally clinging to before.