She Was at the Top of Her Career. Then She Started Over.
A reflection on Gaby Moreno's new form of ambition that every Midlifer can relate to.
I still remember the first time I knew I could be a writer. I was 14 or 15, and my Spanish teacher had us read an entire novel for each test, with ONE question to fill up a small libreta. Her very well-justified obsession with Luis Rafael Sánchez had me wanting to tell stories as if there were no mañana. Those small notebooks she gave us became my vessel of wisdom.
One thing led to another, and that inquisitive teenager turned out to be a media executive, sometimes a la fuerza. Twenty years, many reinventions (Substack version of Las Imperfectas included), plenty of insecurities, and yes, adult bullying. But hey. no regrets here, conste.
So when I heard Gaby Moreno (our fabulous Episode 4 guest, ICYMI) talk about carrying a teenage dream for over 30 years, I felt seen. Resulta que she was 13 when she visited New York with her family and knew in her bones what her calling was, walking out of a Broadway theater: that was the stage she needed to be on. She carried that dream all the way home to Guatemala. Decades passed. Nine albums, a Grammy, and two Latin Grammys as an independent artist who never needed a stadium to prove she mattered. And then, at 44, her manager forwarded an email asking if she was available to play Persephone in Hadestown on Broadway. Her first thought? “My manager has lost his s**t.”
Well, it was legit. She said yes before she fully understood what she was agreeing to: eight shows a week, moving to New York alone, her husband and dog staying in Los Angeles, learning a principal role in a Tony Award-winning musical, having never done Broadway before. A principiante all over again, at the height of a career the world had already recognized as her identity.
To me, it’s not about the Grammy, not the debut. It’s about her willingness to be seen not knowing something, at a stage in life when most people assume you should have it all figured out.
Knowing who we want to be is a never-ending task. I knew it at 14. Gaby knew it at 13. But it took us both 30-something years to understand what that calling actually felt and looked like, and what to do when it needed to change, because we did too.
We’ve been trained, in both explicit and unspoken ways, to believe that midlife is a time for consolidation, not experimentation. You protect the credibility you’ve earned. You wear your label(s) carefully. Because you’ve f***ing earned them. But that label doesn’t determine your next step. It serves only as a prompt to nurture your intuition and red-flag the road ahead.
For Gaby, being a beginner again was “liberating” once she allowed herself to be open to it. She had to release the image she’d been carrying and curating for years, and in doing so, she remembered something she’d somehow forgotten: growth doesn’t have a ceiling, and there is something genuinely profound about allowing yourself to not know.
Gaby Moreno, a woman with decades of creative authority, chose to go back to the room where she knew nothing. She chose it not despite what she’d built, but because of it. Because she trusted herself enough to survive the discomfort.
That, my Sabias, is leadership.
Nobody Puts Ambition in the Corner
When Ana brought up the word ambition, Gaby didn’t reach for scale, market share, or visibility. She talked about growing inward, deepening toward herself and toward a definition of success that finally includes her as a person, not just as a product.
She was honest that this isn’t the ambition that gets celebrated. What Gaby described as choosing a 400-seat theater over a stadium is a form of ambition that rarely gets called by its name. But it is absolutely ambition: the audacious, clear-eyed kind.
I could write a book about the ways I’ve excluded myself from my own ambition, mostly out of fear of seeming like I had an inflated ego. What I learned from our conversation is that including yourself is not a smaller ambition. It’s a harder one. We create for others, perform for others, build for others, so fluently that we forget to ask what any of it costs us or whether we’re actually in it alongside everyone else. And I know Ana has a few things to say about this, too (shameless plug: Done With the Hustle, bestselling book coming soon!).
Gaby, in her 44th year on a Broadway stage she first imagined at 13, had figured out how to stay in it. That’s a form of wisdom that doesn’t arrive until you’ve lived enough to recognize it. Echando a perder, included.
The Moment of Yes
“I didn’t have to audition!”
Yet, Gaby wasn’t performing I-have-my-shit-together. The internal struggle was real, the fear was real. But the fear didn’t get the deciding vote. The 13-year-old girl who walked out of that theater did.
We begin every episode of Her Wisdom Era with a flashback, wanting to understand what that younger version of our guests was like, because we believe she’s still in there, informing everything.
Honoring who you were before the world started telling you what was and wasn’t realistic takes more courage once you’ve built something real, because now you have something real to risk.
The stakes are higher.
And you go anyway.
Gaby walked onto the Walter Kerr stage in midlife, carrying thirty years of a dream she never let go of, completely and unapologetically herself.
Whatever your Broadway is: the business, the degree, the book, the relationship, the city, the creative project engavetado, the version of yourself you’ve been afraid to be too loudly. Remember: there is no expiration date.
A dream you write down in your journal, tuck into a Spanish test notebook, and keep alive through nine albums, two Grammy ceremonies, and decades of building something extraordinary on your own terms, that dream doesn’t expire. It waits.
And when the email arrives, you say yes. F**K YES, baby girl.
¿Seguimo’?
Mucho love from this proud 47-year-old finally investing in herself,
Cristy
Listen to our full conversation with Gaby Moreno HERE, on Spotify, Apple Podcasts & YouTube.