Lemme guess, your trip back home over the holidays was restful and left you feeling like Mom and Dad don’t need your help at all. Not the case and you’ve found yourself needing to pack up more than decorations? We gotchu. We promised a part two on downsizing and like Santa on Christmas Eve, we’re here to deliver the goods.   

New here? Check out part one on how to actually talk with Mom before the boxes are broken out.

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🥳 Gray Monster celebrated its first birthday. Our editor reflected on it here.

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You survived the first conversation. No one got paint-canned in the face. Your mom might’ve side-eyed you, but the seed was planted. Now comes the hard part, actually doing it.

We spoke with our pals at Downsizable again and they shared that the biggest mistake families make is waiting until there’s a crisis — a death, a fall, or a home that suddenly needs to be sold yesterday. Grief and urgency are a brutal combination. You don’t want to make lasting decisions in the worst moments. If 2026 has you looking at helping Mom move somewhere safer and more manageable, we’re here to talk you through how. 

Where do you start?

Begin where it’s easy, on purpose. Don’t go for the garage. Don’t start with the primary bedroom. Start with the guest room. The JV team of belongings lives there: books no one reads, sheets from the ‘90’s, maybe a lava lamp. The point is to pick a space that feels emotionally neutral. And start small, think 20-minute work sessions with your Mom sitting nearby (mobility chair, snacks, pep talk optional). You’re clearing space and building stamina, hers and yours.

Build a weekly rhythm.

Best case? You live close enough to show up weekly and have the bandwidth to help. Even better? Make it the same night each week. Tuesday evenings. Saturday mornings. A predictable rhythm builds trust, momentum, and accountability. And if you can’t be there in person, consider hiring help. Downsizing professionals exist for a reason: time, logistics, emotional overload, sibling dynamics…pick one or all.

Pickups over piles.

Plan for donations before they overtake the house. Schedule a February pickup in January. Set a goal and stick to it. Designate a staging area. And know who takes what — Big Brothers Big Sisters, Vietnam Vets of America, local Buy Nothing groups. Got a sort-of helpful, but long-distant sibling? Tag them in for research and coordination. Kate and Blair from Downsizable made this handy guide they can work on while you pack. Pro tip: donate early and often. Mom feels better knowing her things are being used, not trashed. Everyone wins.

Let go of the guilt chair.

“I promised I’d take Mom’s rocking chair, but I don’t want to spend $1,000 to ship it cross-country.” Sound familiar? You’re not alone. The pressure to keep every hand-me-down isn’t just about legacy, it’s logistics too. If it’s not meaningful and manageable, it’s okay to let it go. Not all memories live in a Lazyboy.

Safety isn't an accusation.

Fall risks. Isolation. Stairs. The trick isn’t shaming Mom into leaving a house she loves, it’s about showing her what’s next. Tour the new place again. Focus on the wider hallways, better lighting, and new friends. Agency matters a lot, especially when it feels like everything else is changing. Help her choose what she can about her new digs. 

And if Mom still wants to age in place? Cool, with conditions. That means grab bars, first-floor living, decluttered stairs, and actual social plans. If you’re going to be the one that gets the call, a “stay here and hope for the best” approach isn’t a helpful plan for either of you. 

Now what?

Even without Kevin McCallister-style booby traps, downsizing can feel scary.

With the house packed up, and the dishes donated, Mom’s making the move. If you or a loved one can, be there. Bring coffee. Stay for dinner. It’s a life shift for everyone. Let her mourn what she left and look forward, together, at what’s ahead.

Helpful care-focused finds we’ve identified and researched so you don’t have to. 

TimeSlips, a non-profit founded by Anne Bastings, Emerita Professor of English at the University of Wisconsin Milwaukee, trains care facilities across the country to inspire and support caregivers in learning to unlock the meaning and joy in elder care through creative engagement. 

Understanding so much care happens at home, TimeSlips provides a  free course for family caregivers, designed for anyone caring for a loved one with dementia — helping spark connection without relying on memory.

You said it. This week’s submissions.

“Dad said thank you. He never says that. Taking it as a win!”

“Mom has taken to telling me all about her bowel movements...you gotta laugh! TMI.”

“Although difficult, I've had the sudden realization that I'm thankful for the opportunity to serve my parents.”

“Grandma agreed she acted like a toddler when asked to shower...we had a good laugh about it!”

“This past Christmas, my mom couldn't find her phone. We called it and realized she accidentally wrapped it.”