By: Amy Smith
For many women, the question isn’t whether they love their careers or their children more; it’s how to hold both without losing themselves. The balancing act between ambition and motherhood can feel impossibly delicate, and every family arrives at its own answer. Some women push forward. Some step back. Most do a complicated dance somewhere in between. For Ann Kittredge, winner of the 2026 MAC Awards (Manhattan Association of Cabarets) for best female vocalist, the decision came at a moment when her performing career was thriving. She had momentum, recognition, and a growing artistic voice. And yet, when her children were young, she made the deeply personal choice to pause, to redirect her time and energy toward parenting and community advocacy. What followed was not simply a break from the spotlight but a transformative chapter that reshaped her artistry and deepened her purpose. Now, celebrating ten years since her return, Kittredge reflects on what it means to step away, to come back, and to discover that sometimes the long road home leads exactly where you’re meant to be.
We sat down and discussed music, motherhood, and her unique journey:
You stepped away from performing at a pivotal moment in your career to focus on raising your young children. What was that decision like emotionally and did you always know you would return to the stage one day?
When my youngest, my son Robby, was about two years old, I made an unexpected career choice and took a leave of absence from performing while they were young. Even though I appreciated being able to focus my time on parenting, which did not come naturally to me, and volunteering, it didn’t mean I wasn’t suffering from a little career withdrawal.
When I made the initial decision, I absolutely thought it had an expiration date. But I really got caught up in advocacy and community building, and at some point, I wondered if I would ever return. Once my children reached the age where they didn’t want me hanging out with them anymore, I began imagining stepping back in. I truly missed it. It was quite a journey to return, but I am absolutely pumped that I did. It’s been such a joy ride. I learned during my hiatus that it was much easier to play a mom than to be one, and yet, being one is immeasurably rewarding.
Many women struggle with the tension between personal ambition and family life. During the years you were offstage, how did you stay connected to your artistic identity while fully embracing motherhood?
I volunteered at my children’s school, directing performances and graduations, and became involved on a city level in various roles to create value for NYC students. I also worked with the American Songbook Association, which allowed me to continue sharing music with children who might otherwise not have exposure to the great music of the past.
One moment I will never forget was securing tickets to Twelfth Night on Broadway for an eighth-grade class studying Shakespeare. Families donated so that everyone could attend, and we arranged for a cast member to visit the school beforehand. Watching those students, many from Queens, take the subway home in tears because it was their first Broadway show… that visceral, emotional reaction stays with me. Art is essential. Sharing it during those years kept me connected in a different, deeply meaningful way.
How has becoming a mother deepened or reshaped your interpretations as a storyteller in cabaret? Are there songs you sing differently now because of your lived experience?
Everything I sing is approached differently now because of my lived experience, but what changed most was my focus. Before my children were born, I was so passionate about the work that I’d sometimes be surprised when we left rehearsal, and the audience began contributing their part. I was very tunnel-visioned.
When I returned, I had a deep appreciation for the audience. I’ve made it my mission to serve them intentionally, using the skills I’ve been given to provide a respite from the world’s craziness for 75 minutes. They still surprise me. But now they surprise me because of how much they offer. The relationship that develops between performer and audience in such a short time is glorious. I can’t wait to serve my next audience.
Celebrating ten years in cabaret after such a meaningful pause feels symbolic. What message would you share with women who fear that stepping away might close the door on their dreams?
When I first stepped back in, full of doubt and insecurity, Broadway director Richard Jay Alexander told me that age doesn’t matter. You can start at any time if you have the passion and the skill.
I’ve grown so much over these ten years. It’s funny to look back and cringe at some early mistakes, but I truly needed to sing. I truly needed to create value for others through my music.
Luck plays a part, and I’ve been lucky. The talent that surrounds me is extraordinary, and I know they work with me because they believe in me. That’s a remarkable place to stand.
But it isn’t all luck. I believe deeply that I am worthy. I don’t want to take, I want to give. I’m only challenged by how many people are available for me to give to. I’m still building a reputation that never ends, and it is a joy to create meaningful music along the way.
See video of Ann’s recent celebration performance at Don’t Tell Mama in New York City at: https://www.annkittredge.com/video and hear her music on Spotify.
