Ep 272: Jonathon Penn
Jonathon Penn: Leaving Wall Street to Pursue Music | Episode 272
The Popko Project Podcast • Episode 272
What happens when you leave a successful career to pursue the thing you can’t stop thinking about? Singer-songwriter Jonathon Penn joins Popko to talk about stepping away from finance, reconnecting with music, and finding purpose through creativity.
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About This Episode
Walking away from an established career comes with plenty of questions. For Jonathon Penn, that decision opened the door to a renewed relationship with songwriting. In this episode of The Popko Project Podcast, we explore his journey from Wall Street to independent music and the experiences that shaped his album, It Took a Long Time to Get Young.
Jonathon opens up about returning to creativity after years away, working through self-doubt, and learning to trust his artistic instincts. We talk about the challenges of changing direction and what it means to make room for music while balancing family life and personal ambition.
Fatherhood and the loss of his dad also became part of that creative journey. Our conversation explores how those experiences influenced his perspective and the stories he brings into his songs.
We also get into the realities of releasing music independently, navigating the streaming era, and building a creative life on your own terms. Along the way, Jonathon shares the stories behind songs including “Hawk Circling,” “Wildfire,” and “Gold Rush.”
Whether you’re discovering Jonathon’s music for the first time or considering a creative leap of your own, this episode offers a personal look at the decisions, doubts, and experiences behind the songs.
In This Episode
- Leaving a career in finance to pursue music
- Rediscovering songwriting after years away
- The making of It Took a Long Time to Get Young
- How fatherhood and grief influence creativity
- Balancing family, ambition, and artistic fulfillment
- Life as an independent musician in the streaming era
- The stories behind “Hawk Circling,” “Wildfire,” and “Gold Rush”
About Jonathon Penn
Jonathon Penn is a singer-songwriter whose return to music followed a career in finance. His album, It Took a Long Time to Get Young, draws on personal experiences with family, loss, and rediscovering his creative voice.
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