The best way to make progress clearing clutter is to first look for items that are easy to clear, the “no brainers”, those things you know you could have and should have gotten rid of a long time ago. Looking for those things that are easy to clear will help you get moving and keep you from getting bogged down in the decision making process.
Once you have gotten rid of an initial layer of items, the energies in the space will shift. You will find it much easier to organize what is left. It’s quite common for people to return to an area where they had done an initial clearing and find themselves rethinking the value of items that didn’t make the first cut.
So, be gentle with yourself for not getting rid of all that you could get rid of during your first pass of clutter clearing. Know that given time and the energy shift caused by the initial clearing, you may find yourself returning and clearing yet another layer.