stack of boxes waiting to be sorted

Chronic disorganization case study: Jason’s story

“Want to give me the tour?” I asked as Jason stood in front of me, shifting his weight from one foot to the other. I’d seen photographs of his house already and we’d talked about his organizing goals but I could see how stressful it was for him to finally let someone into his space. He’d taken a while to open the door and we were standing in his front hallway, surrounded by piles of clutter that lined the walls as far as I could see.

The two bedroom ranch was on a quiet cul-de-sac and although it was a beautiful, sunny day, all the shades were pulled firmly down. Jason wasn’t interested in giving the neighborhood rumor mill any more fodder than it had already gotten from the collection of random items scattered outside his house.

As Jason showed me round, we talked about his dreams for the space. He wanted to be able to work in his home office, to set up a dining room, and to “tidy up” the spare room, which he wasn’t comfortable showing me right then. 

Jason clearly regretted the state of affairs in his home. He got overwhelmed whenever he thought about trying to change things. We’d been emailing back and forth for some weeks now and I was happy he’d finally felt comfortable enough to interview me in person. 

He’d let the clutter go for years but now he’d received an ultimatum from his partner. She was adamant that he “clean up the mess” before she would even start to think about merging their households. They’d tried to work on it together but Jason had quickly realized it was going to be like teaching a spouse to drive – better to hire a professional and save a relationship.

READ MORE >>> Living with a packrat

On my way out, he asked if I was willing to see the garage. It sounded like an afterthought but I quickly understood it was the main reason Jason was considering working with me. He didn’t really mind the clutter in the house but he’d just bought a new car and was determined to find room for it in his garage. 

He led me out to the front of the house and slowly raised the garage door. The garage was densely packed, with randomly stacked boxes from floor to ceiling filling the entire space. A layer of dust covered every box. He smiled apologetically and told me he’d been keeping all his hobby materials here. They needed “a bit of sorting” to be really useful, he said. 

And so our journey began. I arrived every other week and Jason and I went through everything, box by box. We worked in three-hour sessions. Just long enough to see a difference, just short enough for Jason to be able to tolerate the process. He knew I wasn’t going to make him throw out anything he didn’t want to, and he knew he wanted to fit his car inside that garage. We evaluated each item based on that end goal. 

We were lucky that Jason’s timeline wasn’t set in stone. He wanted it done “soon” but he there were no external deadlines bearing down on him. 

He was also fortunate that his partner was willing to give him the time he needed to get this done. Although in her mind, it was just a matter of taking a couple of long weekends and sending 90% of the items to Goodwill, she knew this strategy had been less than successful for Jason.

Jason and I knew that it was going to be a slower, steadier pace. I’d let him know about the research on hoarding disorder, which repeatedly confirms that hurried clean outs are highly traumatic and inevitably result in the re-accumulation of even more items.

We spent many a session going through boxes and sorting Jason’s things into categories.  Without a system to keep things organized, Jason was never confident about what he had. He knew he had a lot of orange extension cords but when they’d all been spread out throughout the garage, he hadn’t been able to picture just how many there were. So he’d often picked up new cords on sale, wanting to make sure he had enough.

READ MORE >>> How to declutter and organize

Once the categories narrowed from “in the garage” to “for the workbench” and “bird feeder supplies”, he could update his mental map and feel more confident he’d be able to find things. This cut down on the flow of new items into his space and meant that he felt more and more confident decluttering and letting things go.

Each session focused on making sure the space we’d already cleared was kept organized. Jason made strenuous efforts to avoid setting anything down on the patches of clear concrete we’d uncovered and so the garage project moved forward.

His decision making muscle strengthened as he got the practice of deciding over and over again, evaluating each item to see if it still served him. He sent me away after each session with a car full of donations, always finding it easier to release something if he knew where it was going.

We continued for months. He began to see progress and to believe that the changes were going to stick. We figured out a strategy for him to persuade his sons to give up their rent free storage units in Dad’s garage. We talked about shopping as a hobby and finding ways to cut down on overspending. The garage was emptying out. Winter was coming and there was a good chance Jason’s dream of never having to scrape ice off his windshield on a bitterly cold morning again would become a reality. We continued to work carefully and at a pace that Jason felt comfortable with. 

READ MORE >>> What does chronically disorganized mean?

One day, the garage door was shuttered and there was a long wait at the front door after I knocked. At last, he threw the door open and invited me to come inside for a few minutes. He was dancing with excitement. He was committed to his decluttering and organizing project but the biggest smiles I usually saw were when I waved goodbye after packing his donations in my car.

Jason ushered me in and proudly showed me a clear dining room table. It was set for four, with place mats and napkins. He gestured towards the living room and I saw a couch and a recliner arranged around a coffee table. The carpet was spotless and there was a small stack of books on the coffee table. 

While we had been working together in the garage, he’d been working in the house by himself, practicing what we’d been doing together in our decluttering sessions. The papers were boxed up in his home office, ready for us to sort. “I put all the medical papers in these boxes and all the insurance papers are in here,” he told me proudly as he pointed towards the stacks of bankers’ boxes neatly arranged against the far wall of his office. Jason had created broad categories for his paperwork, just as he’d learned to do in the garage.

The furniture had been a windfall from a relative who was upgrading and he had decided to make what he called a “proper” front room. The contrast between that initial room, which had felt like a huge junk drawer (his words) and the well appointed space he’d created made me cry tears of joy and pride. Jason had learned to declutter. He had taken ownership of the process and was looking forward to inviting his partner over for dinner later that week.

As we returned to work on the garage, Jason was still beaming. He leaned over with a shy grin and asked if he’d shown me the basement yet? There were a few things down there we might want to take care of…

Key takeaways

#1 Find the right organizer for you

Jason waited years to call a professional organizer and when he did, he was cautious about showing them the whole space. He took the time to interview several organizers. This is the most important part of the decluttering process. If your goals and timeline don’t align with your organizer’s skill set and interests, the result is never going to be what you want. 

Jason made sure I had training and experience in working with people with significant amounts of clutter. With the best will in the world, an inexperienced organizer who doesn’t know how to pace a large decluttering project will falter, get overwhelmed and either try to rush you or lose interest in your project. 

READ MORE >>> What does chronically disorganized mean?

Jason tested my patience in the email dance before our consultation, not consciously or to be unkind but to make sure I was the kind of organizer who knows these things take time. If I’d given him a three week timeline to clear his house, that would have told him what sort of organizer I would be. If Jason had wanted to clear his place out within three weeks, and I’d told him my process is slow and steady, that would have told him to continue the search. It’s all about communicating clearly so everyone knows what the expectations are.

#2 Understand that organizing is an investment

Jason was willing to put time, energy and money into regular and ongoing decluttering sessions. He trusted that the slow and steady way would be the most productive and economical investment for him in the end.

#3 Know your learning style

Jason had read all the books, subscribed to the blogs and watched all the shows. He found none of it translated into action when it was just him and his stuff. To make lasting change, he was willing to try the apprenticeship model, where he worked side-by-side with a professional to learn a skill.

Please note: Jason is a composite character compiled from my experiences with clients who struggle with chronic disorganization. He’s none of my clients and he’s all of them.

Please also note: my policy is not to share before and after photographs of client projects. They only capture a moment in time, and I always want to know where all the stuff you decluttered went. Did it get pushed out of the camera’s view or was it truly dealt with?

by Lucy Kelly


  1. What an uplifting story about patience, learning, and change. I love the ways you supported Jason as he developed his decision-making, sorting, and decluttering skills. It also highlights the importance of finding an organizer that is the right fit. And in this case, Jason clearly did!

  2. Great post. You really “clicked” with Jason and worked hard to move towards his goal. The fact that he worked inside his home with the skills he learned from you must make you so proud. Yes, organizing is an investment, just like eating right, exercising and budgeting. But the investment pays off in the end.

  3. This is amazing! Your style is “goals”, as the kids say. Hahaha. You tell the story of what the possibilities are from our work so well!

  4. This is fantastic, Lucy! You’ve shown us a very clear picture of what it’s like to work with you and the results you can help your clients achieve.