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How to Know If Downsizing Is the Right Thing to Do

By Jennifer Thompson November 24, 2023 Lifestyle

Richard and Jane Brown decided it was time to downsize and sold their four-bedroom home in the suburbs. And moved into a new two-bedroom condominium. In their 60s and still active, they chose this condominium for its amenities. It was two blocks from the ocean.

No more mowing lawns, less house maintenance, more time for golf, and travel. But, within two years of moving into their condominium, they sold it. It was way too small. And their neighbors complained about the noise when the grandchildren came over.

The Browns’ believed they had downsized too soon and too much. They sold the condominium and purchased a townhome. They gave up the proximity to the ocean for more space. This time their grandchildren were free to stay over as long as they wanted to. There was even a yard.

Richard took up membership at a gym close by to make up for the lack of amenities at their townhome. They told me this time they had reached a happy medium.

So, how do you know it’s time to downsize?

When Your Vision for the Future No Longer Aligns with Your Current Home

What’s your vision for the next 10 to 20 years of your life? What are you hoping to achieve in this stage of your life? More travel? More time with grandkids? Part-time work? Returning to school to pursue a new passion?

Before you decide to downsize, you should consider how your current home fits into your vision for the next 10 years.

And don’t forget that homes have an emotional pull. They hold memories of the children growing up, of your happy (or not so happy) times with your spouse. How do you view your home? Is it your castle? An anchor? A soft place to land or a place to lay your head?

While we may all value family, how we want it to show up in our lives may be different. Will you play a significant role in the lives of your grandchildren? Do you need extra space to have them in for a sleepover?

Knowing what your core values are is essential when it comes to downsizing.

For some, the idea of moving is very daunting. Especially if they have accumulated years of “stuff.” But you need to realize that we will all need to move at some point… or be moved.

When You Can No Longer Manage

Many of you managed to maintain a large family home for 40 years. But now you are finding it challenging to keep up with the lawn and repairs around the house. If that is the case, it may be time to move.

Would you be able to manage if your partner were no longer able to help you keep up with maintaining the place? Consider your finances and your physical abilities.

Downsizing to Access Equity in Your Home

The first 10 to 20 years of retirement is when you are most active. Downsizing will free up equity from your house to use in other ways.

Use this cash to achieve some of the goals you’ve put off for years. Or to pay for escalating health care costs.

Needs and priorities may have changed. Accept that there will be trade-offs in downsizing. For instance, you may need to move closer to a health care provider.

Reasons Not to Downsize

You may decide against downsizing if you need the space to accommodate a wheelchair or two. Or if the community you’ve been living in for the past 40 years could be an integral part of your life.

If you are considering downsizing, start by asking yourself, “What would compel me to downsize?” This may shed some light on whether it’s time to downsize or not.

Let’s Have a Conversation:

Are you considering downsizing? Why? What has prompted the notion? What are your priorities at this time in your life? Are you in need of less space, more space, better location, or something else? Please share with our community!

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We have explored some of the over 55 communities in our area as the extras from fitness, to interesting classes and little to no exterior maintenance are very tempting. However put on full stops when we read the “small print” of the communities. So many rules, such as grandchildren could only swim in the pool on one day of the month, to controls over hours of visitors and everything from not allowing candles to mandated meeting attendance.
So once again, buyer beware! Read the very detailed print…and have a friend or even a lawyer review before you buy.


We downsized in our 50s almost 10 years ago. This was mainly because one room in our house was an office for our business, but working from home was becoming difficult as clients were contacting us out of hours knowing we were there all the time. We decided to rent an office in a serviced building.

The house we bought is on a small private gated estate, we moved there because the grounds and properties were kept maintained so no gardening to do, we also thought it would be secure as it’s walled off in a conservation area.

It has not been a happy move, a gated estate needs the right mix of people and many who moved in did not gel together. The residents who arrived first think they should have all their own way on decisions between us and the management company and have tried to turn it into a retirement village. Other properties have been rented out, one is to a family with teenagers but it’s not a suitable development for kids and this has caused problems (we’ve had teenage friends climbing over the gates to get in and breaking the mechanism). Another property has been turned over to short term letting which is another headache and at one point there was an antisocial tenant renting a flat who had to be removed.

We moved overseas for work reasons and now keep it as a holiday home but my plan is to sell on retirement. I never want to live on a gated estate again, it feels too much like being hemmed in.


This has been on my mind lately. I just turned 62 and my husband will be 65 next month. We are living in my father’s home from long ago, where he added on rooms and levels. Lots of up & downs (lots of sets of stairs) all over the property and so much accumulation of “stuff”. I like the area very much (quiet and in the woods), but it is far away from resources which requires 35-40 minutes to drive every time I need something. Realizing that this will not be my forever home. Great article to ponder….

The Author

Jennifer Thompson worked as a financial advisor for over 20 years before starting her own consulting business. She can be reached at

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