100 Songs or Bust: A Songwriter’s Journey

For 50 years, I did not give myself permission to write songs.
I thought songwriters had to be tortured people touched by lightning or some special hardship I would never know.

Then I woke up.
I decided to invest in my own dreams and spend my time doing what makes me happy: music.

I started learning more about singing with my old New York friends Isaac and Thorald Koren.

I met Jen Ayers at a show and was amazed by her voice—she agreed to teach me.

During the pandemic, I wandered into a piano store and impulsively bought a piano so I wouldn’t be bored at home. At first, I tried reading sheet music, but my ADHD brain knew better. I had to learn systems and play from the soul. So I called up an old college friend, Danny Kolke, an extraordinary talent, and began piano lessons.

And then I set a crazy goal, for no good reason:

100 Songs or Bust

When I set out to write and release 100 songs, I wasn’t aiming for perfection. I was aiming for honest songs that give me goosebumps. Each track is a snapshot of where I was in that moment—grieving, laughing, raging, doubting, or simply trying to make sense of the world.

Here’s the road so far.

  1. Run with the Dog (2/4/2023)
    Written after losing my best friend, Bill. A song of grief, loyalty, and memory—the first to set me on this path. I played drums on this, and Isaac and Thorald Koren helped with the music and soulful guitar part. It’s hard for me to listen to this one still, as my vocals are pitchy in parts. A friend of mine tells me he loves to hear the pain in my voice, so I leave it up forever as a recording of this fragile time as a songwriter.

  2. The Song I’m Afraid to Write (10/14/2023)
    Facing the shadows we’d rather avoid. Vulnerability turned into melody. This song was produced entirely at home.

  3. Broken Down Bus (October 2023 – Reel Songs project)
    Inspired by Little Miss Sunshine. It’s about how things somehow work out even when life feels fragile and absurd. I borrowed from the film’s self-help jargon, which hit close to home since I’ve written a book of my own.

  4. Down River (1/7/2024)
    Written about a year after my father passed in 2019. This song reflects on fishing with Dad and the last thing he ever said, “I’ve got to get across this river.” The most intimate moment I ever had with my father was when he took my hand as we crossed the river way out in a faraway river in Idaho. Father-son relationships are complex, and we were not exempt from misunderstandings, judgmental feelings, and a longing to be closer.

  5. Over the Line (3/29/2024)
    Inspired by The Big Lebowski— we are like tumbleweeds, rolling as cowboys, and sometimes just pushed way over the line by mysterious forces. This is the first song where I recorded my vocals at London Bridge Studio.

  6. Way You Make Me Pay (4/12/2024)
    My first song on guitar was learning the G and C chords. I couldn’t finish it there, though, because I heard more harmonic complexity, so I moved it ot the piano. This song wrestles with the confusion of relationships.

  7. Angry Eyes (8/30/2024)
    Born out of a rough night with my son, written in one breath at the piano. Instead of fighting, I turned to song. Recorded my vocals at London Bridge Studio.

  8. Green Room (9/23/2024)
    About losing my friend Brad Houser, bassist for Edie Brickell & the New Bohemians. It’s about us assuming we are in the green room, before the show and not realizing we are actually in real life, right now, living for the last time. Brad taught me so much.

  9. Ticket to Ride (10/11/2024)
    A song about longing, conflict, and the hope of opening up. Heaven is where the heart is.

  10. Irony Sings (12/20/2024)
    A conversation with my friend Irony. It’s about youth wasted on the young, and the lessons life sings back to us. I recorded a beat-up old piano at London Bridge, along with my vocals with this song, and then recorded the rest at home.

  11. Sweet and Complicated (3/14/2025)
    Arrived in a single night. The story of meeting the right person at the wrong time in a club. I had fun getting my band, Greenwood Music Collective (Jack Quick, Michela Miller, and Mike McDermott), and my friend Gina Zukoski to play piano on this.

  12. Meet Me in the Mourning (3/21/2025)
    This just felt like it had to be the title track of my first solo album as a songwriter. So many things came together. A meditation on grief, letting go, and moving toward healing. I recorded these drums and vocals at Lonon Bridge Studios with Jonathan Plum at the controls.

  13. The Price of Love (4/30/2025)
    A philosophical lament—love is costly, but always worth it. A special song to me. Love the tones on this one aided by Plum yet again.

  14. Zombie Lover (4/23/2025 – Bandcamp)
    My ode to doom-scrolling in the time of shameless politics, greed, and the parts of our souls that get sucked in. I ran my drums through guitar pedals and played some synths to create the music. My friend Greg Hoy played some ornery guitars.

  15. Trees and Memories (6/27/2025)
    A collaboration with my wife’s guitar teacher, Jonny Akamu, who sings lead and plays gorgeous guitars. About walking with our memories in love. We had a blast creating this song from thin air and pushing it over the finish line with Jonathan Plum’s help on the mix.

  16. St. Catastrophe (7/4/2025)
    Written with Jeff Haris and Chris Sahlin at Andrea Stolpe’s songwriting camp. I played drums and organ. At its core, the song is about the worship of demagogues and the chaos that devotion creates.

  17. Love Each Other Fine (8/29/2025)
    A reminder that love is fine—not like the movies, but beautiful, true, and real. We make it up as we go, knowing we can’t fix our parents. We just love and support one another, forever. Jonathan Plum did a beautiful job co-producing this track, playing guitars and bass along with my keyboards and drum programming.

  18. Fake Ruse (August 2025 – Reel Songs project)
    Written after Suburban Fury. A reflection on political shame, repeated failures, and the cycles we can’t seem to break. I plan to re-record this and release it this year.

  19. Couldn’t Tell (Planned September 2025)
    This song came quickly as I recorded a voice memo of me singing while patting my chest for a beat while birds chirped overhead. That recording is still there, buried inside the track. This song is my most innovative to me at least, and holds a special place for me. I’ll let the song lyrics and emotion speak for themselves. This song was produced by the great Jeff Fielder, who also played guitar, bass, and added drum machines. It was mixed by old dear drumming pal Gary Thompson, who produced Inflatable Soule’s So Sad album back in the 90s.

  20. Last Horse in America (Planned October 2025)
    A song that showed up in dreams night after night. For me, it’s a metaphor—the cost of leaving good things behind, or the cruelty of kicking someone who is already down. Produced by Jeff Fielder as well.

Rear View Mirror

Looking back, I’ve released 17 songs so far, and have at least 3 more planned for this year. Here’s my scorecard:

  • 3 songs in 2023

  • 7 songs in 2024

  • 7 (so far) in 2025 with 3 more coming

I’ll take it. I don’t plan on stopping, and I think I’m learning more about what’s possible each month. In Brian Eno’s songwriting class in January 2025, he said he believes his best work is still ahead of him. That’s a healthy way to look at life, no matter if it is true or not.

Looking Ahead

Every song so far has been a step toward 100. Some came through joy, some through grief, others through irony or outrage. Together they form a journal in music—a record of where I’ve been and a compass for where I’m going.

100 songs or bust? Well, I’m still on the road.

To follow my journey, please sign up for my Bandcamp account or follow me on your preferred streaming service.

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Andrea Stolpe on Finding Your Sound and the Courage to Keep Going

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