For nearly two decades, Bosky Mukherjee played the career game the way many high achievers are taught to: work hard, climb the ladder, and never leave without a backup plan.
She rose to the C-suite, became a company president, and built a reputation as the person who could always push through. But behind the success, her body was telling a very different story.
In this episode of Second Act, Bosky shares the moment she realized staying had become riskier than leaving, how a heartbreaking question from her young son changed everything, and why she finally walked away from corporate life with no next job lined up.
We talk about burnout, identity, women in leadership, the glass ceiling, sponsors vs. mentors, commercial fluency, and how Bosky built her second act as the founder of PM Dojo and She Trail Blazes.
This conversation is for anyone who has ever wondered:
What if the life I worked so hard to build is no longer the life I’m meant to live?
In this episode, we discuss:- The health scare that forced Bosky to stop and reassess her life
- Why high-achieving women often become “workhorses”
- The difference between work ethic and unhealthy proving
- Why women hit the glass ceiling
- Why mentors are not enough — and why sponsors matter
- What commercial fluency means for senior leaders
- How Bosky built a business without waiting for the perfect idea
- Why paid pilots matter more than praise
- How to start building optionality before you need it
If this episode resonates with you, subscribe to Second Act for more conversations about identity, reinvention, ambition, and life beyond the job title.
Chapters00:00 Can I leave?
00:38 Meet Bosky Mukherjee: From C-Suite to Second Act
01:09 When Staying Became Riskier Than Leaving
04:16 The Turning Point: Health and Family
04:41 The Workhorse Identity and the Cost of Proving Yourself
09:57 Bosky’s Mission to Help Women Break the Glass Ceiling
12:26 Why Women Hit the Glass Ceiling
16:15 Mindset, Strategy, and Letting the Right Balls Drop
18:36 Why Work Harder Stops Working: Sponsors, Influence, and Commercial Fluency
26:27 After the Health Scare: Choosing the Next Move
29:44 Building a Real Business: Paid Pilots, Storytelling, and Scrappiness
44:03 Advice for Anyone Considering Their Second Act
50:45 Future Aspirations and Personal Growth
About Bosky MukherjeeBosky Mukherjee is a founder, product executive, advisor, and coach helping women leaders and founders build influence, revenue, and optionality in a changing world of work.
She is the founder of PM Dojo and She Trailblazes, where she leads programs like Leadership Edge for senior women leaders and Founders Edge for women building revenue-generating businesses. Her work blends commercial fluency, storytelling, product strategy, and lived experience as a former C-suite leader, working mom, and immigrant.
Through her work, Bosky helps women break the glass ceiling — whether that means rising into bigger leadership roles or building a business of their own.
Links:
She Trailblazes:https://www.shetrailblazes.com/
LinkedIn:https://www.linkedin.com/in/bosky/
Tags: Second Act podcast, women in leadership, career reinvention, C-suite burnout, women founders, leaving corporate, commercial fluency, Bosky Mukherjee
