#339 Jennifer Selby Long: Gen X Wisdom for Saboteur Survival

In this final installment, Gen X executive coach Jennifer Selby Long goes deep on the real decision behind office politics: should you stay or should you go? Drawing from decades of experience guiding leaders through complex change, she lays out the subtle dynamics that determine whether a culture is salvageable—or just stuck. From the hidden toll of hybrid models to bosses who subtly push out high performers, Jennifer offers tools for cutting through confusion. And with a memorable framework inspired by civil rights leader Clarence Jones, she helps listeners evaluate not just what they want—but whether the system they’re in will ever let them have it. For Gen Xers caught in the gray area between loyalty and realism, this episode offers clarity with no illusions.>>Why Toxic Cultures Repeat“People leave a bad boss… only to land in a similar situation.”Jennifer explains how unaddressed internal patterns can reappear in new jobs—and what to do before making another move.>>Hybrid Work, Hidden Agendas“If your team isn’t working together in person, politics won’t disappear—they’ll just change form.”She discusses the tradeoffs of hybrid workplaces and how physical distance can mask, not eliminate, power struggles.>>When the Best Performers Leave“I’ve seen bosses quietly engineer ways to push out brilliant people.”Jennifer and Vince unpack the dynamic where insecurity—not excellence—shapes who gets to stay.>>Conflict is Not the Enemy“Most people waste time fighting battles that could’ve been solved with a conversation.”She breaks down how conflict-avoidance fuels politics—and why stepping back to understand styles and misalignment is essential.>>Clarence Jones’ Test for Staying or Leaving“You won’t prevail unless the powerful majority sees that what you want is in their interest.”Jennifer shares hard-earned political wisdom: how to evaluate whether your values and goals can survive the system—or if it’s time to walk._________________________Connect with us:Host: Vince Chan | Guest: Jennifer Selby Long  --Chief Change Officer--Change Ambitiously. Outgrow Yourself.Open a World of Expansive Human Intelligencefor Transformation Gurus, Black Sheep,Unsung Visionaries & Bold Hearts.EdTech Leadership Awards 2025 Finalist.15 Million+ All-Time Downloads.80+ Countries Reached Daily.Global Top 3% Podcast.Top 10 US Business.Top 1 US Careers.>>>150,000+ are outgrowing. Act Today.<<<

In this third installment with Gen X executive coach Jennifer Selby Long, we zoom in on one of the messiest, most misunderstood realities of modern work: office politics. Jennifer breaks down why politics often stem less from individual egos and more from structural dysfunction, emotional disconnection, and leadership blind spots—especially in hybrid teams. She explains how outdated views of leadership, chronic misalignment, and even cost-cutting decisions like slashed T&E budgets can quietly poison team trust. But this isn’t just a takedown—Jennifer arms listeners with a real-world playbook to navigate power struggles without becoming part of the problem. For seasoned professionals tired of performative team building and empty culture talk, this episode reframes politics not as inevitable—but as solvable.>>Politics ≠ Power-Hungry People“The majority of leaders are not political animals.”Jennifer challenges the stereotype that all office politics are about ego—revealing how misaligned strategy and trust gaps often create dysfunction.>>Remote Work’s Invisible Cost“You might not feel like getting on that plane… but complex decisions require in-person time.”She explains how budget cuts, virtual distance, and hybrid habits are quietly damaging team cohesion.>>Toxic by Design“I’ve worked with clients who were pretty mercenary at first… but some became the most dedicated leaders.”What happens when cold-blooded management isn’t an accident—but a strategy?>>Five Moves to Navigate a Political Culture“Stop venting. Start observing.”Jennifer offers a practical five-step approach to surviving—and even reshaping—a political workplace, starting with curiosity, not complaints.>>Why Some People Don’t Struggle with Politics at All“There’s a portion of the population just wired to be unbothered by it.”From temperament to neural wiring, she explains why some Gen Xers are naturally equipped to handle the drama without burnout._________________________Connect with us:Host: Vince Chan | Guest: Jennifer Selby Long  --Chief Change Officer--Change Ambitiously. Outgrow Yourself.Open a World of Expansive Human Intelligencefor Transformation Gurus, Black Sheep,Unsung Visionaries & Bold Hearts.EdTech Leadership Awards 2025 Finalist.15 Million+ All-Time Downloads.80+ Countries Reached Daily.Global Top 3% Podcast.Top 10 US Business.Top 1 US Careers.>>>150,000+ are outgrowing. Act Today.<<<

Jennifer Selby Long is no stranger to messy transformations. With three decades of experience in executive coaching, digital change, and tech leadership, she helps seasoned professionals navigate the personal minefield that comes with professional change. In this second installment, Jennifer dives deep into neuroscience-backed insights on why we sabotage ourselves—and how to stop. She breaks down how our brains are wired for fear, how to spot the voice of the “judge,” and how misplaced loyalty to bad bosses or toxic companies keeps people stuck. But she doesn’t stop at analysis—she arms Gen Xers with tactical empathy, reframing techniques, and political savvy to make their next move smarter. Because in a world where everyone’s changing, the winners aren’t the loudest—they’re the most self-aware.>>The Science of Self-Sabotage“Those negative voices? They’re not you. They’re old neural pathways—and you don’t have to obey them.”Jennifer explains how childhood-formed saboteurs derail adult decision-making—and what to do about it.>>How Judgment Blocks Reinvention“If you’re judging yourself or others, the judge neural network is in charge—and it’s contagious.”Learn how to spot the “inner judge” sabotaging your growth and weaken its grip before it wrecks your next chapter.>>Escape the Bad Boss Loop“Most people don’t leave bad bosses—they recreate them.”Jennifer outlines five traps professionals fall into when trying to escape toxic leadership—and how to break the cycle for good.>>Office Politics Without Selling Your Soul“You’re not imagining it—some power games are real. But empathy is your best defense.”From defensive email habits to managing power dynamics with grace, Jennifer offers non-sleazy tactics for Gen X leaders navigating messy org charts.>>Redefining What ‘Winning’ Looks Like“Change that sticks often doesn’t look like the win you planned—but it’s the win you needed.”A fresh lens on how to reframe wins, even if they come in smaller, slower, or stranger packages than you expected._________________________Connect with us:Host: Vince Chan | Guest: Jennifer Selby Long  --Chief Change Officer--Change Ambitiously. Outgrow Yourself.Open a World of Expansive Human Intelligencefor Transformation Gurus, Black Sheep,Unsung Visionaries & Bold Hearts.EdTech Leadership Awards 2025 Finalist.15 Million+ All-Time Downloads.80+ Countries Reached Daily.Global Top 3% Podcast.Top 10 US Business.Top 1 US Careers.>>>150,000+ are outgrowing. Act Today.<<<

Jennifer Selby Long has spent 30 years helping leaders navigate change—long before “change management” became a buzzword. In this episode, the Gen X executive coach reflects on how she stumbled into her calling during the early days of IT transformation, and why emotional intelligence—not just operational efficiency—is what drives successful digital change. Drawing from her own career pivots and coaching experiences, Jennifer explains how change must be mastered on a personal level before it can be led across an organization. For Gen Xers who’ve seen multiple waves of tech disruption and economic downturns, her story reminds us: experience isn’t old news—it’s the operating system for modern leadership.>>The Accidental Change Manager“I became an accidental change manager in the early 90s.”Jennifer shares how a basic IT training request exposed a deeper problem—one that launched her decades-long journey into change leadership.>>Coaching Tech Leaders Through the Chaos“We help leaders win at change.”From digital transformation to cybersecurity to user experience, Jennifer explains why leadership—not just management—is the biggest missing link in most change initiatives.>>A Gen X Career Rooted in Both People and Process“I kept trying to do stable things, but the change kept coming at me.”She describes how she went from resisting change to becoming its strategic champion—shaped by trial, error, and real-world messiness.>>The Power of Performance Psychology“Coaches aren’t therapists. They’re here to help you win.”Her earliest coaching experience came from a sports psychologist—and that mindset still guides how she supports high performers today.>>Understanding the Natural Process of Personal Change“There are three stages: endings, transition, and new beginnings.”Jennifer walks us through Bill Bridges’ model of change—and how leaders often forget their teams are still at the beginning when they’ve already moved on._________________________Connect with us:Host: Vince Chan | Guest: Jennifer Selby Long  --Chief Change Officer--Change Ambitiously. Outgrow Yourself.Open a World of Expansive Human Intelligencefor Transformation Gurus, Black Sheep,Unsung Visionaries & Bold Hearts.EdTech Leadership Awards 2025 Finalist.15 Million+ All-Time Downloads.80+ Countries Reached Daily.Global Top 3% Podcast.Top 10 US Business.Top 1 US Careers.>>>150,000+ are outgrowing. Act Today.<<<

In Part 3, Waverly Deutsch steps into her latest role: founder of Wyseheart, a coaching firm designed to help the most overlooked founders build ventures that last. Focused on meaningful business, not unicorn exits, she brings her full career of coaching, teaching, and hard-won insight to early-stage leaders across age, gender, race, and identity. For Gen Xers who aren’t ready to “retire,” this is a playbook for doing your best work—on your terms, with your values, and no need for external approval.>>What Retirement Really Means to Her“Retirement means you no longer have to work to cover basic necessities… but you work because you want to.”Waverly explains why Wiseheart was never about building a high-growth company, but creating space for meaningful work in the next chapter of life.>>Who Wiseheart Is Really For“I might have a session with you and turn you down as a client.”She describes her ideal clients: early-stage founders with strong ideas and potential—but she’s selective, because she coaches from belief, not obligation.>>Opening Access Where Systems Don’t“I want to make myself available to people who don’t always have access to someone like me.”Waverly shares how Wiseheart is designed to serve women, BIPOC, LGBTQ+, rural, and underestimated founders who often face systemic barriers.>>LGBTQ+ Advocacy Through Data and Action“You can ask: do you choose to publicly identify as an LGBTQ+ founder?”She calls out the data gap and cultural risks still facing LGBTQ+ entrepreneurs—and how her work with StartOut aims to help change that.>>Advising Older Entrepreneurs With Realism“You may have to go back to the work that got you there.”She offers grounded advice to Gen X and Baby Boomer entrepreneurs who face ageism and cost-cutting—and encourages them to translate wisdom into flexible, consulting-based careers._________________________Connect with Us:Host: Vince Chan | Guest: Waverly Deutsch  --Chief Change Officer--Change Ambitiously. Outgrow Yourself.Open a World of Expansive Human Intelligencefor Transformation Gurus, Black Sheep,Unsung Visionaries & Bold Hearts.EdTech Leadership Awards 2025 Finalist.15 Million+ All-Time Downloads.80+ Countries Reached Daily.Global Top 3% Podcast.Top 10 US Business.Top 1 US Careers.>>>150,000+ are outgrowing. Act Today.<<<

In Part 2, Waverly Deutsch opens up about her decades at Chicago Booth, where she helped founders refine not just their business models but their ability to lead. She discusses how emotional connection strengthens logic, why confident delivery isn’t enough, and how AI is changing but not replacing human insight. For Gen Xers mentoring across generations or rethinking their own leadership, this episode is a reminder: great guidance begins with deep listening.>>Coaching Across the Confidence Spectrum“Some people came in over-confident. Some barely made eye contact.”She explains how coaching required tailoring—not templating—entrepreneurs’ thinking.>>Why Love Belongs in Leadership“If you can’t connect with your idea, why should anyone else?”Waverly talks about the human element most founders overlook when presenting.>>Building Trust Across Generations“EMBAs bring wisdom. Undergrads bring fire.”She shares the challenge—and joy—of coaching both seasoned execs and young dreamers.>>Relearning Her Own Leadership“Coaching taught me how much I still had to unlearn.”She reflects on what working with thousands of students revealed about her own blind spots.>>AI Is Here—Now What?“AI can write your pitch. But can it build your conviction?”She discusses how tech is changing communication—and why human trust still drives every great pitch._________________________Connect with Us:Host: Vince Chan | Guest: Waverly Deutsch  --Chief Change Officer--Change Ambitiously. Outgrow Yourself.Open a World of Expansive Human Intelligencefor Transformation Gurus, Black Sheep,Unsung Visionaries & Bold Hearts.EdTech Leadership Awards 2025 Finalist.15 Million+ All-Time Downloads.80+ Countries Reached Daily.Global Top 3% Podcast.Top 10 US Business.Top 1 US Careers.>>>150,000+ are outgrowing. Act Today.<<<

We meet Waverly Deutsch not as a Chicago Booth professor or coach for entrepreneurs, but as a real human navigating career decisions in a world that often asks us to pick between passion and practicality. From falling in love with theater to entering computer science as one of only three women in a class of 30, Waverly’s story is one of blending head and heart across every career twist. She shares the real story behind leaving academia for Forrester Research, breaking down in a meeting and still making her case, and learning how to navigate gut instinct and logic without losing either. For Gen Xers raised on rules, she shows what it means to rewrite your own—with emotional truth and strategic clarity.>>Two Majors, One Mindset“I ended up with two majors—one in theater and one in computer science.”Waverly explains how her early passions—performance and programming—formed a lifelong blend of emotion and logic.>>Early Outsider, Early Awareness“There were three or four women in a class of 30.”She shares what it was like being one of the only women in computer science, and how that shaped her views on identity and acceptance.>>Teaching as a Lifelong Thread“I knew that what I wanted to do was teach. That was truly my calling.”From undergrad to her PhD in theater history, teaching remained her throughline—even as industries changed.>>Forrester and the First Real Pivot“I was employee number 27.”She tells the story of joining Forrester Research during its startup phase, helping it scale through the internet boom, and falling in love with entrepreneurship.>>The Crying Meeting“George, I can cry and think at the same time.”Waverly recounts the pivotal moment when she stopped hiding her emotions at work—and started integrating her whole self into how she leads._________________________Connect with Us:Host: Vince Chan | Guest: Waverly Deutsch  --Chief Change Officer--Change Ambitiously. Outgrow Yourself.Open a World of Expansive Human Intelligencefor Transformation Gurus, Black Sheep,Unsung Visionaries & Bold Hearts.EdTech Leadership Awards 2025 Finalist.15 Million+ All-Time Downloads.80+ Countries Reached Daily.Global Top 3% Podcast.Top 10 US Business.Top 1 US Careers.>>>150,000+ are outgrowing. Act Today.<<<

Dominic Carter, CEO of the Carter Group, shares how a personal frustration with his aging parents’ care became a long-term mission: building real, user-driven aging tech in one of the world’s oldest—and most demanding—markets. From human-centric research to venture studio development, Dominic shows how Gen Xers can lead the future of aging by solving the problems we’re all going to face. This isn’t just eldercare innovation—it’s preemptive, practical system design. For those over 50 building what comes next, this episode is a field guide to action rooted in empathy, not hype.>>From Personal Wake-Up Call to Business Blueprint“I wanted better options for my parents—and for myself one day.”Dominic shares how watching his parents’ struggle with aging became the catalyst for a venture into real, human-first aging innovation.>>Aging Tech Isn’t Just for the Elderly“Aging begins at 50—and the opportunity starts there.”He reframes aged tech not as a niche, but as a massive, underserved market hiding in plain sight.>>Start with the User—or Don’t Start at All“If you don’t listen, you’ll waste time, money, and trust.”Dominic explains why most aging tech fails: founders fall in love with ideas, not problems—and skip the hard part: listening.>>Culture Is More Than Geography“The cultural gap between 55 and 75 is as wide as the one between Japan and the West.”He unpacks why aging solutions must be co-designed with users—and adapted not just to national cultures, but age-based subcultures.>>Building Credibility One Win at a Time“Get the use case. Prove the value. Then scale.”Dominic outlines his venture studio strategy—prioritizing two user-validated products (a friction-reducing linen set and a wearable tremor device) to establish proof before expansion.______________________Connect with us:Host: Vince Chan | Guests: Dominic Carter  --Chief Change Officer--Change Ambitiously. Outgrow Yourself.Open a World of Expansive Human Intelligencefor Transformation Gurus, Black Sheep,Unsung Visionaries & Bold Hearts.EdTech Leadership Awards 2025 Finalist.15 Million+ All-Time Downloads.80+ Countries Reached Daily.Global Top 3% Podcast.Top 10 US Business.Top 1 US Careers.>>>150,000+ are outgrowing. Act Today.<<<

Dominic Carter, the CEO of the Carter Group, didn’t become an aging tech founder by chasing trends—he got there by building slowly, listening deeply, and surviving the kind of early burnout that forces reinvention. In Part 1, he shares how moving to Japan, launching businesses, and failing hard shaped the systems-thinking approach that now powers his work on aging innovation. This isn’t a startup story—it’s a Gen X blueprint: steady, lived, built from purpose long before it had a name.>>Leaving, Burning Out, Coming Back“I opened a Tokyo office at 24—and broke myself in the process.”Dominic talks about how early success nearly ruined him, and why walking away was the start of everything good that followed.>>A Life Rebuilt Through Listening“Research made me better—not just at business, but at understanding people.”He shares how market research and consulting sharpened his ability to listen deeply and solve real problems over time.>>No Pivot. Just Evolution.“Every business I built grew from the one before it.”Dominic explains how his work in research, media, and software wasn’t a series of pivots—it was a slow, deliberate build toward relevance.>>Staying in Japan by Choice“I could’ve gone home—but Japan became the place I wanted to change from.”He reflects on the emotional pull of Japan and how the country’s demographic trajectory mirrored something deeper he was starting to feel.>>When Profit Isn’t the Point“I’ve never been obsessed with money. I’ve been obsessed with meaning.”Dominic explains why mission-aligned work—not exits—has always been his driver, even if it meant a longer, less glamorous path.______________________Connect with us:Host: Vince Chan | Guests: Dominic Carter  --Chief Change Officer--Change Ambitiously. Outgrow Yourself.Open a World of Expansive Human Intelligencefor Transformation Gurus, Black Sheep,Unsung Visionaries & Bold Hearts.EdTech Leadership Awards 2025 Finalist.15 Million+ All-Time Downloads.80+ Countries Reached Daily.Global Top 3% Podcast.Top 10 US Business.Top 1 US Careers.>>>150,000+ are outgrowing. Act Today.<<<

This episode offers you $79 worth of value—completely free. Read till the end for the gift.In Part 2, Kevin introduces the core ideas behind his latest book, Flexible Leadership. He explains why leading isn’t about finding the perfect style—it’s about flexing based on the situation without abandoning your principles. We break down how intention, context, and flexors all work together, why rigid leadership labels backfire, and why the best leaders never stop adjusting how they show up.Key Highlights of Our Interview:Why Human Nature Hasn’t Changed“The tools have changed. People haven’t.”Start with Intention“Flexibility doesn’t mean random. It means choosing your leadership moves on purpose.”Context Is Everything“If you don’t read the situation right, no style will save you.”Flexors, Not Labels“You’re not just a ‘visionary’ or a ‘coach.’ Labels can help, but they can also trap.”Compliance vs. Commitment“Sometimes you need quick compliance. Sometimes you need lasting commitment. Know what you’re asking for.”____________________________Connect with us:Host: Vince Chan | Guest: Kevin Eikenberry>>>Your $79 free gift is here for you to accept -- not a scam, it's a personal gift from Kevin to you.  --Chief Change Officer--Change Ambitiously. Outgrow Yourself.Open a World of Expansive Human Intelligencefor Transformation Gurus, Black Sheep,Unsung Visionaries & Bold Hearts.EdTech Leadership Awards 2025 Finalist.15 Million+ All-Time Downloads.80+ Countries Reached Daily.Global Top 3% Podcast.Top 10 US Business.Top 1 US Careers.>>>150,000+ are outgrowing. Act Today.<<<