We had too much stuff.

There was no way that all that had accumulated over 32 years of marriage, three kids, and a big home was going to fit into our retirement island home. We had been flirting with downsizing for a few years – now it was time to get serious.

A friend told me that downsizing would be liberating (it is) and that it would be time-consuming (also true). I was eager to begin, though some specifics did give me pause. One big one: What would I do with the wedding dresses that I had carted around for my entire married life? One dress belonged to my mother, who wore it when she married my father almost 70 years ago. The other is my own dress that I wore 33 years ago. My mom’s dress is loosely packed in a cardboard box (horrible storage, I know, especially for a Florida home) and mine is dry cleaned and sealed in a $100 box, which seemed like a fortune at that time. I’ve actually never even opened that box. Wouldn’t it be a hoot if it wasn’t even my dress?

Thankfully, my niece wanted her grandmother’s dress, so I packed it up and shipped it out before she could change her mind. I am happy that the dress is with family and its destiny is now in her hands.

Down to one wedding dress, someone told me to sell it on eBay. Have you looked at the almost 10,000 pre-owned wedding dresses on eBay? A beautiful dress costs less than $100. A “vintage” dress (which is sometimes just a nice way to say outdated and old) is $10-50. Oh, and no one is buying them.

Which brings me to a few of my “aha moments” about downsizing:

Things are only worth what someone is willing to pay you.

People aren’t collecting like they used to and our children are not using china and crystal. My kids don’t want excess stuff to be responsible for. They are spending their money on experiences, not “stuff”, and I happen to think that’s outstanding!

If it means something to you, keep it.

No one is judging you. Well, at least until you die and they have to go through the mess you left… And then, who cares, right?

Be generous.

If a loved one wants an item, give it to them now unless you’re in love with it or are still using it. I’ve found that to be much more fulfilling than items sitting in a forgotten box.


If it means nothing to you, don’t waste your precious storage space on it.

One of my friends takes a picture of her stuff when she says goodbye to it. She eventually deletes the photos too.

Take a realistic look at your closets.

If you haven’t worn it in a year, you should probably get rid of it. Set out what you would pack if you were going on two separate month-long trips. One trip is in the summer and one is in the winter. If it doesn’t make the cut, you probably don’t like it enough to keep it.

Adjust your attitude about donating items.

You are donating it because someone else is able to use it NOT because there is something wrong with it or because you don’t like it. An added bonus is that your local charity is benefitting from your donation. Remember to get a tax receipt. The deduction isn’t much, but it all adds up!

Throw away those things that you are pretty sure no one will ever use.

Goodwill does not want your chipped mug or your Lily Pulitzer sweater with the bleach spot. C’mon! You really don’t even consider it usable/wearable. You will save time for the donation centers who sort and throw away unusable items if you are realistic in your giving.

NEVER pay for storage space!

Your used furniture is worth next-to-nothing. Sell the furniture on Craigslist. Have a garage sale. Use the money for a fantastic trip. Put the rent that you’d pay for a monthly storage space into a fund for next year’s vacation. The only exception to this would be our friends who sold almost everything and are living on their boat. They did keep a storage unit but still win the Outstanding Downsizing Award. Imagine fitting everything you own onto a boat! My husband dreams that we will do this one day. We shall see about that…

–   –   –

I’m a work in progress. I still have too much stuff. Everyone has a different twist on what’s important to them. Life events certainly play a part. I’ve lost loved ones. I’ve settled many estates and disposed of belongings, houses, and farms. One of my brothers lost his life and worldly possessions, including many family heirlooms and keepsakes, in a tragic house fire. Random stuff just doesn’t seem that important now. At the same time, the important – meaningful – things in my life seem priceless.

And if there’s a point to this rant, that’s it. We simply have to decide what is important enough to stay in our lives and what isn’t.

So if you’re contemplating your own moving to an island downsizing strategy and you’re deciding what’s important, remember to live a little. Take the trip. Buy the shoes (you’ve gone through your closet and made room for them, right?). And certainly, eat the cake. Always eat the cake.

My beautiful mom (left) & me (right)


Did you downsize before moving to your island? Was the experience liberating for you too?

Written By:

Current Rock of Residence:

Islamorada, Florida Keys

Island Girl Since:

Part time since 1984; Full time since 2016

Originally Hails From:

South Dakota, then Florida

Can you really live full time in the Keys? Cindy and her husband Lat are about to find out. After having a second home in the Keys for the past 20 years, they are now moving full time to Islamorada to begin a new stage in life – retirement!

While Lat is a 6th generation Floridian (how many of those do you know?!), Cindy grew up on a farm in South Dakota and has lived in Florida since they were married in 1984. They have always lived where shopping centers, malls, and entertainment were within a short drive. Their communities have been filled with people just like them with growing families and a lot of kid-driven activities. If that wasn’t enough, they had their own business and work took every minute of the time they had left.

Now, they’ve sold their business, their 3 sons are grown, and their beloved dog has died. They are now on their own! It’s a little scary but they’re looking forward to doing the things they always thought they’d love to do. And they’re going to see if they can do them on an island! To follow more of their adventures, check out Cindy’s blog, Tropical Life, Food and Fun.

Want to read more posts by this writer? Click here.

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