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As a professional organizer, Cheryl Larson knows the draw of giving your home a big, dramatic overhaul. Clients overwhelmed by stuff come to her in the hopes that one good organizing session is all that stands between them and a clutter-free life. The dream is real: All you need is to clear out that jam-packed closet, haul 10 bags off to Goodwill and figure out where to put all of those odds and ends that have no home.

She also knows it’s not that simple. It’s one thing to get organized, and quite another to stay that way. That’s why some people have long-standing relationships with professional organizers, or in some cases hire them again and again.

“With one man, it took us four years of going every week to get him organized,” says Larson, whose company, <a href="https://cherylsorganizing.com/" target=_blank>Cheryl’s Organizing Concepts</a>, is based in D.C. and the Baltimore metro area. “He’s probably my biggest success story because he keeps it that way.”

It started with some window treatments. Before working with Larson, the client, who had been living alone since his wife died, hired an interior designer for some help, but there was just one problem: She couldn’t get around the piles of boxes to access the windows. The designer called in Larson, who could see right away that it was a huge job; the basement alone would take years to sort through.

“He had no idea what was down there,” Larson says. Much of the solution lay simply in digitizing his files and setting him up with personal finance software. Luckily, he was an enthusiastic learner. “He’s just so proud of how everything looks now,” she says.

Some people seem to naturally excel at maintaining systems and routines at home. For others, it’s a lifelong issue that even hiring a pro doesn’t fix. What sets these two groups apart? While it could be a simple matter of time and will, there may also be a deeper issue at play. For instance, <a href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8312593/" target=_blank>traumatic life experiences can create a tendency to hoard possessions</a>. And staying organized presents specific challenges for people who are <a href="https://my.clevelandclinic.org/health/symptoms/23154-neurodivergent" target=_blank>neurodivergent</a>. That includes the <a href="https://www.jmcp.org/doi/full/10.18553/jmcp.2021.21290" target=_blank>more than 8.7 million U.S. adults</a> who live with attention-deficit/hyperactivity disorder (ADHD). In any case, understanding the reasons behind your organization struggles can help illuminate solutions.

Larson likens getting organized to other major lifestyle changes, including healthy eating habits or even quitting smoking. Indeed, research shows that behavioral change can be frustratingly difficult. Most of our behavior is <a href="https://hbr.org/2021/02/what-does-it-really-take-to-build-a-new-habit" target=_blank>governed by habits</a> — actions that we take without really thinking about them. That includes habits at home, such as promptly recycling mail or putting your keys in the same place every day. When we’re not used to a routine, it can take a while to get to a point where behaviors are automatic. As psychologist Mark E. Bouton <a href="https://www.sciencedirect.com/science/article/abs/pii/S0091743514002102?via%3Dihub" target=_blank>wrote</a> in the journal Preventive Medicine, “changing behavior can be an inherently unstable and unsteady process; frequent lapses and relapse should be expected to occur.”

Yes, messy people can learn to be tidier. Here’s how.

All that change takes motivation, and Larson says she can tell when a client’s heart isn’t in it. Sometimes, that’s because a spouse or relative has pressured them into getting organized. “If you’ve decided on your own to make the change, you’re more likely to stick to it,” she says. That applies to everyone in the household. If a spouse or kids won’t get onboard, it’s going to be tough to keep it up.

One of Larson’s clients couldn’t get her three daughters to organize their rooms. Exasperated, she paired them with Larson, who could tell that the eldest, a teenager, had no interest in the project. Nonetheless, a few weeks later, a transformation seemed to have occurred: All three girls were keeping their rooms spic and span. The adults later discovered that the eldest had been paying the youngest to clean for her. As far as the mother was concerned, if it meant a tidy house, it worked for her. After all, a system is only effective if everyone follows it.

“One thing we do when working with a client is to check to make sure they are maintaining whatever we organized at the previous visit,” Larson says. “If not, we have to figure out why.”

While that family’s solution was a bit unorthodox, figuring out what motivates everyone is key. Some of Larson’s clients hire her on a recurring basis because they like the external accountability, like the woman who had her come four times per year. When Larson arrived, the house would look tidy already, but the client said it was only because she had scheduled the appointment.

When motivation is weak, a simpler system may help. For example, rather than attempting to alphabetize DVDs or sort clothes by color, it could be more realistic for some to just get everything on shelves or in bins and consider that a success. After all, continually feeling like you’re falling short can lead to avoidance, killing motivation: You might feel guilty, then distract yourself to feel better, then feel guilty again when the goal goes unaddressed. Recognizing negative self talk and practicing self compassion is the first step, says <a href="https://www.harmonicdivergence.com/about" target=_blank>Camil Aponte</a>, an ADHD coach.

Rather than trying to work yourself up to a big task, Aponte advises, set your timer for just five minutes to see what you can get done during that time. Starting with small tasks also allows you to rack up small wins to help you feel good. You could even write down each accomplishment as you go. (Some refer to this practice as a “ta-da” list because it is essentially the opposite of a “to do” list.)

No matter what, hiring a pro isn’t a cure-all. If you don’t follow the systems they teach, or if you keep bringing home more stuff than you have space for, you’ll be back to square one before long. Larson says her most successful clients follow the “one in, one out” rule: every time you bring something new into the home, you have to get rid of something else. That can be hard if you’re sentimental or wince at the thought of tossing your kid’s art in the recycling bin. Setting parameters, such as saving one item per month, can make doing so easier, Larson says.

The relationship between mental health and organization

Sometimes, the challenge goes beyond a simple lack of time or will. For instance, when someone seems to have an emotional attachment to everything they own or they shuffle things to another area, such as the garage, attic or basement, instead of getting rid of stuff. “That’s a big red flag,” says Tiffany Smith of <a href="https://www.simplyputorg.com/" target=_blank>Simply Put Organizing</a> in Indianapolis.

Occasionally, Smith refers clients to a mental health professional when she senses that they have a more complicated relationship with possessions. “Maybe they didn’t have a lot growing up, so they overcompensate, or maybe they lost things, or they lost people, and everything became emotionally attached to them in some way,” she says. “So yes, some people absolutely need deeper help.”

Others may have an especially hard time sticking to routines because of how their brains work. Aponte says creating novelty — or making tasks feel new or fresh — is crucial for maintaining motivation.

“If you have ADHD, things tend to lose their sparkle after a while,” Aponte says. Because she lives with ADHD and autism herself, she applies a personal lens to her advice. She helps clients add “sparkle” to tasks they don’t want to do, perhaps by buying attractive organizing products or playing fun background music. Most importantly, she says, don’t be too hard on yourself because that can lead to a vicious cycle of avoidance and guilt.

“Just say, ‘Wait, this is the way my brain works, but it’s not that I’m lazy,’” Aponte says.

<i>Annie Midori Atherton is a writer in Seattle who covers culture, lifestyle, business and parenting.</i>

Annie Midori Atherton

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Pro organizers say some people can’t stay tidy, even with help

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