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Having Trouble Downsizing? These 3 Questions May Help You to Simplify and Move Forward

By Sara Hart October 11, 2022 Lifestyle

Simplifying, downsizing, decluttering… these topics seem to be very popular. Why is this such an issue for so many people?

When I went through a major downsizing several years ago, one of the things I learned was that I needed a very small percentage of the things that I had accumulated over the years.

This is absolutely not to say that it was easy to sell, donate and throw out piles and piles of things that had been – and in many cases still were – important to me.

As I’ve explained in my book, The Upside of Downsizing: Getting to Enough, that sorting and disposing process was very painful at times; however, now that I’m on the other side of it, I realize how little I actually need in order to feel perfectly satisfied – to feel as if I have just enough.

Do We Own More Than We Need?

Why do many of us keep piling in possessions way beyond the point of need? Why do we cram more and more things into closets, drawers, garages, basements and attics?

And, when all that gets full to the bursting point, why do we rent an external storage unit for which we pay not an insignificant amount of money every month?

Each of us will have our own answer for that. I invite you to spend some time with these questions if you’re one of the many of us who have accumulated way more stuff than we need.

As I’ve talked to people about downsizing and simplifying, some version of the following story seems to be fairly common:

Jane, a composite of many people who told me their story, grew up with parents who had lived through the great depression, and so were very frugal. As a child, Jane remembers having very few (by today’s standards) clothes and three pairs of shoes: Sunday shoes, play shoes and school shoes.

Every year, she and her sister each received three Christmas presents from Santa. One usually was either something for school (a new book bag), underwear or pajamas. She had one much loved doll whose stuffing was falling out.

She and her sister shared a wagon. And since everyone around Jane lived pretty much the same way, she was satisfied most of the time.

Does Technology Impact Our Purchasing Habits?

Over the decades, our world has changed significantly. Perhaps one of the most significant changes is the impact of television and the Internet. We now have ready access to images of how people live in places very far from us.

We see poverty, of course, but we also watch nightly sitcoms where seemingly average people are living in ideal apartments in New York or Paris or London.

We are flooded with ads for all the things we can buy that will make us beautiful, successful, desirable, sexy, younger… all we have to do is buy that thing. And we have ready access to fairly inexpensive things in a burgeoning number of megastores that are close by.

So, in the middle of all this is Jane, who grew up with three pairs of shoes, and now often can afford to buy many pairs of shoes at any number of outlet stores or with one quick click of the key at Amazon and have them delivered in two days.

We simply have lost track of what is enough.

This story, or some variation of it, may help explain the current situation for Jane, but what is at the heart of this? For those like Jane, there are two causes: 1) our tendency to compare ourselves with others and/or with an idealized self and 2) our fear of not having enough or of being without.

Each of these can be explained from the story of Jane above. Jane grew up comparing herself with those in her immediate environment, not with those thousands of miles away who were living very different lives than she was.

Additionally, she was not hourly being inundated with information about all the things she could buy that would make her ‘better’.

In Jane’s case, she also may have heard stories her parents told about not having enough or of having to go without. Today, she remembers very well a childhood where there was significantly less than what she has gradually become comfortable with and used to.

What Is Our Particular Story?

This is Jane’s story. Yours may be very different. I’ve heard dozens of explanations for why stuff seems to accumulate in our homes. What’s yours?

If, over the years, you have amassed far more than you need and can reasonably use on any kind of a regular basis, why do you think that is? Are you comparing yourself to others that may have much more than you do? Do you have trouble making decisions?

Do you have an image of yourself that seems more desirable than the current image you have of yourself? Did you experience significant loss in your childhood?

Are you afraid of not having enough or of running out of things you need to keep yourself comfortable? Is comfortable enough or is there more that you’re striving for?

If you’re starting to feel as if it may be time to begin downsizing your home, now or in the near future, these are some questions you can begin asking yourself so when the time comes, you’re ready to face the difficult feelings that may arise.

And, if downsizing doesn’t seem to be in the near future for you, it still is an excellent time to think about these questions and begin to get rid of unused things and stop acquiring new ones unless something is realty necessary.

You may find this process challenging, or even painful, so consider providing yourself with some extra support. Ask a non-judgmental friend to help you by sitting with you and asking you what’s important as you reflect on the issue. Or consider hiring a coach like myself to help you.

You can do it! Good luck!

Let’s Have a Conversation:

Have you started the process of downsizing yet? Are you even considering it? What’s the first thing you would get rid of, if you were to start downsizing your stuff? Please let us know in the comments below.

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I see several questions there within this article . . . Specially, which are the six to which the title refers?


I paid a lot of money to an organizer to help me a few years ago and I am still depressed about it. I felt like my whole life was being deleted. I’ve moved a few things back but feel I spent so much I don’t want to undo everything. I use Asian ingredients almost every day so why are they stored so high up that I need a stool? I’m still waiting for the lighter feeling, especially in te kitchen.


I’m not an organizer, so keep that in mind… This organizer might not have been the right person for you. I have a friend who’s a huge pack rat and I’ve helped her downsize and pack before three moves. This was a long process each time. I had to gently suggest what might need to go, listen, understand what held extreme sentimental value for her and what she wasn’t able to let go of for whatever reason, then move on to what was next. Much was purged, but much also remained. This continued on with each move until her stuff became more manageable. She had to do this in her own time. As for organizing, that too, has to work for the person involved. In your case, I would suggest that you gradually move things to a better location, but try to continue the idea of being organized. This isn’t money wasted. It’s all about discovering what works best for you. And only you can decide this.

Connie Troupe

Downsizing actually makes your whole outlook on life feel lighter. Try it, you’ll see and feel better.

The Author

Sara Hart is a business owner, speaker, author and coach. Her project, the Sign of Enough, is designed to help us answer the question, “How will I know when I have enough?” with a focus on the emotional side of downsizing, not the practical. Please visit here https://signofenough.com/blog/

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