Jenny Bentley and Jennifer Dewis have a lot in common, beside their first names.
They moved to Westport on the same day in 2008. They met while dropping off their 3rd graders at Greens Farms Elementary School. (The girls became longtime friends.)
Both women were good at helping friends’ parents downsize their homes. As their organizational skills grew, their separate reputations spread.
Inevitably, they joined forces. Today, their business — 2Jens Organizing — thrives. Empty nesters themselves, they fill a great niche: taking the stress out of moving from a large house to a smaller one.
Jenny and Jennifer take on side tasks too with gusto, like bringing small items to Goodwill, calling auction houses and hanging art. They’ve been hired to organize young children’s rooms, too.

Jenny Bentley (left) and Jennifer Dewis take on many tasks with smiles.
But their bread and butter is the daunting task of helping older folks downsize.
The process begins with questions: What should I bring? What should I donate, and where? What can I throw out?
Well-meaning adult children cannot always help. Sometimes they hurt. They’re too close to the situation.
The Jens provide 2 sets of objective eyes. And years of experience in helping folks make plans, then carrying them out. (The plans, not the clients.)
“A lot of this is intuitive. We’re very good listeners,” Jenny says. “We consult. We advise. But we’re very respectful of people’s wishes.”
The women know it can be hard to part with memorabilia. Gently, they help sort through it. If there are 75 pieces of artwork from elementary school, perhaps 10 are enough to keep?
Much of that memorabilia is all over the place too: refrigerators, mantels, basements, attics. The Jens are geniuses at sorting it, putting it in bins, and labeling it.

Setting up a new, well-organized space.
Moving can be a fraught experience. Clients invite Jenny and Jennifer into their personal space. But they don’t want to feel criticized or judged.
“Whatever works for them is fine,” Jenny says. She leaves out the second part: Even if we don’t like it ourselves.
What they do is largely “problem-solving,” she adds. “We have independent eyes, we come up with a game plan, we communicate it with them, and then we work on the timing of everything.”
Once a client has moved into a new home, the Jens are there. They’ll organize, say, a kitchen. They bring their expertise, but stop often to ask: Does this work for you?
A recent client (though probably gratis) was Jenny’s mother, Nina Bentley.
A noted assemblage artist, she did not want to part with anything in her garage. So the 2 Jens emptied, swept and vacuumed it, then put everything back in an orderly way.
Now her tools, paints and skulls (!) are organized. “It doesn’t look Instagram-perfect, but that’s the reality of how an artist work,” Nina’s daughter says.

A 2 Jens garage: before and after.
Some of the kitchens and laundry rooms they work on do look tidy. But not every room.
“Not every client wants then,” Jennifer explains. “They want to live their lives in a way that works for them.”
The women’s expertise comes from their own lives. Both women have moved often. They’ve set up their own homes, and helped their 6 children (combined) move into new bedrooms, dorm rooms and apartments.
Deciding what to sell or donate — or whether to have an estate sale, or send items to consignment — is challening.
“Clients can be overwhelmed,” says Jenny. “We have a lot of patience, and a deft touch to make them feel at ease, every step of the way.”
The women charge by the hour. Clients can stop the clock any time, and not feel locked into a contract.
However, Jenny notes, “jobs tend to get bigger as we go. Once we get started, people realize they need more things done.”
Downsizing is never easy. There’s a lot of stuff in those closets, basements and attics.
The 2 Jens are ready to help make sense — and well-organized, clearly labeled bins — of it.
(For more information on 2Jens Organizing, click here.)
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Can one actually make a living doing this and pay property taxes in Westport? I mean how much can you charge for doing this?
I’m sure they’re carrying a lot of insurance! What would happen if they accidentally broke a $100,000 dollar object?