Alison Kero Says Clutter Is a Decision Problem.

For anyone who has read the books, watched the videos and bought another bin, and found that nothing stuck.

One client lived in a four-bedroom apartment and used the smallest, darkest bedroom in it. The room could barely hold a single bed, and the bed was so covered with belongings that she could barely fit on it. The larger bedrooms were brighter and had bay windows, and they weren’t being used the way they could have been.

“On paper, the solution might have looked obvious,” says the organizer who worked with her. “Move the stuff. Clear the room. Use the bigger bedroom. But that’s not where we started.”

The pattern isn’t hers alone. In a 2020 study of 290 US office workers, researchers at the University of New Mexico and DePaul University found that indecision was part of how heavy workloads turned into cluttered desks.

Alison Kero, Founder of From Clutter to Confidence, has been a professional organizer since 2004 and now coaches people online, from Myrtle Beach, South Carolina, to get organized and stay organized. Her work starts with the decision, not the room. “People rarely keep things simply because they don’t know how to organize,” she says. “If organization were just a matter of knowing the right system, most of us would have figured it out by now.”

The people she most wants to reach are those who have watched the short organizing videos, read the books and tried on their own, and found that nothing stuck. “They may feel as though they’re failing at organizing,” she says, “but the exact opposite is true.” In her view, it’s the system that has been failing them. She has put the argument in two lines: “Maybe you don’t have an organizing problem. Maybe you have a decision problem.”

Why Another Bin Rarely Helps

There are two things, Alison says, that most people don’t consider when they get organized. The first is order. “If you don’t declutter first, you’re just moving your stuff around hoping that a new storage container or storage space will make the difference,” she says. “It rarely will because usually the bigger issue is you have too much stuff you aren’t actually using.”

The second is feeling. “We hear a lot about keeping items with joy, but what rarely gets discussed is how hard it is to part with items that cause fear, shame, and guilt,” she says. “These emotions can cause you to freeze and stop your work. That’s what leads to indecision, the emotions no one ever counted on experiencing.”

The cost of that freeze isn’t only physical. She has written that “those unresolved decisions don’t just take up physical space. They take up mental space, too.” Research points the same way. A 2025 survey of 501 adults in the Journal of Environmental Psychology found that people who rated their homes as more cluttered reported more negative feelings and lower mental well-being and life satisfaction, though the effect was modest.

It’s a conclusion she reached standing in other people’s homes.

What You See From Inside the Room

“I’ve stood in people’s homes and watched what happens when they are asked to decide whether something stays or goes,” Alison says. “I’ve watched someone pick up an object and immediately tell me why they can’t get rid of it. Sometimes the reason makes perfect sense. Sometimes even the person saying it knows it doesn’t.”

From inside the room, she says, you see what a productivity system can’t always capture: the box of things from a parent who has passed away, the clothes from a version of someone they used to be, the gifts someone feels guilty getting rid of, and “the expensive item they bought because they were convinced they would eventually become the person who used it.”

A filing system or the one-year rule can be useful, she says. “But none of them can automatically answer the question: ‘What does this item mean to you?’” she says. “That’s where the real work often begins.”

That is where she started with the client in the four-bedroom apartment. Rather than moving everything into the bigger bedroom, they worked on helping her make smarter decisions about what actually deserved space in her life. As she learned those skills, Alison says, she became more confident in her decisions, and the skills didn’t stay inside her own home. She shared what she had learned with her sister.

“The goal isn’t to create a perfect room. The goal is to create a person who feels more confident making decisions about their space.”

Alison Kero, Founder, From Clutter to Confidence

“That’s the difference I see between simply organizing someone’s belongings and teaching someone how to organize,” she says.

Ten Years in Storage

Some clients, Alison says, let things go easily. Others have a history of trauma, grief or other tough emotions, and their belongings have become part of their identity, even when that identity is decades old.

One client had kept items she and her husband collected during their marriage in storage for ten years. They were put away as the couple moved into a new phase of life, and he passed away soon after. “She felt stuck with all of the unexpected emotions and it made the decision process that much more difficult,” Alison says. “There was a lot of anger and grief involved.” She had expected her children to help or to take some of the belongings, but they were grown, with belongings of their own.

“It took a lot of work to help her realize that it was okay to let go of the items,” Alison says. “Her memories of her family, her achievements, and her life with her husband were still there. The items being let go didn’t take anything away from that.”

Her approach is to go in expecting resistance, guilt, fear and shame, with tools and guidance ready, and to begin with the easier, less emotional items. By the time a client reaches the harder ones, they know the process. “You’ll then be able to truly use and enjoy the items you choose to keep,” she says.

What Should This Room Make Possible?

When someone stands in a room they’ve been avoiding for months, Alison doesn’t begin with where things will go. “Instead of asking: ‘How do we fit everything into this space?’ I often want people to consider: ‘What do you want this space to make possible?’” she says. Maybe a bedroom where you can actually rest. Maybe simply walking in without immediately feeling overwhelmed.

One client had big dreams of hosting dinner parties. Her living room barely held three people comfortably, yet her tiny kitchen held enough plates and glasses to host twenty. She was making her decisions for a distant future dream rather than her current reality, Alison says. Once they talked about what she needed now, she cleared space, and what she kept became easy to keep organized. It took one session, and she left, in Alison’s words, knowing her life at that moment “was pretty awesome, too.”

“The hardest part of organizing usually isn’t knowing where something goes. It’s deciding what deserves a place in the life you’re living now.”

Alison, Founder, From Clutter to Confidence

“The goal isn’t necessarily to have less,” she says. “You don’t need to want less. You need to make space for what you truly want.”

She doesn’t treat organization as a personality trait. “You aren’t either an organized person or a disorganized person. Organization is a skill. And skills can be learned.” Her own habit is a five-minute rule: when she doesn’t have the time or energy to tackle something fully, she does what she can in five minutes. “Small, consistent actions keep clutter from becoming overwhelming.”

Her favorite quote is a familiar one: “Insanity is doing the same thing over and over again and expecting different results.” “Often small changes can create those different results,” she says, “but you have to be willing to take a look at what isn’t working and find out why first.”

In People’s Homes Since 2004

Before she coached online, Alison ran Alison Kero Organizing, working from Rehoboth Beach, Delaware, between 2019 and 2023. The work was hands-on: decluttering, space planning, moves and downsizing for homes and offices. She worked with people who hoard, helping them learn healthy habits so they could take back control of their lives, health and homes. She also built online courses, among them one on packing up and preparing a home after someone passes.

She studied with Jack Canfield Success Coaching in 2009 and 2010, and co-authored Step Into Your Brilliant Purpose, released in March 2022, sharing tips on decluttering your home and life.

The person who most shaped how she works was a client. For more than ten years, Alison worked with a woman who ran her own business, and watched how she ran it. “She was kind, helpful, and great at what she did. But she also had high boundaries with her clients,” Alison says. The client encouraged her to keep going when things got hard. She has since passed away. “I learned a tremendous amount about myself and how to run a business thanks to her.”

Asked about a time things went wrong, she talks about the business itself. She learned, she says, that “people pleasing in this business is a one-way street to burning out really quickly.” When something goes wrong, she puts it as a choice: “You can either blame yourself for being human and making a mistake or be curious as to what worked and what didn’t so you can correct what went wrong and move forward.”

Where Alison Is Now

In July 2025, Alison started From Clutter to Confidence, an online coaching business created to help busy people identify what holds them back. As she puts it on her profile, “So many of us are making decisions based on fear, guilt, and shame.”

She has built it with several ways in. “I’m looking to grow and expand my business so that everyone who needs help can get it in some form or another,” she says. Free monthly events and a weekly newsletter are for people who want to learn more but aren’t ready to commit or don’t have the budget. Her coaching now runs in three- and six-month programs. She used to work with clients for six to twelve months, but, she says, she thinks people prefer faster results.

She is a graduate of the 12-week Milestone Circles program at the Nasdaq Entrepreneurial Center, which, she has written, gave her “clarity, community, and the tools to elevate my business with confidence.” As part of her milestone that quarter, she increased her access to capital and was featured on the Nasdaq Tower in Times Square. She is a member of the Entreprenista League, and she co-authored her most recent book, Boss Moves Only: 17 Women Who Did It Their Way and Changed the Game, which came out in August. She plans to write her own book next year.

Outside work, she loves to travel, and the goal on every trip is to bring back one or two items that are useful and that she’ll enjoy for the long term. “That way, I get the memories without the clutter.”

What comes next, in her words: “I’m taking what I’ve learned from decades of helping people declutter and turning it into a movement to help more people make space for the life they want.”

“You’re not just cleaning out a closet,” she has written. “You’re letting go of what no longer serves you so you can make room for who you’re becoming.”

Am I organizing this, or avoiding a decision? If you keep reorganizing the same closet, counter or pile of paperwork, the thing you’ve been putting off may be the decision about what deserves to stay.

What do I want this space to make possible? Rest, focus, a meal, or simply walking in the door without feeling overwhelmed.

What am I ready to let go of that no longer serves me? Asked this way, decluttering becomes about making room rather than losing something.

Does this support the life I’m living now? A home arranged around a distant dream can be hard to keep organized in the life you actually have.

What can I do in five minutes? Small, consistent actions keep clutter from becoming overwhelming.

From the Diary of Alison Kero

Alison Kero is a Myrtle Beach, South Carolina-based online home organizing coach and the Founder of From Clutter to Confidence.

“Making room for who you’re becoming.”

Editor’s Note

Executives Diary chose Alison Kero for an argument she has tested in other people’s homes since 2004: that clutter is a decision problem rather than an organizing one. What convinced the editors was the detail in her answers, from the bed in the smallest room of a four-bedroom apartment to a kitchen stocked for twenty in an apartment whose living room held three. She now teaches the skill behind those decisions online, to people who have tried the books and videos first.

Executives Diary, Editorial