Have you ever had to clean out the home of a loved one who has passed away?
Have you ever served in the role of executor of an estate for a friend or family member?
In a strange way, if you have not, you’re missing out on life education that has the potential to help you and your family and friends to one day leave behind love, legacy, and memories rather than a “dumpster fire,” as Rachel Donnelly, our friend, founder, and author of Late to Your Own Funeral, has been known to say.
Read on for one family’s true story. We’ve made modifications along the way to protect their privacy.
Honoring a Bachelor’s Legacy
Emily was always close to her cousin Joseph, growing up in neighboring towns, spending many weekends together at the family’s cabin. Time passed, Emily moved away (three towns over), married and started a family, and had a fulfilling career, keeping her busy, but never too busy for her cousin. In contrast, Joseph remained a proud bachelor, well-liked by his neighbors, and ever the humble host.
“Joe’s place was a gathering place. People just showed up with a cooler of drinks to shoot the breeze on his back acres, enjoying the lake view. You could see two dozen different birds just relaxing by the lake.”
Joseph’s affable nature and pride in his numerous collections related to pyrotechnics and war—think Civil War through WWII guns and other historical artifacts—meant he was also well known far beyond his local area.
So, when Emily got the call that Joe had passed away, she sprang to action.
"He joked all the time that I was going to get all his s*** one day, but he was better prepared than you might expect given his other bachelor ways. All of the items in his collections were labeled. And he had shared with me the names of antiques dealers and others he bartered and traded with over the years. I had a head start on what to do with everything valuable.”
We asked Emily, “But where did you even start? How did you know where to start?”
“Well, I’ve seen this movie before, being the executor for my mom’s estate and helping my husband with his sister’s, too, so I knew the basics. And I wasn’t alone.”
Here are Emily’s 5 steps to a DIY estate cleanout, bachelor style:
Step 1. Security. Joe lived out in the country in a modest 2-bedroom rambler, and didn’t really worry about locking his doors. Everyone knows everyone. Everyone looks out for everyone. But of course, Joe’s reputation as a collector was known far and wide. Not only were his collections valuable, but, if improperly handled, some pieces were dangerous. So, as executor, Emily immediately sent a family member to stay at Joe’s home to ensure his belongings were secured.
Step 2. Make it legal. Joe had a Transfer on Death Deed (TODD), otherwise known as a beneficiary deed. As such, because he planned ahead and named Emily to receive his home and all of its contents, in a matter of days the property was legally in her name, neatly nipping a prolonged probate process in the bud.
Step 3. Dust (and tidy). Emily’s lifelong bachelor cousin was not much for cleaning, but this isn’t only about dusting away the cobwebs. His extended dining table was also his home office and the most likely place for her to find bills and statements, her clues to the financial assets and liabilities that were now left to her to sort out. Finding bills to be paid was foremost on her mind. If only this part of his life was as well organized as his war memorabilia!
Step 4. Grief and ‘stuff.’ “Joe was always telling stories. He loved history. And because the things he collected had stories, I wanted it all to have good homes. We easily could have gotten a dumpster. But how would that honor Joe’s memory, help his close friends grieve, or have been good for the planet? You can’t just throw it all in a landfill!”
A few weeks after the funeral, Emily arranged for a celebration at Joe’s house. While he had no immediate family, the neighbors, other collectors, and extended family were eager to gather to remember their friend. Emily also invited them to select mementos to remember Joe.
This gathering was then the steppingstone for a broader community initiative to find the right auction houses, antique dealers, and yes, pyrotechnic experts, to liquidate the more valuable (and explosive) assets from Joe’s estate.
“Some things went at auction for only $1 or $5, many more sold in the $50-75 range, and then there were exceptions hitting $2,000 or more. We used Facebook Marketplace, too, because it’s fast, local, and you’re not giving up 20% or more to an auction house.”
Step 5. The dump. Well, not only the dump. Yes, some items were trashed, but they could re-sell steel, aluminum, and copper scraps from Joe’s various projects, recycle electronics, and bring home goods to Habitat for Humanity’s ReStores.

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At the end of our conversation, we took Emily back to the beginning to ask if she had considered hiring a professional to do all this work at any point during the cleanout.
“No. Maybe it’s a trust issue, worrying they’d just toss stuff out. But really, I had the time—I’m retired—I already knew what was what inside his home, and I was not doing the work alone. I had my husband’s support. He could have said, ‘Hell with it, I’m not helping. Just sell the place!’ And Joe’s wide network of friends and neighbors helped at every turn, too.
To tell you the truth, in the end, it feels good.”
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Did you miss our first installment about estate cleanouts? Read it now -->
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