One Step Forward, Two Steps Back

I got really organized a while ago, but I just couldn't maintain it! What did I do wrong? Am I a hopeless case? How do I know this will work for me?

Backsliding into disorganization is a lot like yo-yo dieting. You made major progress, felt good about yourself, but then slowly things got away from you, and you're back to where you started. Or worse. Ugh. You wonder if this is just the way things are going to be for you. I have good news: you can totally figure out why it happened, and find ways to fix it and prevent it from happening again! If you've backslid recently, it probably comes down to one or more of these reasons:

You didn't get rid of enough the first time around.
  The less stuff you have, the harder it is to get disorganized. If you only had five outfits (hypothetically; I'm not that hardcore!), you can bet you'd be keeping up on your laundry. If you only had two sets of dishes and silverware, you'd never be overwhelmed by an overflowing kitchen sink.
  What to do? Get rid of more stuff. I know, I know, but there's just no better solution. It's vital that your total amount of stuff fits into your storage space, including a good 10-20% or more of "breathing room." The empty space is crucial, as it makes things less stressful to put away. (We'll talk about that more down below, keep reading!) If you're having trouble letting go, take a look at my worksheet Learn to Let Go and explore what's holding you back.

You've acquired more since you did your initial organizing.
  Okay, so while we're on the topic of that empty 20% of your storage, I'm reminded of an organizing TV show that was on TLC in the early 2000s called "Clean Sweep." At the end of the show, they'd always proudly display this empty space, which they called "room to grow." Nooooooo. Stop. This is not "room to grow." It's not there so you can cram more stuff into your space! It's there so it isn't a total pain to get books back onto your bookshelf, or fit your t-shirts back into their drawer. It prevents wrinkles, frustration, and collapsing towers of whatever you've stacked up.
  What to do? Like above, get rid of more stuff. But how do you prevent filling it up again? 1) Embrace the empty space. Learn to see the beauty in it and appreciate how it helps you keep your space tidy. 2) Some people still have a desire to fill in any empty space, though. If you absolutely must fill the space, I recommend placing something there that you already own, and that will live there permanently; either something that adds beauty or showcases a memento. You can relocate a beloved teddy bear from a box in the closet to your sock drawer, or a picture frame or souvenir to your bookshelf. If you can't seem to keep a flat surface clear, consider covering it with a clear blotter and place favorite artwork or photos underneath it, to remind you not to let piles grow on your work surface. 3) When you do buy new things for yourself, practice one-in-one-out. If you bring in three new shirts, donate three shirts. In addition, I really recommend only buying things you absolutely LOVE, and maybe cost a little more than you'd typically spend. Having two pairs of "investment jeans" is so much better than having six from Ross that are just okay. Finally, if you just want to shop as a stress reliever or something to do with friends, try doing gift shopping. Plan for Christmas, your mom's birthday, or your next anniversary. You'll be more prepared for the occasion, and more likely to find the perfect present when it's not a last-minute chore.

Your storage or systems weren't efficient enough. They were either too time-consuming, or took more energy than you could put into them.
  This probably happened because you were expecting too much of yourself, you were more interested in beautifying than making things easy, or you didn't leave that crucial 20% space. Like crash dieting, if you go crazy creating exhausting systems for your to-dos, you'll burn out. 
  What to do? 1) Make putting away easy. As a rule, you shouldn't need to move another object to put something away. Don't stack things or layer things deep on a shelf. Even refrain from using lids when you can! (Put the lid under the container if you want to keep it around.) Ideally you'll get rid of enough stuff to adhere to this rule, but if you must, you can also consider additional storage systems. Consider whether switching from shelves to drawers would be beneficial, or if you can add an extra shelf or hook somewhere. 2) Store the item where you use it. If you always manage your bills at the kitchen counter, don't stack them up on the desk in your bedroom. If you exercise in the living room, make a place right there to keep your yoga mat and weights. (Seriously: I'm too tired to move my five-pound dumbbells when I'm done working out. All I can manage is rolling them into the corner of the room with my foot. Making something that much easier to put away is really all it takes sometimes.) 3) Remember to assess a new system for at least a few days or weeks to see what's working and what's not. If you're not sticking with it, it's not because of you; it's because the system needs more adjustment.

You're spiraling instead of looping in the natural cycle of organization+doing. 
  In a functioning system, you will find yourself in a cycle of living in your space and then tidying it. If you don't ever get around to this occasional tidying, the disorganization will creep up on you until you don't know where to start managing it. If you've truly cut down your belongings successfully and made a home for everything, it won't take you more than ten or fifteen minutes to get a room back to your ideal level of tidiness.
  What to do? It's okay to have projects on the table, events you're planning for, a business you're growing. Please use and enjoy your home; that's what it's for! But remember to make a habit of putting things away. 1) Make it a ritual. I like to take a few minutes at the end of the day to put everything "to bed" in its home. I sleep better when I know I'm waking up to a calm, organized space. 2) Create "transition spaces." Have a tub you keep by the front door for things that need to leave the house, baskets at the top and bottom of the staircases, and a bin next to your workspace that can hold a project that's in progress. Make sure that these bins are emptied regularly, either by finishing the project or putting them back in their homes.

You didn't actually finish organizing! 
  You might have hid the questionable items out of the way in a box or closet last time, and they've come back to haunt you. "Miscellaneous" is not a category of things, sorry!
  What to do? This is a good time to enlist some help. Sometimes you just need an outside perspective to talk through your options with those mystery items. Enlist a friend or a professional!

Something has changed in your life that has affected your time and/or energy levels.
  Okay, obviously if you've just moved or had a baby, you're going to be overwhelmed and lose track of some of your organization systems. But it doesn't have to be a major life change to throw you off course. Have you been traveling and not had time to unpack your suitcase? Have you been spending less time at home due to a new hobby, a gym membership, a relationship, or a work project that's been keeping you at the office late? Physical and mental health challenges can take a serious toll, too, whether it's a breakup, a nagging cold, anxiety, or depression.
  What to do? 1) Not to sound like a broken record, but again, cutting back on stuff and making systems easier will make a world of difference. Lord knows it can be especially hard to make a change when you're already struggling to do the bare minimum, though. Set tiny goals for yourself: spend ten or twenty minutes a day on small goals. Set a timer and attack a stack of papers. 2) Give yourself a break. When I have low energy, I like to think of myself as having a "low battery." If I'm at 20% battery, of course I can't get to everything on my list. Try saying "no" more often, and practicing self-care. Be nice to yourself, and take baby steps. 3) Again, enlist help! Whether it's a friend, a partner, or a professional, having some support is going to be key to your success.

Take some time to think over where your systems aren't flowing, and take small steps in the right direction. Donate one thing, delegate or decline one obligation, or set a timer for ten minutes. Do it right now.