Clutter Tales – Musically Rolling Along (Guest post)

Book open to title page "Clutter Tales - Musically Rolling Along" with picture of iPod
Clutter Tales12 Comments on Clutter Tales – Musically Rolling Along (Guest post)

Clutter Tales – Musically Rolling Along (Guest post)

Welcome to Volume 8 of Clutter Tales, a series where we tell the stories of our lives through our clutter. Today, I have another guest post and, as a music lover, it’s one I definitely relate to. This post comes from my dear friend Cher at The Chicago Files who shares the story of memories sparked by finding her old iPod. There’s nothing like musical memories to transport you back to a different time and place!

This post was originally published in July 2021 and updated in July 2024.

About today’s guest blogger

Cher and I have been friends for many years. It’s a special friendship that has stood the test of time and distance. You can find her blog at The Chicago Files where she provides a Canadian perspective on living in the windy city. She regularly shares stunning pictures of the skies over Lake Michigan that she captures from the window of her condo.

Cher inspired me to start this blog and was a huge help when I was getting started. I might never have got this blog online without her help!

Book open to title page showing "Musically Rolling Along" with an image of an original iPod

Cher’s Clutter Tale – Musically Rolling Along

I enjoy Michelle’s posts so much, and her Decluttering 52-Week Challenge, Cluttering Tips, and Clutter Tales are no exception. 

Intrigued by the thought of following Michelle’s excellent advice, I decided to ‘get serious’ about getting rid of clutter. I began with the dreaded bathroom cupboards, followed by the clothes closet. Then I moved onto little nooks and crannies, which I was certain would result in mayhem since I hadn’t given them a second thought for eons.

Have you ever heard the term, “Hiding in plain sight?” Despite the fact that this sounds counter-intuitive to my “nooks and crannies” comment, it is actually (in this case) the same thing. 

Case in point: I have a little tray of sorts that sits in a corner of my dresser. The number of items in this tray are unknown to me, as spillage happens quite often, and I usually either find another place for an item, or I try and squish it back onto the tray.

With decluttering at the forefront of my mind, I took a huge, deep breath, grabbed the tray, and tossed everything onto the dresser.

My eyes stared directly at a purple/bluish item; well now, what do we have here?

Immediately I was taken back in time; eleven years, to be exact. It was my iPod. I smiled as I picked it up, and felt such nostalgia (for lack of a better word).

I bought it soon after I moved from Canada to Chicago. Everything was so big, intimidating, and exciting all at the same time. I spent a lot of time on the elevated trains and buses, exploring my new home. Everywhere I went I had my iPod in tow. The music somehow made me feel calm, at ease, and part of the city. No longer a tourist, this was me, riding the trains, a resident of the City of Chicago, and my tunes brought a sense of the old blending with the new.

Curious to see what songs I actually listened to ‘back then,’ I charged it and waited to see what would appear (I only used my iPod for the first couple of years after moving here; it was replaced by a musically inclined smartphone).

I searched under, “Most Recently Played.” I grinned from ear to ear. Not only was it a song by a Canadian band, but they happened to be from Winnipeg (where I moved from).

Original iPod with playlist showing "Share The Land"

“Share the Land” by the Guess Who was at the top of the list. My mind now wandered back to Winnipeg, a place that (despite the exceptional Arctic blasts of frigid winter temperatures) will always have a warm spot in my heart. I was having such fun thinking back to my Winnipeg days, then my ‘new’ days here in Chicago.

This all came about because of Michelle’s decluttering challenge. Thank you, Michelle. You have given me so much to recall in song and memories. 

Now, where did I put my headphones? I need to ‘guess who’ else is on my playlist!


Let’s keep in touch! Join my mailing list and I’ll email you when I add a new post.


Thanks again to Cher for sharing this story with us. It brought back musical memories of the days when I travelled around town listening to tapes on my Sony Walkman. I really wish I had kept it – and those tapes. Now that would have been an awesome Clutter Tale!

I hope you enjoyed this installment of Clutter Tales. If you’d like to write a guest post for Clutter Tales, please get in touch. I’d love to give you the opportunity to properly thank your clutter by sharing its story too!

What song do you remember listening to on your iPod, Walkman or smart phone? Tell us about your musical memories below.


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Hi there! I’m Michelle and I live in Kitchener, Ontario, Canada. I am married with two young adult daughters. I’m a big fan of reducing waste, using less plastic, decluttering and simplifying life as much as possible.

12 thoughts on “Clutter Tales – Musically Rolling Along (Guest post)

  1. I have kept multiple voice mails from folks on my phone. So, when I upgrade or change phones I am faithful to make sure they are “switched over”. Unfortunately, I did not have them all backed up to my Forever account and when I clicked on “Optimize Space” the voice mail from my sister who has passed away was deleted. She’s been gone for 8 years and I have listened to it on my birthday for all these years. So, warning if you are saving voice mails! Don’t optimize on your smart phone or they will go away. Upload to your photo server (if they accept mp3’s) so that you can keep them safe!

  2. I love discovering old music collections like this! I have no idea where my old iPod is but I’m certainly inspired to open up my old iTunes to see if there’s any gems on there! x

    1. There’s nothing like old music to bring back memories. It’s one of the things I love about Spotify – searching a specific year and seeing what songs come up!

  3. Thank you so much for including me in your Clutter Tales series, Michelle! I am super grateful to share my decluttering music story.

    Thank you also for including me in your blog journey!

    Cher xoxoxo

  4. I almost listened to my ipod this weekend as a special birthday treat. I guess I really need to charge the poor thing and give it a chance after this post. I’d say I probably haven’t added any songs to it since about 2014, but we’ll see what I find!

I'd love to hear your ideas. Drop me a comment below.

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