Today I want to talk about a recent Wall Street Journal article titled, “Meet the Army of Staffers Who Manage the Mansions of the Ultrarich.” The article outlines how owning a luxury property is not about peace and quiet—it is about managing a private enterprise. The ultrarich hire full-time chefs, housekeepers, landscapers, tech specialists, estate managers, and even interior designers to keep everything running smoothly.

But here is where we shift the lens—back to you, the real retiree.

Many people approaching retirement decide to finally buy the home they have always wanted. It might be bigger, fancier, newer—or just filled with potential. But what they do not always consider is this: a big house is a small business, and retirement is not the best time to start managing a complex operation.

You do not have a chief of staff or a personal assistant. You have you. And maybe a part-time lawn guy or a cleaning service. But nobody is syncing calendars, coordinating vendors, or supervising repairs. So when something breaks—and it will—you are back on the phone, hunting down estimates and waiting for callbacks.

And here is the part most people overlook: even if you have the money, you may not have the energy.


Every room in your home is a to-do list. Every feature—a responsibility. And as we age, those responsibilities multiply faster than our desire to deal with them. What once felt like a rewarding project can quickly turn into overwhelming noise. I have seen it time and time again—people begin letting things go. First the gutters. Then the bushes. Then the light bulbs. Eventually, the flowers become fake, and the charm gives way to clutter.

And let us not forget the physical risk. One missed step on a ladder, one slip on wet tile, and you could be in rehab for months—or worse. You cannot buy back time, and you cannot afford unnecessary injuries. Ask yourself: is your home serving you—or are you serving it?

Simplifying is not giving up. It is getting smart. It is about taking control while you still can.


So here is my advice:

1. Be honest about what you can handle. A large home may be affordable, but that does not make it sustainable.
2. Streamline your surroundings. Smaller, efficient, well-maintained spaces bring peace, not pressure.
3. Designate a point person. Do not hire ten people—hire one who can oversee them when needed.
4. Plan for a hands-off future. Your home should be livable without your constant supervision.
5. Redefine the dream. The best retirement home is one that serves you—not one you serve.

Remember, you are not supposed to mimic the mansion crowd. They have staff. You have freedom—if you protect it. Downsizing is not failure. It is clarity. It is wisdom. It is the beginning of a new, better chapter.

So the next time you walk through your house and feel overwhelmed, ask yourself:

Are you living in your dream home—or managing your nightmare?