How to Let Go of Something You Feel Obligated to Keep

Birds symbolizing my real-life lesson in letting go.
Birds symbolizing my real-life lesson in letting go.

Quite some time ago, I interviewed Karen Young, the psychologist behind the mental health blog Hey Sigmund. I liked her site right away because A) the name and B) she writes truly helpful posts about depression, anxiety and mental wellness. Anyhow, one of the things she said really stuck with me:

Stop hanging on to what’s trying to let go of you.

I think she’s probably talking about stuff like a bad relationship (romantic, friendly, or with a toxic family member), a job that’s keeping you down, or really anything that’s causing emotional strife. But for whatever reason, these words brought to mind something I’d been struggling with for the last 12 years.

This story begins at UW-Madison, where I somehow earned a degree in journalism and mass communications without sacrificing my partying.

My parents were so proud.

During my sophomore year, I started dating a guy I’d met working at the newspaper. He wasn’t my type at all. A total hipster before hipsters were a thing, small enough to wear my jeans, and an art major. My parents disliked him, most of my friends thought he was weird (he was) and even I was often like what am I doing right now? To be fair, I don’t think many of his people thought much of me.

College is a time of curiosity. You can date a starving artist and a musician and a football player and whoever the hell you want. That is what college is all about: learning who you are as an adult. That and education, of course.

I dated art guy for about six months. He was nice, and we had fun for awhile, and then the relationship ran its course.

We broke up a week before my 21st birthday.

I did the breaking. When my birthday rolled around, he text me and asked if he could drop something off at my apartment. I said sure. A half an hour later, he showed up with this:

The infamous chair.
The infamous chair.

Yeah, so.

A month before The End, he’d started painting the chair for me as a surprise. It was supposed to be the two of us. He looked exactly like himself. I ended up looking like a mix of Mariah Carey and myself, and not in a good way. I was pretty shocked that he’d given it to me after the breakup, but I guess what else was he going to do with it?

Bewildered, I accepted the chair.

Since receiving The Chair, I’ve moved six times. I’ve dated people, I eventually got engaged and married. And The Chair has been there for all of it.

Do you drop off a piece of furniture with a painting of [sort of] your face at Goodwill? Or throw it away? Or what?! I just wasn’t sure. It felt weird to just get rid of it… like when you see people’s framed personal photos at a thrift store. Yet it also felt weird to have a chair with a painting of me and my ex-boyfriend sitting in the house I share with my husband.

As I write this, I see the ridiculousness of the scenario.

I should’ve gotten rid of the chair long ago. Instead, I bought a seat cushion for it from Ikea and stuck it in our guest bedroom.

It’s not that I was really attached to The Chair in an emotional way (except I did love showing it to people at dinner parties. A fantastic conversation starter!). I never truly liked the thing, though maybe I was attached the gesture? Nobody else has painted something with my face on it, and I sincerely doubt it will ever happen again. Maybe it’s like how Sharona feels every time she hears the song, “My Sharona.” I was once thought of as so awesome it inspired ART! I felt obligated to keep the damn thing.

A few months ago, as I was KonMari-ing my house, I happened upon The Chair.

It was then I realized it must go.

It gave me no joy whatsoever. It gave me the opposite of joy. And it really, really bothered the guy who I’d vowed to honor and respect ’til death do us part.

I considered repainting it, but quickly ruled out that idea. No matter what it ended up looking like, it would always remind me (and my husband and friends and anyone else who knew the story) of my college boyfriend’s strange declaration of his affection.

Instead, I was reminded of my friend Carter’s words. He owns a vintage furniture store and once told me that “any furniture you put in your back alley will eventually get picked up by someone.” What I would think if I saw a random painted wooden chair sitting in a back alley? I’d probably love it! I’d wonder about the people on the chair, why someone might get rid of such a thing, and proudly display the odd piece in my entryway or something.

Before I could change my mind, I picked up The Chair and put it at the end of our driveway. But not before I wrote a note on it and taped it to the bottom.

My college boyfriend painted this chair for me in 2003. We’ve long since broken up. I’m married (to someone else, obviously) and just need to get rid of it. Hope you enjoy this quirky piece of my history. 

Goodbye, chair.
Goodbye, chair.

Two days later, it was gone.

I finally stopped hanging on to what was trying to let go of me.

It felt surprisingly satisfying. I have no idea where it ended up, but it tickles me to think of this weird little chair sitting in someone else’s house, spurring conversations about who may have owned it, and how someone could’ve ever just thrown away something so personal.

But this chair was never personal to me.

That’s why it’s important to ask yourself WHY you’re hanging on to certain things. Who cares if it was your great-grandma’s tea set if you don’t like it? Or an ill-fitting itchy sweater your aunt Linda knit for you in 1998? If you don’t like it, or it’s done serving it’s purpose, get rid of it! You can’t be forced to feel a certain way about a gesture, heirloom or a gift. Even if your face is painted on it.

Besides, that’s not my face. It’s Mariah Carey’s.


After posting this, I got a response from Chair Guy’s college roomie. Made my day!

Hey Molly, Art Guy’s college roommate checking in. I did a double take when I saw this chair. Amazing memory!! I thought I’d never see that chair again – it is legendary – I’m shocked you didn’t burn it in a dumpster fire shortly after receiving it! 

A few points of clarification: i) we (his roommates) counseled Art Guy strongly against giving you this item – we thought its sheer weirdness went beyond the pale, even for him; ii) if my memory serves me, Art Guy spent months on his likeness, but only a small fraction on yours (hence the Mariah Carey affect) but I am sure this does not surprise you at all; iii) the cringe was palpable when we learned of the chair’s fate and I’m sure the look of utter befuddlement on your face upon receipt was priceless; and iv) contrary to what you wrote, we all thought very highly of you.

Nice post, thanks for the memory!

* * *

Want to get rid of things? Me too! Here’s how I got rid of tons of my clothes (nearly pain-free, too!), plus where to get rid of your unwanted crap.



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Comments (9)

  • Harmony 5 years ago Reply

    I’ve always thought you looked remarkably similar to Mariah.

    molly mogren katt 5 years ago Reply

    riiiight. We have the same engagement ring tho…

  • Liz 5 years ago Reply

    Oh I hope the new owners someday find this blog – this is a This American Life in the making.

    molly mogren katt 5 years ago Reply

    YOU ARE SO RIGHT! I kind of have a sneaking suspicion that this thing will resurface at some point. That’s just the way things work. I sincerely hope it had something to do with Ira Glass.

  • Alleria 5 years ago Reply

    Very interesting story, and a good lesson to learn. After my mother died, it was hard to divest myself of the things she left me (some of them, anyway) simply because they were hers. I STILL have some of that stuff, to be honest. But it’s better to let it go than let it clutter up your house and your emotions.

    I do have a maybe-impertinent observation, though. I think it’s kind of odd that Josh was upset that you kept the chair. You broke up with the dude, and you eventually married Josh. So what’s to be jealous about or upset about? And I guess I’m overlaying this with some of the stuff I’ve heard on the podcast, too, where Andrew comments about how Josh is kind of a jealous guy (and you’ve concurred). So what’s the deal there? Jealousy is about trust, and you seem absolutely trustworthy; I guess I’m just not getting where this jealousy comes from.

    molly mogren katt 5 years ago Reply

    It was not about jealousy. I think it comes from not wanting to picture of your wife with another guy. And in this case, it was literally a picture. 🙂

    molly mogren katt 5 years ago

    Also, he kinda felt bad when I got rid of it. But not that bad.

    Katherine Harris 5 years ago

    "I think it comes from not wanting to picture of your wife with another guy."

    This. Which is perfectly normal and not ‘jealous behavior’ in my book.

  • Sarge in Charge 5 years ago Reply


    That is all.

    Oh, and this will DEFINITELY resurface somehow.

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