Of Sad Dad Music and Mixtapes
I saw a video on Instagram the other day: a mom pulling old mix CDs out of storage, playing them for her teenage daughter. The daughter's face as she listened. The questions she asked. It looked like archaeology.
So I went to our basement.
I pulled out a stack of old mix CDs from a box that hadn't been opened in years. Handwritten labels. Slightly scratched plastic cases. One of them stopped me cold. The cover was a found photograph from a thrift store, a black and white image of a young boy on a tricycle, tucked into a sleeve that read in handwritten script: "it's your BIRTHDAY when I say it's YOUR BIRTHDAY." Below it: "a gift for TJ Lawson."
Sarah Legas (now Sarah Newman) had made this for my birthday in 2005. The whole thing had a zine aesthetic, that very specific early 2000s mix of earnestness and irony. I flipped it over. The back was a handwritten tracklist, twenty-one songs, some highlighted in yellow. At the bottom: "I hope you had a good Birthday! Enjoy your gift. Thanks for being great all these years. Your friend, Legas."
I brought the stack out to our old 2012 Kia Soul, the one feature my kids consider "vintage" being the CD player. Most of the time it just sits there unused, a relic from a previous era of dashboards. But when I slid Sarah's disc in, it became the most interesting piece of technology in the car.
My kids did not just listen to the music. They studied the object.
"How did she make this?" "You mean she chose all these songs?" "She found that picture at a thrift store and put it on there herself?"
They were fascinated by the mechanics of it. Burning a CD. Designing the insert. Writing the track list by hand. In their world, music appears instantly. It streams from nowhere. It is infinitely editable, infinitely disposable. There is no friction.
This had friction. You had to decide. You had to commit. Once you burned it, that was the order. That was the statement.
And then something more interesting happened.
We were on track five when "Spent On Rainy Days" by Bright Eyes and Britt Daniel came on. The song finished, and my 13-year-old looked at me from the backseat.
"Wow, Dad. She must really know you. She knows you like sad dad music."
I laughed. Because she wasn't wrong. Sarah had nailed it. Stars. Yo La Tengo. Broken Social Scene. Iron & Wine. Every song on that disc was proof that someone had paid attention to who I was in 2005, what I was feeling, what I needed to hear. And twenty years later, my daughter could hear it too.
"Sarah's probably a bit of a sad dad at heart herself," I told her. "Which is exactly why she knew what songs to put on this thing."
That's when I realized what my kids were really responding to. Not nostalgia. Not the novelty of a physical disc. They were responding to evidence of being known.
The mix CD wasn't just a playlist. It was a document. It said: someone cared enough to curate this. Someone sat down and asked, "What songs belong together? What songs belong to you?" And then they made something you could hold. Something with a thrift store photograph and hand-drawn letters and yellow highlighter on the songs that mattered most.
We talk a lot about the convenience of digital life, and rightly so. Streaming is objectively better in almost every functional way. But in smoothing out the friction, we've also smoothed out some of the artifact. Our playlists don't age. They don't sit in boxes waiting to be rediscovered. They don't say "I made this for you in 2005" the way a scratched silver disc with a found photograph does.
Driving around in that old Kia, listening to Sarah's mix, I realized the most meaningful part of the moment wasn't the music. It was the bridge.
The bridge between who I was and who I am. Between a friend in 2005 and my kids in 2026. Between being known then and being seen now.
Now, on the way to school in the morning, my kids ask which CD we're going to listen to. They have favorites. They request specific mixes. They've started asking questions about the people who made them, the stories behind them, what I was like back then.
The algorithm will never ask them that. The algorithm doesn't know what I was like in 2005. It doesn't remember that Sarah Legas knew me well enough to put Stars and Yo La Tengo and Broken Social Scene on the same disc, or that she'd find a random kid on a tricycle at a thrift store and decide that was exactly the right vibe for my birthday.
But my kids can hear it. They can hold it. They can see the evidence.
Maybe we don't need to go back to CDs. But we do need to create artifacts that outlast the moment. Things that can be found again. Things that say, "This is who I was. This is what I loved. This is who knew me."
Because one day, your kids might pop it into an old car and press play. And they'll hear you. Not just the music. You.
And if you're lucky, they'll ask to hear it again tomorrow.
What mix, playlist, or unexpected artifact has helped someone else see who you really are?
About Enthusiastic Generalist: This blog explores ideas across disciplines: science, leadership, faith, parenting, book reviews, personal essays, and the occasional deep dive into mix CDs from 2005. It's an eclectic mix of whatever I find interesting about the world. If you enjoyed this post, subscribe for more deep dives into the unexpected connections that make life worth paying attention to.
