These Two Crucial Questions will Change the Way You Declutter (Forever)

It's not 'purging' — it's surrounding yourself with what you love

by Samantha Pollack

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“If I didn’t already own this, how much would I be willing to pay for it?”


Or, try this one on for size: “How much do I love this thing? How much joy does it bring me on a daily basis?”

And there you have it. Two (okay, three) questions that will redefine how you declutter your kitchen/office/closet/schedule.

See ya!

HA. As if.

Truth is, you can read 17 articles about how to declutter, and they all focus on the same negative process of elimination.

  • Have you worn this (gorgeous, expensive) pair of shoes at all in the past year?
  • How often do you use this fancy food mill? (Or…do you even know what this fancy food mill is for?)
  • Do you really need to keep your collection of U2 CDs now that we’ve gone digital?

It’s kind of shaming, right? It feels a bit finger-waggy. Shame on you, for hoarding this useless crap.

Do you ever stop to wonder why the same decluttering content gets regurgitated year after year? Why you continue to click those links when you know what the article’s going to say? And then go home to your clusterfuck of an office, shrug your shoulders, and say, “Maybe next year?”

It’s because these approaches are tired. AND they don’t work. Not for lasting declutter.

Instead, you can turn decluttering into an exercise in what you love.

In my office, I have a little black-and-white postcard of Marilyn Monroe in jeans, bare feet, and a bikini top — bench-pressing.

I’ve carried this flimsy piece of cardboard to three different apartments, from Boston, Massachusetts to Asheville, North Carolina. It’s pinned on my wall just to the right of my computer station, and I look at it all the time.

Its monetary value? Non-existent.

On the other side of my computer hangs a framed certificate from the Institute for Integrative Nutrition.

I paid almost $5,000 for that piece of paper. I poured at least that much into my health coaching practice, not to mention boatloads of my time. But when I had my a-ha! lightbulb moment and realized I was meant to be a writer, I made the decision to shut down my coaching practice without batting an eye (no regrets).

Now if you asked me to choose — keep Marilyn? Or keep this IIN certificate? I would choose Marilyn in a heartbeat. (Wouldn’t we all?) Because I fucking love it. Because it inspires me. It’s powerful and gritty and freaking hot.

My $5,000 health coaching certificate? Meh.

“If you didn’t already own this, how much would you pay to obtain it?”

This question comes from Essentialism: The Disciplined Pursuit of Less, by Greg McKeown — a book that is currently (literally) changing my life.

The crux of Essentialism is: you need to stop scattering your energy across many things and focus in on the one thing that truly matters to you. And yes, this applies to decluttering your closet (that’s the easy part). It also applies to your career, your social life, and your financial planning.

This isn’t just about basic needs. No one needs U2 CDs for basic survival (although…arguable). But YOU might need them, because Bono is more important to you than than water.

For example, I’m a writer. What’s the #1 MOST IMPORTANT thing for me to do, every single day? Write.

It’s more important than taking a meeting with someone who wants to talk about my writing. It’s more important than reading books about writing. It’s more important than replying to emails, doing my laundry, or decluttering my office (ha).

See, those are all good things. Great, even. But in the end, they become distractions from #1. And that’s not how you make progress.

“How much do I love this item? How much joy does it bring me every day?”

Awwwwww yeah. This is the one where you get to keep those (gorgeous, expensive) shoes you never wear.

This is loosely based on some of the principles found in Spark Joy: The Life-Changing Magic of Tidying Up, by Marie Kondo.

What if you got rid of everything in your closet that you don’t absolutely, 150% love?

I’d be left with a pair of grey skinny jeans, cowboy boots, and and an old, frayed Black Crowes t-shirt. Brown leather jacket, and lots-o-scarves. It could work.

This approach to decluttering takes the traditional method, throws a blindfold over its eyes, spins it around three times, and sends it wandering off into the woods alone.

Rather than the negative, you focus on the positive. What if the items you surrounded yourself with — all of them — inspired you like my Marilyn photo?

Talk about up-level. Your office would become like that ice place where Superman goes when he needs to recharge.

Your daily planner? Full of activities that fuel your creativity, honor your self-care, and really move the needle in your business and life.

See, once you’ve found clarity on what really matters, it’s easy to identify all the objects and obligations that aren’t that. And ditch ‘em.

And bonus! Not only has decluttering just become a no-brainer, you’ve also more or less eliminated any future decisions around what to keep and what to scrap. Which is good, because decisions are hard.

Stop focusing on what to get rid of. Instead, get crystal clear on what you want to keep.

That’s how you declutter your life. For life.

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Samantha Pollack
Samantha Pollack traveled a winding road through personal training, health coaching, and the restaurant business, before hitting her stride as a full-time writer. In 2010, she bid a fond “peace out” to her demanding career in Boston and relocated to the mountains of Asheville, NC. Since then, she’s launched (and more

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Read 3 comments

  1. Matt

    Great article!
    My decluttering tip is to buy a buy a large notebook and divide your page into two columns – “Essential” and “Non-Essential Items”.
    Then go around the room and put every single item in one column or another.
    When you have finished your “hit-list”, move the offending items (from the non-essential section) to a designated collection point to get your room “clutter-free”!!!
    Matt recently posted…Declutter your crib with these surprisngly easy home organizing ideas!!!My Profile

  2. Kelli

    ooo – I forgot about that on3e8#2&0; can you still get it? I had to order Backup by Jim Butcher as soon as I could as that was only getting a limited amount of printings. Though rumour has it that a collection of Dresden Shorts is on the way!

  3. Monica Rios

    OMG… I LOVED this! I have a clutter problem… I keep everything! I keep thinking ” Oh, but what if I need this someday?” and someday never comes! lol It just gets so overwhelming at times and I just do not know where to start. Well, now I do. Reading this was my ” aha!” moment. Thank you!