Deering Rose Organizes Calm Out Of Chaos

Everyone’s life has ups and downs. Deering Rose’s has more highs and lows than most.

She was a Staples High School soccer star. She was a marketing expert, movie production assistant, sponsored snowboarder, world traveler and outdoor adventurer. Now a talented home organizer, she’s just opened a pop-up store specializing in estate sales.

Deering also survived a near-fatal automobile accident. She was addicted to crack. She was arrested for stealing money from a friend’s home.

Deering Rose

She speaks about her life — all of it; the good, the bad, and the very ugly — with candor and clarity. She wants people to know she is not the same person now she once was.

That’s not easy to do. Particularly in the town she grew up in, and where nearly everyone knows her.

Or thinks they do.

Deering’s roots run deep. Her mother moved here at 11, and graduated from the Bolton School in 1951. Generations of Westporters know Barbara Rose as the founder of the Sea Squirts summer program.

One of the first female soccer stars in town, Deering graduated from Staples in 1984 and headed to the University of North Carolina. The Tar Heels were just beginning their long dynasty in college women’s soccer. Deering felt overwhelmed. She moved to New York, lived with her father, and finished her degree in business and communications at NYU.

After working for a real estate development firm, then in theatrical advertising, Deering landed a job as a production assistant. Her films include “The Ambulance,” “Prince of Tides” and “For the Boys.”

A guy on a camera crew invited Deering to Vail. She’d never snowboarded. But within months she made Vail’s team, with sponsors like Burton.

At 28 she was in a horrific car crash. She lost her spleen, left kidney and half her pancreas; many of her facial bones were shattered.

It took 2 years to recover. In constant pain, she lived on morphine. Eventually Deering used a holistic approach to get off drugs. She opened an indoor golf facility in Vail.

When she was 35 she sold the business. With no idea what to do next, she set out to see the world. From Spain and Italy to Thailand and Australia, she had an unforgettable time. She hiked, waterskied and scuba dove.

Five days before returning to the US from New Zealand, she met a man who ran outdoor adventures. He asked her to help with a business plan. She stayed — and spent the next few months riding helicopters, jet boating and surfing all around the beautiful country.

Back in Vail in 2001, she dated someone who was “not a good person.” He introduced her to crack.

But she managed to function. Moving back to Westport 17 years ago, she got a job with a real estate firm. One October — “bored and lonely” — she met a man. Two months later, he moved in. Soon, she was pregnant.

He was verbally abusive. “I used that as an excuse to cover my feelings again,” Deering says.

She went out several times a week. She smoked a lot of crack. She thought she was fooling everyone.

When Deering’s son was 5, she started a home organizing business. She was a natural. But she used most of her income to party.

One day while high she walked into a friend’s kitchen, and stole money. A camera recorded the scene.

The friend asked for no jail time; she just wanted Deering to get better. She was put on probation; the arrest was erased the following year. But her name was all over the news.

“This was a friend I did a horrible injustice to,” Deering says. “I’ll never go back to the person I was before rehab. I’ll never leave my son again.”

Once she got clean, an organizing client asked if Deering had ever run an estate sale. No, she said — but she’d been to a few.

Her first one was very successful. Soon she moved into full service mode: helping people who were moving decide what to keep, sell, donate or dump; then arranging how to do it all.

Deering’s business boomed. She does multiple organizing jobs and estate sales each weekend. She ran the Cobb’s Mill sale this past winter.

She has 5 employees, and has branched out into helping people move into new homes, staging and decorating it while working with handymen, electricians and more.

“I’m blessed,” she says heartfully. “My clientele know my history has nothing to do with the person I am today. My family is behind me 100% in everything I do.”

Everything she does now includes that pop-up estate sale store. Located at 877 Post Road East — in the plaza between Sherwood Diner and Shearwater Coffee — it’s crammed with artwork, china, Steuben glass, Rolex watches, mirrors, furniture, household accessories, lamps, clothing, camping equipment, clocks,, jewelry, handbags, rugs and more, from 6 estates.

Deering Rose shows off a beautiful chest at her pop-up store.

It’s open from 10 a.m. to 4 p.m., Thursday through Sunday, this weekend and next. Whatever is unsold on June 26 will be auctioned off that day at 5 p.m.

One view of Deering Rose’s store …

The next day, Deering Rose will turn to her next project. In a life of so many ups and downs, she’s headed in only one direction now: the right one.

(Deering Rose’s business is called Chaos2Calm Home Editing: Organizing Your Chaos One Room at a Time. Email; call 203-604-7118.)

… and another.

11 responses to “Deering Rose Organizes Calm Out Of Chaos

  1. Cheryl McKenna

    I live a redemption story as much as the next guy but those handmade signs of “multi family estate sale “ on the post road ( and all over the place) are misleading and I think free advertising that our local retailers would be fined for. It’s a store and littering our beautiful town with neon – pink signs every week. Real families have a two day sale and remove their signs after the weekend…. thoughts?

  2. Dan Donovan

    I’m thankful for those pink signs. I saw one and headed to Cobbs Mill Inn a few months ago. I ran into my old friend Deering and found a really cool sign from the restaurant to give to my wife for Christmas because that is where we had our wedding reception 27 year ago.

  3. Betsy Phillips Kahn

    I JUST LOVE THIS STORY!!! yayyyy Deering!

    I met Deering RIGHT as Covid hit our town and I have to say- to All:
    I had a terrific experience with her! I furnished nearly an entire beach house from one of her tag sales and it was so incredibly well handled. They actually wrapped and delivered our things- so carefully!!!

    This is a difficult job and (in my opinion) she was top notch and I highly recommend her company.

    I wish you much success, Deering! And- I am so proud of you- that’s an amazing ‘redemption story!’

  4. Deering Rose

    Cheryl, I’m so sorry you do not like my bright pink signs. I only have procured a retail space as a pop up shop for the month of June. I am not a retailer. I have clients that were not able to have their sales in their homes for multiple reasons, I was given this opportunity graciously and jumped on it. It will be finished and closed after this coming weekend. I have been managing estate sales/moving sales for over 6 years now and have a following because of my pink neon signs. They are up in Ffld County almost every weekend throughout the year advertising clients sales. I hope to see you at one of them, maybe I have.

    • Cheryl McKenna

      Deering Thank you for the update . Seems to me true tag estate sales take place at the actual home. You were smart to jump on this opportunity as I doubt other real estate owners want this disingenuous advertising attached to a real retail space . I wish you luck and I hope this was taken in the spirit of our town and it’s real tag sale signs yours in the future included .

  5. Great story! I wish our family had known Deering after our mom passed a few years ago- it sounds like Deering would have handled our estate sale in a stellar fashion & really have been helpful : ) I wish you’d take consignments, Deering, because we may have a few things left lol!

  6. Melissa Augeri

    May temporary pink signs posted around Town by a local entrepreneur be Westport’s BIGGEST problem! Oh how I wish.
    Thanks for sharing another interesting story Dan.

  7. Deering Rose

    I know see my life in full- the good and the bad and a so grateful for it all. My life is a success story thanks to my family, my son, his father and most importantly me.

  8. Peter Noonan

    Thanks, Dan. Deering always was a piece of cake. So glad she’s doing well!

  9. Heather Traber

    Absolutely courageous to share this. Good to hear you are doing well Deering. Sending you my best.

  10. Tracy Flood

    I’ll take the pink signs any day – particularly having read her story. You go, girl. Those hand scrawled Build You Shed signs are not nearly as festive!