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?

• 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.

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

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

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.

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

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.

• 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

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

Tightknit — https://tightknit.ai

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