In the past eight years, I moved from a 2700-square-foot condo to a 900-square-foot home with a full basement to a 900-square-foot home with no basement to an 825-square-foot apartment.

So I know a little something about shedding possessions to fit into a smaller space. 

These days I live in my mother’s house. She died three years ago, after a full  life that lasted nearly 102 years. And now I’m cleaning out her abundant things, a task I foresee will take me into next year.

Downsizing, decluttering, purging….whatever you want to call it, getting rid of your own or your loved one’s possessions can be overwhelming.

Each time, I start the process with vigor and regret. Vigor, because I’m often facing a deadline, like the arrival of the moving van. Regret, because every time I make a decision to give something up, it takes an emotional toll.

Memories come flooding back, of the day I bought something, or the person who gave it to me. In my mom’s case, picturing her in places where she wore one of her 60 pairs of shoes, which she stored in their original boxes, each shoe wrapped in tissue paper.

But I’ve also learned some valuable lessons from experts who do this for a living. I’m sharing them here in hopes you can avoid some of the angst I’ve gone though.

See the thing, not the person

This is a critical requirement, says Shari Robards, a personal organizer based in Chelsea, Mich. The process of getting rid of the artifacts of a life—even if it’s your life—is “such an emotional thing,” she says.

When she begins working with clients, Robards encourages them to talk about where they are in life, and their goals for accomplishing a purge.

But she often runs into roadblocks when she helps someone clear out the home of a parent who has gone to a nursing home, or recently passed away.

She often has clients, she says, who will look at an object and say “Oh, that was my mom’s” in such a melancholy tone that she ends up gently saying: “Do you look at it and see your mom, or do you look at it and see a thing?’”

Take it in steps

Robards says she doesn’t force her clients to part with anything they feel is precious. One of her tactics is work in multiple sessions, rather than try to get everything done in one swoop.

“Everybody says they’re ready to do it, but there’s a limit. Sometimes, only within a couple of hours, emotionally they can’t handle any more,” Robards says.

She knows the feeling, having recently moved.

“You feel like you’re ripping your arm off, at some point,” she says. “Deciding is exhausting.”

Meet your new friends

A key tactic for organizers is to help clients set limits on what they can keep.

“If you go into a project knowing that you can only keep X number of things, or enough of one item to fill a box, it becomes a lot easier,” says Chloe Longstreet, an experienced organizer based in southern New Hampshire.

“Labels and boxes and baskets can be your friends,” she says, although she admits “Although you can get to a point where you hoard these things as well.”

“Learning to downsize is a process that you aren’t going to master overnight.”
Chloe Longstreet
personal organizer

If you’re moving from a larger place to a smaller one, Longstreet says it’s important to know just how much space you’ll have and pack only what will fit. Even the most streamlined people can still have issues, however. 

“There are people who have downsized to live in tiny homes or RVs who say they are still figuring out what to downsize years after making their move,” she says.

In other words: “Learning to downsize is a process that you aren’t going to master overnight.”

Ask yourself: will you use it?

In 2016, Marie Kondo made a splash with her book, The Life-Changing Magic of Tidying Up, and her famous de-cluttering advice, “Does it bring me joy?”

Robards isn’t crazy about that criteria.

“If you have 50 things from your mom, do they all give you joy?” she says. “Or, are you just putting them in a box? When are you going to look at them?”

She believes it is smarter to see where your parents’ things fit into your lifestyle. And you can do that with your wardrobe, too.

“If you have 50 things from your mom, do they all bring you joy?”
Shari Robards
personal organizer

Jacobs tells clients to look at their laundry basket and dry cleaning pile, and figure out what they say about the way they currently live.

Do you like to dress up for work? Do you dress glamorously to go out? Have you abandoned business attire for a casual look? Is your life now spent in leggings and tunics?

There’s no point in keeping a closet full of suits and ball gowns if you wear them once a year. Select a few that you particularly love, and which fit, and sell or donate the rest, Robards says.

Take photos of any you will particularly miss, she adds.

Choose between sell and donate

These days, there are many ways to make money off your own things, or items from your parents that you no longer want.

You can call in an estimator, who will look over an estate and give you one price for everything they haul away. You can approach local consignment shops, who will subtract their cut, then pay you for whatever sells (many now ask for photos before they will accept your items).

You can sell items on used clothing sites such as ThredUp, and sites for used household goods, such as EBTH: Everything But The House, which bills itself as an online estate sale

You can hold your own garage sale, which happens to be one of my favorite ways to clear things out. For the past decade or so, I’ve held two sales a year, one in the spring and one in the fall. I accept cash, checks, PayPal and credit cards via Swipe, and note that in the Craigslist ad.

It’s important to be realistic about how much you can make, because people want rock-bottom prices. One of my tips is to think about what you’d pay if you were shopping at a garage sale. Also, consider special prices to get rid of multiple items.

“There is truth to life being easier with less things.”
Chloe Longstreet
personal organizer

I sort small things like lipsticks (yes, people buy cosmetics) and hotel shampoo bottles into bins, and charge 25 cents each, or five for $1. That gives kids something to buy. I also mark everything half off during the final hour of the sale. You can read more of my garage sale tips here.

All that will take some time, and it still means you will be making decisions about what stays and what goes.

After all that, you still might not make that much money. Some of my garage sales have netted hundreds of dollars; others only about $75 for a full Saturday’s work.

It might simply be easier to shed, and there are countless charities who will accept boxes and bags of your used items. One place I’ve used is Donate Stuff, an especially good place to send household linens (make sure it’s all clean).

Remember the point

Longstreet and Robards agree that downsizing has one main goal: to make your life simpler.

“There is truth to life being easier with less things,” Longstreet says. “It will be an adjustment at first, but you will be much happier.”

Adds Robards: “It’s almost like drama to have a lot of things. We don’t need drama in our lives, right?”

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