From Eyes-Closed to Camden Yards, and the Song She Was Afraid to Write with Rachel Druckenmiller
Episode Details

Today I talk to Rachel Druckenmiller, keynote speaker, songwriter and recording artist I met at a recent songwriting retreat.  You know those people you meet that seem kind and approachable, and then as you learn more you realize, oh I think she’s a really big deal.  Well, that’s Rachel.  In the 3 short months since we first met, she lived out a childhood dream of singing the national anthem for her hometown Baltimore Orioles.  We hear about all the seemingly small things she said yes to, things that didn’t seem to have any point to them, but together landed her on that field in front of 31 thousand people.  And when she got that opportunity, she didn’t waste it. She went all in.  


She also talks for the first time about the song she wrote at the retreat, something so deeply personal she had never said it out loud before.  But when she put her phone on airplane mode and reconnected with herself and nature, it just poured out of her.


This is a conversation about the power of saying your dreams out loud, borrowing other people's belief in you when your own runs short, and why, now more than ever, authenticity beats perfection every time.


Key Takeaways

  • Say your dreams out loud — you never know who's listening. Rachel once told a stranger at a conference that her dream was to "speak and sing in stadiums." That offhand admission set off the chain of events that eventually put her on the field at Camden Yards. Kept-inside dreams can't be caught by the right person.
  • Be strategic with your yeses — but don't let strategy veto what makes you feel alive. Her first anthem gig failed every strategic test. Rachel's gauge: if it's going to make you feel alive, do it.
  • You already have the evidence — use it. Rachel had practised the anthem 200+ times and already sung it once in that exact stadium. Scale spooks us into forgetting we've done a version of the thing before.
  • Borrow other people's belief in you. When her own confidence wavered, Rachel deliberately reached out to people who understood high-stakes performance.
  • An anthem is a celebration, not a funeral march. Rachel's whole preparation was built on one intention — "renew joy" before every line — and on singing with her whole body, face, and hands.
  • Alienating people is a sign of good art. (Peter Katz's line, which lands twice in this episode.) Rachel worried her retreat song was too specific to relate to. The specificity is exactly why it connects, with mothers and non-mothers alike.
  • In the age of AI, imperfection is the signal. A little grit, a note caught slightly under — the human imperfections are what make people trust the art now.
  • "Allow the unfolding." Rachel takes intentional action toward what she wants, then stays receptive to how it shows up rather than forcing it. Every action is a vote for the person you want to become (a nod to James Clear) — she spent years saying she wanted to be a singer while casting no votes; the last eighteen months have been nothing but votes.
  • Get out of the audience of your own life. The through-line of Rachel's year: building a foundation strong enough to support a bigger life, and choosing to participate rather than observe. Legacy doesn't require the path everyone assumes — she points to the late Dolly Parton, who mothered millions without children of her own.


Resources & References


Connect with Rachel Druckenmiller


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The Restless Leader Newsletter on Substack: https://bobmathers.substack.com/

Episode cover art for From Eyes-Closed to Camden Yards, and the Song She Was Afraid to Write with Rachel Druckenmiller
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