Decluttering is far easier when we're focused on the lives we're living today, who we are, where we live, and what truly matters to us.
It's sometimes too easy to hang onto things because we've always had them or we used to use them or we connect these items to people who used to be in our lives. But our stuff can't take us back in time. And things can only spark memories, they aren't the memories themselves.
FOCUS ON WHAT WORKS NOW
When you catch yourself unwilling to let go of too many things that are part of your past, shift your focus to what matters in your current circumstances. For example, if you're pulling clothing from back of your closet and reminiscing about times you wore it years ago, spend some time assembling four or five fabulous outfits using the best items you currently wear. Plan those looks from top to bottom, including jewelry, ties, belts, shoes, handbags, etc. Now, carefully put these items away where they belong, and arrange them as attractively as you can so your favorite pieces shine. Next, add in similar and complementary garments and accessories. Keep going until you have a range of items and outfits at the ready. If you'd like, make a short list of items of clothing you'd like to purchase to make your wardrobe even more flattering or versatile.
Only when you've finished assembling a pleasing wardrobe that meets your current needs (notice it only needs to be pleasing, not perfect) should you return to your sentimental clothes or items making you feel indecisive. Anything that doesn't fit your lifestyle (or literally doesn't fit) or isn't in good condition will fade in comparison to your current favorites.
SET LIMITS TO MAKE SPACE FOR WHAT MATTERS NOW
If you genuinely have room for it, there's nothing wrong with dedicating space for keepsakes and sentimental favorites. The key is to ensure that the majority of clothing storage space is reserved for what is truly useful and attractive. Allow yourself one fabric bin, drawer, or garment bag, etc., where you store items that are especially meaningful. And remember that if you have photographs of you wearing your old favorites, those are actually more satisfying than than the unwearable items of clothing themselves.
SOMEDAY, SOMEDAY, MAYBE
It sometimes feels wasteful to give up on things we might use or keep meaning to read or will surely fit into someday. But in trying to avoid one kind of guilt, we often take on another, storing items that crowd our closets and shelves and nag us. That book cost almost $30 and practically everyone you know read it months ago and you could only get through 40 pages of it. This all bothers you every time you see this book on your nightstand, so you keep thinking you'll read it someday.
No one only picks up books they love. We all choose duds here and there. We all purchase cooking gadgets that end up being too inconvenient to use or clean, skincare that doesn't work well with our skin, toys kids grow out of, and so on.
Commit to learning from your mistakes and move on. You may feel bad about throwing away an expensive bottle of moisturizer you hardly used, but that feeling won't last long. Isn't it more important to move on to a product that is healthier for your skin? Why not donate your someday items or sell them or give them to someone who might actually enjoy it? I guarantee you that book will not continue to nag you once you have sent it on its way to another reader.
AGAIN, SET LIMITS
Create a reading list for the current month or season; add one or two "someday" books. If you haven't read them when the month or season is up, it's probably time to move on. (I like to make reading lists on rifflebooks.com or you can just create a list on your phone or in your planner.)
MAKE SOMEDAY TODAY
Take the time to figure out what you can wear with that expensive silk scarf, and choose which day you will wear it this week.
Bookmark a recipe or two that would make good use of that fancy marble rolling pin you bought and used once. If you haven't made the recipe in a month's time, you can add the rolling pin to the donate bag. And if you do end up baking a delectable batch of lemon sugar cookies or a pot pie with a perfectly flaky crust, enjoy every minute of it in the here and the now.