Downsizing Guru Marie Kondo has got it wrong. She says you should touch everything you own and get rid of anything that doesn’t bring you joy. But for us folks of a certain age, the “joy-ploy” doesn’t always work.

I recently hired a professional estate sale company, and although I got rid of some of my stuff, it wasn’t painless. I discovered a lot about my feelings and attachment to things. As I spoke with friends, it confirmed the difficulty folks were having with the overload of items cluttering their lives, even if they had no intention of moving. And if they were moving, it seemed overwhelming to sort through a lifetime of both trash and treasures.

One of my friends broke out in a rash trying to purge, and another swears she broke her ankle because she was so distracted by the thought of cleaning out.

Why is it so hard for us to downsize? And why is getting rid of stuff a bit different at 50+ than at 30? Each of us has our reasons for the difficulty. Some that seem universal are…

#1. Attachment to the past. Interior designer and sculptor Julia Hyman calls stuff that you’ve been keeping since childhood “Mom and Pop.” Here is a picture of my actual Mom and Pop.

And my “Mom and Pop” stuff.

The bookcase still smells of the liquor my folks kept on the bottom shelf more than 60 years ago. They served the good stuff only for company. My Dad was a Democratic politician in Brooklyn. Abraham Beame, who eventually became Mayor of New York City, and Brooklyn Borough President Stanley Steingut and other political figures often visited us. My Mom would offer knishes, homemade by her sister, my Aunt Rose.

My Dad poured the Scotch. The men spoke in whispers and made deals that could affect the lives of thousands of Brooklynites. That cabinet witnessed family history and political history. How can I call Habitat for Humanity for a pickup just because it doesn’t fit in with my decor?

This is my Dad’s desk. I have no idea how a 300-pound man could be comfortable working there, but I was tiny enough to hide under the desk hole when I was sad or playing hide and seek.

I would never buy either of these pieces today. But I have nothing else of my Dad’s. He died when I was 11. No, Marie Kondo, it does not cause me joy to touch them—but it would cause me sorrow to dump them.

#2. Money does matter. It’s tough to swallow that the value of your “expensive” things has plummeted. But tastes change…and so do you. For example, I’ll come out of the politically correct closet and talk about furs. I wore furs in the venal 1990s when I was practicing law. Remember, Greed is Good? Lawyers, particularly female corporate lawyers, were judged by how prosperous they looked. Furs were in. I “looked” prosperous.

For moral reasons, I have not worn furs for decades. But that $20,000 lynx coat is hard to merely discard at $75 (although I did it). Eventually, I found companies like ReMinke that converts furs to teddy bears, pillows and more. I donated mine to Good Grief for children to take when they enter the child-grief program. It made me feel better.

No such luck with my no-longer-trendy brown furniture. The $1,600 bed I bought in 2000 can’t even be given away.

#3. The stuff is not yours. How many kids, sisters and cousins have left stuff in your house? How many times have you asked if they want it back and gotten a vague answer? How reluctant are you to dump other people’s stuff? Will they be hurt or angry if, after a millennium, you get rid of it? If you know how to get your children to take their stuff back, please drop me a line.

#4. You don’t want your stuff to be insulted. Look, no one wants your stuff, not even you. Still, you hate to think of your things as trash. Even organizations for Vietnam Vets and people with lupus can reject your stuff, although their reputation is they take anything. The driver will leave items because they are too big or they are not on the “willing to take list.” Surprisingly, this includes TVs over 19 inches.

Thrift shops are generous in accepting items but only if they have no stains, rips or tears. Things were rejected by the local club because the volunteers had no clue of the value of what I was bringing. It was quite embarrassing to hear, “No, we don’t take that kind of thing.” So be careful in your largesse.

#5. House sales are scary. In my latest house sale, things went reasonably well. I used a highly recommended firm that was sensitive to my feelings. I sold less than expected but not anything that I regret—except that in the excitement, they sold a vintage sweater valued on Etsy and eBay at $6,500 for $15. I showed the sales operator the information before the sale, but it never registered. Still, I did not make a fuss. I was grateful to have purged at least some items.Why not?

A wise man once said that our possessions possess us. I am valiantly trying to be finished with all that. My dearest wish is that my kids have nothing to throw out when I‘m gone. Ultimately, I agree with Kondo on one point—there is immense freedom and satisfaction in purging your stuff.

So, to help you, here are a few tips I learned along the way…

Don’t dump anything…instead give it away. Remember when President Clinton took a deduction for his underwear? It was allowed. You can take charitable deductions over several years, so don’t think that it’s useless to you if your current income is low.

Only give to a charity that gives you a receipt for your tax deduction with the charity’s IRS number. Make an inventory of your donations, including the current value of the item—your tax deduction is based on the value at the time of donation. Get an appraisal for things worth more than $500.

If you are planning to sell, categorize your stuff…

  • Items worthy of an auction sale or private collector
  • Items worthy of a consignment shop or dealer purchase
  • Items suitable for a house sale
  • Items to simply give away

Then choose your selling outlet…

Auctions. An auction house takes between 5% and 15% of the sale price. If you have a representative to help you, he/she may add 10% to that figure. If you set a reserve, you will get the stuff back if it does not sell, and you will have to pay the auction house a handling fee as well. You will also have to pay insurance, usually 0.5% to 1% of the estimated value of the items, and a shipping charge, unless you bring the stuff to auction yourself. The good news is that almost all of this is negotiable.

Selling apps. MaxSold, LetGo, eBay and higher-end sites/stores like The Real Real, Invaluable and many more are available if you have the time to sort, evaluate, post and wait for a buyer. With many of these sites, the attraction is that the buyer comes to your home and takes away the item. With the rural location of my home, I decided against these alternatives. I felt that the amount of travel the buyers would have to endure would make the auction unsuccessful. In addition, I wasn’t comfortable having total strangers come to my door. Of course, a house sale isn’t much better. But at least there is no chance of being alone in the house when strangers arrive. My best advice: If you have a private buyer coming, make sure that another person is with you at the appointed time for pick-up.

House Sale: Read the magazines that deal with the stuff you want to sell (collectibles art, antiques, etc.), and place ads in those magazines and newsletters. Use a local paper, or place an ad in the edition of a national magazine that goes only to your nearby zip codes. This will get you a discount on otherwise expensive ads. Even if you use a professional to help with the sale, you must know the value of every item yourself.

Consignment: You’ll get about 50% of the sale price, and it may take longer than an auction, but you’ll have greater control over the price, and a consignment store may take many items that no auction house will take.

For everything that remains, hold a downscaling party. Let friends and family take what they want as long as they pick up the delivery charge.

Finally…play the George Carlin monologue on “stuff.” Then give the album away.