I've spent 15 years in women's closets.
I know that sounds weird, but stay with me. I own a consignment boutique in Vermont, and for 15 years, women have been bringing me their stuff. Their "pre-baby weight" jeans. Their "I paid way too much to get rid of this" handbags. The dresses that they haven't worn in ten years but somehow keep making the cut every time they clean out their closet.
And here's what I've figured out after all this time: your closet tells the truth about your life. Even when you won't.
The Confessions
The things women say when they're cleaning out their closets... it's never really about the clothes.
A woman pulls out a pair of jeans and sighs. "I keep thinking I'll lose the weight. But... it's probably time to just let them go."
Another one holds up a dress and says, "This is what I wore to my son's wedding." I ask, "When was that?" She goes, "Fifteen years ago."
Someone hands me a whole pile of blazers and silk blouses. "I used to wear this stuff to the office when I lived in Manhattan. But those days are over now."
And then there are the women who call or come in asking about the consignment process, and they get this overwhelmed look on their face and say, "I have SO much stuff."
That "so much stuff"? It's never really about the stuff.
Sound familiar?
The Mirror
Here's what I've learned from 15 years of these conversations:
We keep clothes that don't fit because we hope we'll change to match them.
We hold onto the skinny jeans thinking our body will shrink. We keep the corporate blazer thinking maybe we'll want that life again. We save the fancy dress for "someday" thinking someday is actually going to show up.
But here's what really got me—and this is the part that changed everything:
We do the exact same thing with our lives.
We hold onto roles that don't fit anymore. Commitments we've totally outgrown. Relationships that squeeze too tight. Versions of ourselves that are, honestly, two sizes too small for who we're becoming.
We keep adding. We keep squeezing. We keep hoping we'll somehow shrink to fit the life we built ten years ago.
And then we wonder why we can't breathe.
The 7 Categories
Over the years, I've noticed that everything in a closet falls into one of about seven categories. And these same seven categories show up in our lives too:
1. What you actually wear — the go-to pieces that work. In life: how you actually spend your time.
2. What you're holding onto "just in case" — the stuff you haven't touched in years. In life: the obligations you keep out of fear.
3. What doesn't fit anymore — the pre-baby jeans, the goal weight dress. In life: the job, relationship, or identity you've outgrown.
4. What you're saving for "someday" — the fancy dress with tags still on. In life: rest, joy, the hard conversation you keep putting off.
5. What represents who you used to be — the corporate wardrobe from a career you left. In life: the overachiever, the people-pleaser, the "always available" friend.
6. What you bought to fix something — retail therapy. In life: overworking, over-scheduling, scrolling, staying busy to avoid feeling.
7. What you're keeping to remember — the wedding dress, the graduation outfit. In life: traditions no one enjoys, relationships you maintain just to hold onto the past.
Start Here
This week, go stand in front of your closet. Not to organize it. Not to purge everything. Just to look.
Ask yourself:
- What am I holding onto that doesn't really fit anymore?
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What am I saving for some imaginary "someday"?
- What am I keeping out of guilt or fear or obligation?
- What would it feel like to actually let it go?
And if you're stuck—if it all just looks like stuff and you can't get any clarity—grab a friend. Someone you trust. Let them come in and ask you the questions. Because when you have to explain out loud why you're keeping something, you'll know if you're telling the truth—or just making a case.
Start with your closet. But don't stop there.
Listen to the full episode: YOUTUBE LINK
Download the free Closet-to-Life Audit workbook: LINK