Don’t Wait for the Chaos: How to Tackle Clearing Out Your Parents’ Home Over Time

Let’s talk about something no one likes to think about… but everyone in the sandwich generation eventually has to face.

Clearing out your parents’ home.

Whether they’re aging in place or starting to downsize, chances are their house is filled with decades of memories, mismatched Tupperware, sentimental treasures, expired spice jars, and maybe a few questionable knick-knacks (hello, porcelain clown collection and tiny spoons).

The idea of sorting through it all after they pass is not just daunting—it’s emotionally and physically exhausting. And if you’ve ever watched someone try to do it all in one emotionally-charged weekend after a funeral… you know that’s not the time to be deciding what to do with 40 years of tax returns and 12 chipped “World’s Best Dad” mugs.

That’s why I’m a huge fan of the slow and steady approach. Start now, little by little, while your parents are still here and able to share stories, make decisions, and maybe even have a few laughs along the way.

Clearing Out Your Parents’ Home: Why You Shouldn’t Wait Until It’s Too Late

You might be thinking: “But my parents are still fine! Their house is clean, and they’re not ready to part with anything.”

Totally fair. But here’s the thing: The process of clearing out isn’t just about clutter—it’s about control, preparation, and peace of mind. You don’t have to strip their house down to the studs today. You just have to start the conversation—and take the first step.

Starting now means:

• Less stress during an already emotional time

• More time to ask about the meaning behind items

• The ability to donate or distribute things with intention

• Fewer family arguments about “who gets what” later

Plus, it gives your parents a say in what happens to their stuff—before decisions are made without them.

Step 1: Start Small & Start With a Story

Don’t march in with garbage bags and a label maker like you’re on a reality show. Start with a sentimental invitation:

“Mom, I’d love for you to tell me the story behind some of your favorite things.”

Choose one drawer. One box. One shelf. Sit together and go through it. You’ll likely uncover items with memories attached—letters, photos, recipes, or souvenirs from that trip your dad still talks about. Ask questions. Listen. Write things down.

You’re not just decluttering—you’re preserving their legacy, one memory at a time.

Step 2: Create a “Keep, Toss, Donate, Decide Later” System

This method works wonders because it gives everyone permission to not have to make 100% of the decisions in one go. Use labeled bins or boxes for:

• Keep: Items that are used, needed, or loved

• Donate: Useful items they no longer need

• Toss: Broken, expired, or unsentimental items

• Decide Later: The “I’m not sure yet” pile that keeps momentum going

  
  

Pro tip: The “Decide Later” bin keeps the process moving without guilt. Just revisit it every few months together.

Step 3: Tackle One Area Per Season

This is a marathon, not a sprint. Pick one small area to go through each season. Not a whole room—just a focused section like:

• The bathroom medicine cabinet in spring

• The holiday decorations in summer

• The kitchen junk drawer in fall

• The linen closet in winter

This bite-sized approach prevents burnout and keeps progress moving throughout the year.

You can even tie it to seasonal routines:

“Since we’re putting up the tree, let’s sort through the decorations while we’re at it.”

Step 4: Digitize the Memories

That box of old photos under the bed? Those VHS tapes? The scrapbook from 1981?

Now’s the time to preserve them. Use your phone or a photo scanner to digitize photos. Record your parents sharing the story behind certain heirlooms. Convert old videos to digital files.

This part isn’t just decluttering—it’s preserving family history in a way you and your kids can actually enjoy later. And if you’re lucky, you might even catch your dad getting teary over his high school football photo.

"Polk High, 4 touchdowns in one game" - Al Bundy

Step 5: Ask What They Want Done With It All

It might feel awkward, but having a conversation about their wishes now avoids guesswork—and family drama—later.

Ask questions like:

• Are there any items you’d like passed down to specific people?

• Would you want us to sell or donate your things if you didn’t need them anymore?

• Is there anything you want to be buried with, or that has deep meaning for you?

  
  

These conversations are tender, yes—but they’re also empowering. It gives your parents a voice and gives you peace of mind.

Step 6: Let Go of Guilt (Theirs & Yours)

You’re going to run into emotional speed bumps.

Your mom might say “But that’s my wedding china!” even though it hasn’t seen daylight since 1983. Your dad might insist he’s saving that broken lawnmower “just in case.”

Guilt shows up—both theirs and yours. But remember this:

You are not disrespecting their legacy by letting go of things. You are protecting it.

Keeping everything doesn’t honor their memory—keeping what matters most does.

Step 7: Make It a Tradition

You don’t have to call it “decluttering.” Maybe it’s “Story Sunday” or “Memory Monday.” Maybe you order takeout, pour some wine, and dig through a box together while you laugh (and cry) at what you find.

Make it a ritual. Make it meaningful. Make it manageable.

One Day, You’ll Be So Grateful You Started Now

When the time comes, and it always does, you’ll be thankful you took the time to ask, to listen, and to clear the clutter with love and intention.

You won’t be drowning in boxes of unknown items, wondering, Should I keep this? Would Mom care if I toss it?

You’ll know. You’ll have the stories. You’ll have the plan. And most importantly, you’ll have peace.

Ready to start the process?

Grab one of the many free resources on my website to help you get started, plan ahead and prepare for the unknown.