Introduction: A Lesson from Grandpa’s Boxes

This is part of Stewie's Guide to Ruthlessly Declutter Your Clothes Today.

Hey there!

I come from a long line of packrats and entry-level hoarders. Not the extreme, reality-show kind—no crumbling walls, no dead animals under mountains of junk. But still, we’ve had our fair share of “Why are we keeping this?” moments that make you question family genetics.

Take my Grandpa Bill. The man held on to newspaper clippings. Not just a few here and there, but boxes of them. He saved articles from USA Today, Investors Business Daily, San Jose Mercury News, and every financial magazine he could get his hands on.

These boxes were everywhere—in the garage, under the stairs, in his tiny home office (which we all called “the cubby hole”). Eventually, they filled a shed.

Did he ever go back and read those clippings? No, of course not. Why would he? There was always more fresh financial news arriving the next day.

But everything changed in July 1996.

Grandpa and Grandma had finally retired and decided to move from California to Utah, but they couldn’t take everything with them. Those boxes of newspapers? They had to go. And I will never forget the look on my Grandpa’s face as my Dad loaded box after box onto a trailer headed for the city dump.

Grandpa shook his head, pointing at the mountain of paper, and muttered, “There’s a lot of good information in there.”

In the decades since, that moment stuck with me. Because isn’t that what we all do?

We hold onto things—not because we need them, not because they’re useful, but because we tell ourselves a story about them.

But what if “one day” never comes?

That moment—watching my Grandpa wrestle with the weight of things he never actually used—helped me fight my own impulses to keep everything. Like those boxes of computer parts I swore I’d turn into a supercomputer one day. Spoiler: I didn’t.

I started asking, “Why am I keeping this? No, but seriously… why?”

And when I first tackled decluttering my clothes, I had to face the same uncomfortable questions.

The Closet That Forced My Hand

At one point, my closet and dresser were overflowing. I was running out of space, faced with two choices:

  1. Buy another dresser.
  2. Get rid of the clothes I never wore.

Luckily (and with some gentle nudging from my wife), I chose decluttering.

It wasn’t easy, but fast-forward five years, and my closet is the one area I’ve managed to keep (mostly) clutter-free. And it feels amazing.

So much so, that if I ever invent a time machine, this would be the first book I’d hand my younger self.

But before we dive in, here’s a heads-up.

My Extreme Take on Decluttering Clothes

You’re not going to agree with some of what I’m about to say. That’s okay. Take what works, leave what doesn’t. But if you’re looking for permission to finally let go, consider this your sign.

Here’s what I believe:

  1. You should get rid of most of the clothes you never wear. Right now.
  2. It’s better to trash unwanted clothes today than to cling to things with the vague intention of mending, selling, or donating it “someday.”
  3. If you don’t declutter today, you won’t declutter tomorrow. Excuses have a way of following us into the future.

I also believe your situation is unique and not every idea will work for you. No one doling out advice on the Internet can tell you precisely what you should do.

But hey, you’re an adult, so use good judgment.

For example, you might keep more clothes if:

Or you might be even more ruthless with decluttering if:

Because here’s the thing…

Letting Go is Freedom

If you’ve ever stood in front of your closet feeling frustrated, overwhelmed, or guilty, I get it. I’ve been there.

But here’s what I’ve learned: life is better without the clutter.

Every unnecessary item you let go of lightens your load—physically, mentally, emotionally. It clears space for what actually serves you. It clears mental bandwidth for decisions that matter.

And it clears room for the person you are now—not the person you used to be, or the one you think you should become.

So open that closet. Take a deep breath. And start letting go.

Because today is always the best day to start fresh.

Final Thoughts: A Challenge for You

If this chapter spoke to you, I have a simple challenge.

Tonight, go into your closet and pull out five items you don’t wear. Put them in a bag. Tomorrow, donate, trash, or pass them on.

See how it feels.

I promise—it gets easier. And before you know it, you’ll be looking at a wardrobe that actually works for you, instead of one that weighs you down.

Are you ready?

Next steps…