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We’re not the lost generation. We’re the underestimated one. While the internet obsesses over Gen Z and glorifies Boomer dominance, Gen X remains the generation history keeps skipping. This show...
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We’re not the lost generation. We’re the underestimated one.
While the internet obsesses over Gen Z and glorifies Boomer dominance, Gen X remains the generation history keeps skipping. This show changes that.
Gen X Legends features real Gen Xers: coaches, creators, founders, executives, and reinvention artists who’ve outgrown the old playbook and designed careers worth living.
Forget the hype, the hustle-posting, and the midlife glow-up myth. This is the generation that weathered dot-com crashes, financial crises, and digital disruption without performative reinvention—and came out smarter, sharper, and still in motion.
We don’t chase virality. We design for longevity.
If you’re tired of the noise and hungry for honest, grounded, human wisdom…You’re in the right generation. And now, you’re on the right show.
show less
While the internet obsesses over Gen Z and glorifies Boomer dominance, Gen X remains the generation history keeps skipping. This show changes that.
Gen X Legends features real Gen Xers: coaches, creators, founders, executives, and reinvention artists who’ve outgrown the old playbook and designed careers worth living.
Forget the hype, the hustle-posting, and the midlife glow-up myth. This is the generation that weathered dot-com crashes, financial crises, and digital disruption without performative reinvention—and came out smarter, sharper, and still in motion.
We don’t chase virality. We design for longevity.
If you’re tired of the noise and hungry for honest, grounded, human wisdom…You’re in the right generation. And now, you’re on the right show.
Episodes & Posts
Episodes
Posts
Transcribed
16 JUN 2025 · Meetings are endless, your manager’s Slack tone feels like a personal attack, and quitting sounds like the only escape plan. But Gen Xers know better than to throw it all away without a backup parachute.
In this episode, executive coach and author of Red Cape Rescue, Darcy Eikenberg offers an alternative to resignation: reinvention from the inside. Drawing on years of coaching and a dose of neuroscience, she shares how to shift your mindset, rewrite your story, and reclaim your power—without updating your résumé.
For anyone who’s ever whispered “I can’t take this anymore” during a Zoom call, this is your comeback plan.
>>The Red Cape Isn’t a Costume—It’s Control
“When your shoulders go back and you feel in charge—that’s your red cape moment.”
Darcy reframes confidence as something you create, not something you wait for.
>>Your Brain’s Lying. Kindly Ignore It.
“Our lizard brain doesn’t know the difference between a tiger and a Slack ping.”
She unpacks how fear hijacks our workday—and what to do about it.
>>Change Starts with Three Levers
“We only control what we say, what we do, and what we think. That’s enough.”
Forget fixing your boss or your org chart—Darcy redirects attention to what is in your control.
>>The Jar Label Problem
“You can’t see the label from inside the jar.”
She offers a surprising exercise that helps you step out of your stories and into clarity.
>>Rescue Yourself Without Leaving the Company
“One client didn’t get the promotion. She didn’t quit. She spoke up—and now leads the agency.”
Darcy shares real-world examples of reinvention without walking away.
>>Fear Strategy Beats Fearlessness
“You don’t need to be brave. You need a plan.”
Instead of idolizing courage, she teaches how to prepare for fear when—not if—it shows up.
>>Burnout Is Not One-Size-Fits-All
“One person’s burnout is another person’s boredom.”
She closes with a reminder that self-awareness is the ultimate Gen X leadership edge.
_______________________
Connect with: https://www.linkedin.com/in/darcyeikenberg/
Transcribed
16 JUN 2025 · What happens when the company you’ve devoted half your life to suddenly disappears?
Benedikt Oehmen spent 17 years at Blizzard Entertainment, moving from gamer support to managing teams across seven languages. But when corporate priorities shifted and layoffs hit hard, he didn’t just walk away—he rebuilt.
In this episode, Benedikt shares how he turned a painful downsizing experience into a mission to help others, building a coaching practice and writing a book centered on his signature “Big Three” framework: Be Kind. Be Present. Be Open. It’s a mindset that’s not just for career survival—but for reinvention with soul.
>>From Gamer to Guide
“I thought I was taking a semester off from physics. It turned into a 17-year journey.”
Benedikt recounts how a student gig at Blizzard became a defining career. From player support to managing pan-European communities, he found joy in collaboration—and in building something that felt like family.
>>The Culture Shift No One Saw Coming
“We were all passionate. Then the merger changed everything.”
After Blizzard merged with Activision, the company’s soul began to shift—from people to profits. The once-collaborative culture gave way to numbers-first decision-making, culminating in layoffs that wiped out entire departments—and the community spirit with them.
>>When Family Gets Downsized
“We went from 10 community managers to one. It broke our hearts.”
Benedikt describes the emotional toll of watching his close-knit team vanish under corporate restructuring. But instead of retreating, he leaned into leadership—guiding others through the grief and uncertainty.
>>Coaching as a Way Forward
“I didn’t want to just survive—I wanted to help others do the same.”
The experience sparked something new: a desire to coach others through job loss and change. He pursued certification, built his practice, and found a new mission—supporting the “geeks and quiet warriors” navigating their own career crossroads.
>>The Big Three: Kind. Present. Open.
“Writing the book wasn’t the goal. Becoming an author was.
”His philosophy is simple but profound. Be kind—to yourself. Be present—in your journey. Be open—to what’s next. Whether coaching a client or finishing a book, Benedikt’s framework turns fear into forward momentum.
_______________________
Connect with: https://www.linkedin.com/in/benedikt-oehmen/
Transcribed
15 JUN 2025 · In the second half of his conversation, Collin Plume moves beyond financial products into financial legacy—sharing how Gen Xers can teach resilience, ownership, and critical thinking to the next generation. From diversifying income streams to protecting family futures with real assets, Collin reveals why wealth isn’t about a flashy portfolio—it’s about building something that lasts, even when systems shift.
For Gen Xers tired of flashy advice and ready to raise wiser, stronger humans, this episode delivers the quiet tools for lifelong financial independence.
>>Inflation, Instability, and the Fight for Financial Control
“Gold has kept up with the cost of living for over 150 years.”
Collin explains why owning tangible assets isn’t just smart investing—it’s a fight for personal freedom and future-proofing your life against system shocks.
>>Diversification Isn’t Optional Anymore
“The mistake isn’t just losing—it’s being stuck in one idea forever.”
He shares why today’s market demands diversified thinking, constant learning, and rejecting loyalty to any one asset class—including real estate.
>>Retirement Will Never Look the Same
“People aren’t retiring—they’re reworking life.”
Collin talks about the shifting realities of work, aging, and how side gigs, flexible income, and purpose-driven work are rewriting retirement for Gen X and beyond.
>>The Rise—and Risk—of Finfluencers
“Algorithms reward appeal, not expertise.”
He calls out the dangers of taking financial advice from unverified influencers, and why critical thinking is the real currency in today’s information economy.
>>Teaching Kids the Real Value of Money
“Experience and education over stuff.”
Collin shares how he’s raising his three kids to value assets over toys, experiences over things, and knowledge over hype—with gold and silver as real-world teaching tools.
__________________________
Connect with https://www.linkedin.com/in/collin-plume/
Transcribed
14 JUN 2025 · Collin Plume didn’t build Noble Gold to chase hype—he built it to restore trust in a system Gen X knows can break.
In this first of a two-part series, Collin shares how early lessons from insurance sales, real estate, and recession-era survival shaped his people-first approach to wealth building. He explains why real assets like gold and silver aren’t just investments—they’re anchors of ownership in a world increasingly built on debt and paper.
For Gen Xers who value resilience over rhetoric, and control over hype, this episode delivers the human side of financial security.
>>Learning the Hard Way
“Customer service wasn’t a department—it was survival.”
Collin reflects on early lessons selling insurance and real estate, where trust and loyalty mattered more than shiny marketing.
>>Why People Stay—and Why They Leave
“Employees don’t stay because of ping-pong tables. They stay because they’re seen.”
He shares how mentorship and genuine relationship-building shaped his leadership style at Noble Gold.
>>Selling Without the Sleaze
“I don’t care what you’re selling—if you don’t care about people, you lose.”
Collin talks about why prioritizing people over products isn’t soft—it’s the only strategy that survives downturns.
>>Precious Metals: The Ownership Play
“When everything else feels intangible, gold and silver are still yours.”
He explains why real assets like precious metals offer Gen Xers a hedge—not just against inflation, but against an unstable system.
>>Family, Fear, and Financial Freedom
“You’re not just buying an asset—you’re buying options.”
Collin connects gold ownership to a deeper human need: protecting family, future, and dignity through real, controllable wealth.
__________________________
Connect with https://www.linkedin.com/in/collin-plume/
Transcribed
13 JUN 2025 · 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 Wyseheart was never about building a high-growth company, but creating space for meaningful work in the next chapter of life.
>>Who Wyseheart 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 https://www.linkedin.com/in/waverlydeutsch/
Transcribed
13 JUN 2025 · 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 https://www.linkedin.com/in/waverlydeutsch/
Transcribed
12 JUN 2025 · Waverly Deutsch, the former Clinical Professor of Entrepreneurship at the Chicago Booth School of Business, didn’t follow a path—she composed one.
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 https://www.linkedin.com/in/waverlydeutsch/
Transcribed
11 JUN 2025 · 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 https://www.linkedin.com/in/jenniferselbylong/
Transcribed
11 JUN 2025 · 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 https://www.linkedin.com/in/jenniferselbylong/
Transcribed
10 JUN 2025 · 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 https://www.linkedin.com/in/jenniferselbylong/
We’re not the lost generation. We’re the underestimated one. While the internet obsesses over Gen Z and glorifies Boomer dominance, Gen X remains the generation history keeps skipping. This show...
show more
We’re not the lost generation. We’re the underestimated one.
While the internet obsesses over Gen Z and glorifies Boomer dominance, Gen X remains the generation history keeps skipping. This show changes that.
Gen X Legends features real Gen Xers: coaches, creators, founders, executives, and reinvention artists who’ve outgrown the old playbook and designed careers worth living.
Forget the hype, the hustle-posting, and the midlife glow-up myth. This is the generation that weathered dot-com crashes, financial crises, and digital disruption without performative reinvention—and came out smarter, sharper, and still in motion.
We don’t chase virality. We design for longevity.
If you’re tired of the noise and hungry for honest, grounded, human wisdom…You’re in the right generation. And now, you’re on the right show.
show less
While the internet obsesses over Gen Z and glorifies Boomer dominance, Gen X remains the generation history keeps skipping. This show changes that.
Gen X Legends features real Gen Xers: coaches, creators, founders, executives, and reinvention artists who’ve outgrown the old playbook and designed careers worth living.
Forget the hype, the hustle-posting, and the midlife glow-up myth. This is the generation that weathered dot-com crashes, financial crises, and digital disruption without performative reinvention—and came out smarter, sharper, and still in motion.
We don’t chase virality. We design for longevity.
If you’re tired of the noise and hungry for honest, grounded, human wisdom…You’re in the right generation. And now, you’re on the right show.
Information
| Author | Gen X Legends |
| Organization | Gen X Legends |
| Categories | Society & Culture , Personal Journals , Careers |
| Website | - |
| genxlegends2025@proton.me |
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