Second Act: Lives Beyond the Job Title

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 lifeWhy high-achieving women often become “workhorses”The difference between work ethic and unhealthy provingWhy women hit the glass ceilingWhy mentors are not enough — and why sponsors matterWhat commercial fluency means for senior leadersHow Bosky built a business without waiting for the perfect ideaWhy paid pilots matter more than praiseHow to start building optionality before you need itIf 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 Act01:09 When Staying Became Riskier Than Leaving04:16 The Turning Point: Health and Family04:41 The Workhorse Identity and the Cost of Proving Yourself09:57 Bosky’s Mission to Help Women Break the Glass Ceiling12:26 Why Women Hit the Glass Ceiling16:15 Mindset, Strategy, and Letting the Right Balls Drop18:36 Why Work Harder Stops Working: Sponsors, Influence, and Commercial Fluency26:27 After the Health Scare: Choosing the Next Move29:44 Building a Real Business: Paid Pilots, Storytelling, and Scrappiness44:03 Advice for Anyone Considering Their Second Act50:45 Future Aspirations and Personal GrowthAbout 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

In this episode of Second Act, Zach Hawtof shares his journey from Salesforce to building Tightknit — and the deliberate decisions that led him there.Instead of jumping straight into a startup, Zach chose to first move to a smaller company to get closer to customers, product, and the realities of building. What followed was a journey that was far less polished — and far more real — than most startup stories you hear.We talk about what it actually takes to start from scratch: the messiness, the uncertainty, the early chaos, and the moments that make it all worth it.If you’ve ever thought about leaving a “safe” path to build something of your own, this conversation will give you a grounded, honest look at what that really means.🎯 Key TopicsZach’s journey from Salesforce to building TightknitWhy he deliberately moved to a smaller company before startingThe reality of startup life: why it’s always messyWhy you don’t need to be a genius to build a companyThe importance of talking to customers early and oftenWhy handshakes beat scale in the early daysThe case for starting with services before building a productEarly struggles: side hustles, financial trade-offs, and uncertaintyThe first customer moment — before anything was readyWhy founders should chase problems, not ideas⏱️ Timestamps00:00 - Introduction: Choosing building over the safe path00:32 - From developer to PM to founder01:02 - What Tightknit does01:37 - Early days at Salesforce02:41 - Discovering Slack and community building04:14 - The idea behind Tightknit05:13 - Finding the right co-founder06:39 - Why it gets harder to leave big companies09:47 - Making the move toward entrepreneurship09:55 - The first startup idea that didn’t work11:53 - First customer chaos (before onboarding existed)12:46 - Why handshakes beat scale early14:07 - Service-first validation15:17 - Surviving financially in the early days17:48 - The moments that made it worth it20:03 - The reality of startup life22:30 - When everything breaks23:52 - Managing time as a founder25:22 - Building community beyond the product26:41 - Rethinking traditional planning frameworks28:37 - How AI changed the game30:48 - Features customers actually value32:18 - Why Slack is the center of work33:50 - Advice: Chase problems, not ideas35:52 - Zach’s vision for Tightknit🔗 Resources & LinksTightknit — https://tightknit.aiLinkedin https://www.linkedin.com/in/zhawtof/

After years as a product leader in tech, Fabrice found himself at an unexpected crossroads: a layoff.Instead of searching for another tech role, he took a risk he’d quietly dreamed about for years — starting a food business centered around traditional French butter cookies.In this episode, we unpack:How he evaluated financial and emotional risk before making the leapThe surprising economics of running a food businessWhy his first product wasn’t his final productThe power of marketing and storytelling in building demandHow AI tools now power everything from operations to contentWhat it really means to “fail fast” outside of techThis is a story about identity, reinvention, and courage — about choosing passion without abandoning discipline.If you’re navigating your own second act, this conversation will resonate deeply.Keywords: entrepreneurship, food startup, product launch, AI in business, marketing strategy, startup journey, business pivot, personal growth