Most of us struggle with keeping a tidy home because we have too many things. We’re not talking about things that are easy to throw away or recycle like spoiled or expired food, empty rolls of paper towels, or cracked and broken dishes. The sentimental or “I might need this one day” are what make us give up and ignore the clutter.

We spoke to an organizing expert to gather the best questions you should ask yourself before you toss or get rid of an item.

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Will I regret not having this one someday?

“People often think that organization is the hardest part of what an organizational professional does,” says Carson. “The truth is, however, that the cleanup process is far more emotionally and mentally draining for everyone, including clients and organizers.”

Regret is a difficult emotion to resolve and almost impossible to respond to. Hoarding items or a “better safe than sorry” mentality can derail the goal of a clean home. Carson reminds clients that you can’t predict what you’ll feel or need in the future. Instead, she recommends asking yourself these important questions when deciding whether an item should stay or go.

Can I save memories while playing this item?

Carson said that she keeps two sentimental pieces of clothing that she will never wear again: her wedding dress and the dress she wore to bring her son home from the hospital. Since there are only two dresses, the collection is strong. However, you can’t hold on to every piece of clothing, book, or piece of china.

She recommends these methods to retain the memory but let go of the subject.

• Take a photo of the item. Place the printed photos in an album or digital file with a note about the item.
• Create something new. Repurpose Grandpa’s shirt to make a stuffed toy, holiday ornament, or part of a quilt.
• Frame it. If you don’t have room to keep a full set of china, frame a plate that reminds you of family dinners and hang it in your kitchen or dining room.
• Put it to another use. Use your mother’s prized silver tray to organize items on your dresser. You will see and use it every day.

Is it something I can find online if needed?

This question is especially useful for paper clutter. Owner’s manuals, bank statements, investment information and insurance documents can all be found online. Carson says when it comes to documents, ask yourself: Can I find them online? If yes, throw it away.

Documents that you may need in an emergency or legal documents should be stored in an easily accessible fire and flood resistant box.

The IRS recommends keeping individual tax returns and records for three years. It’s a good idea to keep some documents longer, such as records related to the purchase or sale of a home, stock transactions, IRAs, and business or rental property records. However, if the records are destroyed, you can request copies online from the IRS.

Can this be digitized?

Some documents such as birth certificates, death certificates, social security cards and marriage licenses should be kept in their original form. Carson still recommends making a digital copy and storing it separately in case of disaster.

For sentimental items such as birthday cards, invitations and letters, a digital copy will last much longer than the original paper and take up much less space.

Would I notice this item is gone? If so, how upset would I be?

Carson asks, “If you keep something for sentimental reasons but never look at it, what purpose does it serve?”

She encourages clients to use or display sentimental items until they become clutter. Her number one rule for determining whether a sentimental piece should stay or go is this: If this item were lost to fire or damage, how much would you notice and how upset would it make you? If you would be destroyed, keep it, but keep it right. She advises that guilt or obligation should not affect your true commitment to the subject.

“Your loved ones wouldn’t want their items or gifts to become a burden,” adds Carson.

Who am I saving this for?

Carson’s clients have attics, garages and basements full of things they are “saving for their children or grandchildren” which is often just an excuse because they are not ready to let go.

“The reality is, your kids or grandkids aren’t going to want all of those things,” Carson says. “If you’re really saving something with the intention of passing it on, ask the recipient who wants it. They might just want a few special pieces. They might want everything. You won’t know if you don’t ask.”

Whether you’re keeping things because you’re not ready to let them go or because you haven’t asked others what they want, always be honest about why you have an item.