When It’s Time to Make a Change, What’s Next? Where Do I Go?
In December, I wrote about my friend Jackie. This is part two of her story, still unfolding in real time. I wish I could tell you everything turned out smoothly, but I can’t. Like many life transitions, this one has been layered, emotional, and far more complicated than anyone expected.
After years of thinking about it, Jackie made the move to Merrill Gardens. Leaving her home of 35 years was no small decision, but the stairs had become too much for her. I constantly worried about her falling. She lived alone and rarely had visitors. Something had to change.
Still, choosing a senior community meant more than a new address. It meant being surrounded by people after a lifetime of independence and solitude. Jackie is a bit of a loner, so this was going to take adjustment.
The move itself was stressful, but the real hurdle came after the boxes arrived. Unpacking became overwhelming. Finding a place for everything felt impossible to her — and she would not accept help, not even with putting away a single plate, because then she “wouldn’t know where it was.” Five months later, she still isn’t settled.
Both her financial planner — who had recently moved his own mother into a facility — and I offered professional organizers. She refused.
Then, about a month ago, Jackie fell.
She landed in the ER at a Kaiser Permanente. After a short stay, she was sent back to her apartment, though it was clear she couldn’t safely manage on her own. Getting to the bathroom, managing medications, arranging meals — all of it was too much. Somehow, she ended up back in the ER again. I’m still unclear on the details, but it seemed like the only way to trigger the next level of care.
Kaiser transferred her to an assisted living facility where she remained mostly bedridden. I’m her friend, not family or an official advocate, but I could see things weren’t right. I asked a nurse about physical therapy. “She’s getting it daily,” they told me. Jackie said she wasn’t. It became hard to know what was accurate and what wasn’t.
Jackie has since returned to her independent living community — but she is no longer independent. She needs assistance now. And this is where we are today: facing the reality of care needs, resistance to help, and the very real concern about cost.
I’m sharing this to help you prepare for what may lie ahead.
We plan for college. We plan vacations. We make lists for holiday meals. But do we truly plan for aging? For the day errands become exhausting? When driving feels unsafe? When managing medications gets confusing?
Ask yourself:
Will I keep my car?
How will I get to the bank?
Who will pick up prescriptions?
How will I get to doctor appointments?
Who will help with taxes, bills, laundry, and meals?
Do loved ones know my passwords and how to access medical information?
The list goes on. Tasks that once felt simple can quickly become overwhelming. Often, these transitions happen suddenly. A fall. An illness. A moment that changes everything. Please start the conversation now, while you’re healthy and clear-minded. It’s one of the greatest gifts you can give your family and yourself. A lifetime of memories, belongings, and decisions doesn’t sort itself out in a crisis.
Just as we use professionals to plan travel or manage finances, there are caregivers, advocates, organizers, and senior service experts ready to help with this stage of life. Planning is the key to making an emotional transition as smooth as possible. It’s never too early to begin. And one day, you’ll be grateful you did.
Debbi.DiMaggio@corcoranicon.com • DiMaggioBettaGroup.co • 510.414.6777 • DebbiDiMaggio.com





