Decluttering After 50: What to Keep and What to Toss

If you’re an empty nester, I have a question for you. What are you doing with all the stuff your kids left behind? I’m talking about the boxes of childhood artwork, old report cards, sports trophies, books, clothes and everything else we’ve carefully saved because we thought someday our children would want it. And then there’s our stuff: the china, silver, furniture, collections and family heirlooms we’ve accumulated over decades.

Here’s the reality that might surprise you: Our kids probably don’t want most of it.

That was one of the biggest takeaways from my conversation with professional organizer Ann Sullivan on this week’s episode of Living Ageless & Bold. Ann has spent nearly three decades helping people organize their homes and lives, including busy families and celebrities in New York City. At 59, she launched a second business, FotoStori, helping families organize, digitize and preserve their photographs and memories for future generations.

As someone who recently went through a major home renovation after living in the same house for 25 years, I could relate to just about everything Ann said. I’ve saved more than my fair share of childhood memorabilia, collected things I haven’t used in years and discovered boxes of photographs I didn’t even remember having. What I loved about Ann’s approach is that she isn’t telling us to throw everything away. She’s helping us think differently about what we own, why we’re keeping it and whether it’s making our lives better.

And for those of us navigating life after 50, that conversation is about much more than organizing our homes. It’s about making space for the next chapter.

Decluttering After 50: Why Your Kids Don’t Want Your Stuff

Ann was pretty straightforward about what she’s seeing with her clients. The next generation generally doesn’t want our stuff, especially the formal household items that were once considered essential wedding gifts or valuable family possessions. They don’t necessarily want china that has to be hand-washed or silver that needs polishing. As Ann put it, they want white plates that can go in the dishwasher and microwave, and they’re perfectly happy with that.

The same thing often happens with childhood memorabilia. Ann told me that when her clients ask their adult children whether they want their old artwork, school papers and other keepsakes, she estimates that about 90% respond by telling their parents to decide what to keep and get rid of the rest. Of course, there are exceptions, and some adult children are extremely sentimental. But the assumption that our kids will eventually want everything we’ve been saving for them simply isn’t realistic.

I experienced this firsthand when we renovated our home. I had saved everything from my children’s school years, and going through it was an enormous project. At one point, I nearly threw away my daughter’s high school sports letter, but my husband suggested I ask her first. It turned out that was something she actually wanted, so we saved it in her bin. That experience taught me something important: We shouldn’t automatically keep everything, but we also shouldn’t make every decision without asking.

How to Start Decluttering After 50 Without Getting Overwhelmed

If you’ve ever stood in front of an attic, basement or garage filled with decades of possessions, you know how overwhelming the idea of organizing everything can feel. The project seems so enormous that it’s easier to close the door and promise yourself you’ll deal with it another day. Unfortunately, that day can keep getting pushed back for years, especially when there’s always something more interesting or urgent to do.

Ann recommends beginning with an assessment of your home and identifying what’s serving you and what isn’t. Rather than randomly pulling things out of closets, she suggests creating a plan that considers your lifestyle, priorities and available time. She compares it to building a house. You wouldn’t begin construction without some kind of blueprint, so it makes sense to approach a major organizing project with a similar level of thought.

After my children moved out, I decided to tackle one drawer or cabinet every week. That was it. I wasn’t going to spend an entire weekend sorting through everything we owned, but I could manage one small space at a time. I went through games, kitchen items and things we hadn’t used in years. I certainly didn’t finish the entire house, but I made progress, and Ann said that’s exactly the kind of approach she encourages.

She also recommends starting with something that isn’t emotionally difficult. For some clients, that might mean gathering all the magazines scattered throughout the house and deciding which ones are worth keeping. She’ll sometimes suggest giving someone a couple of months to read the magazines they’ve been saving, then putting a date on the calendar to let them go. Starting with an easier category helps people experience the satisfaction of clearing space before moving on to more sentimental or complicated possessions.

Organizing Your Home Doesn’t Mean Becoming a Minimalist

One of the reasons I enjoyed talking with Ann is that she doesn’t believe everyone should become a minimalist. She isn’t interested in walking into someone’s home and judging them for what they’ve purchased, collected or saved. Her philosophy is that our homes should reflect who we are and support the way we want to live, which means different things to different people. What feels comfortable and meaningful to one person might feel overwhelming to someone else.

Ann developed this perspective partly through her own experience living in New York City. At one point, she lived in a 350-square-foot apartment and learned how to use every inch efficiently. She loved being out in the energy and excitement of the city, but she also appreciated coming home to a space that felt peaceful and secure. That desire to create environments where people feel comfortable and function at their best became a driving force behind her organizing business.

While Ann isn’t pushing minimalism, she does believe we need to challenge ourselves. Do we really need every piece of artwork our children created, or could we select a few meaningful examples from different stages of their lives? Do we need 20 decorative wine glasses when we haven’t used them in years? Sometimes we hold on to things simply because we’ve had them for so long that we stop questioning whether they still belong in our lives.

The Surprising Freedom of Letting Things Go

During our renovation, I started noticing how many things I’d accumulated that no longer had a place in my everyday life. I had collected decorative wine glasses for birthdays, Christmas and other occasions, along with Longaberger baskets that were so popular years ago. They were perfectly nice things, but when I stopped to think about the last time I’d used them, I realized some had been sitting untouched for years.

My best friend was renovating her home around the same time, and our conversations helped me look at my possessions differently. Instead of asking whether something was attractive or valuable, I started asking whether I actually wanted to keep it. I found a local consignment shop and began making appointments to bring in things I no longer needed. Before long, I’d made a couple thousand dollars selling items that had been taking up space in my house, which made the whole process surprisingly enjoyable.

Ann described that feeling as liberation, and I think she’s right. There’s something satisfying about taking control of your belongings instead of feeling responsible for maintaining things you don’t particularly want or use. She also asked a question that really resonated with me: How do you want to spend your time, maintaining your things or living your life? At this stage, when so many of us are excited about travel, new experiences, friendships and opportunities, that’s worth thinking about.

Downsizing After 50: What Should You Actually Keep?

One of the most meaningful parts of our conversation came when I shared something I’d done before a family trip. My husband, son and I were preparing to go on a safari, while our daughter was staying home. As I thought about the trip, it occurred to me that if something happened to the three of us, she wouldn’t necessarily know which possessions in our house were important family heirlooms and which were simply things we’d accumulated.

So I took out my video camera and walked through our home, identifying five things I would want my children to think twice about before getting rid of them. One was the original railroad china belonging to my husband’s grandfather, who worked for Norfolk Southern Railroad. Another was a beautiful hooked rug made by a great-grandmother, representing a craft and a family connection I wanted my children to understand. I also included a fur stole my father had given my mother, something especially meaningful because my dad passed away 30 years ago.

I explained the stories behind those possessions and why they mattered to me. Then I told my children that everything else was up to them. They could sell it, donate it or give it away, but at least they’d know why those particular pieces had been important to our family. Ann loved the idea and encouraged people to consider documenting their homes and possessions, especially the items whose meaning might not be obvious to the next generation.

That conversation reinforced something I’ve come to believe: Preserving our family history doesn’t require keeping every object we’ve ever owned. Sometimes the most valuable thing we can pass along is the story behind a possession, rather than the possession itself. A piece of china might not mean much to someone who doesn’t know its history, but learning that it belonged to a great-grandfather who worked on the railroad gives it an entirely different significance.

Why Getting Organized Is a Gift to Your Adult Children

Ann made another point that I think every parent of adult children should consider. Getting our possessions and affairs in order is one of the greatest gifts we can give our kids. We spend years accumulating things, often with the best intentions, but eventually someone has to decide what happens to everything. If we don’t make those decisions ourselves, that responsibility may fall to our children at an already difficult time.

This doesn’t mean we need to empty our homes or stop collecting things we love. It means recognizing that our possessions are our responsibility and taking reasonable steps to manage them. Ann believes that whether someone lives in a tiny apartment or an enormous house, they should be thoughtful about what they own and how they want their home to function. For empty nesters, this is also an opportunity to rethink spaces that were designed around raising children but may no longer serve the same purpose.

If the project feels too big to handle alone, Ann suggests finding someone to help. That could be a professional organizer, but it could also be a friend willing to trade organizing sessions. Sometimes it’s much easier to sort through someone else’s possessions because we aren’t emotionally attached to every object. Having another person there to ask questions, offer perspective and keep the process moving can make an enormous difference.

What to Do With Old Family Photos, Slides and Negatives

Now we get to the part of our conversation that I was especially excited about: family photographs. If you’re anywhere near my age, you probably have boxes and boxes of printed pictures, along with old slides, negatives and albums that haven’t been opened in years. I have all of those things, and during our renovation, I kept discovering photographs tucked into drawers and closets. Eventually, I started putting everything into boxes because I simply didn’t know how to organize it.

Ann says this is an incredibly common problem. People begin sorting through their photographs with the best intentions, but the sheer volume quickly becomes overwhelming. They spread everything across the floor, realize how much work is involved and eventually put it all away again. The photographs remain in their boxes, but the memories aren’t being enjoyed, shared or passed along in a meaningful way.

This challenge inspired Ann’s second business, FotoStori, which she launched at 59. She had already spent years organizing printed photographs as part of her residential organizing work, but during the pandemic, she began thinking about how families could do more with those collections. She realized there was an opportunity to help people not only organize their photographs but also digitize them and create something their children and grandchildren could enjoy for years to come.

Reinvention After 50: How Ann Sullivan Started a Second Business

Before becoming a professional organizer, Ann spent years working in the court system. Eventually, she decided she wanted to do something creative and build a business of her own. She even visited a career counselor, who told her she had no marketable skills. Fortunately, she didn’t let that assessment determine her future, because she went to the library and started researching businesses she could launch with very little money.

She discovered professional organizing at a time when most people weren’t familiar with the industry. In fact, she often had to explain that she wasn’t a union organizer or community organizer. She started by offering organizing services as gifts to friends who were getting married or having babies, and those early clients began referring her to others. Eventually, a referral led to helping an Oscar-winning director and actor coordinate a major household move while his wife was expecting a baby, opening the door to more clients in the entertainment world.

Decades later, Ann recognized another opportunity and created FotoStori. I love that she didn’t look at turning 59 as a reason to slow down or avoid starting something new. Instead, she took everything she’d learned from her first business and used it to solve another problem for her clients. It’s a wonderful example of how our experience can become the foundation for an entirely new chapter.

How to Digitize and Organize Family Photos

One of the most fascinating stories Ann shared involved a client who sent her more than 30,000 printed photographs. I couldn’t imagine where anyone would begin with that many pictures, but Ann explained that her team follows a systematic process. They inventory the collection, look for clues about when photographs were taken, identify duplicates and work with the family to determine which images are most meaningful.

Even the physical appearance of a photograph can provide clues about its age. Ann explained that different decades had recognizable printing styles, including white borders and rounded corners, which can help establish a timeline. From there, the team can narrow down large groups of similar photographs, organize the collection and prepare it for digitization. The process is time-intensive, but the goal is to turn an overwhelming collection into something people can actually navigate and enjoy.

What impressed me most was that FotoStori doesn’t simply scan everything and return thousands of digital images in no particular order. Ann explained that her team can organize and tag photographs so family members can search for specific people and events. Imagine preparing for your daughter’s 30th birthday and being able to find photographs from different stages of her life without digging through dozens of boxes.

FotoStori can also combine printed photographs with existing digital collections, creating a more complete family photo library. Depending on what the family wants, the finished collection might include digital files, traditional albums or beautifully organized photo books. Some clients want their original prints returned and stored in archival boxes, while others are primarily interested in having digital copies they can share with their children.

Preserving Family Memories for Future Generations

Here’s something I found especially interesting. While Ann says adult children often don’t want their parents’ furniture, china or collections, she’s seen a very different reaction when families receive organized photo books. Children who might not be interested in inheriting a dining room set can become completely absorbed in looking through photographs of their childhoods or learning about relatives they’ve never met.

Ann described seeing children light up as they looked through family albums and asked their parents to tell the stories behind the pictures. Sometimes they wanted to go through the books again because the photographs sparked conversations they might never have had otherwise. That really struck me because it shows that our children may care deeply about family history even if they don’t want to inherit all the physical objects we’ve associated with it.

FotoStori also creates legacy books that can incorporate letters, handwritten notes and other memorabilia alongside photographs. I think that’s a beautiful idea because so much of our family history exists in small details that can easily disappear. A handwritten note from a grandparent, a photograph from a family celebration or a letter saved from decades ago can help future generations understand the people who came before them.

And there’s a practical reason to preserve these collections digitally. Ann recommends creating backup copies and storing them in separate locations so that a fire, flood or other disaster doesn’t destroy everything. We can’t always protect the original photographs, but taking steps to digitize and back them up can help ensure those memories survive.

Don’t Forget About Your Digital Clutter

We also talked about a modern organizing problem that I discovered during our renovation: old electronics. Somehow, we’d accumulated multiple MacBooks, phones and other devices, and nobody remembered the passwords. I didn’t want to donate or recycle anything without making sure our personal information had been removed, but figuring out how to access some of those devices was another project entirely.

Ann explained that recovering information from locked computers can be complicated and sometimes expensive. Her company works with technology professionals when clients believe old devices contain photographs or other important files, but she acknowledged that recovery isn’t always possible. That’s why she encourages people to think ahead about password management and make sure someone they trust can access important information if necessary.

It’s a reminder that organizing our lives today involves more than closets, cabinets and paperwork. Our digital possessions need attention, too, especially when they contain family photographs or information that would be difficult to replace. Just as we wouldn’t want to leave our children a house full of unidentified possessions, we probably don’t want to leave them a collection of inaccessible computers and devices.

Empty Nest Organization: Making Space for Your Next Chapter

As Ann and I wrapped up our conversation, I kept thinking about how much this topic connects to the bigger message of Living Ageless & Bold. When we’re raising children, our homes revolve around their needs. We have spaces for homework, sports equipment, toys, games, school projects and all the other things that come with family life. Those years are wonderful, but eventually our children grow up, move away and begin building lives of their own.

That transition gives us an opportunity to think about what we want our homes to look like now. Maybe a former bedroom becomes a home office, a creative space or somewhere to pursue a hobby you’ve always wanted to try. Maybe clearing out the basement means you can finally use it for something you enjoy. Or perhaps you simply want a home that feels calmer, lighter and easier to maintain, without the constant reminder of projects you’ve been putting off for years.

Ann’s advice isn’t to erase the past or get rid of everything that reminds us of our families. It’s to be intentional about what we keep and recognize that the things we own should support the lives we’re living today. We can preserve meaningful possessions, document family stories and organize photographs while still letting go of the things that no longer serve us.

For me, that’s what makes this conversation about so much more than decluttering. We’ve spent decades creating homes for our families, and now we have the opportunity to create spaces that reflect the women we’ve become. We can keep the memories, honor the people and experiences that shaped us, and still make room for new adventures.

Because after 50, the goal isn’t to spend the rest of our lives managing everything we’ve accumulated. It’s to make room for everything we still want to experience.

You can learn more about Ann Sullivan’s photo preservation services at FotoStori.com. And be sure to listen to our full conversation on Living Ageless & Bold wherever you get your podcasts. If you have a friend who’s staring at an attic full of memories and wondering where to begin, share this episode with her. Maybe you’ll inspire each other to finally tackle that first drawer.

Watch her full episode here: