Say the word ambition, especially around women, and it brings up a complicated mix of emotions and beliefs.

If you’re not succeeding, you’re not ambitious enough. If you are succeeding, wanting a lot, and going for it, you’re too ambitious, and you get penalized or punished. It happens at work, at home, and in the communities we move through every day.

There are so many mixed messages about ambition and success coming at us from every direction. And it’s not just imposed from the outside.

For many women, those messages get internalized and shape the way we present ourselves and communicate about our work and personal lives. We start to police our own ambition, and we police each other’s ambition.

My guest today names the invisible norms around women’s ambitions, and calls out the ways that organizations perpetuate bias, even as they think they’re playing fair. Her work is extensively researched, tracing the roots of the tension around ambition, and also offers language and an opportunity for us to reclaim our ambitions together.

Stefanie O’Connell is an award-winning journalist and author of The Ambition Penalty: How Corporate Culture Tells Women to Step Up– and Then Pushes Them Down. Her work dismantles the myths keeping women from equitable pay, leadership and power — one data point at a time. 

Listen to the full episode to hear:

• The material costs of what happens when women speak up, lean in, and get ambitious
• How implicit and gendered double standards around power keep women out of leadership
• Why encouraging ambition in girls doesn’t translate into celebrating ambition in women
• How people and organizations that believe they are meritocratic end up reinforcing the most bias
• Why we can’t self-optimize our way out of systemic inequality, and why we need collective action
• Six key elements for reframing burnout as an environmental problem, not a personal one
• Why we need to push back against framing women being pushed out of the work force as “empowerment” and challenge sexism in our everyday lives

Learn more about Stefanie O’Connell:

• Website
• Too Ambitious on Substack
• Instagram: @stefanieoconnell
• Threads: @stefanieoconnell
• TikTok: @stefaniemoconnell
• The Ambition Penalty

Learn more about Rebecca:

• rebeccaching.com
• Work With Rebecca
• The Unburdened Leader on Substack
• Sign up for the weekly Unburdened Leader Email

Resources:

• EP 155: Hidden Cost of Caretaking at Work: Nilofer Merchant on Invisible Norms Limiting Your Leadership
• Stop Punishing Women for Being Ambitious | Bloomberg
• Maslach, Christina. (1998). A Multidimensional Theory of Burnout. 10.1093/oso/9780198522799.003.0004. 
• My Mother’s Daughter: Finding Myself in My Family’s Fractured Past, Tracy Clark-Flory 
• Ragtime (2025 Broadway Cast Recording)
• Mad Men