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 After Memorial Day weekend, I planned to write a story about how it felt to get rid of a decent chunk of my wardrobe. My apartment is small; my clothes are many; and I figured I'd feel happier if I just purged a bunch of them. I even had a jazzy headline picked out: I just got rid of one-third of my wardrobe — and I can't believe I didn't do it sooner. That Sunday morning, I emptied my dresser drawers onto the bed and prepared to go in for the kill. My prey: stained shirts; sweaters I've owned since high school; and a suffocatingly tight leotard that I bought when I took a ballet class freshman year of college. An hour later, I'd gotten rid of four tee-shirts. Actually, I didn't get rid of them; they're currently sitting in my living room until I "have a chance" to take them to Goodwill. (The leotard remains in my bottom drawer.) This was, in a word, humiliating. Everyone else is winnowing their possessions down to the very few that "spark joy" in their hearts, and here I can't part with a ruffly piece of white fabric that I'm still not sure is a dress or skirt. For some insight and advice, I called Josh Zerkel, a certified professional organizer and the director of global community and training at Evernote. Zerkel didn't sound especially concerned when I shared my predicament. In fact, he applauded me for taking the first step in decluttering my dresser: picking out the oldest and stained-est of the T-shirts and readying them for either donation or the trash. "It is really, really okay to start small," he said. "This isn't the type of thing where you need to upend your entire home, or your closet, or your desk in a weekend." It's worth noting here that I'd met Zerkel a few weeks earlier and consulted him about another organizational challenge I'd been facing: clearing the papers off my desk at work. Zerkel's advice at the time had been similar: Start small. Spend five to 10 minutes every day on the project. Whatever you do, don't expect to come in on a weekend and spend eight hours getting the whole thing done. I was behind on the paper challenge, mostly because five minutes worth of organizing seemed like removing a single shovelful of snow off Mount Everest.  But when I spoke to him about my wardrobe issue, Zerkel hammered home the point: "It can absolutely feel great if you do the weekend project. I just have seen vanishingly few people do it successfully without creating a big mess that they feel more overwhelmed by along the way."
In other words, if you try to take on too much organization at once, you're all but dooming yourself to failure. In fact, if you do the thing where you dump out the contents of your closet or your desk drawers and dive in headfirst (ahem), often "it ends up being worse than when you started," Zerkel said. All that decision-making — Should this shirt I wore to my cousin's college graduation go in the donation pile? Is this pizza stain actually visible? — can be "daunting," he added. Start with the most obviously unnecessary items; then take another day to delve into the "maybe" pile; and so on. Ultimately, my takeaway from my conversations with Zerkel is really just to give myself a break. There's no way I can declutter my home and workspace overnight. This is hard for me to accept, but I'm trying. In the meantime, if you know of any organization fairies who can transform your life with the wave of a wand, please do send them straight to me. SEE ALSO: A professional organizer says too many people think of 'organization' all wrong | 
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