Meet Rachel Simmons

As the daughter of a refugee, I was raised with deep gratitude for my family’s sacrifices. Early on, I grappled with the dilemma of wanting to fulfill their dreams and listen to my own. My parents wanted me to live a conventional life. I won a Rhodes Scholarship in 1998, was accepted to law school, and looked for a husband. I couldn’t shake the feeling that I had become a passenger in my own life. I chose another path. 

I have always loved to write and listen to others’ stories. I wrote my first book, Odd Girl Out, in 2002, which became a New York Times bestseller. After co-founding the national nonprofit Girls Leadership, I spent nearly a decade teaching leadership skills to girls. In 2010 I wrote The Curse of the Good Girl: Raising Girls with Courage and Confidence, also a national bestseller.

As I got older, so did my students. I led the Phoebe Lewis Leadership program at Smith College, then wrote Enough As She Is: How to Help Girls Overcome Impossible Standards of Success to Lead Healthy, Happy, Fulfilling Lives.

In 2017, I joined the faculty of the Google School for Leaders, where I moved from preparing young women to lead to supporting women in the trenches. I was trained as an executive coach at the Hudson Institute and joined Cultivating Leadership, a global firm that teaches complexity fitness and adult development theory to corporate and nonprofit clients. In 2020, I began designing programs for male allies to serve as sponsors to women and other non-dominant groups. That’s when I fell in love with coaching men.

When I reached midlife, I hit a wall. The identity I had built — the speaker, the doer, the achiever — no longer felt like it fit. The drive that defined my success began to feel like a burden. Suddenly, my tools and beliefs began to fail me.

So I did something I’d never done before: I slowed down. I questioned everything I thought I knew about success, worthiness, and what it means to be enough.

I started to hear a voice that had been with me all along — not the voice of achievement, but of authenticity. Then I began to follow it. I journaled, sat with my fear and discomfort, and studied the psychology of midlife. I set small experiments in my relationships and work, imagining new ways of contributing and connecting – then made moves to bring them to life.

In depth psychology, this midlife moment is understood as a normal and necessary passage of individuation—becoming more fully yourself. Carl Jung described it not as a breakdown, but as a reorientation of meaning—when the structures that once organized identity begin to loosen so something more integrated can emerge.

I’ve spent decades listening closely to how people make sense of themselves, their ambition, and their place in the world. I built The Clearing because, after years of achievement, I couldn’t find language or support that reflected what I was actually going through.