As we get older, many of us find that we’re more interested in getting rid of things than in acquiring more. At a certain point in our lives, we look around and realize that we’ve accumulated a lot of stuff: shelves stuffed with books we’ll never read; closets filled with clothes we’ll never wear; and cabinets, attics, garages, and basements stacked with an array of leftover, left behind, outgrown, slightly damaged things. There are a number of reasons to downsize or right size, the most common being a prelude to a move. But even if we’re staying in our home, we may want to step back, evaluate what we have, and give away or get rid of what we no longer need or want. Although the experience can be physically, mentally, and emotionally exhausting, it can also be a satisfying and gratifying expression of our values and a gift to our heirs.

As a home organizer, I have supported people of all ages by helping them make thoughtful decisions about what to let go, what to hold on to, and what to give away. As they let go of the clutter and belongings blocking their space, internally and externally, they have gained a deeper appreciation for what truly holds meaning in their lives and a greater understanding of the symbolism and history of the belongings that are of true value.

The process of decluttering has a resonance with the pre-Passover preparations of removing chametz (products that contain leavening) from our houses. Symbolically, chametz is not just yeast or flour, but represents things that “puff us up.” As we look around our houses, how can we get rid of the things that bloat us? Before Passover in my Brooklyn neighborhood, I witness families burning their bread in garbage cans in preparation for the holiday. It makes me think about my clients who at first are afraid that they will have to let go of things that matter to them, only to discover in the process what truly does matter to them.

Where to Start?

How do you sort through all your possessions and determine what do with them?

I recommend starting in your home’s storage units—the attic, basement, and garage; we often stuff items in these spaces because we don’t want to deal with them—then move on to closets, cabinets, and drawers. Divide things into the following four groups.

GROUP 1: THINGS YOU WANT TO CONTINUE USING AND/OR ENJOYING

Items in this group are easy to identify because you know what you use and enjoy. When you’re unsure about an item’s usefulness or aesthetics, give it the time test: If you haven’t used or worn something in a year, give it away. Or follow the advice of Marie Kondo in her best seller The Life-Changing Magic of Tidying Up: The Japanese Art of Decluttering and Organizing and consider whether the item “gives you joy.”

GROUP 2: THINGS YOU WANT TO GIVE AWAY TO SPECIFIC PEOPLE

This category includes items you want to give away, either now or later, to specific people because they reflect values, experiences, or sentiments important to you. They tell the story of your life, so decisions surrounding them can be difficult. Before you begin, ask yourself: What do you want or consider to be your legacy?

I asked both my mother and a long-term client this question. My mother is a Swedish minimalist, and my client is a “collector.” In both cases, the question led to oral histories of family, love, and identity, and a list of their most important possessions—a museum catalog of their lives.

My mother put it simply but beautifully: “I want my legacy to be love: the love of my family and the love of my friends; the love I felt for them, and the love I received from them.” She determined the value of things she loved by who gave them to her and whether they made her feel loved. For instance, she loved the furniture from my grandmother, my father’s mother, who welcomed her into the family when she was not Jewish and who became a surrogate mother to her when she moved to the United States. My mother remembered and held on to this act of kindness and love even through the rough times. In the end, my mother identified about 5 or 10 items that she wanted my siblings and me and my children to have. Through asking my mother what her legacy was and what she truly valued, I gained a deeper appreciation for the purity of the love my mother gave us all, and I made a commitment to keep the few things that meant so much to her.

When I asked my client, the collector, what she wanted her legacy to be, her answer was “worthiness.” Together we created a list of items to be given to friends and charities. For three years I had been helping this client sort and clear out items from her vast collection. A former actress, and a lover of words, she said, “I live in the word, whether spoken or written. It feeds me and it informs me and wraps itself around any material things I own.” For her, any meaningful gift comes with a story. We decided that we would dedicate a portion of each session to writing dedications for heirlooms to be given to friends or relatives. My client then took it to the next level, not only writing descriptions of the objects, but also including letters to the individuals expressing to the individuals expressing the love she felt for them and how they influenced her life. By letting your friends and family know what you would like to pass down to them, they will better understand the symbolism and meaning of the things that matter to you. Consider having these conversations one-on-one, and be mindful of the recipients’ needs, interests, and capacities. When my collector client was considering leaving something to a dear friend who has himself become overwhelmed by his own stuff, she thoughtfully decided to leave him only one item.

Holiday gatherings or family get-togethers are great opportunities to have these conversations about leaving a legacy, although it is probably wise to let family members know in advance that this is part of your agenda. You may start by saying, “I have been thinking about my legacy and what I value, and this is why these things matter to me.” GROUP 3: THINGS THAT ARE USABLE BUT ARE NOT LEGACY ITEMS We all have lots of beautiful, valuable, or usable stuff. But not everything will have such personal, sentimental, or symbolic value for you that you want to keep it in the family or give it (and its stories) to particular people. Trust your gut and keep a sense of humor. If your thought is “Why the heck did I keep this?” give it away or throw it away.

First, ask your friends and family if they would like anything that you are not keeping or giving to other people. If they don’t respond, that is their answer. It does not mean your possessions are not valuable; they just might not fit into their physical spaces or lifestyles. Don’t take it personally.

Second, donate. After decluttering, all my clients feel comforted by the idea that other people will benefit from their donations. Knowing that furniture, clothing, housewares, and other material possessions are going to worthy organizations makes letting go less painful. A dear friend of mine volunteers and contributes excess furniture to A Sense of Home, a Los Angeles–based nonprofit that sets up apartments for young adults who have aged out of the foster care system. My Swedish aunt and uncle donated their collection of traditional Christmas decorations to the ski club of which they were longtime members. A former client donated her civil rights academic library to a prison that was starting an education program. Another client donated her entire work wardrobe to an organization that helps women get back into the workforce after recovering from addiction and poverty.

GROUP 4: THINGS THAT ARE BROKEN, UNREPAIRABLE, OR OF NO POSSIBLE VALUE TO ANYONE ELSE

What you cannot give away, dispose of in an environmentally positive way. Your local city or town has places where you can recycle fabrics, electronics, and toxic materials.

Additional Considerations There is no one approach to decluttering. It helps to attune ourselves to special circumstances and be flexible in how we handle things.

Couples. Rarely do I find couples who have the same attachments to their possessions. One might be the collector, the other the minimalist (who might actually have spent decades resenting his or her spouse’s collections!). I work with couples separately when downsizing a house. I encourage them to focus on their own “stuff” first and make joint decisions on shared items later.

Children’s things. You may find that your home has become a storage unit for your adult children’s memorabilia: yearbooks, trophies, sports equipment, school papers. Send your adult children's photos of all the items that they have in the house and ask them if they want their stuff, or if it can be donated or trashed. If the kids want some of their things, set a firm deadline for them to pick up what they want or arrange with them to have the items sent.

Paperwork. Begin by buying a fireproof safe box. As you sort through your paperwork, secure in the box your important identity and financial papers, such as birth certificates, death certificates, military service records, long-term care instructions, wills, Social Security cards, passports, insurance policies, and the deed to the house. Decluttering can be exhausting and anxiety-producing. It is easy to become overwhelmed and forgetful. Knowing that all your documents are in one safe and secure container will bring you peace of mind. (See chapter 18, “Getting Your Stuff Together.”)

Photos. Keep the photos, ditch the frames. Only keep photos and memorabilia that are truly significant to you. Make sure to write down the dates, the history, and the names of people on the back of photographs or frames of artwork. If you are looking at a photograph and have no idea who the person or people are in it, throw it out.

Organizing digital photographs is even more complicated and time-consuming than organizing physical photos. Because storage space on an external hard drive or in the cloud is so vast, you may tend to keep everything. This doesn’t make for a coherent legacy, however. As with physical photos, it’s worth going through them carefully. For this task, dedicate short periods of time over a number of days or weeks, so you don’t get exhausted by the experience. Delete duplicates and only keep those photos that have value or meaning to you. Then label the files with information about who is in them, where they were taken, and when.

Journals. Clients often ask what I recommend they do with their personal journals. If your journals are simply travel logs and you don’t mind your children or spouse reading them, go ahead and keep them. If your journals hold parts of your story that you would not want your loved ones to read, let them go. It is freeing.

Gifts and things passed down to you. We hold on to so many things that weigh us down. This is a time in your life when you deserve to focus on yourself and feel lightness and joy. Throw out the guilt and make thoughtful choices. If someone gave you a gift and it’s not your style, donate it. If you have Aunt Esther’s furniture in your basement and you hate it, donate it or put it out on the curb. You can find great peace in letting go of things that no longer have meaning or value to you.

I already know what I would like of my mother’s: a blue blown-glass cat in her dining room. It’s not because I am particularly fond of cats, but rather because I cherish the story attached to it. My mother, who is a giver and truly the most generous person I have ever known, was in Stockholm with my aunt and spotted this cat. She wanted it but could not justify spending the money. My aunt grew tired of her indecision and told her, “If you don’t buy it for yourself, I will.” My mother bought it for herself. My mother told me it was her favorite thing now. To me it symbolized my mother giving love to herself, and that is something I want to hold on to. What is your legacy, and how do your things tell your story?

Deborah Goldstein

‘Excerpted from Getting Good at Getting Older © 2019 Richard Siegel and Laura Geller; Behrman House’