Confessions From the Underground #20: Obsolescence

**This column originally appeared in our July 2026 issue**

For those keeping track at home, yes, this column looks a little different this month. For one, it takes up 75% less space (sorry/you’re welcome). This is solely due to time restraints, and needing to prioritize this month’s exciting cover story. Even though I didn’t have the chance to have an in-depth conversation with anyone this month, I figured I could ruminate on a topic anyway. While I know I’m nowhere near as interesting as any of the folks I have the pleasure of speaking with each month, I’m grateful I have a platform to do something like this, because I’m way too busy to start a Substack. Thanks for tuning in.

Lately, I’ve been thinking a lot about obsolescence. You know what I’m talking about. It’s like when Apple announces a new iPhone and suddenly your reliable two-year-old model starts acting real weird. That’s what’s known as planned obsolescence.

What I’m here to discuss is the other kind of obsolescence. The unplanned kind that seems to naturally sneak up on us. Like those moments where you think to yourself, “Technology has eclipsed me; I give up.” As someone who’s always been pretty tech-savvy, it’s a weird feeling to suddenly recognize you’re behind the times. It’s even weirder to lose the desire to catch up.

When I was nine or ten years old, I started playing Little League. I was an above-average player — not the best, but basically the equivalent of being a reliably in-the-pocket, not-too-flashy musician, which I also consider myself to be. Clearly, some things never change. On top of that, I enjoyed the game. Baseball was the one sport I followed, while all others never held my interest outside of a Playstation or Nintendo 64 environment. I played in the spring, fall, and even traveled with a couple All-Star teams during the summer. Naturally, as I got older, things became more competitive, and when I got to high school, my peers and I all aged out of Little League and had to try out for the school’s team. 

I was the first one to get cut. I couldn’t run (still can’t), and where other kids were bulking up and becoming more athletic, I was doing whatever the opposite was. I was deemed not good enough and, looking back, this was my first experience with obsolescence. The other kids had eclipsed me and I lost something that I truly enjoyed doing.

But, if there’s any point at all to this newspaper column you’re currently reading, it’s that obsolescence does not have to mean defeat. 

It was around this time that I first picked up a guitar. And with my calendar now blank, I suddenly had more time to devote to this other interest and make it a full-blown passion. Cover a Stratocaster in stickers. Dye the hair blue. Write a whole lot of emo songs about girls. I think three examples is enough, let’s move on.

At the risk of sounding self aggrandizing, especially when I’m more of a quiet-voice-whispering-‘you-suck’ guy, I’ve done more with music in the last twentysomething years than I ever could have with baseball. If you count my first forays into writing and releasing original music in high school — which you shouldn’t, but I’ll do it for the sole purpose of this article and then never again — I’ve released 17 LPs, eight EPs, and a dozen or so singles over the course of that time, spanning 10 different projects. And while some should be burned in the dumpster fires of history, I’m proud of the sheer volume of that output because it shows a willingness to stick with something and always aim to improve. That’s not a trait I’d otherwise consider myself to have. And along the way, I’ve felt a lot of things, often —  imposter syndrome, uncool, naïve — but I’ve never really felt obsolete.

Until recently.

Next year, I’ll be turning 40. And while the music industry has certainly gotten a lot less ageist in recent years, there’s still that inherent feeling lingering from the days of yore when, if you weren’t a hot young artist releasing a chart-topping single on the radio and debuting in the top 10 of TRL, you might as well be a dinosaur. 

It’s so much more than just an artificial age thing though, and this is where the obsolescence, and my confession, really kicks in: it feels more and more lately like no one cares. Like I’ve overstayed my welcome, and it’s time to move on. I assure you that’s neither a self-deprecating statement meant to encourage praise (please don’t), nor a slight aimed at anyone who does or does not care. It’s a sign of the times we live in as creatives. Please read on before you hate-post at me.

On a recent episode of my favorite podcast Smartless, special guest Nick Jonas made some brief comments on how the music industry has changed since his teeny bopper days. This one really stuck with me:

“When [the Jonas Brothers] first started putting music out in the early 2000s, on any given release day, there would be anywhere from 30 to 50 new releases. There are now thousands. Every week.”

Think about that for a second. Thousands. In the grand scheme of things, it’s hard to not feel a sense of sheer impossibility for a tiny, no-name artist to float to the top of that many releases. More importantly, I could never expect anyone to devote their most valuable resources — time, attention, etc. — to someone so far down the food chain. The more you spiral with this line of thinking, the more it feels like the thing you love doesn’t really love you back. Cue one of those aforementioned emo songs.

To make a long story a little bit longer, I’ve been thinking long and hard about taking a step back for mental health reasons. Pivot to other dreams that have quietly lived rent-free in the back of my brain in favor of continuing on the path that’s defined me for more than half my life. 

I happened to mention some of this to my family in the car the other day, apologizing for being busier than normal and assuring them that I wanted more time together. I’ve been feeling a sudden surge of creativity, which has resulted in spending a lot of my time either composing, mixing, rehearsing, or performing. It’s been great, but I can’t be in two places at once because #science. My nine-year-old especially has been feeling a bit neglected, and so I was surprised with what she said to me that day. To paraphrase: “I don’t want you to stop doing music; that’s who you are and I don’t want you to change.”

Suddenly, I didn’t feel so obsolete anymore.

And while I don’t really have any advice to offer at this point, I’m assuming there are others out there who feel the same way that I do. Raging against the dying of the light, maintaining any and all semblance of creativity and youth as devoutly as possible. What my nine-year-old showed me is that it’s probably all in our heads. If we, the obsolete, can overcome those voices and keep pushing forward, maybe we’re making a long-lasting impact after all: showing the younger generation that sticking with something past your “prime” isn’t uncool, it’s dedication. That’s what I’m choosing to believe, anyway.

And if nothing else, maybe I have a future in children’s music. My first single will be called “Counting To Four” and will only weave in and out of 3/4 and 7/4 time. How’s that for obsolescence?