Risky Conversations with Jamie Lee
The Ingenious Ways Senior-Level Mothers Cope with the Intense Pressures of Corporate America with Journalist Shalene Gupta and Executive Coach Jamie Lee
Jun 18, 2026
Episode 128
What happens when the pressures of work intensify AND parenting intensifies at the same time? Senior-level mothers are caught in a two-way trap—and many are quietly burning out, believing it's a personal failure rather than a systemic one.
In this episode, I talk with Shalene Gupta, staff editor at Fast Company, about her groundbreaking investigation into how senior-level women are coping with the impossible. After putting out a call on LinkedIn, Shalene received over 100 responses—48,000 words' worth—revealing both the ingenuity and the despair of working mothers trying to have it all.
Discover the creative solutions that are actually working: job-sharing arrangements that have lasted 13 years, radical transparency about boundaries that builds trust, and companies (like Cakes) that are redesigning the workplace from the ground up. But also understand why these individual hacks aren't enough—and why the real answer requires systemic change.
If you're a working parent, an ambitious woman in corporate America, or someone who wants to understand what's really happening behind closed doors, this is a conversation you need to hear. Because as Shalene says: "It's not you. The system is broken. And it can be redesigned."
Featuring:
SHALENE GUPTA BIO:
Shalene Gupta is a staff editor at Fast Company covering work life and leadership. Her investigative journalism on women, work, and wellness has appeared in The Atlantic, Fortune, Harvard Business Review, ESPN The Magazine, and TIME. She is co-author of The Power of Trust and author of The Cycle: Confronting the Pain of Periods and PMDD. Shalene holds an MS from Columbia Journalism School, a BA in creative writing and psychology from Johns Hopkins University, and is a Fulbright grant recipient. Her work focuses on the systemic barriers women face in corporate America—from motherhood to menopause—and the creative solutions women are building to survive (and thrive) in broken systems.
Connect with Shalene on LinkedIn: https://www.linkedin.com/in/shalenegupta/
Connect with Jamie on LinkedIn: https://www.linkedin.com/in/leejieunjamie/
Text me your thoughts on this episode!
Enjoy the show?
Connect with me
- Book a free hour-long consultation with me. You'll leave with your custom blueprint to confidence, and we'll ensure it's a slam-dunk fit for you before you commit to working with me 1:1.
- Connect with me on LinkedIn
- Email me at jamie@jamieleecoach.com