If you have been following me, you may remember that the final quarter of 2025 had me selling my home and putting most of my belongings into storage. (You can refresh your memory here.) This past week I arranged to have everything taken out of storage and brought to a warehouse where Ruth Hartmann of Ruth’s Reselling will price everything in preparation for a gigantic sale beginning on March 5. I want to share the lessons I learned so you, too, can downsize joyfully if you (or someone you love) are preparing for a similar transition.
Work with a Trusted Professional
I hired another professional organizer to work with me.
Yes. It’s true.
I am an experienced professional organizer. I can be objective with someone else’s things, but I knew I would make faster progress if I had someone there with me — someone I trusted who would prompt me to think differently.
I hired Shanon McAulliffe from Purple Dragonfly Organizing. Shanon and I have worked together before. I trusted her completely.
If you want to downsize joyfully, don’t underestimate the value of having steady, compassionate support beside you.
Lessons from Three Experts on Hoarding Disorder
ICD (Institute for Challenging Disorganization) held a virtual three-hour event on Saturday, February 21st. Each of the three hoarding disorder experts gave a fabulous one-hour presentation. I kept some of their tips in mind as I opened boxes.
To be clear, I do not have hoarding behaviors. I, myself, am more of a minimalist. As a Certified Professional Organizer in Chronic Disorganization, I want to know as much as possible about hoarding behaviors. I believe everyone can benefit from insights shared by experts when preparing to downsize joyfully.
Congested Spaces
Dr. Mary E. Dozier used the word congested to describe spaces that are over-full.
When I think about the word congested, I picture a traffic jam or someone with a head cold and congested nasal passages. These images were incredibly helpful. I don’t want any part of my home to feel congested.
That visual alone helped me make clearer decisions.
Sit with the Discomfort
Dr. Randy O. Frost talked about letting go of our acquisitions. He shared videos from a patient named Marni describing her discomfort while parting with belongings.
He reminded us that almost everyone struggles with letting things go, especially items that tug at our heartstrings. Sitting with discomfort is part of the process. Notice how long the feeling lasts. Acknowledge it. Tell yourself it will pass.
I actively practiced this as Shanon and I unpacked boxes.
Some things were easy to set aside to sell. I didn’t want to keep any extra glasses or plates because I had already taken what I needed before my belongings went into storage.
Other items were much harder.
I had saved a baby blanket my Aunt Daphne made for my son, Alex. It is adorable and has the alphabet with cross-stitched animals. The thought of selling it was uncomfortable.
I told Shanon to put it in the “keep” pile. She gently asked, “What are you going to do with it?”
I paused. I realized it would simply sit on a shelf in a closet. I had no use for a baby blanket now.
And so, it went into the “sell” pile.
That moment was a turning point in my ability to truly downsize joyfully.
Motivation Is Something You Do
Dr. David Tolin spoke about Motivational Interviewing. He reminded us that motivation is not something you have, it’s something you do.
You can’t spur someone else into motivation. It must come from within.
As Shanon and I worked from 9–5 for two days and 9–12 on the third, there were moments when my energy flagged. I wasn’t sure we would finish opening, sorting, and labeling all the boxes.
During those moments, I questioned myself:
Why am I making this effort?
I thought about some of my clients (or their children) who have said they just want to be rid of everything without going through the sorting process.
My answer was simple: I want to live with the things I love and use and be happy to let go of the rest.
I was ready to downsize joyfully.
Tell the Stories
One of the greatest benefits of working with someone you trust is that you can tell the stories behind the items.
Not every object has a story. But when you come across one that does, sharing that story often makes it easier to let go.
Two large solid wood chests of drawers had belonged to my father. They became mine when my father died. These chests were used in my sons’ bedrooms. They traveled to Singapore, Connecticut, and finally Atlanta without a scratch.
Talking about my father and the journey of those pieces helped me acknowledge that they simply would not fit in my smaller home.
The memories remain even without the furniture.
Say “Thank You” and Good-Bye
Years ago, I remember Marie Kondo suggesting we thank our belongings for their service before letting them go. At the time, I didn’t give it much thought.
But as I walked through the warehouse one final time, I found myself softly saying “thank you” as I passed each table.
I am not sad. I am grateful.
I used and loved these items. Now they will benefit someone else.
When I left, I turned and said, “Good-bye.”
That simple act helped me downsize joyfully and I hope it will help you, too.
FAQs About How to Downsize Joyfully
1. What does it mean to downsize joyfully?
To downsize joyfully means making intentional decisions about what to keep and what to release without resentment, guilt, or regret. It’s about focusing on what you’re moving toward, not just what you’re giving up.
2. Is it normal to feel uncomfortable when letting things go?
Absolutely. Discomfort is part of the process. Acknowledge it. Sit with it. Notice that it passes. That awareness helps you move forward with clarity.
3. Do I need professional help to downsize?
Not always — but having a trusted professional can speed up the process and help you stay objective. Even professional organizers benefit from support when it’s their own belongings.
4. How do I let go of sentimental items?
Tell the story. Take a photograph. Keep one representative sample instead of the entire collection. Honor the memory, not just the object.
5. How do I know if I’m ready?
If you can answer the question, “Why do I want to make this change?” you may already be ready. Motivation is something you do — not something you wait to feel.
Ready to Downsize Joyfully?
If you are preparing for a move, helping a loved one transition, or simply ready to live with less congestion and more intention, I would be honored to support you.
You don’t have to do it alone.
Whether you need hands-on organizing, virtual coaching, or a steady sounding board while you make decisions, let’s talk.
Together, we can help you downsize joyfully.
I love the way you describe — and humanize — this process. We may be professional organizers, but we’re people with nostalgic hearts and deep emotions first, whether we’re minimalists or collectors. Of course, we pause at letting go of all that has filled our lives and spaces across the decades. But you are an exemplary role model and teacher, both for clients and for our colleagues.
The lessons you took from Drs. Frost, Dozier, and Tolin apply to all of us and not just thoughts with complicated relationships with our possessions. The fact that you availed yourself of Shannon shows that we all benefit from the same kind of support (in one way or another) that benefits our clients. Thanks for giving us a window into your experience. I know your memories will be with you forever, without you having to dust or polish the items in question.
Thanks so much, Julie
Wow, that is great, Diane! Good luck with the sale. I am a big fan of the saying thank you and good-bye. I like to do this with items that have special happy memories. Also, I like to shred or burn papers that bring negative emotions to me. Both work well. I have had clients shred documents and journals from workshops they were in, where they were working to let go of something tragic. It was very enlightening for them. And, they were grateful for the suggestion.
Thanks, Sabrina. It felt good to do that.
I’,m not looking forward to the time we have to leave this large apartment to go somewhere smaller, but I know it will happen eventually. Thank you for this inspiring post reminding me that I don’t have to keep something in order to keep the memories and feelings associated with it. It’s always better to focus on joy!
Thank you, Janet. It’s even easier if you can go through your things a little bit at a time.
Wow, Diane! Your story is so inspiring. I love how you took the learnings from ICD’s Virtual conference and used them for your personal downsizing process. By the way, it was a fantastic conference. Thank you for all the work you put into making it happen.
We spend our lives collecting things. But at a point, the time comes to depossess. Sometimes we are the ones making the choices. Other times, that process gets left for our loved ones. Yet how empowering to be the decider of your things. I love how you hired someone to help and recognized that it’s easier to have support. The added benefit was that you got to share your stories as you said your goodbyes to your belongings.
I can only imagine how much lighter you feel. Bravo and congratulations!
Thank you very much, Linda. I am very happy to be the one making these decisions. I’m also delighted to know you enjoyed the virtual conference!
Thank you for sharing your personal story.
I love the comment, “Dr. David Tolin spoke about Motivational Interviewing. He reminded us that motivation is not something you have, it’s something you do.”
You are an inspiration to many of us.
Thanks, Jonda
When I hear the word “congested” I think of my sinuses when I have a cold. Can you tell my family has had a “sickly” winter??
Anyway, I love that you invited someone else into the process. I love organizing, but decluttering alone is hard even for me, especially with the sentimental stuff. We saved it to relive the memory, which is always more fun when we have someone to share the memory with. I’m not yet at the downsizing moment, but I know it is coming. In fact, this year as I took down Christmas decorations, I was making mental notes about what I would really want to keep if I downsized, and which decorations I would be willing to donate.
I love the gentle question your organizer asked, “What will you do with it?” Why we keep things is an important question we need to be able to answer. So often we hold on “for the grandkids” or “because it came from so and so.” Years later, the thing we saved has deteriorated, when it could have served someone else. I would let go of much more if I were starting my adult life all over again.
Thank you for sharing this “joyful” perspective on the process. So often we feel it is all loss, but it truly isn’t. It’s so helpful to have a positive perspective and remember these decisions are to enhance the life we are living today.
Thanks, Seana – It’s so important to think about the current circumstances and have the things that support the way you are living now.