Push Pull Podcast

Varun Rajan
  • 5.0 (2)
  • CAREERS

Interviewing successful professionals about what drove their career transitions

  1. Beyond Resumes: Helen Huang on identity, what AI can't answer, and building Trove

    MAY 20

    Beyond Resumes: Helen Huang on identity, what AI can't answer, and building Trove

    Helen Huang on Trove, Behavioral Identity, and Building an Authentic Life in the Age of AI On today’s episode, we speak to Helen Huang, a product leader and two-time founder building Trove, a “behavioral identity layer” that helps people understand and represent themselves through what they do rather than what they say. Helen recounts immigrating from China to Canada, studying earth science at Waterloo, pivoting into product roles at Zynga, Microsoft, and GitHub, then bootstrapping edtech company CoLab to seven figures while graduating 2,500+ learners before taking a 2024–2025 gap year to learn AI and explore playful experiments (including a garbage-bag fashion show). She describes Trove’s interactive story “Tangles,” early traction and intense user responses, and her aim to invert typical AI use: AI prompts us, and we supply instinctive answers. All while fundraising and hiring a founding team! 00:00 Show Mission Shift 00:48 Meet Helen and Trove 02:38 Reconnecting and Background 06:05 Earth Science to Tech Pivot 08:14 800 Applications and Resume Limits 10:28 PM Lessons to Founder Leap 14:55 Building CoLab and Scaling Education 18:19 AI Hype and Learning Friction 24:59 Gap Year Doubts and Rediscovery 28:01 Garbage Bag Fashion Show 28:26 Immersive Fashion World 29:44 Fun Over Goals 31:48 Civic Tech Detour 34:11 Finding Trove Mission 35:46 What Trove Is 37:54 Actions Reveal Identity 39:58 Early Drops And Metrics 41:59 Real Life Impact Stories 44:47 What Comes Next 46:25 AI Prompts Us 49:36 Use Cases And Ethics 52:51 Closing Reflections

    56 min
  2. Building Change Capacity: Jillian Reilly on creating a permission-rich culture and staying optimistic (pt 2)

    MAY 13

    Building Change Capacity: Jillian Reilly on creating a permission-rich culture and staying optimistic (pt 2)

    Building Change Capacity: Jillian Reilly on Permission, Automation, and Portfolio Careers Earlier this year, I interviewed Jillian Reilly, author of The Ten Permissions: Redefining the Rules of Adulting for the 21st Century about why people change (or don’t). And how “permission” and agency shape behavior more than resources, training, or workshops. In part two of my conversation with Jillian Reilly, we talk about why “change management” often becomes performative and why real transformation depends on building ongoing capacity for change. She describes her role as a catalyst who creates conditions for teams to have hard, honest conversations, run experiments, and rebuild trust, emphasizing that leaders must explicitly allow disagreement and learning rather than rely on one-time programs. We discuss how automation will replace repeatable “corporate cog” work and increase the value of human adaptability, critical thinking, and innovation.  Jillian frames the current era as an “unraveling” of old social and career scripts and a “renaissance” of choice that requires agency rooted in clear-eyed optimism. She offers practical career guidance: design flexibility early, think in portfolios (“I can” vs. “I am”), build temporary/project-based value like a DJ reading the room, and experiment without dopamine-chasing by matching focus to one’s current season. 00:00 Change Management Trap 01:17 Consultant as Catalyst 05:19 Permission Over Performance 09:26 Building Change Capacity 11:00 Automation Ends Cogs 12:48 Unraveling and Renaissance 21:10 Optimism Creates Agency 27:15 Reclaim Local Control 28:21 Designing Flexible Careers 31:47 Portfolio Skills Mindset 35:14 Build Temporary Projects 40:57 You Already Know This 45:11 Experimentation Versus Dopamine 51:41 Closing Takeaways

    53 min
  3. Giving Yourself Permission: Jillian Reilly on trusting your gut and foregoing regret (pt 1)

    MAY 6

    Giving Yourself Permission: Jillian Reilly on trusting your gut and foregoing regret (pt 1)

    Earlier this year, I interviewed Jillian Reilly, author of "The Ten Permissions: Redefining the Rules of Adulting for the 21st Century," about why people change (or don’t). And how “permission” and agency shape behavior more than resources, training, or workshops. She recounts leaving a prescribed path and law school plans to go to South Africa during the of apartheid, followed by two decades in international aid across Africa. During that time, she led an HIV/AIDS program in Zimbabwe, where she saw how cultural and safety constraints make “novel choices” dangerous. She describes disillusionment with the kind of change driven by funding incentives, moving into consulting, and later prioritizing motherhood despite career trade-offs. We explore the ideas of permission, conviction over certainty, experimentation, avoiding regret through intentional choice, and building “permission-rich” environments in villages and boardrooms alike. 00:00 Why Permission Matters 00:17 Meet Jillian Reilly 01:59 Ten Permissions Explained 04:53 Leaving the Midwest Script 08:11 Aid Work Lessons 10:03 Zimbabwe and Permission 13:32 Agency and Modern Careers 17:46 Moving to South Africa 22:33 Conviction Over Certainty 24:02 Feel Your Way Forward 27:05 Transition to Consulting 27:28 Aid Work Disillusionment 29:39 Spending Versus Impact 31:52 Leaving the Dream Job 36:09 Consulting as Truth Teller 36:55 Permission and Change 41:12 Motherhood and Tradeoffs 46:33 No Regrets Framework 50:57 Returning Through Experiments 53:22 Frontiers and Explorers Way 55:50 Closing Reflections and Tease

    58 min
  4. On Trust: How dishonesty derails the Job Search and the Industry at large

    APR 29

    On Trust: How dishonesty derails the Job Search and the Industry at large

    The Trust Tax: Reframing Your Story and AI Layoff Narratives Today I unpack a LinkedIn post about declining trust in ourselves and each other, showing how it appears in job searches and in how companies explain AI-driven change. Drawing on Stephen M.R. Covey’s The Speed of Trust, I argue trust is has a tangible impact across our careers and the broader economy. I share a coaching conversation I had with an ops professional moving toward data analysis who calls his interview narrative “spin,” and reframed it as honest conviction and initiative rather than performance, linking this to Covey’s first “wave” of trust: self-trust as the foundation for relationship and organizational trust. I also critique companies spinning layoffs as AI-driven when they often reflect pandemic overhiring, warning that spin breeds cynicism and slows real adoption. 00:00 The Big Idea 00:55 Trust as Economic Force 01:50 Coaching Story Spin vs Reframe 04:49 Self Trust Comes First 05:40 Layoffs and the AI Narrative 07:29 Low Trust Tax at Work 08:36 Five Waves of Trust 10:31 Culture Leaks to Customers 11:49 Conviction Over Certainty 12:37 Closing and How to Reach Me

    13 min
  5. Empathy at Scale: James Warren on the benefits of emotional archeology (pt 2)

    APR 22

    Empathy at Scale: James Warren on the benefits of emotional archeology (pt 2)

    Empathy at Scale: James Warren on Building SEEQ, Trust, and the Emotional Data Behind Work This week, we continue our conversation with James Warren, who left a successful corporate career and built Share More Stories (SMS) alongside an investor/partner through a decade-long, sometimes exhausting dual-company arrangement that required relinquishing control, building trust, and personal growth. James explains SMS’s evolution from storytelling workshops into SEEQ, a productized platform that captures employee and customer stories and analyzes emotions to reveal the “why” behind metrics like NPS and engagement scores. After launching in late 2022, the company faced market re-education in 2023, gained momentum in 2024, and is now scaling with added generative-AI capabilities such as SEEQ GPT for rapid, high-context analysis. He describes how leaders must model healthy vulnerability, and shares a case where employee and customer trust curves mirrored, linking employee experience to customer experience. The host closes by reflecting on SEEQ as infrastructure for measuring an organization’s emotional layer. 00:00 Part Two Setup 01:40 Arranged Marriage Partnership 02:56 Letting Go Of Control 06:25 Two Businesses One Gearshift 07:43 Startup Hiring Build Mode 08:53 Going Full Time SMS 10:03 Being Early In Market 11:05 SMS Origins And Pivots 12:45 Workshops To Tech Breakthrough 15:06 First Big Pitch And API Demo 18:49 Launching SEEQ And Reeducation 23:29 Empathy At Scale Value 26:08 What Stories Reveal At Work 29:11 Psychological Safety Signals 30:05 Facilitating Live Storytelling 30:49 The Magic Moment 32:39 Leaders Embrace Vulnerability 35:18 Asking Better Questions 37:03 Selling Employee Experience Value 40:41 Trust Links EX and CX 45:01 Emotional Archeology 47:06 SEEQ GPT Breakthrough 53:56 Advice For Feeling Stuck 57:26 Trust Reflection Outro

    1 hr
  6. The Road to the Right Work: James Warren on storytelling and entrepreneurship (pt 1)

    APR 15

    The Road to the Right Work: James Warren on storytelling and entrepreneurship (pt 1)

    We kick off Season 2 of the Push-Pull Podcast, we widen the lens from career transitions to how people build durable careers amid rapid change. In this episode, I interview James Warren, founder and CEO of Share More Stories, who is a storyteller committed to helping organizations understand their employees’ and customers’ experiences. James recounts early storytelling and entrepreneurial interests, studying at Princeton before transferring to Columbia for creative writing, and learning persistence through rigorous workshops. After marrying young, he entered corporate roles at MetLife and then Altria, where self-advocacy and mentorship fueled moves from communications to brand/marketing to sales, revealing shifting generational expectations about “job hopping.” He eventually left Altria with a package to pursue entrepreneurship, describing a difficult first year, early failed ventures and a failed crowdfunding campaign, and a pivotal partnership that provided the material and experiential resources to build Share More Stories. 00:00 Season Two Mission 00:50 Building Durable Careers 02:24 Meet James Warren 04:19 James Today Snapshot 05:14 Early Storytelling Roots 07:41 Writing Path to Columbia 09:59 Pressure Intuition Pivots 15:07 First Corporate Breaks 18:48 Altria Growth and Moves 23:52 Jump to Brand and Sales 29:53 Sales Role Reality Check 31:50 Resentment In The Field 32:26 Work With Lunch Lesson 33:42 Reorgs And Returning HQ 35:40 Choosing To Leave Corporate 37:19 First Year Entrepreneur Reality 39:36 Origins Of Share More Stories 45:32 Crowdfunding Failure Wakeup 47:31 Mentors And Finding Ken 51:48 Partner Deal And New Runway 53:10 Host Reflection And Wrap

    56 min

  7. SEASON 2 TRAILER

    Empower Yourself: Announcing Season 2

    Announcing Season 2 of the Push Pull Podcast. In the world of rapidly evolving AI tools, and the expectations and market disruptions that come with them, ignore the losers trying to scare you. Find what matters to you and be the champion of your own story.

    5 min

  8. 08/27/2025

    Season One Reflections and Reset

    The past few weeks I soft-launched a hiatus, and today I'm making it official. Keep your eyes peeled for Season 2 of the Push Pull Podcast!

    4 min
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About

Interviewing successful professionals about what drove their career transitions

Information

  • Creator
    Varun Rajan
  • Years Active
    2025 - 2026
  • Episodes
    29
  • Rating
    Explicit
  • Copyright
    © 2026 Push Pull Podcast
  • Show Website
    Push Pull Podcast