Heartbreaking Bravery

Heartbreaking Bravery is in the midst of its return, but it’s showing—and will continue to show—a slightly different bent.

In my initial presentation of Heartbreaking Bravery, it was—first and foremost—a near-daily music blog. I published over 1,000 standalone pieces (including several featuring guest author submissions), released a meaningful, 100-track benefit compilation, and strung together a number of momentous achievements that still seem improbable, even in retrospect. I don’t take that for granted.

Towards the end of Heartbreaking Bravery‘s first lifetime, I accepted a job at Tone Madison. Working there took me from being a general freelancer at the publication, to the music section’s lead writer, to its editor, to becoming one of the publication’s co-owners. I unofficially stepped down from my position within Tone Madison‘s internal ranks in the final quarter of 2025. After publishing Tone Madison‘s annual best-of lists for local Madison music, my decision to leave was formally announced in the back half of a photo essay that contained a portion of my reasoning.

I have spent over 15 years writing professionally about music, in some way, shape, or form. This included writing for everything from Hot Lunch Collective to True Endeavors to Muzzle of Bees to PopMatters to Playground Misnomer to Consequence to Fvck The Media to AdHoc to Heartbreaking Bravery to The Grey Estates to Post-Trash to Tone Madison to a number of other in-between one-offs. A sizable percentage of my early adulthood has been dedicated to deconstructing and interrogating recently-released music. Over this (ongoing) stretch, I would estimate the present number of my published, music-focused pieces falls somewhere between 3,500 and 5,000.

That’s… a lot.

My relationship with music became more complicated over the course of those years, but the draw to its potency never wavered. Still, my interests in other areas expanded; photography (in all of its distinct forms), politics, wildlife, athletics, and other forms of culture all factored into the equation. At certain points, the appeal of continuing to unspool a never-ending string of new music to write about lost a bit of its lustre. But music, more than any other medium, still found a way to inspire strong innate feeling and productive, creative action. Tone Madison provided a platform that pushed me to engage with music in new ways, and it was an instructive experience that was worth the effort of honoring. But its guardrails eventually became incompatible with an increasingly demanding, time-intensive schedule. And my thoughts, in turn, went to carving out a space that could offer broader compatibility with my aims as a writer, and my interests as a musician and photographer. A space that could serve as a springboard for appreciations of the arts and culture—especially in cases where they’re less visible or appreciated—that spark inspiration.

It didn’t take long to realize that space already existed.

So Heartbreaking Bravery, as you may have noticed, is back. And it’s still going to celebrate music, but it isn’t going to be geared towards track or album writeups, as was once the case.

A track or album review may still appear on occasion, should my feelings about a given release become particularly strong, but this revived version of Heartbreaking Bravery will be primarily tethered to photojournalism. All of the pieces that are published from here on out will feature original photography (inclusive of live video), unless otherwise noted. Music will still be a prominent part of that lineage, as you may have gathered from the previous two posts, as will editorializing, as you may have gathered from my general inability to shut up and leave well enough alone. 

Going forward, Heartbreaking Bravery will be driven by first-person visual essays on arts and culture events. Music will still be the most consistent focal point, for a number of reasons, and I’m excited to unveil some things that have been in the works for years. In accordance with this reframing, the majority of the publication’s upcoming content will be directly connected to Madison, WI, with some stray forays into Milwaukee, Chicago, Minneapolis, and beyond. (I am not a static person, and the content of Heartbreaking Bravery will continue to reflect wherever life takes me, as a musician, photographer, or traveller.)

Expect a lot of Flickr links, YouTube embeds, and editorial meditations. Don’t be shocked to come across an errant interview, retrospective, or other scattershot format deviations, either. I’ll also be putting more effort into Instagram, where you can access a more visual, less copy-driven version of what’s being published on a week-to-week basis. Speaking of: expect to see a new post or two every other week, with productivity scaling up as Heartbreaking Bravery regains momentum.

It’s my hope that a number of those reading—and a number of those who were once kind enough to give Heartbreaking Bravery their time and attention—will be willing to click the proverbial radio on and enjoy the ride. There’s a lot of wide-open road ahead.

In the meantime, enjoy this playlist, which is composed of 100 tracks that were instrumental in steering Heartbreaking Bravery‘s first extended run (with a few recent tunes thrown in for good measure):

Keep the dial tuned, and be on the lookout for another future, playlist-including post celebrating exceptional music from this decade.

Editor’s Note: in the course of revisiting the above playlist, it became apparent permissions for several of the included videos had been shifted since their initial uploads, resulting in non-display. Please enjoy this bonus playlist that rescues each of those songs. All but two were able to be re-compiled, with the remaining exceptions having incredible music videos that are worth the click(s).