One of my favorite clients, Shirley, found herself at a crossroads. After the death of her husband, she came to a painful realization: the home filled with decades of memories could no longer be part of her future. What finally pushed her to act wasn’t a dramatic event, but a seemingly small one—paying $400 to have someone rake and remove leaves. Vulnerable at the time, the expense lingered with her, not because of the money alone, but because it symbolized how overwhelming homeownership had quietly become.

Most of us have an insurance plan. We have a financial plan. But how many of us have a housing plan?

Yes—a housing plan.

At my seminars, I’ve asked this question of hundreds of senior homeowners. Almost without exception, the response is the same: a blank stare. Yet housing is one of the most important aspects of our lives, and too often we leave it to chance. We wait for circumstances to dictate when and how we will make our next move. Unfortunately, circumstances can change quickly—through unexpected health challenges, mobility issues, or financial shifts.

This article addresses the often-emotional interactions between adult children and their parents when the time comes to sell a home that has held decades of memories. These observations are drawn from my experience guiding hundreds of families through this deeply personal process.

When I sit with senior homeowners who have lived in the same house for decades, I often hear the same quiet truth: leaving a home feels like losing a best friend. It stirs many of the same emotions—and just as deeply.

There are four primary reasons many seniors delay making the decision to move to a lifestyle that better supports their needs, health, and happiness.

There often comes a time in the lives of older adults when remaining in their longtime home is no longer the safest or wisest choice. Perhaps the stairs have become difficult—or impossible—to manage. Maybe the upkeep of the home feels overwhelming. Or health concerns have begun to interfere with daily living. Yet far too many seniors continue to live in homes that no longer support their physical, emotional, or practical needs.

Many of my clients tell me they feel overwhelmed and uncertain when deciding where to move and what life will look like in a new home. Most want to maintain their independence and privacy—and often hope for more opportunities to socialize than their current situation provides. Understanding the different senior housing options available can bring clarity and confidence to this important decision.

Below is an overview of the most common senior housing options available throughout the Greater Milwaukee metro area.

Living in Wisconsin offers natural beauty, changing seasons, and—at times—challenging weather. This past winter, followed by the heavy rains in June, has been especially concerning for many longtime homeowners. I’ve spoken with numerous seniors who worry about what winter ice may have done to their roof or walls, or what record rainfall may have caused in basements, window wells, or sewer systems. When these concerns are combined with uncertainty about today’s real estate market, it’s easy to feel overwhelmed and hesitant to even consider selling.

In my years of speaking with senior groups and their families, one theme comes up again and again: procrastination. Not because people don’t care, but because change feels uncomfortable—especially when it involves leaving a home filled with memories. Yet when it comes to one of the most important aspects of our lives—where we live—waiting for a “sign” can unintentionally lead us straight into crisis mode.

Lately I find myself doing a lot of reflecting. I suppose that’s natural as we get older and become more aware of how much time we have left. The truth is, there are regrets—plenty of them. But there are also so many wonderful moments too. Somehow, though, the regrets have a way of trying to steal the spotlight.

I began my journey helping seniors and their families about 35 years ago. It started when I gave my first talk at a senior community to a group of seniors and their families. My talk encompassed the emotional aspects of making a move from their long-time as touching on the overwhelming emotions experienced prior to making their decision to stay or move from their homes.

Anyone owning a home today is thrilled to see the incredible appreciation over the last 5 years. Just this year we have seen a 19% increase in home values! That can put a smile on your face but as we all know too well, what goes up must come down.

There are so many factors that play into a decision to a change of address, but the most significant is overcoming fear of change. I often hear from my clients that they know the time is coming to find a new home that fits who they are today, but just can’t go beyond that feeling of dread when entertaining the thought of moving.

There could be several reasons why homeowners have decided to stay put for the last 4 years.

The pandemic has certainly played a role in those deciding to wait for that perfect time to move. Are you one of those would-be sellers? If you are, here are some reasons based on my interviews with potential sellers:

Every new year I assemble a vision board with inspiring graphics and goals that transport me into the realm of possibility.  I know.  It’s an idealistic venture, but it’s my personal opportunity to reconfigure in a hopeful way.  And then there’s real estate. Each new real estate year brings some preparedness, but equal parts buckling up for total uncertainty. I once heard the saying, “if you can’t be good, be consistent.” Thus, 2023 is just another consistent year of riding the volatile market wave.  

The holidays are here and what is going through your mind right now? Are you anxious? Do you have unfounded fears that seep through your usually logical mind? Will family get along this year? Do you think you have changed in a way that makes you wonder how you will react when family gathers this year? Are you playing an old tape in your mind that is not who you are today? Does your current living situation reflect who you are both physically and mentally? What does the coming year mean to you? Is your current lifestyle a reflection of who you truly are today? Do you have a spouse or partner that has had health changes and assessing the future in both housing and needs?

No matter where you go or who you talk to, everyone has a different take on the future of our money and direction of home prices. Any homeowner today, especially long-term owner, has had the fortune of watching your home equity rise over the last 14 years. It seems like yesterday, but the financial crisis of 2008 is over a decade in a half in our past! Remember as you grew up your parents would always tell you how time speeds up as you age. Boy was that true!

Young people today find it hard to believe that interest rates reached a staggering number or almost 20% for a fixed rate 30-year mortgage. On top of that, the bank charged 3% of the mortgage amount upfront, just to have the privilege of securing that incredible debt. On a $350,000 mortgage, that would have been $10,500 in loan costs for that 20% 30-year fixed rate mortgage in 1981!

Inventory is at all time lows. Affordability is approaching historical highs based on home prices, interest rates, and competition amongst the large pool of potential young homeowners. That sounds good for anyone thinking about selling your long-time home and moving out of state to enjoy the fruits of a lifetime of work and saving.

Look, we all feel about 20-30 years younger mentally, but our true age is known by all body parts! You know what I mean. We make that turn, that move that we have done for most of our lives and ouch! Where did that come from. Next thing we know it’s rehab. My point is that when thinking about where we live, our homes should match who we TRULY are TODAY.