For me, there were several issues in play. The first issue was my lack of maturity. I hadn't had the chance to try a million things and discover what I was truly passionate about. I was young, and full of energy. I wanted to be passionate about gourmet cooking, and heirloom sewing and quilting. I wanted to grow my own herbs, and raise chickens and goats, and make my own cheese. I wanted to scrapbook all my photos, and play the guitar, and learn to cane chairs. I wanted to homeschool my children, and use cloth diapers, and...and....and.....you get the idea. Now I am old and mature, and I realize that I cannot be passionate about everything. I certainly can't use my aptitude as a measuring stick for what I should be passionate about, because I can do many things well. Far too many things to have passion for all of them. Over time I have winnowed down the list to a few things I really love or need to do. All the rest have gone away, and with them, all the gear and geegaws needed to perform them. The few things I really DO, I let myself have the good stuff, like a really nice sewing machine, which has earned its bit of real estate inside my teeny bedroom closet. Or the bins of excellent quality fabric stored under my bed. Like the chocolate molds that eat up the whole cabinet over my refrigerator. Like the books that line soooo many of my walls. But so many other things have disappeared. Some things I have sold, some given away to a friend who would use it, some donated. I don't miss the things that are gone.
Maturity and experience have also taught me that I do not need many of the things I once thought I did. Neither do my children. We live with far less clothing and linens. I do laundry every single day. We do not need one of everything for every child. They can learn to share. I do not need to own things I can borrow or rent. The list goes on and on, and applies to nearly every area. But in the beginning I thought I had to have it all.
I have a system for ongoing purging. Usually I purge the house deeply, twice a year. One of the best times is right before the holidays, but after the New Year will work too. Pre-holiday is ideal, because I clear space for incoming gifts, and mentally tally who has what, and make mental notes of what they may want or need. The whole rest of the year, I do constant maintenance purging. I cycle through the whole house, room by room, cupboard and drawer, closet and bureau. I always have a donation bag or box set up, and am constantly adding to it. Anything beyond repair goes into the trash immediately. Outgrown clothing, unwanted books, unused toys get dropped into the donation box. Another bag or box is set up for "things that don't live here". This is for items that belong to other people...things that got left behind, or borrowed items, or things we plan to pass on to a specific person. When I plan to pass the thrift store, I drop off the donation box. When I plan to see a person who owns something in the other box, I try to remember to give it to them.
I have other boxes too. I have a "wait and see" box. This is where I store things I am unsure about. Things I think I want to get rid of, but still have doubts. If I don't go back for it in a few weeks, it's probably safe to let it go. At times I have had "yard sale" boxes. Right now I live in the sticks, so it is not practical to have yard sales. If you really will carry through and have the yard sale, and you have the space to store the stuff until you do it, by all means, have a yard sale. We have made lots of vacation spending money this way. Currently I have E.bay boxes, because I have had success selling certain items using that forum. Another tip I would offer, is that I put my boxes out in a visible, and mildly annoying location. This inspires me to keep the stuff moving out the door, rather than sitting buried and forgotten somewhere. (Kind of like the laundry baskets in the middle of the living room floor inspiring me to fold it and put it away.)
Another sticking point to paring things down, is the children. Children and their stuff take up a lot of space. Especially if you homeschool them. In some ways you have to relax a bit about this, because everything about them is always in a state of flux...a messy state of flux. They are always growing, and so their closets and drawers need constant supervision, rotating out that which is outgrown or worn out. If you are passing clothes along to younger siblings, you must decide how much you can reasonably store. In the past, I found myself storing everything, in fear that I would "need" it. I stored ugly clothes that I did not like. I stored very specific clothing that had nothing to match it, or would hardly ever be worn. I stored clothes that suited one child's body type, but would never suit their younger sibling. In other words, I wasted a lot of precious time and space, because I was afraid I would be found lacking later on. Now I only save that which is in top condition, that I know for a fact will be used. I am also constantly sorting through their toys and books, weeding out the ones they have outgrown. I only save that which is classic and beloved. Things that they have passed over for newer pursuits go into the donation box. I used to save every homeschool book and teaching aid. Those things are crazy expensive, and what if I find myself teaching at that level again? But as that has happened again and again, I have found myself not returning to the materials I had previously used because I found something that worked better for me, or for a different learner. Now I use the materials, and if I don't have specific plans to use them again soon, I pass them on to other homeschool moms.
I have only touched on a few areas, and made a few suggestions. You must figure out what works for you. The most important thing I have learned along the way, is that it is an ongoing process. You will purge, and it will feel good. Then you will purge again, more deeply, and it will feel even better. Spaces will open up, and you will feel freer. Eventually it will become routine, and you will feel as though you are just skimming bits off the top. But you will never arrive at some place of perfect order. There will always be things you are toying with getting rid of, things you are aware will need replacement soon, things you wish you had. For me, it has been getting to a place of calm and contentment about this ebb and flow. I feel like I am controlling it to some extent, rather than being washed away by it.