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

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

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

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

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.

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!

Today we revisit a couple of “near misses” — where a combination of solid preparation and luck led my guests to thrive or pivot quickly in the face of turmoil in their organizations.

Omar Dinar discusses joining Lehman at the onset of the financial crisis, and the impact of the bank's bankruptcy on his career. Being in the real estate division allowed him participation in the acquisition negotiations by Barclays where he excelled for a solid portion of his career.

We then revisit our discussion with Annalyn Cruz, at the point where she had years of advising university students under her belt. At a crossroads, she made the tough call to take a pay cut to go into Learning and Development when she had the option to move to a Director-level role. This choice didn’t save her from impending layoffs, but future-proofed her resume to work in corporate spaces.

00:00 Introduction to the MBA Journey
00:25 Landing the Dream Job at Lehman Brothers
02:04 The Financial Crisis Unfolds
02:57 Experiencing Lehman's Collapse
08:07 Transition to Barclays
08:32 A New Path: Semester at Sea
09:49 Pivot to Learning and Development
12:04 Challenges and Growth in L&D
18:03 Final Reflections and Career Transition

Navigating the Ups and Downs: From Consulting to Startups and Facing Burnout

Today I revist discussions where my guests faced significant adversity in their work lives. 

Shalini Chander talks about pivoting to the startup world — and while she gained valuable industry knowledge, the experience was marred by financial instability and unethical practices by the company's founder. This difficult stint was followed by a brief period at another startup focused on diabetes care, where funding issues led to job instability. Ultimately, the she found stability at Abbott, successfully pivoting to Product Management for the rest of her career. 

Marshall Robins was a tech Account Executive. In his last couple of companies in this role, he encountered high-pressure environments driven by venture capital expectations and an economic downturn. He understood the importance of taking a step back from his career and getting meaningful rest when he was driven to burnout.

00:00 Shalini Leaving Consulting and Joining a Startup
00:57 Red Flags and Financial Instability
03:29 Lessons Learned and Moving On
05:57 Transition to Diabetes Startup
08:35 Marshall’s Burnout and Career Reflections

In this episode I continue my conversation with Dr. Jess Mendoza, cognitive psychologist and UX researcher. Upon wrapping up Dr. Mendoza's transition from academia to UX research, we explore her efforts building community within her new company, and her advocacy for AI literacy across the org. Jess shares insights on the role of critical thinking and communication in prompting, the importance of a supportive work environment for pursuing side projects, and the unique challenges faced by different groups in the job market. You’ll hear Jess emphasize the value of fostering human connections at work and give solid advice for navigating career switches.

00:00 Introduction and Recap
00:46 Shifting Gears: Current Workplace Dynamics
01:03 AI in the Workplace
02:51 Building Community and Support Networks
27:35 Navigating Career Challenges
31:38 Final Thoughts and Shoutouts
35:36 Conclusion and Reflections

Today I interview Dr. Jess Mendoza, a cognitive psychologist turned UX researcher. Dr. Mendoza shares her inspiring story of being a first-generation college student, pursuing a doctorate, and eventually transitioning into the tech industry. We explore her academic journey, including conducting social experiments and presenting research globally, to making the leap to user experience. Key topics include the emotional challenges of moving away from family, the impact of community and networking, and the importance of persistence and curiosity in navigating career transitions. Jess also highlights the value of feedback and networking in successfully pivoting careers. 

00:00 Introduction to the Push Pull Podcast
01:30 Meet Dr. Jess Mendoza: From Academia to UX
02:09 Jess's Early Life and Education
03:20 Discovering a Passion for Research
07:59 The Journey to Graduate School
11:49 Life and Challenges in Graduate School
19:54 Exploring Opportunities Beyond Academia
25:31 Navigating Online Security for Kids
26:31 Developing Educational Curriculums
27:39 From Grad School to Career Decisions
29:13 Discovering UX Research
30:03 The Grad School Dissertation
33:49 Networking and Career Pivot
38:48 Landing the First UX Job
44:49 Adapting to the Corporate World
49:02 Conclusion and Next Steps