Would You Buy It Again? The Ultimate Life Decluttering Hack

by | Dec 12, 2023

Our Overflowing Closets

Do you have clothes in your closet that you never wear? That old college hoodie, the dress bought on sale that isn’t quite your style, those jeans that are just a size too small? Even though we never wear these unused and unloved items, it’s tough to get rid of them. We keep these belongings for a variety of reasons: attachment to fond memories, hope we may wear them again someday (especially if they are a smaller size), or our evolutionary tendency to overvalue our possessions. Whatever the reason, for most of us, our closets and drawers are graveyards of unworn clothes.

Solid advice for declutting a closet includes discarding clothes you haven’t worn in a year and Marie Kondo’s guidance that you should evaluate each item of clothing on the basis of whether it brings you joy and donate or sell those that fall below that standard.

Would You Buy It Again?

But the most powerful way IMO to evaluate your clothes is to ask whether you’d buy them again. If the answer is no, you wouldn’t re-buy, it’s probably best to get rid of it. I think this question is a better way of evaluating whether to keep clothing than asking whether it brings you joy or if you’ve worn it in a year. For example, I may not wear my tux for over a year, yet its an essential part of my wardrobe. Similarly, some clothes that don’t bring joy are utilitarian like your painting clothes or that dark suit you just wear to funerals. So, try applying the “would I rebuy this” question to items in your closet.

The Question Is Powerful In Many Areas

This question of whether you’d rebuy something is powerful beyond closet decluttering — it is clarifying to ask it in other areas of our lives:

  • Household Items: Just like our clothes closets, our basements, pantries, and shelves easily become stuffed with unused and unloved items. Apply the “Would I rebuy this” to all your household items.
  • Relationships: would I choose to be friends with this person if we didn’t know each other? If the answer is no, maybe it’s time to move on.
  • Employees: This question is also interesting at work: would I rehire this person knowing what I know about them if they re-applied for their job?
  • Our jobs: Knowing everything you know about your company and job, would you re-apply for the position? Sure, work is called work for a reason, but if you wouldn’t re-apply for your job, maybe it’s time to reevaluate your career.

How The Question Can Improve Your Investing

Asking whether you’d rebuy something is also useful in investing, especially when you’re having trouble selling an investment at a loss. Here’s a story about that from my book, The Uncertainty Solution:

About five years ago, I met with a client who owned millions of dollars in a struggling company. The stock was way down from where he bought it. We’d been advising him to reduce his ownership of this stock for years, but he was reticent to lock in his loss. At each meeting, he said he wanted to wait to sell when it returned to positive territory. After he again refused to sell, I proposed the following: “Given your strong belief that this company’s stock will rebound, would you like to buy more of it?”

“No,” he said quickly. “I don’t think that’s a good idea. This stock has been dropping for years, and the outlook for the company is poor. There’s no way I’m buying more of it.”

I said, “But in effect, you are rebuying this stock each day you don’t sell it.”

That finally got through to him. He realized this wasn’t a good stock to own if he had such a strong aversion to buying more. The next day we made the trade, and within two years, the company had declared bankruptcy.

The story’s point isn’t that you should sell every investment when it’s down; inactivity and patience are generally better investment practices than tinkering and trading. The lesson is that you should be mindful of your loss aversion when making investment decisions. Asking yourself, “Would I buy more?” can help you make a more rational decision.

The Uncertainty Solution: How to Invest With Confidence in the Face of the Unknown

1 Comment

  1. hi John, John and I just downsized as we moved from our home of 45 years to a two bedroom apartment. You can imagine the downsizing we had to do to make this possible. I appreciate your article because there are things that I brought with me that still need to be reckoned with. I’ll get on it as soon as I can. thanks

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