At Silver Pathways, I work with two main groups: (1) older adults who are actively navigating the process of decluttering and downsizing, and (2) their adult children who are stepping in to help.
My team and I mostly fall into that second group—members of the Sandwich Generation, balancing the changing needs of our parents while cheering on kids who are preparing for launch.
If that sounds familiar, your calendar might look something like this: one day you’re moving your young adult into their first apartment, and the next you’re in your parents’ attic—sorting through holiday decorations from the ’70s, fine china no one uses, and greeting cards from every birthday since 1963. Who knew the Sandwich Generation would require so many moving boxes?
And if you’re anything like me, you’ve probably made a quiet vow: I won’t leave this kind of task for my own kids someday.
And yet… I walk past that stack of stuff in my own garage seven days a week.
Here’s the thing: the advice I give to older adults about simplifying their lives? It’s just as relevant to the rest of us. The best time to start preparing for the future isn’t when you’re overwhelmed or in crisis—it’s now, while you still have time to be thoughtful and intentional.
In today’s post, I’m sharing the practical, doable steps that can help you age well, live lighter, and make things easier for the people you love. So while you’re helping your parents get their ducks in a row, let’s take a moment to organize your ducklings, too.
Plan Now, Thank Yourself Later
Here are four things you can do now to make life easier on everyone down the road.
You can: Declutter as you go.
Your parents’ home may be full of decades’ worth of furniture, paperwork, and sentimental items that made up the bits and pieces of their lives, but now, these things have become a burden to sort through. Take note of problem areas in their home that require extra time, and make a commitment now to avoid the same fate.
Start small—one closet, one drawer, one shelf at a time. Regular decluttering ensures that when the time comes to downsize (or just simplify), you won’t be buried in excess stuff.
I cover the emotional and the practical sides of decluttering in this two-part series directed at seniors, Letting Go & Living Light. Click here for tips on the emotional overwhelm of decluttering and here for practical steps towards reducing the clutter in your home.
There are lots of nuggets of wisdom applicable to you in those two posts, and here are a few I would call out for our generation specifically:
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- Use the 5-Year Rule. Our lives evolve, but our stuff often lingers long after a phase has passed. If you haven’t used something in the last five years, ask yourself honestly—will you need it in the next five?
- Downsize in place. Even if you don’t plan to move anytime soon, reduce what you own as if you were. Keep only what serves a purpose or brings you joy in each space. Let go of large or unused items like furniture, outdated electronics, or yard equipment that might complicate a future move.
- Give with purpose. As you declutter, create Keep, Sell, Donate, and Give Away piles—but don’t stop there. Follow through and find the right home for each item. Think about what you might pass along to friends or family now, especially if your children are setting up homes of their own. When you can match a cherished item with the right person, it becomes more than a hand-me-down—it becomes part of your living legacy.
- Organize photos and important documents. One of the biggest challenges for families is sorting through years of unorganized photos and paperwork. Digitize or organize as you go—into albums, labeled folders, or even framed displays. Starting now means you’re not scrambling later.
From my client notes: Decluttering doesn’t have to be painful—in fact, it can often be healing. One generation can inspire the next in ways we don’t always expect.
I’ll never forget one client—we’ll call him Paul—who lost his wife suddenly. As his family sorted through their belongings, his adult daughter, Sarah, grieved that her mother would never have the chance to see her using the collection of teacups that had been tucked away in boxes for years. That fall, she sent me a photo of the colorful vintage bedsheets she was passing down to her college-bound daughter. “I’m following your advice and giving with intention!” she wrote. A simple yet powerful reminder that letting go can also be a way of passing love forward.
You can: Get your financial, medical, and legal ducks in a row.
Here are those ducks again… they follow us everywhere.
While your parents may be reviewing their wills, powers of attorney, and long-term care plans, this isn’t just a task for their generation—it’s just as important for ours. Having your own affairs in order ensures your wishes are clear, your loved ones aren’t left guessing, and you maintain control if life takes an unexpected turn. Think of it as future-proofing your life: when everything is organized and accessible, it’s easier to navigate a crisis with confidence instead of chaos.
Here are the key steps to take now:
- Create or update your will and beneficiary designations. Make sure these reflect your current stage of life, especially if they were created years ago.
- Assign powers of attorney. Choose trusted individuals to handle financial and medical decisions if you’re ever unable to do so yourself.
- Organize your medical documents. This includes advance directives, a list of current medications, and health insurance information.
- Review long-term care options. If you’re considering long-term care insurance, the earlier the better—premiums rise with age.
- Consolidate and simplify finances. Streamline where possible, automate bills, and keep account details easy to find.
- Create a central file—digital or paper—for essential documents. Include your will, powers of attorney, medical directives, insurance policies, and key account info. Make sure someone you trust knows how to access it.
For more on how to tackle this process with confidence, check out my blog: The Power of Planning: Securing Your Future, Whether You Stay or Go.
You can: Create a home that supports you for decades.
With a little forethought, you can make small, gradual changes to your home that will help it remain safe, comfortable, and easy to maintain over time.
- Plan for accessibility before you need it. Simple upgrades—like improved lighting, lever-style door handles, and having essential spaces on the main floor—can make a big impact without a major renovation.
- Right-size your lifestyle. Keep only what adds value, comfort, or joy to your daily life. Letting go of excess makes your space easier to navigate and maintain—and more aligned with how you want to live now and in the future.
From my client notes: I worked with a lovely older couple who were heartbroken to leave their family home, but it had become too difficult to navigate—cramped bathrooms and multiple steps made mobility a challenge. As we went through the moving process, their son noted that if they had made some modifications to their home when they were younger, they could have safely stayed in it longer. Since he was in the middle of building a new house himself, he made some small adjustments to the blueprint to ensure his home would be more accessible as he aged.
You can: Build the life you want to age into.
It’s not just about clearing out the garage (though, we know that’s on my list.) Aging well means shaping a life you enjoy—one that supports your well-being, connection, and independence.
Here are a few areas to consider:
- Stay socially connected. Friendships, community involvement, and hobbies can keep you engaged and energized. Invest in the relationships and activities that bring you joy.
- Prioritize your health and mobility. Regular movement, balanced nutrition, and staying on top of preventive care all build a strong foundation for the years ahead.
- Plan for future support. Start thinking now about what kind of help or living situation would feel right later—whether that’s bringing in support services, modifying your current home, or exploring a move to a walkable or lower-maintenance community.
You can: Initiate meaningful conversations.
Don’t just think about your future, talk about it with the people who matter most to you. Whether it’s your spouse, siblings, or adult children, open communication about your wishes—like where you’d like to live, how your finances should be managed, or who should make medical decisions on your behalf—can make a world of difference later.
Remember, these aren’t conversations for “old” people—they’re for prepared people. The earlier you begin, the more control and peace of mind you’ll have later.
- Be intentional. Schedule a family conversation about your long-term plans.
- Put it in writing. Write down your wishes for living arrangements, healthcare, and finances.
- No secrets. Share the location of key documents with trusted loved ones.
- Revisit the conversation as needed. It’s not a one-and-done!
For more ideas on how to talk through these topics, click here to check out my blog: When Roles Reverse: A Guide to Having the Aging Conversation With Your Parent
Give Your Future Self a Little Love
If you’ve helped your parents sort through years of belongings or navigate big decisions about their care, you already know—it’s a lot. And it often stirs up more than just dust. That kind of experience has a way of making you pause and think:
What do I want this to look like for me someday?
Here’s the good news—you don’t have to figure it all out at once. Small, thoughtful steps now can make life feel lighter and clearer, both for you and for the people who may one day step in to help. This isn’t about being perfectly prepared. It’s about paying attention to what matters and choosing to make things a little easier down the road.
And if you’re not sure where to start? That’s where I come in!
At Silver Pathways, I help people just like you—adult children juggling aging parents and growing families, as well as individuals in their 50s and 60s who want to take control of their next chapter. Whether you need help decluttering or planning a future move, I bring both the heart and the how-to.
If you’re ready to lighten your load and build a more sustainable, organized future—for you and for those you love—I’m here to help. Let’s take the next step together!
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ABOUT ME
Hi, I’m Jill Hart.
In my work as a professional organizer and senior advisor, I’ve helped people in every stage of life downsize, organize, and relocate to new homes.
From childhood visits with my grandmother to my career in real estate, I’ve always been drawn to supporting those entering new life chapters. When I realized that downsizing is about so much more than selling a home, I knew I had found my calling.
My clients aren’t just moving—they’re making tough decisions about what to keep, donate, and pass on. They’re navigating emotional transitions while juggling family opinions, logistics, and timelines. That’s why I created a service that goes beyond real estate.
My team and I handle the planning, organizing, packing, cleaning, and selling—so you don’t have to do it alone. No matter your situation, we’re here to make downsizing a smoother, more manageable process.
Click Here to Schedule a Discovery Call
Learn more at downsizingwithhart.com.