The Things We Leave Behind: A Little Less Stuff, A Lot More Love

Part One: A Little Less Stuff, A Lot More Love

The first thing I noticed was her slippers.

They were sitting beside the couch, right where she had left them.

Such an ordinary thing. A pair of slippers in a living room. But they stopped me for a moment.

I was standing in the home of a woman I had never met, surrounded by the things that had made up her life. Her furniture, photographs, paperwork, and all the little pieces of a life lived.

And somehow, it had become my responsibility to figure out what happened to them.

I didn’t know which things she treasured. I didn’t know what held a special memory or what she would have happily given away years ago. I didn’t know what she would have wanted saved, donated, sold, or simply thrown away.

I was a stranger, trying to honor a life I knew almost nothing about.

And I couldn’t stop thinking about those slippers.

Because here’s something I’ve come to understand, both through losing my own parents and through the work I’ve done helping families navigate what comes afterward:

When we leave this world, we don’t just leave behind the people we love. We leave them decisions. Thousands of them.

And sometimes, those decisions become an enormous burden at the very moment those people are least equipped to carry it.

I’ve Been on Both Sides of the Front Door

I lost my father when I was 23. I watched my mother navigate the grief of losing her husband while making decisions about the things he left behind.

Twenty years later, I lost her.

My mother was an extraordinary planner. She had a will, organized documents, written instructions, and even index cards explaining exactly what she wanted us to do.

She had planned her funeral, selected the music and readings, and identified which special belongings she wanted her children and grandchildren to have.

She had even given one of my sisters an envelope years earlier, with instructions to open it when the time came.

Honestly, she could have taught a master class in preparing your family for the inevitable.

And yet, despite all of that preparation, it was still incredibly difficult.

There were seven of us. Seven grown women with jobs, families, responsibilities, and lives that didn’t suddenly stop because our mother had died.

We spent months sorting through belongings, making decisions, arranging donations, and trying to honor her wishes.

Our group text became a never-ending parade of photographs.

Does anybody want these placemats?

What about this tablecloth?

Does anyone remember where this came from?

Do any of the grandchildren want this?

Seven sisters. Seven opinions. One group text that I’m fairly certain deserves its own chapter in family history. If you’ve ever tried to get seven women to agree on anything, you can imagine how smoothly this went.

It wasn’t that we needed these things. We were grown women with our own homes, our own furniture, and, quite frankly, plenty of our own stuff.

But we were terrified of throwing away something that might matter to someone else.

So we asked. And asked. And asked.

Sometimes we kept things simply because getting rid of them felt wrong.

Apparently, grief has a way of convincing you that you absolutely need a tablecloth you haven’t seen since 1987. And then, years later, you’re standing in your own basement wondering why on earth you brought it home.

I’ve found myself letting go of some of those very things.

Not because they weren’t meaningful to my mother, but because I finally understood that I didn’t need to keep every object to keep the memory.

And here’s the part that stays with me:

My mother did almost everything right. And it was still that hard.

Imagine what happens when there is no plan at all.

The Other Side of My Work

After more than 25 years in real estate, I’ve seen what happens when families are left to figure everything out themselves.

I’ve worked with children who live hundreds of miles away, executors who are overwhelmed, and families who are struggling to agree on what should happen next.

I’ve also worked with families whose loved ones are still alive but have moved into assisted living or memory care and can no longer participate in decisions about their homes.

Sometimes the responsibility falls on one person.

I recently sat across from a young woman who had lost her father. She was an only child, lived out of state, and had just weeks before she needed to return to work.

When I asked how she was doing, she said, “I’m fine.”

But what I saw was someone who didn’t have the luxury of falling apart.

There were accounts to close, assets to manage, a house to maintain, and an entire lifetime of belongings to sort through.

She had no siblings to share the work. No clear direction about what her father wanted done with his possessions.

And no time to stop.

I’ve seen families become divided over these responsibilities. I’ve watched disagreements about who did what, who kept what, and who made which decisions create lasting hurt.

And I’ve seen perfectly useful belongings end up in dumpsters because time, money, and circumstances left families with few other options.

These aren’t necessarily families who don’t care.

Often, they’re families who care deeply but are simply overwhelmed.

The House Doesn’t Stop Living

Here’s something people rarely think about.

When someone dies or moves permanently into a care facility, the house doesn’t simply pause.

The lawn still needs mowing. The snow still needs plowing. The insurance, utilities, taxes, and maintenance don’t disappear.

Unfortunately, nobody tells the lawn that its owner has passed away. It just keeps growing. And the snow? It certainly doesn’t care that you’re grieving.

The refrigerator still has food in it. The basement still has boxes. The garage still has forty years of things someone thought might come in handy someday.

And somebody has to deal with all of it.

All while working, raising children, managing their own households, and, in many cases, grieving.

It isn’t a weekend project.

Sometimes it takes months.

And the emotional toll can be just as significant as the physical work.

This Isn’t About Living With Nothing

Before anyone starts worrying that I’m coming for their Christmas decorations or their grandmother’s china, let me be clear.

I’m not suggesting we all become minimalists.

I love beautiful things. I love sentimental things. I understand why people keep objects connected to memories.

But there’s a difference between keeping things because they bring meaning to your life and keeping things because you simply can’t bring yourself to make a decision.

That basement full of boxes you haven’t opened in thirty years?

The extra sets of dishes?

The furniture you’ve been storing because maybe someone will want it someday?

I’m not suggesting you get rid of your grandmother’s china. But perhaps we can all agree that the collection of takeout containers without matching lids doesn’t need to become part of anyone’s inheritance.

At some point, somebody is going to have to decide what happens to those things.

Why not make some of those decisions while you’re here to make them yourself?

And better yet, why not invite the people you love to help?

An Act of Love, Not a Morbid Conversation

I know these conversations can feel uncomfortable.

Nobody wants to sit down with their parents and talk about what happens when they’re gone.

And many parents don’t want to think about it either.

But talking about death doesn’t make it happen.

Avoiding the conversation doesn’t prevent it.

What it can do is leave the people we love with questions they may never be able to answer.

Looking back, I wish we’d had more of those conversations with my mother.

Not because she failed to prepare us. Quite the opposite.

But because even with all her careful planning, there were still things we didn’t know.

And sometimes, just hearing someone say, “I don’t care what happens to those old dishes. Please don’t feel guilty getting rid of them,” can be an enormous gift.

It’s permission.

Permission to let go.

Permission to make decisions without second-guessing every one of them.

Permission to grieve without feeling responsible for preserving every object a person ever owned.

Where Do We Start?

Here’s what I want you to do this week.

Not next year. Not when you retire. Not when you finally get around to cleaning out the basement.

This week.

If you’re the person who will someday leave these things behind:

Choose one small space. A drawer, a closet shelf, a box of old photographs.

Ask yourself three questions:

1. Do I actually use or enjoy this?
2. Is there someone who genuinely wants it?
3. If I weren’t here tomorrow, would I want someone I love spending their time figuring out what to do with it?

If the answer to that last question is no, perhaps it’s time to make the decision yourself.

If you’re the person who will someday be responsible for someone else’s belongings:

Start a conversation.

Not a dramatic, sit-down-at-the-kitchen-table conversation about death.

Something simple.

“Hey, would you like some help going through those boxes in the basement? Maybe we could spend an hour together next weekend.”

And then show up.

Don’t just tell someone they need to get organized.

Help them do it.

An hour a week. One drawer. One box. One conversation at a time.

Because the goal isn’t to empty someone’s house while they’re still living in it.

The goal is to make sure that when the time comes, the people left behind have fewer unnecessary decisions to make.

A Little Less Stuff, A Lot More Love

My mother’s passing anniversary was last month. My father’s was just last week.

Maybe that’s why all of this has been weighing on me lately.

I’ve been thinking about what they left behind, what we learned, and how those experiences have changed the way I look at my own home.

My sisters and I have become much more mindful about what we keep. We purge, we donate, we ask questions, and we try to think about the people who may someday have to make decisions about our belongings.

Not because we’re expecting something terrible to happen.

But because we understand what it feels like to be on the other side.

I can’t promise that planning ahead will eliminate grief, disagreements, or difficult decisions.

It won’t.

But I do believe it can make an extraordinarily difficult time a little more manageable.

And maybe that’s one of the greatest gifts we can leave behind.

Not another box of things someone might want someday.

But a little less work, a little less guilt, and a little more room for the people we love to simply miss us.

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Welcome to The Things We Leave Behind, a weekly series exploring the emotional and practical realities of preparing our homes, belongings, and families for life’s inevitable transitions. Through personal stories, professional experiences, and practical steps, we’ll explore how a little preparation today can make an enormous difference tomorrow.

COMING NEXT IN THE SERIES

The Conversation Nobody Wants to Have

How do we talk to our parents, spouses, or adult children about the things we’ll someday leave behind—without making everyone uncomfortable?

Next week, we’ll explore how to start those conversations, what questions are worth asking, and why a little honesty today can spare our families a lot of uncertainty tomorrow.

Part Two of The Things We Leave Behind — coming next week to Vicariously Sisters.