Song Challenge Week 22 — A Song You Listen To When You’re Sad


The latest entry in my 30 Day Song Challenge weekly project.


Song Challenge Week 22 — A Song You Listen To When You’re Sad

“Even If It Breaks Your Heart,” Will Hoge

A song I listen to when I’m sad? Well, what am I sad about?

Historically, this one is a very situational thing for me. If I’m sad, changes are I’m sad about something. And that something is frequently loss. And often in those moments, I can gravitate towards songs that speak to what it is I’m sad about losing.

In college and thereafter, I couldn’t listen to 10,000 Maniacs’ “How You’ve Grown” without crying. I had a baby brother growing up that I rarely got to see living a state away, and that song drove home what I was missing — “Every time we say goodbye, you’re frozen in my mind as the child that you never will be again.” I came home each time to a different person than I left.

As my marriage fell apart, another 10,000 Maniacs song got played a lot (my music library was less diverse back in those days), “Jezebel” — “I’m not saying love’s a plaything; no, it’s a powerful word, inspired by a strong desire to bind myself to you.”

In the wake of the divorce, there was Lori McKenna’s “If You Ask” reminding me of all my shortcomings. And in the years since, in other situations, there’s been Rascal Flatts and Sugarland and more Lori McKenna.

And then, there are the songs that lift up instead of pulling down.

In younger days, it was as simple as singing to myself. “It is well with me soul.”

The first songs I listen to that came to mind, I actually just used a few entries back, “All Will Be Well,” by the Gabe Dixon Band.

So to avoid repeating it, I’ll go with another one that occupies a similar emotional landscape for me, “Even If It Breaks Your Heart,” by Will Hoge. (There’s an Eli Young Band cover that’s had more success, but I still prefer the way I first heard it.)

Hope isn’t always the road out of heartache. Sometimes it’s the road into heartache. But it’s still worth hoping.

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