The Question That Changed My Life (and Could Change Yours)

How one simple question shifted everything I thought I knew about success, belonging, and leadership

In the summer of 2020, I joined a book group for the first time in my life. I didn’t actually read most of the books except one: Untamed by Glennon Doyle. I devoured it in a week of rest and vacation, and one passage stopped me in my tracks.

Glennon asked herself a question: “What do I really want?” She admitted it was the first time, as a woman in her 30s, that she had ever asked herself that question. And she wrote about how most women never do.

I kept reading for a few chapters, but the question followed me. I flipped back, reread it, and felt… angry. Disturbed. My first reaction was: Of course I know what I want.

After all, I was a homeowner in Boston. I had a high-powered, well-paying job in a field dominated by men. I had degrees from top universities, including an Ivy League master’s. My marriage looked like a J.Crew ad. By every conventional measure, I was successful. Surely all of this was proof that I had been clear about what I wanted and gone out and achieved it.

And yet the question would not let me go.

When I Looked Closer

The more I sat with it, the more I realized: many of my biggest life choices had not come from my truest desires. They came from external forces and fear.

• My career path? It wasn’t because I dreamed of that work. It was the one offer I got in Boston, where my boyfriend (later husband) already lived.

• My choices? They were shaped by what would make my parents proud, keep a relationship intact, or earn society’s approval.

• My priorities? They were filtered through the fear of financial instability, a fear I carried from growing up without it.

None of those reasons were “bad.” They gave me stability my family had never known. But they were not the whole story. Even after I had financial security, the fear kept running the show. My answers to “What do I want?” were really answers to “What will keep me safe? What will make me acceptable?”

The Turning Point

I realized I had been living inside this paradigm for nearly 15 years. It had worked for a while. It got me stability, achievement, and accolades. But it wasn’t working anymore.

That question — What do you want? — cracked something open. For the first time, I had the privilege, the safety, and the courage to ask:

• What do I want beyond security?

• What would make me feel fulfilled at 80, looking back?

• What definition of authentic success would actually be mine?

It didn’t spark an overnight transformation. At first, it led to small, incremental shifts. But those shifts compounded. Over time, they reshaped my life and became the foundation of my personal reinvention.

The Transformation

Five years later, the difference is staggering.

I went from:

• A condo in Boston, a stable corporate career, and a conventional marriage.

To:

• Divorced, queer, living in Europe.

• A business owner prioritizing community, relationships, and self-care over capitalism.

• Someone who claims disability as part of my truth, after discovering I’m both dyslexic and autistic.

It wasn’t one big leap. It was a thousand micro-choices, each guided by that question. Every time I asked, “What do I want?” I had to sort what was really mine from what was fear or conditioning. Slowly, I began steering my own ship.

The seas were rough at times. But they also revealed beauty I never could have imagined. They offered gifts, growth, and a sense of belonging to myself. It was a true career transformation, but more importantly, it was a life transformation.

Why I Coach

That question didn’t just change my life. It gave me the clarity to realize what I most want now: to help other women ask it too.

Because here’s what I know:

• You can look wildly successful on paper and still feel restless inside.

• You can check every box society told you to check and still ask, “Is this it?”

• You can be a high achiever and still crave a deeper, truer life.

My clients are often at that turning point. They are women leaders who are ready for professional and personal reinvention. They want to climb up to the bow of their own ship, grab the compass, and finally steer toward their true north.

I didn’t always have a guide when I needed one. I pieced together help from friends, therapists, and moments of grace. But I often wished for someone who had walked this path before. Someone to push from behind when I was stuck, or to reach down and pull me over the next hurdle when I was tired.

That is why I built Eleva. To light the candle, to remind you to ask the questions, and to walk beside you as you write your own definition of authentic success.

Your Turn

So I’ll leave you with the same question that changed my life:

What do you really want?

Sit with it. Let it disturb you. Let it follow you. See what begins to shift.

And if you are craving support for your own career change journey, coaching for women is one of the most powerful ways to find clarity. Asking yourself the right questions is the first step in learning how to find fulfillment at work and in life.