Step 5: Save the Best—Toss the Rest

Meaning, keep one to represent many. Madere points out that there are some things that we're inclined to hang on to in bulk, when a sample might be more powerful. "Sometimes clients will say, 'I can't throw that out—it's a card my mother gave me!' But it might be a boring card signed 'M.' Instead, save a letter and toss that card,” says Madere. The same principle can help you winnow down a collection. Let's say you have a load of inherited teapots. Pick a favorite that you would most want to see on a shelf in your home.

Marisa Cohen, a writer who lives in New York City, cherished her children's baby clothes, as well as her own kicky urban–single-girl outfits. Clothes are sweetly painful proof that time waits for no one. Teeny babies become towering tweens. But Cohen had to learn to open her hand. "I've hung on to three things," she says. "The green T-shirt I was wearing the night I met my husband and the baby hats my daughters wore home from the hospital. I keep them in the bottom of the under-bed boxes where I store off-season clothes. So twice a year, when I'm switching from winter to summer or vice versa, I hold them, have a moment, then put them back."