Heather Aimee O'Neill: The Observer
Heather Aimee O'Neill on the vulnerability of ambition, the challenge of living an authentic life, and the strange transition from observer to protagonist.
"I began wanting to write about grief, but the more I was writing it, the more I began to see I was writing about the journey of these three women trying to live an authentic life.” - Heather Aimee O’Neill
How well do you know your friends?
Heather Aimee O’Neill is my friend.
For more than a decade, we’ve shared meals, cups of coffee, family vacations, and countless conversations about how to build a creative life in the midst of domestic reality. We have talked about marriage, children, ambition, art, money, time management, and the strange business of trying to make things while simultaneously living a life.
I know I have revealed much of myself to Heather over the years, often huddled at the end of her long dining table in the Bed-Stuy apartment she shares with her wife, Caroline.
I would tell her about balancing commercial work, the podcast, tour life, and my own songwriting ambitions. She would tell me about her work as a teacher, editor, and writing coach, and about how she balanced all of that with her own writing practice.
Which is why, when sometime last year she announced that she had sold her first novel, I was stunned. She sold a novel? She wrote a novel? How had I missed this?
Looking back on it, I suppose Heather had been telling me all along.
I found a text exchange from October of 2024 where she wrote: “I have a character in my book who speaks Spanish. Can you tell me if this is correct?”
I answered her matter-of-factly, never stopping to consider the larger story hidden inside the smaller one. What book?
It turns out that while we had been talking about creativity for years, Heather had quietly been writing a novel. Not telling her students, not telling most of her friends, not telling me. Just writing it, mostly - as she later explained - on Thursdays.
Heather once told me that as the youngest of three sisters growing up on Long Island, she never felt like the main character in her own life. She felt like an observer. And I think that has been one of her great gifts. She was paying attention while the rest of us were busy talking. I didn’t notice her noticing me. That’s a superpower that she has.
When someone you love makes something, there is always a risk that you won’t love it as much as you love them.
So when Heather’s debut novel, The Irish Goodbye, arrived in the fall of 2025, I cracked it open with equal parts optimism and apprehension.
I said a small prayer: “Please be good.”
And it was. Very good.
The Irish Goodbye tells the story of three sisters returning to their family home on Long Island for Thanksgiving, each carrying grief, guilt, and unresolved questions surrounding the death of their brother years earlier. It’s a novel about family, memory, secrets, loss, and ultimately the challenge of living an authentic life.
I saw pieces of Heather in it. But what surprised me most was how quickly I surrendered to the story and forgot about the person who had written it. It was a gift to discover that I wasn’t only proud of my friend. I was also a fan.
As it turned out, I wasn’t alone. The Irish Goodbye became one of the most celebrated debut novels of 2025.
The week of its publication, Heather asked me to help her launch the book at a bookstore in Brooklyn. Preparing for that event, I had the chance to ask her about the writing process, the characters, and what she felt the novel was really about.
And as I watched her that evening in front of a packed room of family, friends, students, and readers, I began to really notice her. The Heather I knew was still there: thoughtful, observant, curious. But alongside her sat someone else. A novelist completely in command of her own narrative.
As much as I loved the story she told in the book, I found myself increasingly curious about the story she hadn’t been telling me all those years. Or maybe the story I hadn’t been listening carefully enough to hear.
We got together recently to talk about all of it.
