Declutter and ‘Rightsize’ Your Life in 5 Easy Steps

Declutter and ‘Rightsize’ Your Life in 5 Easy Steps

As a 53-year-old divorcee and former TV news anchor, I took my fourth and final child to college last fall. This prompted a huge life decision: I decided to empty a five-bedroom family home in Cincinnati and move to a 1,200-square-foot apartment in downtown Chicago. Preparing to move into such a dramatically reduced living space made one thing clear — it was time to start decluttering my life.

Lauren Chesley
Lauren Chesley

It doesn’t matter if you are moving down the street or moving your whole life, getting ready for a new baby or responding to the lure of an empty nest and the excitement of city living, the art of getting organized offers newfound freedom. It is the gift of conscientiously picking and choosing the stuff that matters most.

Whether we call it decluttering, organizing or downsizing, it feels wonderful to get rid of “stuff.” We have somehow collected our kids’ stuff, our parents’ stuff, their parents’ stuff. Sometimes it’s just an accumulation of endless amounts of junk we hold onto — just in case we may “need” it one day.

The task is daunting. Letting go is hard. But how many high school papers do you really need to keep? How many pairs of shoes do you need that never really fit? If they just remind you of blisters, start sorting.

One drawer at a time, I found a system that actually works. It’s called the 5 Ps.

1. Plan

Know where you are going and be realistic. Get a good measuring tape. A 90-inch wall will not fit a 94-inch couch. Size up the kitchen cabinets. Do you need an eight-piece toaster? It takes up half the kitchen counter. Plan ahead. It makes all of the following steps so much easier.

2. Pile

Be prepared to make choices. Piles mean organization. First pile or label the “must-haves.” These are the irreplaceable things like family heirlooms, photographs, gifts from friends, your favorite funky red coat. Pile and choose.

Piles should include the “keep,” the “donate,” the “kids’ stuff they need to claim” and the “selling” pile.

3. Purge

This is where the heavy-duty garbage bags are a necessity. Throw it away (or recycle). We’re talking old papers, contents of junk drawers and boxes that haven’t been opened since your last move. If you think you will have a lot, Bagster is a dumpster-sized bag from Waste Management that comes with delivery and pick-up service. Don’t overthink it. Toss it and get it out of your house so you are not tempted to sift through it a second time in the middle of a sleepless night.


By now we should know what we are keeping, storing, pitching and donating. Be organized. Invest in good magic markers, tape that doesn’t get twisted, bubble wrap and sturdy boxes. With supplies in hand, be mindful when you label the box. Don’t just write “clothes.” Be specific. Write “winter sweaters, gloves, hats.” What exactly is in the box labeled “kitchen?” This is also a good place to enlist help from a professional organizer or downsizer. They are awesome at keeping you on task. Chances are if you’re paying someone for help you will stay much more focused and not wander onto Facebook.


There are too many homeless shelters, youth crisis centers, schools and organizations that are in great need. Clothes you don’t wear will delight someone else. Your old suit could help someone find a job. Your daughter’s old prom dress will be loved by another 18-year-old who would otherwise not have one. A conversation with charities you already support may uncover needs you didn’t even know about. Many charities regularly have trucks in your neighborhood and can pick up your clothes and small furniture and appliances. Zealous Good is a website that lets you post items you have to donate and then 300+ charities can look and respond based on their needs.

Be generous. Be creative. Be supportive.

Where Do I start?

Figuring out where to start can be daunting. After all, it may have taken years to accumulate all you have. “Start in the area of the home that doesn’t have as much sentimental connection, such as the garage, basement or bathroom,” says Mary Kay Buysse, executive director of the National Association of Senior Move Managers (NASMM). NASMM members specialize in moving older adults but have seen a recent increase in Baby Boomers downsizing and moving for more urban living. Some may even upsize to move into the home they have always dreamed of. College students moving out of state and busy professionals juggling careers and family are also among those who may enlist a professional to make a move manageable.

“Start with a sweep of your home,” Buysse says. “What is absolutely something that hasn’t been used in five years, or what doesn’t have a home?” If it’s not being used in your current home, chances are it won’t be missed in your new one. This is true whether you are moving into a new space that is larger, smaller or the same size as the one you are leaving.

It’s about “rightsizing,” says Terri Albert, owner and professional organizer at The Chicago Organizer. “Maybe you are just starting a family or are no longer raising kids, maybe your hobbies are changing,” Albert says. “It’s about having the right amount of possessions for the current space and life you are leading.”

Albert also recommends annual purges — before you are under the gun with a move. “Go through your filing cabinets every single year and get rid of one more year of tax information, travel brochures or things you can get online, manuals for items that you sold or replaced.”

And that mini-skirt you bought and never wore? Time to get over it and get rid of it.

Should You Sell or Donate?

As far as selling goes, it takes time. But that money does add up, especially if you have designer stuff. Luxury Garage Sale (a Best of 2016 winner) is a great option for consigning designer clothing, shoes and handbags, but you will have to wait for the paycheck. Designer Resale in Chicago will buy some items outright.

If your timeframe permits, take your time and sell your stuff to the best buyers. Art and antiques have value. For example, do the research on who is actually buying Wedgwood dishes or what the market is for sterling silver. See how much things are going for on eBay. Get an appraisal from an auction house or estate sale.

That said, limit your expectations on what your “stuff” is actually worth. “People usually think their stuff is way more valuable than it is,” Albert says. “There’s a glut of china and silver because people don’t want it because it can’t go into the dishwasher.”

A quick call to your accountant may also help you decide if it’s worth the time and energy to sell items or if you might better be served with a tax-deduction on your charitable donation.

When You Have to Have It, But There’s No Space

Unfortunately, sometimes there is simply not enough space, even for the most cherished items. This is where an experienced professional may help, Buysse says, because they have probably seen it before. How do you know if other family members will want something? Post photos of everything on a cloud-based platform so family members dispersed around the globe can have a chance to claim things before a move. How do you honor the memory of a collection that has been in the works for years? Buysse recalls a story of a client with a collection of 85 teapots. The favorite teapot was selected and then a beautiful poster was made of the other 84 to honor the memory without having to find a place for the rest. “The goal is to give the process the dignity it deserves.”

A Life Unencumbered

The bottom line is once we begin, it is incredible to see how much stuff we have accumulated and how much we can do without. Letting go allows us a clearer vision of new beginnings.

After all, once you clear away the clutter you can actually see what’s in the closet.


Have you recently “rightsized”? Share your tips in the comments below.

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