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Second Act: Lives Beyond the Job Title

Second Act: Lives Beyond the Job Title

By: Gayathri Geetha
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Second Act: Lives Beyond the Job Title

Sometimes the next level isn’t higher — it’s wider.

What if the life you worked so hard to build isn’t the final form of who you’re meant to become?

You can earn the title. Lead the team. Hit the milestone.
And still feel a quiet pull toward something more — not instead of your success, but beyond it.

Second Act is a podcast for high-performing, mid-career professionals who are expanding their identity without abandoning what they’ve built.

Each episode traces the real arc of a second act: the internal shift, the first imperfect move, the tradeoffs and constraints, the craft behind the work, and the tools or teams that made growth possible. We end with grounded insights for those ready to widen their own path.

This isn’t about quitting.
It’s about range.

If you’ve ever thought, “Is this it?” — this conversation is for you.

2026 Gayathri Geetha
Career Success Economics Leadership Management & Leadership
Episodes
  • She Left the C-Suite With No Backup Plan | Bosky Mukherjee on Burnout, Power & Reinvention
    May 26 2026

    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.

    Chapters

    00:00 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 Mukherjee

    Bosky 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

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    52 mins
  • Keep the Job, Build the Art: Cielo De La Paz’s Second Act
    May 9 2026

    What if you didn’t have to quit your job to build a deeply creative life?

    In this episode of Second Act: Life Beyond the Job Title, I sit down with Cielo De La Paz — UX leader at YouTube, photographer, filmmaker, educator, and creator — to talk about what it really means to build a creative second act while keeping a full-time career.

    Cielo shares the story behind her photo being featured in Apple’s Shot on iPhone campaign, what happened when she tried to take photography full-time, and why she eventually realized that not every passion needs to become a business. We also talk about imposter syndrome, building a YouTube channel, teaching what you know, using AI tools as a creator, and why your job can sometimes be the “angel investor” for your art.

    This conversation is for anyone with a creative dream, a side project, or a quiet part of themselves they are ready to take more seriously.

    Chapters

    00:00 Cold Open: Photography as Art vs. Business
    01:12 Meet Cielo: UX Leader, Photographer, Creator
    01:45 The Red Umbrella Photo That Went Global
    04:15 Becoming a Creator and Facing the Camera
    05:38 Imposter Syndrome and Sharing Your Work
    07:28 What Happened When She Tried Photography Full-Time
    10:48 Building a Course Business — Then Walking Away
    14:06 Your Job Can Be the Angel Investor for Your Art
    15:19 How to Create While Working Full-Time
    18:03 AI Tools and the Future of Creation
    22:00 Finding Community Through Art
    24:12 Long-Term Goals and Aspirations in Art
    26:17 A Bridge, Not a Leap
    28:32 Is YouTube Too Saturated?
    29:52 Why Being Multi-Hyphenate Is an Advantage

    Tags: Second Act, creative career, career reinvention, side hustle, creator economy, YouTube creator, photography, AI tools, creative life, multi-hyphenate, personal brand, imposter syndrome, UX leader, women in tech, career and creativity, passion project, creative entrepreneurship, art and work, building in public, life beyond the job title, Cielo De La Paz

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    31 mins
  • From Salesforce PM to Startup Founder: Zach Hawtof’s Second Act
    Mar 25 2026

    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 Topics
    • Zach’s journey from Salesforce to building Tightknit
    • Why he deliberately moved to a smaller company before starting
    • The reality of startup life: why it’s always messy
    • Why you don’t need to be a genius to build a company
    • The importance of talking to customers early and often
    • Why handshakes beat scale in the early days
    • The case for starting with services before building a product
    • Early struggles: side hustles, financial trade-offs, and uncertainty
    • The first customer moment — before anything was ready
    • Why founders should chase problems, not ideas
    ⏱️ Timestamps

    00:00 - Introduction: Choosing building over the safe path
    00:32 - From developer to PM to founder
    01:02 - What Tightknit does
    01:37 - Early days at Salesforce
    02:41 - Discovering Slack and community building
    04:14 - The idea behind Tightknit
    05:13 - Finding the right co-founder
    06:39 - Why it gets harder to leave big companies
    09:47 - Making the move toward entrepreneurship
    09:55 - The first startup idea that didn’t work
    11:53 - First customer chaos (before onboarding existed)
    12:46 - Why handshakes beat scale early
    14:07 - Service-first validation
    15:17 - Surviving financially in the early days
    17:48 - The moments that made it worth it
    20:03 - The reality of startup life
    22:30 - When everything breaks
    23:52 - Managing time as a founder
    25:22 - Building community beyond the product
    26:41 - Rethinking traditional planning frameworks
    28:37 - How AI changed the game
    30:48 - Features customers actually value
    32:18 - Why Slack is the center of work
    33:50 - Advice: Chase problems, not ideas
    35:52 - Zach’s vision for Tightknit

    🔗 Resources & Links

    Tightknit — https://tightknit.ai

    Linkedin https://www.linkedin.com/in/zhawtof/

    Show More Show Less
    37 mins
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