Part Two of the “Am I Ready?” Series:
Moving From Thinking to Doing
You thought about it last week when you opened up that crowded linen closet, full of items you haven’t used for years. You think about it every time the yard needs extra attention. You thought about it today
“I’m tired of rattling around this big house all by myself.”
“I think I’m ready to downsize.”
In last month’s blog, “Thinking About Downsizing? Why Just Considering It Means You’ve Already Started,” I talked about emotional readiness and how it doesn’t always arrive like a bolt of lightning. Often, it shows up quietly, subtle thoughts, small nudges, or a recurring longing for less. It might feel like weariness or wishing you could cross some tasks off your list for good.
If you recognized yourself in that post and you’re ready to explore your options, you might be asking: What comes next?
You’ll be glad to hear you don’t need to overhaul your life in one weekend, and because you are choosing to work on your own timeline, you’ve given yourself the gift of intentional sorting.
This blog is about taking those first real steps—moving from thinking to doing, gently and thoughtfully. I’ll walk you through a framework I call Space, Stuff, and Speaking Up. These three areas help bring structure and clarity to what can otherwise feel like a big, overwhelming transition.
Let’s talk about your space.
Where are you going?
This is one of the most important questions you can ask yourself: Where do you want to go? The parameters of your decluttering are set by choosing your future space, so taking steps to explore your options will give shape to this process.
Whether you’re thinking of moving from a large home to a smaller one, joining a senior living community, or even moving in with family, your future space will guide nearly every decision you make.
Start by researching what fits your needs, think about your lifestyle, finances, location preferences, and the kind of community you’d like to be part of. Even if you’re not ready to commit, reach out for brochures or inquire about joining waitlists (sometimes there are perks!). If you have friends or family members who have downsized, give them a call! Talk to local Realtors, and consider meeting with a senior move specialist who can talk through steps to take now. These conversations can help demystify the process and clarify what’s realistic for your timeline.
If you’re selling a home, now’s a good time to ask yourself: Do I want to sell it as-is or make repairs or updates to improve the sale price? Selling a home as-is may sound easier, but it likely will affect your sales price by a large margin. If you decide to make repairs to your home, working with a professional can help you decide what kinds of work will boost your sale price and what kinds are hard to recoup. Starting early gives you breathing room and options.
Let’s talk about your stuff.
Start with the spaces you’ve been avoiding.
Most people begin decluttering where they spend the most time, kitchens, closets, or bathrooms. That’s fine for a quick tidy-up, but when you’re preparing for a move, those areas aren’t your biggest challenge.
Instead, begin with what I call “ambush zones” the places that sneak up on you right before a move and steal your energy. Attics, garages, crawlspaces, basements, sheds, and those boxes of photos and paperwork tucked away for “later.”
These spaces hold the things you’ve had trouble getting rid of, often with good reason—they don’t just hold stuff. They hold decisions that don’t get easier with time. In fact, I’ll bet you moved those same boxes from a storage area in the last place you lived to the storage area here, and you haven’t touched them since. Time to dig in!
Attics, Garages, Storage Sheds, Crawl Spaces
Enlist some help to bring items to a safe, comfortable area for sorting. As you sort, be realistic about items you have kept for “someday.” Picture where and how you would use something in your newer, smaller space.
Work quickly through unwanted items! It is easier to make space in your head for decisions when you spend a short amount of time on the things that don’t require much thought. This can make the entire process feel lighter.
- Trash it. Empty boxes and items that are moldy, broken, or damaged by temperature can be thrown away.
- Arrange for pickup. If you are storing items for other people, give them a call and set a date for pickup.
- Sell, give away, or donate usable items. Be realistic about items you think others might want. Passing along keepsakes to friends and family is a beautiful way to create memories!
- Dispose of old paint and building materials. Wood scraps, chemicals, and other materials leftover from home projects can be dropped off at your local disposal center.
Documents and Paperwork
Decluttering paperwork requires constant decision-making—what to keep, what to shred, what might matter later. This uncertainty can create a mental block, causing even the most motivated person to stall out before they begin. Taking care of these tasks early prevents them from becoming a drain on your time later and keeps momentum going.
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- Check the dates. Your tax advisor and attorney can advise you on the length of time to keep important documents.
- Shred or destroy outdated and irrelevant paperwork.
Photographs
Family photos are emotional speed bumps, not just tasks. You can lose hours sorting through them, so doing this early in the process is a sentimental gift to yourself. Begin now, with small manageable piles. Focus on progress, not perfection.
As you sort, keep these guidelines in mind.
- Save quality photos. Keep only clear, meaningful pictures that tell a story.
- Pare it down. Discard duplicates and multiple pictures with the same subject matter.
- Set limits. Consider keeping a set amount of photos per year, or designate a box or album and limit yourself to the amount that fits inside.
- Be easy on yourself. If the collection feels overwhelming, set a timer and work 20-30 minutes at a time.
- Enjoy the process. Sometimes it’s enough to honor the memory before letting it go, so make yourself comfortable and pour a cup of tea while you sort! Consider inviting a family member who would enjoy helping.
Tackling these “invisible” zones, like attics, basements, paperwork, and photographs, first can build momentum for the rest of your move. Once those heavy areas are behind you, the easier parts of the home feel faster and more manageable, giving you a real sense of progress. You’ve already proven you can do the hard stuff—now the rest feels doable!
From my client notes: One of my former clients, Marsha, met with me and began her process two years before she planned to move. Acting on my advice, she started with the attic—boxes she hadn’t opened since the ‘90s—and slowly made her way through the garage and basement. When the time came to list her home, her realtor told her it was the easiest pre-listing walkthrough she’d ever done. More importantly, Marsha said she felt calm, not rushed, and even enjoyed reminiscing through old photos without the pressure of an impending deadline.
Now, a word about speaking up.
Thoughtful communication is the way to go here.
Downsizing isn’t just about changing your address, it’s about changing your life. That means the people close to you should know what’s on your mind.
Speaking up about your plans isn’t about giving up control. It’s about keeping everyone in the loop so your choices are understood and respected. When you share your goals and values with family, friends, or trusted advisors, you help set the tone for collaboration, not confusion.
When you speak up, you create a shared vision. You allow others to walk with you instead of watching from the sidelines.
If you’re not sure how to start those conversations—or how to handle family who may not agree, this blog post can help. Click here to read “Stay in Control: How Thoughtful Communication Protects Your Independence.”
This is your next chapter. Speaking up ensures your story is told the way you want it to be.
Next step? Just keep moving forward.
You don’t need to pack a box today or schedule a move next week. But… I invite you to take one step in the next few days.
Look up a senior living option you’ve been curious about. Call a handyman to fix those pesky projects. Toss those rusted paint cans. Set aside one box of paperwork to sort. Check in with a Realtor about the current market. Every action—no matter how small—builds momentum, and momentum builds confidence.
Let’s do this!
| 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, REALTOR®, 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.