…With Children Who Aren’t Ready To Think About It
Let’s face it—no one really likes to talk about the last chapters. Not when you mean the chapters in your life that include big decisions about where you live, how you live, and what you leave behind (both emotionally and materially).
However, you, my wise and seasoned friend, might be ready to talk about what your later years could look like. You’ve lived a life filled with milestones and memories—and now, you’re thinking practically about how to make your golden years beautiful (and with a lot less yard work!).
But there’s one small hiccup.
Your kids aren’t ready. They avoid that conversation every single time you try to work it in.
So what do you do when you’re ready to plan and they’re ready to pretend you’re immortal?
You start anyway—with compassion, a little humor, and a very practical plan.
So, let’s talk about how to approach this important conversation, what topics to cover, and how to nudge your adult children—or other trusted supporters—out of denial and into helpful participation.
First, Why This Matters
Before we get into strategies, let’s get clear on why this conversation is important. This conversation isn’t about dying. It’s about living well until the very end.
You want to:
- Have a home that supports your lifestyle, and doesn’t work against it.
- Know who’s in charge if things get complicated.
- Pass on what matters (memories, heirlooms, stories) and not leave behind what doesn’t (broken blenders and unpaid parking tickets).
- Have peace of mind that your last years reflect your wishes—not just what someone else guessed you might’ve wanted.
This matters because it is important to you to make choices on your terms, and because your children can play a fulfilling role in those choices.
The Big Topics Worth Tackling (Eventually)
You don’t need to sit everyone down at once and hand them a three-ring binder titled Mom’s March to Mortality: An Owner’s Manual, although that could certainly be effective. Instead, think of this as a good book to read aloud, slowly. Let it unfold over time, with moments of real honesty and, hopefully, a little humor too.
Here are the big areas worth discussing—whether with your kids or a trusted advisor:
Where Will You Live?
This is usually the big one. You might be thinking about:
- Moving to a smaller home, condo, or apartment
- Considering independent or assisted living communities
- Staying put but downsizing, or modifying your home to age in place
This isn’t just about square footage—it’s about freedom. You want fewer stairs, fewer repairs, and fewer reasons to curse at your gutters in November.
Let your children know you’re thinking ahead—not because you have to move right now, but because you want options that make life easier and safer.
What Will You Keep (and What Can Go)?
Decluttering can be surprisingly emotional, but it can also be empowering.
Maybe you’ve looked at that garage full of forgotten gadgets and thought, “If I go first, my kids are just going to rent a dumpster and toss it all.”
And… well… they might.
So, beat them to the punch.
Downsizing your stuff can be a gift to your future self and to your family. You’re not getting rid of memories—you’re just choosing which ones to honor and which ones to release.
Start with the “easy” stuff: extra kitchenware, linens for rooms you rarely use, mystery cords to electronics that no longer work. Then, move to the sentimental things—deciding what to pass on, what to donate, and what to photograph before letting go.
Does this part leave you feeling overwhelmed and not sure where to start? That’s where I come in! As a professional organizer who specializes in working with seniors, I’ve helped countless clients make these decisions—step by step, without pressure, and often without needing a single family member present.
Whether you need practical help sorting through the physical clutter or a sounding board for the emotional part, I’ve got you. And if you’re looking for guidance before we meet, check out my previous blogs where I break down the decluttering process—from tackling the easy wins (hello, mystery Tupperware lids) to navigating the sentimental stuff with care and intention.
Click here for practical tips on decluttering and here to work through the emotions as you downsize.
Money, Paperwork, and the Power Players
Okay, this isn’t a fun one. But it’s vital.
Do you have:
- A will?
- A healthcare directive?
- Power of attorney assigned?
- A list of accounts, passwords, and instructions?
These are the documents that keep your wishes from becoming someone else’s logistical nightmare. If your kids squirm when you talk about this stuff, frame it as a kindness. “I want to make life easier for you, not harder.” And don’t be afraid to ask for help getting these things in order. A good financial advisor or estate planner can walk you through all of it!
Legacy and Values
Your legacy isn’t just what you leave behind—it’s what you leave within each of your loved ones.
What values do you want to pass on? What stories should your family remember? Are there traditions, letters, or recipes worth preserving? Is it finally time to pass along the lemon bar recipe everyone loves?
These are the beautiful things that make a legacy, and they deserve a place alongside the paperwork.
“But My Kids Don’t Want to Hear It…”
I understand. They are willing to help you figure out tricks on your phone, but they would rather not talk about this.
Here are a few ways to open the door:
Use humor. Sometimes the best way to tackle a tough topic is to make it a little lighter. Try something like: “Hey, I’ve been watching this show where someone’s mom moves into a treehouse community in Costa Rica. I’m not saying I would… but just in case, you should know where I keep the keys to my safe.”
This invites the conversation without making your children feel like they need to start writing your eulogy.
Share a story. Tell them about a friend or neighbor who went through something that made you think. “Remember my friend Judy? Her kids had no idea what she wanted when her health declined—and it was really hard on everyone. I don’t want that for us. Can we talk about a few things while I’m still feeling great?”
Real-life stories can be easier to digest than hypotheticals. They make the “why” feel more immediate.
Ask for their input. Instead of delivering a monologue, invite a dialogue. Something like:
“I’ve been thinking about simplifying my life—fewer responsibilities, less stress. Would you like to tour some senior-friendly apartments with me to get an idea of what that could look like?
Even if they initially resist, planting the seed lets them adjust to the idea over time.
Schedule it (yes, really). If subtle hints aren’t working, go bold. “I’d like to set up a time next month when we can sit down for an hour and talk about some future planning. Nothing scary, I promise. But I want to make sure we’re all on the same page.”
Sometimes framing it as a “meeting” makes it more official and gives them time to prepare (and freak out less).
The Quiet Upside of Planning Ahead
Here’s the truth most people don’t say out loud: Planning for your final years can be deeply freeing. It’s a chance to reflect on what matters, choose how you want to spend your time, and remove burdens from those you love. It gives you back a sense of agency in a world that can feel increasingly out of your control.
This is about your life. And you’re allowed to be both wise and lighthearted about it.
Take It One Step at a Time (Even Without Family Involved)
Maybe your adult children aren’t ready to talk. Or maybe you don’t have family nearby—or at all. That doesn’t mean you’re stuck. You’re not alone, and you don’t have to figure everything out by yourself.
There are professionals (like me!) who specialize in helping seniors plan, organize, and move forward with clarity and confidence—whether it’s sorting through belongings, exploring new living options, or just creating a plan that reflects your values.
If family isn’t in the picture, it’s especially important to loop in a trusted advisor at some point—someone who can help you make informed decisions, keep your best interests front and center, and be a steady hand if things get complicated. Chances are, you have someone in mind to act in this capacity, but if not, it’s worth finding the right person.
You don’t have to do it all. Just take the next right step, and the rest will follow.
In the End, It’s About Love
This entire process—yes, even the awkward parts—is an act of love.
Love for your family, so they’re not left guessing. Love for yourself, so you can live your later years with peace, dignity, and joy. And love for the life you’ve built, so you can rest in winding down with intention and purpose.
So go ahead—crack open the conversation. Let your kids squirm a little. (Lord knows they’ve made us squirm plenty of times in their younger years!) They’ll adjust. And when they do? You’ll be ready—with a plan, a smile, and maybe a few lemon bars.
| Is it time to downsize? Take this 3-minute quiz to gain clarity on your emotional attachment, organizational readiness, and future planning. Don’t leave this decision to chance—start your journey with confidence! Click here to take the quiz. |
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.