How to Destroy the Clutter in Your Life and Reclaim Your Freedom

An unconventional plan for achieving freedom from possessions, freedom from employment, and freedom from mediocrity

Photo by Rob Bye on Unsplash

Let me tell you a story.

In some ways it’s an embarrassing story because it shows just how much of a mess I am and just how little of a complete handle I have on life.

In other ways it’s a redemptive story, because it shows that I’m making progress.

I guess it starts with a dresser. The dresser itself wasn’t a problem, but it represents the problem.

We got it for free when some friends had moved. Free dresser! Who would say no to that? We already had a dresser that my wife and I used to share, but now we had too many clothes and needed more storage space.

It kind of made our bedroom look cluttered and cramped, because even though there was technically room for it, there wasn’t really any room for it.

But the price was right and it solved a storage problem for us so it’s a win right?

Not too long ago my wife and I became frustrated with how hard of a time we were having keeping the house clean. Maintaining a clean house is no easy feat with two young children, but we noticed it had been getting harder.

It used to be the case that the house would gradually get more messy until we decided to clean it and then would be spotless for a day. Recently it has been that our inspired moments of cleaning have only been able to move the needle to “less messy.”

What’s going on here?

Are we not trying hard enough? Do we need a better system?

The answer to those two question might be yes, but the more I thought about it, the more I realized that there was a root cause that was even deeper: we own way too much stuff.

What’s crazy is that it’s not just us, it’s everyone. When I started to purge all our possessions, I started telling people what I was doing. People at work. People at church. They all said roughly the same thing: “I know, it’s amazing how much stuff just accumulates.” Many of them admitted that they needed to start throwing stuff out too.

The Endowment Effect

One of the problems is a natural human weakness known as the endowment effect. This is where we tend to value things that we own more highly than if we didn’t own them.

One way this has been demonstrated in experiments is buy giving people a coffee mug and then asking them if they want to trade it for a chocolate bar. The bar and the mug are of equal value, but very few people are willing to trade.

Maybe people just value mugs more than chocolate? Not so fast, the people given chocolate refuse to trade it in for a coffee mug. Everyone sticks with the first thing they are given.

This means that I valued the dresser too highly just because I owned it. I valued the clothes that were in it too highly just because I owned them.

The Sunk Cost Fallacy

Imagine this situation: you’re going to see a movie that costs $10, but you realize that you’ve just lost a $10 bill. Would you still see the movie? Most people would.

But now imagine this, you didn’t lose the $10, but in between buying the ticket and handing it over, you lose the ticket. Would you go back and buy another one?

This time most people wouldn’t.

The situations are exactly the same. You have a choice between being down $20 and seeing a movie or being down $10 without seeing a movie, yet according to Nobel winner Daniel Kahneman in his book Thinking, Fast and Slow, 88% of people would see the movie if they lost the $10, but only 46% of people would see it if they lost the ticket.

The two situations are the same, but they don’t feel the same. In the first example you can mentally assign the lost $10 bill to a general ledger of lost cash. It has nothing to do with the movie. In the second example, you’ve mentally assigned the $10 loss to the movie.

This is the same reason people don’t walk out of bad movies. Once you pay $10 for a movie, the money has been lost, but it doesn’t feel lost if you can still “get your money’s worth” by watching the movie.

The sunk cost fallacy doesn’t apply to my dresser, which was free, but it applies to many of the clothes that I didn’t wear that filled the dresser: “I can’t get rid of that, I paid good money for it.”

Loss Aversion

The endowment effect and the sunk cost fallacy are both part of the larger phenomenon of loss aversion.

People try to avoid losing more than they try to pursue winning.

I used to avoid competition- everything from sports to board games- because the fear of losing trumped the excitement of winning.

For a long time I was hesitant about putting my writing out into the world because I was more scared of losing than I was about missing an opportunity.

Our fear of loss is holding us back in so many ways.

In the earlier parts of the decade, millions of people were hooked on a game on Facebook called Farmville because they were scared of losing the fake farm they had built. I hear people would set alarms to wake up in the middle of the night to tend to their fake pastures.

My career has been stunted by my desire to avoid losses. I’ve always hated applying for jobs that I might not get. I’ve been afraid to start blogs that might fail.

And of course, my house has filled with clutter to avoid the slight discomfort of experiencing loss.

The Path Forward

Sooner or later, I had to confront the amazing wisdom of this quote from Jerzy Gregorek:

“Hard choices, easy life. Easy choices, hard life.”

So many people struggle to find the life that they want because the choices that lead to an easier life are the harder ones to make in the moment.

When it comes to the issue of loss aversion, locking in a loss will be momentarily uncomfortable no matter how you look at it, but the only way forward is to take some losses along the way.

In order for life to get better in the long run, it often needs to get more difficult in the short run.

More Difficult Questions

In Thinking, Fast and Slow, Daniel Kahneman points out that human beings have created a fascinating way of avoiding difficult questions: we substitute an easier question and answer that one.

In his wonderful book Essentialism, Greg McKeown lays out a perfect example of this that relates to the specific issue of de-cluttering:

Without a disciplined approach, it’s hard for a non-essentialist to de-clutter their closet. They ask questions like “is there a chance that I might wear this someday in the future?” The essentialist asks more disciplined, tough questions such as “Do I love this?” “Do I look great in it?” “Do I wear it often?”

The easier question leaves you stuck with stuff that you are too scared to get rid of. The more disciplined, but also more difficult questions are the ones that get you the results that you should be looking for.

He also gives a fantastic question to help you avoid the sunk cost fallacy: “if I didn’t already own this, how much would I pay to acquire it?”

If the answer to that question is that you would pay next to nothing, you should be willing to sell it for next to nothing. If you wouldn’t pay for it at all, you should throw it away or donate it.

Some other disciplined questions when it comes to de-cluttering come from the minimalists:

  • The 90/90 rule: have you used it in the last 90 days, will you use it in the next 90? If no, get rid of it.
  • The 20/20 Rule for evaluating “just in case” items: Can you replace it for less than $20 less than 20 minutes from where you are? If so, get rid of it.

Getting Rid of the Dresser

As I began to get rid of all the clothes that I never wore, I began to notice that there really wasn’t much left to put in the dresser.

I had owned this dresser all this time just to hold clothes that I didn’t even need.

I took everything else out of it and we put it up for sale on Facebook marketplace. Two days later it was out of our house and had been replaced by a cool $50.

Based on the number of responses we got, we definitely could have gotten even more for it, but I don’t care. Our house is less cluttered, will be easier to clean going forward, and we are up $50. I’ll call that a win.

The dresser in question

It’s Not Just About Getting Rid of Stuff

There are several lessons beyond getting rid of stuff that come out of this experience, and they carry huge implications for living a good life.

1️⃣ “Stuff” is more likely to make you miserable than happy

There’s a bizarre thing that happens in developed countries where we try to pursue happiness by buying things.

We feel good initially, but the excitement of the purchase quickly wears off and we are right back where we started. Not only that, but we fall right back into the trap by turning around and buying something else.

I think one of the reasons why it’s so hard to learn from our mistakes in this area is because we never come to terms with the fact that we wasted our money. As long as we still have the worthless possession, it feels like we got something for our money.

Once the worthless things accumulate into clutter however, eventually you have to come to terms with the fact that not only have your purchases not made you happy, they are actively making you miserable.

The next time I am tempted to make a foolish purchase, I’m going to remind myself that after the initial excitement fades, the purchase is going to keep making my life worse until I throw it away. Why would I buy something where the most joy I get from it is throwing it away?

I’ve written before that a major key to achieve happiness through spending is to know when cutting back on your spending actually makes you happier:

Spending less and becoming happier is a huge win because it lets you pursue the worthy goal of financial independence with sacrifices that make life better not worse.

As Jim Collins has said:

Money can buy many things, but nothing more valuable than your freedom.

If you can save up 25x your yearly spending, you can be free from the need to earn an income.

When you are free from the control of your possessions and the need to buy things, the amount you can save goes up while the amount you need to save goes down.

Every dollar a year less that you spend is $25 dollars less that you need to save.

2️⃣ Experiences> “Stuff”

Another incredibly useful insight from the Minimalists is the 10/10 Theory:

How important is the stuff in your life?

Your material possessions — those things you’ve worked so hard for by slaving 40, 50, 60 hours a week to acquire — how much value do they actually add to your life?

We bet it’s less than you realize.

Here’s an exercise for you. Take a moment and write down your ten most expensive material possessions from the last decade. Things like your car, your house, your jewelry, your furniture, and any other material possessions you own or have owned in the last ten years. The big ticket items.

Next to that list, make another top ten list: ten things that add the most value to your life. This list might include experiences like catching a sunset with a loved one, watching your kid play baseball, eating dinner with your parents, etc.

Be honest with yourself when you’re making these lists: it’s likely that both lists share zero things in common.

This year my family took a trip to Galveston, Texas and stopped at New Orleans along the way. I’m going to remember that trip for a long time.

I don’t remember a single purchase from this year that I’m thrilled with, but I can already think of several that I regret.

When I think of my dreams for the future, they are focused on acquiring experiences, not stuff:

By the way, in that post I reference two trips to Europe that I took a decade ago. I’m still talking about them. How many things that I bought from those years do you think I’m still talking about 10 years later?

Of course, “experiences” is a broad term, and there’s one key type of meaningful experience I want to make sure I mention. That leads me to the next point:

3️⃣ Accomplishments are among the sweetest kinds of experiences

One of the biggest ways that loss aversion holds people back is through the fear of failure.

Better not start writing that book, you might not finish.

Better not start a YouTube channel, you might get no views.

Better not write down your goals, you might not achieve them.

Of course, the tricky thing about the voices of doubt is that they speak the truth: you might fail.

The thing that’s hard to understand in the beginning is that failure isn’t the opposite of success, it’s a step along the way.

We’ve been trained to think that success and failure are opposites, but that just isn’t true.

There’s a certain type of final, fatal failure that is a true opposite of success, but it’s more rare than you think.

The general way things work is that failures are the outward manifestation of learning, and they mean that success is imminent.

And success feels pretty good. You have to go through a heck of a dip to get there, but it’s definitely worth the effort.

This year I wrote and published my first book on Amazon Kindle. It’s a book about money called Personal Finance That Works For You: How to Build Wealth, Design Your Future, and Make Money While You Sleep.

Like most people, I’ve always wanted to write a book. Like most people, I’ve never done anything before now.

It feels good to have accomplished something difficult.

Don’t be afraid to fail your way into significant accomplishments.


I’m going to be getting rid of more stuff.

I’m going to try to buy less stuff.

I’m going to divert my money toward things that are more meaningful: freedom, giving, travelling, etc.

I’m going to actively fight my fear of failure by doing things that might not work.

The endowment effect, the sunk cost fallacy, and loss aversion are quietly sabotaging your life from the shadows. I shared my story in the hopes to shine a light on them so that you can free yourself from their tyranny.

One last thing…

A big shoutout to Gonzalo Ziadi. This post wouldn’t exist if I hadn’t been inspired by his excellent piece titled “I could live in a box…” I found myself sharing my story as a response and realized that it needed to become it’s own post.

“I could live in a box…” is an article that is definitely worth reading and Gonzalo is a writer that is definitely worth following:

Done settling for average. Now I have my sights set on awesome 😎 Get “The Ultimate Daily Checklist,” my free ebook on productivity:

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