Many people I work with have a really hard time letting go of “things” in their homes.

It comes down to making decisions about what to give away, clean out, donate, and get rid of versus what to keep. I’ve been thinking about how I can help you make those decisions.

Much of the problem has to do with our thoughts, so below are the three magical questions that help you to decide to keep or let go of an item.

I heard a mind-blowing quote from Joshua Becker, “If we keep everything, then nothing is special.”

Mmm… let that sink in for a moment.

We want to surround ourselves with special things, right? We want to surround ourselves and make space for things that are special, not just fill our space with a bunch of stuff – for many of us, too much stuff to be comfortable.

It’s the same as with people, right? We want to surround ourselves with special people – people who we aspire to be like, people that truly support us, or people that we’re helping. But not just fill all of our time with a bunch of people, especially people who are not a good influence in our lives, strangers, crowds, etc.

We can think of our stuff in the same way.

Negative thoughts

If we think about our stuff, some of the thoughts that we might be currently believing are:

  • Letting go is hard.
  • Letting go of stuff is hard.
  • Making decisions is hard.
  • I’m emotionally attached to my things.
  • I’m a sentimental person. So of course, because I’m a sentimental person, letting go of anything is hard.

I also hear this a lot.

  • There was that one thing that I let go of and I’ve regretted it ever since.

My gray slacks

I went through my closet a while back and donated several things. Later, I was looking for a pair of gray dress slacks that I had.

I went to look for them and they weren’t there. They weren’t in my closet. Then, I thought I must have donated them. At that moment, I regretted that decision so much.

Here is what was running through my mind when I couldn’t find them:

  • If I only had those pants, they would look good, of course, with everything.
  • Now I have nothing to wear because I don’t have those dress pants and they were just perfect.
  • I shouldn’t have let them go.
  • That was a terrible decision.

As I continued to look just a couple more places, I opened my cedar chest and there they were! I think I had put them there because I wanted my mom to tailor them.

I tried them on and guess what? They fit terribly! I would never choose to wear those gray slacks out of the house because they looked so bad. They were tight in all the wrong places. I ended up donating them.

Do you see what I did? I had made up this whole story, verbally beating myself up, thinking that I should have kept them.

That’s what happens so often. We let go of something and then we make up this story. It was a mistake. We should have kept it. That was a bad decision I made.

You might even use an experience like that as an excuse. If I let this go, it will be bad. I will regret it. 

I want to throw this out there…. We can CHANGE those thoughts! We don’t have to feel bad.

Thoughts that create abundance

What if we changed those negative thoughts to thoughts that create abundance? 

Here’s a great thought:

  • I always have everything I need.

I mean, we literally, almost every single one of us, always have what we need. Right? If you think about need. We have food, shelter, and clothing. Many of us probably have so much more than we need.

Here are more thoughts you could try:

  • I trust that I will have everything I need when I need it.
  • If I really need it, I trust that I will have it. I could borrow it, go buy it or ask a friend, but I will have everything I need when I need it.
  • I’m creating space in my life. I love that… I am creating space.
  • A decluttered, spacious home is what I really want most of all. If I keep thinking a decluttered and spacious home is what I really want most of all, then it will be easier to let things go.
  • I trust that I will find all the information I need on the internet.

Print some of these thoughts out and hang them up.

Keep practicing these thoughts.

Put a little reminder on your phone and keep practicing.

Three magical questions to ask yourself

With each item that you’re trying to make a decision about – whether to keep it or give it away – ask yourself these three questions. I’ll use a few real-life examples.

1. Is this item my favorite?

You’re going to pick something up and you’re going to say, Is this one my favorite?

If yes, of course, you keep it.

If no, go to the next question.

2. Will keeping this make my space feel de-cluttered and spacious?

While you are in that space, for example, your closet, ask yourself, Will keeping this item make my closet feel decluttered and spacious?

Or if you’re in your craft room, Will keeping this item make my craft area feel decluttered and spacious?

Or if you’re looking over your kitchen drawer, Will keeping this item make my kitchen drawer feel decluttered and spacious?

If the answer’s no, then let it go.

But let’s say you’re teetering in your decision – will keeping this make this area/place feel spacious – and you’re struggling to find an answer. Then go to the next question.

3. How will I be kind to myself if I let it go?

Think into the future and plan how you will be kind when you think back about letting it go.

An Example

Let me explain this with an example. Think of a clothing item – maybe a pair of jeans. That pair that you just love – your favorite pair. You pick them up, you’re holding them, and you ask, (1) Is this my favorite pair of jeans? You answer aloud, “Yep!” Okay. We know you’ll keep it.

Pick up another pair – maybe a pair that’s on the bottom of your pile. Hold it up and ask, “Is this my favorite?” Well, no, I haven’t worn this pair in three years. But I keep thinking that they’re going to work with something I have. Every time I pick them up, I never end up putting them on. Then you go to the next question.

(2) Will keeping this make my space feel decluttered and spacious? Will it make my closet shelf, my closet hanging rod, wherever you keep your jeans, feel decluttered and spacious? Really think about that. Imagine it being spacious. If I hang my jeans in my closet, I would imagine each pair spaced out by an inch hanging on the rod. If I stack my jeans, I imagine a perfect, even stack neatly folded on the shelf. However, you want to imagine a spacious feeling closet that you love.

Imagine – will keeping this pair help me feel that?

Not really. So maybe that’s enough to let it go or, if not, go to the next question. (3) How will I be kind to myself if I let this go?Quote graphic "If we keep everything, then nothing is special."

Maybe you’ll remember how brave you were for making a hard decision.

  • You’re going to come back to this moment and you’re going to say to yourself, I was doing my best. I was trying to declutter my closet.
  • At that moment, I hadn’t worn those jeans in three years and I decided to let them go.
  • You remember it. Put a timestamp on this moment so you remember your brave thoughts.

Another example

Pick something else. Let’s say, you go into your kitchen and you have a vegetable peeler. You pick it up. You ask yourself, (1) Is this my favorite vegetable peeler? No, actually this other one – because I have two – this other one with the black handle is my favorite.

Maybe that’s enough and you can let that one go or you go to the next question. (2) Will keeping it make me feel decluttered and spacious? Will it make this drawer, this space in my kitchen, feel decluttered and spacious?

No, every time I look in there, I grab the other one. I see this one, but it has a little bit of rust on it.

It’s not keeping it spacious, so then I can let it go. But if you still cannot let it go, then move to the next question. (3) How will I be kind to myself if I let it go?

Do you ever have that time when you think, My grandmother’s going to be over next week. I’m going to peel potatoes with her and we need two vegetable peelers. Or you think that maybe there will be a time with your child when you might need two peelers so that you can teach him to peel vegetables.

You have this glorious vision of peeling vegetables together. At that moment, you’re going to apply question #3. You are going to remember that you were creating space at the time, so you let that vegetable peeler go.

  • That was the best choice for me at that moment.
  • Right now, we’ll take turns using the vegetable peeler. We can talk and still enjoy this moment.
  • This actually gives me the time to cut the onions while she peels the potatoes.

Really think through how you’re going to be kind to yourself in the future if you begin thinking about how you got rid of the item.

I know it seems silly, but it’s super valuable.

More examples

Here’s another example. I came across an old cross-stitch that I had started 20 years ago.

I’m holding it and I start thinking about questions. (1) Is it my favorite? I mean, I haven’t done it in 20 years, so maybe that answers the question.

Maybe it’s a math paper that your child brought home. (1) Is it your favorite? I mean, really, is any math paper a favorite? That’s super helpful if the answer is no, but if you’re teetering, go to the second question. (2) Will keeping this make my space, my child’s memory bin, feel spacious and decluttered?

No. We cannot keep every math paper each child brings home. But, what if it’s a unique math paper? Maybe this child really struggled in math and this was the first ‘A’ that they got on a math paper. Then you get to decide to keep it.

If it’s not a special paper and you do choose to throw it away but then remember it and feel bad, ask, (3) how can you be kind to yourself later?

Prepare ahead of time for the obstacle – those negative thoughts creeping in.

The obstacle is your critical self saying, You shouldn’t have gotten rid of that.

Then your future self has a solution ready to share. It’s very beneficial.

Thoughts ready to go:

  • No, I remember that moment when I was being brave deciding to declutter.
  • I have five other important papers showing the hard work my daughter did to overcome her struggle in math. 
  • We were so proud of her when she overcame that struggle. I should text her and let her know how much I love her. 

Those are thoughts that make me feel at peace and calm. These thoughts bring relaxation to my tense shoulders. These preplanned phrases bring clarity and rest to my racing mind.


Use these three magical questions on each item as you decide what to keep and what to donate as you declutter and organize.

1. Is this my favorite?
2. Will keeping it make my specific space feel decluttered and spacious?
3. How will I be kind to myself later if I let it go right now?

If you have a specific item or area in your home you’re thinking about or even thoughts, like those negative thoughts above, that you’re struggling with, set up a FREE call with me. I’ll walk you through it.

The call is free. You’ll know at the end of that call what your next step is. We’ll get it figured out and you can get started on simplifying and organizing your life.

Have a great day.

Tracy Hoth