Step One

Uncover the Stories Behind the Stuff

Did cleaning out Dad's space spark an epiphany that decluttering is my lifelong purpose? Not at all. I was just happy to put off my job search for a few months while I figured things out. I still had no idea how I was going to earn a living. My father, my hero, was gone, and I was lost and wandering-and the only thing worse than being lost in life is being lost in life and broke.

I had one thing going for me, though: a community. People knew my grandfather, they knew my father, and now they knew me. I had my people. The upside of a tightly knit community is that people look out for you when you're down on your luck. The downside is that everyone knows the details of your life. Both realities played into what happened next.

Word got around that I had cleared out my dad's house and that I was looking for work. At church one Sunday, a kindly eighty-year-old woman-we'll call her Etta-came over to me. I'd known her my entire life-she and her loving squad of bridge players, with their immaculate, blue-tinted white hair. No matter what was going on in their lives, these women got their hair done at the beauty parlor every other Thursday afternoon.

Etta told me she'd heard I was looking for some ways to make money and offered to help me out. She lived in an old colonial house like my father's, and her friends were encouraging her to downsize now that her beloved husband, Jim, had died. She was years away from going into senior living, she hastened to inform me. But she figured I could use some extra money. She asked if I could do some work for her.

I quickly agreed, happy to help her out and earn some cash. A few days later, I arrived at her home ready to clear out what I assumed were a few boxes.

Then I stepped inside. Etta's home was a sign of a well-lived life. Dishes and crystal of every type imaginable were stacked in her kitchen and dining room. Cases of wine and shelves of wineglasses. Linen tablecloths and napkins folded neatly. At least ten card tables and dozens of decks of cards. It looked to me like her home held enough to supply a banquet hall.

I had thought, going over to Etta's home, that helping her declutter would be depressing. Weren't we going to throw away a lifetime of stuff, after all? Wouldn't helping her clean out be like helping her write her own obituary?

That wasn't what happened at all. Over the next few weeks, Etta and I took pleasure in her favorite life stories. We didn't bury her best years; we celebrated them. She had an eager audience in me, and she was in control of how the organizational process worked. She took her time. Etta's memories were given another life when she recalled them to me-and in this chapter I'm giving them another life by recalling them to you. This is the most important part of the process-the part most experts miss entirely. If we don't know the stories behind the stuff, we will never be able to freely let go of it.

If you are in the process of decluttering, downsizing, or moving, telling your stories to an interested audience is the magic key. And if you're helping someone else, it's your responsibility to listen. In this chapter, I'm going to show you how to both tell and listen to the tales.

Why Different Generations Collect Different Stuff

If you're cleaning out the home of older generations, you'll likely notice how differently they consumed and collected stuff than we do in our current era. I hadn't realized this until cleaning Etta's home. Etta was an entirely different species from me or my dad. As we talked that day, I understood for the first time the significance of that generation gap.

Etta was a child of the Great Depression. Those of us who have grown up in more prosperous times might not understand what it was like to come of age when scarcity was the norm, not the exception. But those who lived through it never forget it. Soup kitchens and bread lines. Labor strikes and Dust Bowls. "One-third of a nation ill-housed, ill-clad, and ill-nourished," as President Franklin Roosevelt said in 1937. These traumatic memories become part of a generation's DNA. Starting with Etta and continuing for the last twenty-plus years, I have worked with that generation and witnessed the indelible imprint the Depression left upon millions of people. It's not always detectable in their words or actions out in public-but it's visible in their homes.

But I didn't know that yet. So at first, I wondered why Etta seemed to keep everything. Why hold on to those skinny yellow plastic bags tossed on her porch every morning with the newspapers? And the rubber bands wrapped around the armrest of her rocking chair? She had a stack of bulletins from every church service I think she ever attended; it looked like fifty years of neatly stacked Sundays. I was stupefied at the sheer amount of stuff this petite woman possessed.

Starting in the dining room and moving to the basement and the attic, we went to work, packing things up, picking and choosing what to keep and what to donate or discard, and, most of all, talking and laughing.

And crying. Tears welled up in Etta's eyes as she looked at a note from her father, in his rough handwriting, when he'd left home for months to go out in the world in search of work. She showed me his pocket watch, which she remembered him pulling out of a vest pocket often to ensure they'd be on time for appointments. That story led to others: She and her brother splitting a single slice of bread because that was all they had to eat that day. The Christmas when all her mother could afford for her children was a gift of a single orange and a peppermint stick. Etta told me with delight, with gratitude for her good fortune, the luxurious treat of sucking the juice out of the orange through the peppermint stick.

I felt like I was not just helping Etta go through her stuff; I was in the trenches with her. As I got to know her, I began to understand why she had so much stuff: For people who had nothing at one time, anything they have is precious. More than sixty years later, Etta hadn't lost the feeling that one day, abundance might suddenly disappear, leaving her with nothing once again. And then every plastic bag, every last rubber band would be as precious as coins and paper bills.

Wading through her belongings and talking to Etta about her memories of deprivation, I started to understand something that would later become essential to my life's work: People hoard to cover up pain. The scarcity Etta had suffered when she was younger stayed with her for the rest of her life. She wanted to have enough in her home so that she would never, ever run out. And plastic bags and rubber bands aside, she was damned proud of the possessions she and Jim had worked their tails off to earn. That made parting with them all the more difficult.

Etta explained something else to me: As a full-time homemaker for decades, entertaining guests, friends, and family was deeply important to her. That was why she always kept the house spotless and stocked with enough supplies to serve a small army. When I first got there, I wondered: Who could ever use that many card tables? I'd been to some underground casinos in my time, but something told me that Etta wasn't a card shark running an after-hours club in her basement. And enough platters and serving utensils to open a catering business? Now I understood.

Jim had been a big-time tobacco executive. He was a strong, sturdy, reliable man-a pillar of the community. I admired him when I was young. People like him built Richmond into the city it is today. But now I was seeing Etta, too, as a pillar. For decades, even while raising two kids, she was ready at any time should Jim bring a colleague, supervisor, or client over to be fed and charmed. Her home, the items she took such pride in, proved her commitment to her family and community.

After I spent a few hours helping Etta sort through her memories, she began putting her stuff into perspective. This early in the process, we are only subconsciously coming around to the idea that it's not always the pocket watch we love; it's the person who wore it. The goal is not to make any hasty decisions about what to toss and what to keep. It's to begin to build the trust necessary to decide together. By the time Etta had recounted some of her most cherished memories, and I'd listened with an open mind and heart, she felt she trusted me enough for me to start doing my job.

How to Listen Well

Much of this book will outline the unmatchable worth of sharing stories. But the flip side of sharing stories is another vital practice: listening to them. To earn someone's confidence, you have to be fully present. Hour after hour, day after day. There are no shortcuts, and ideally there should be no multitasking. If you are helping people declutter, they might think you do not care about their stories, let alone want to hear about their past in great detail. Your job is to show that you care. Not just to say it, but to show it, which requires earning their trust along the way. And as I always remind my employees, the word "listen" has the same letters as the word "silent."

To listen intently, make sure you leave the technology in the car or at least in another room. I'm old school-I bring a pad of paper and a pen to take notes. I do not, under any circumstances, use an electronic device in front of clients. That includes cell phones, tablets, smart watches, and headphones with music. If I divert my attention every few minutes to check my email or look at an incoming text message, my clients sense my lack of interest. If you must have your device with you, put it on airplane mode and turn off the ringer and vibrator. Think how offensive it is if someone is pouring out his heart out to you and you respond by looking down at your buzzing watch. He now thinks something else is more important than he is, and is less inclined to trust you with his most treasured items as a result.

Be sure to make eye contact and to take mental notes of things to ask about when the person is done talking. Let him know you are writing down ideas or tasks to do later so you don't forget them. I often ask clients to hold on momentarily so I can write down all they are saying, and then I ask them to resume telling me the story. Most important, avoid talking about yourself. This isn't about you; it's about you listening. Don't keep trying to relate your life to his; this is a rare moment when it is 100 percent about him, so just listen and enjoy and be thankful that you are able to have this moment in time. You're helping him make major change in his life, and that's an immense privilege.

On one of the days I was working with Etta, while in her jam-packed attic, I picked up a grainy black-and-white picture of two young couples sitting at a table, smiling at the camera. The women, probably between eighteen and twenty years old, were simply beautiful. They wore pearls, white gloves, and fancy dresses. Both of the men were in military uniform, grinning, handsome, and happy.

"Who's this?" I asked.

Etta smiled. She pointed to one of the couples. "That's me and Jim."

"That's you?" I asked. Etta nodded. The woman standing in front of me was lovely and powerful, but she was a blue-haired eighty-year-old who looked a bit older. I, twenty-five years old and drunk with the delusions of eternal youthfulness, had a hard time squaring the photo with the woman before me.

"Etta," I said, "you were a knockout!" She smiled and then excitedly showed me a pack of matches that were nearly hidden amid the clutter. It bore the logo of a place named Tantilla Gardens. All my life I'd lived in Richmond, but I'd never even heard of Tantilla Gardens. Etta told me that the picture was taken there on the night her then-suitor Jim had just returned from World War II and got dropped off at the train station just up the street.

For Etta, this was the image that the photo brought to mind. For me, the snapshot was just a fading shot of two good-looking happy young couples. For Etta, the picture was a precious reminder of an unforgettable time in her life, an early glimpse of the man she'd spend her life with. It was proof of the world she'd once inhabited. Of the young man she'd once pined for, of the young woman she'd once been, and of the man she deeply loved for a lifetime. No wonder she had held on to it and to everything in her home. They were items that seemed random and unnecessary to me but contained life-affirming memories for her. She wasn't hoarding or holding on to junk; she was celebrating the incredible life that she and her husband had lived together. I was learning that this was more than just stuff. I was starting to realize in fact that it had almost nothing to do with the stuff; it was all about the memories behind the stuff.

She pointed out something in the photograph that I hadn't noticed: a paper bag sitting on the table. There was booze in it, she told me, giving me a mischievous look that made her appear for a moment as if she were eighteen years old all over again. Good Baptist ladies didn't drink in public, I knew-but if they did, they put the liquor bottle in a brown paper bag to be discreet.

"You must have had a good time," I said, winking at her.

"Oh, we did," she said, grinning. "I missed my parents' curfew that night."

Note that we didn't look at Etta's picture on the first day of our decluttering effort. It took some time before we spontaneously created that moment. This is another reason why you want to give yourself lots of time to do this work-so that you can relax and delve into the details of the items. I said earlier in this book that you want to jump into decluttering as soon as possible; don't wait until the last minute. On the other hand, you're going to take your time going through your stuff. This is more than just packing boxes and filling up trash bags. Just like writing a term paper in college, if you wait to cram all the work until the end, your grade will probably reflect that choice, and it will impact your permanent record. Decluttering should not be completed in one long weekend. Plan ahead for the time and people to properly help. Put it on the calendar. By knowing her eventual journey into senior living, Etta gave herself crucial preparatory time to enjoy the move calmly and confidently.