Are generational divides in the workplace and in life driving you crazy?
The Gen Mess with Tess is here to help! Hosted by Tess Brigham—certified coach, licensed therapist, TEDx speaker, author, and mom to a Gen Zer—this podcast tackles the challenges and complexities of navigating life and work across multiple generations. From the unique struggles of Gen Z to the evolving perspectives of Millennials, Gen X, and Baby Boomers, Tess brings her expertise to the table, offering practical advice, expert insights, and real conversations to bridge the generational gap. Whether you're trying to communicate better with colleagues, understand your kids, or just get a clearer perspective on the "mess" of it all, The Gen Mess with Tess is your go-to resource for understanding how different generations think, work, and live.
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Are generational divides in the workplace and in life driving you crazy?
The Gen Mess with Tess is here to help! Hosted by Tess Brigham—certified coach, licensed therapist, TEDx speaker, author, and mom to a Gen Zer—this podcast tackles the challenges and complexities of navigating life and work across multiple generations. From the unique struggles of Gen Z to the evolving perspectives of Millennials, Gen X, and Baby Boomers, Tess brings her expertise to the table, offering practical advice, expert insights, and real conversations to bridge the generational gap. Whether you're trying to communicate better with colleagues, understand your kids, or just get a clearer perspective on the "mess" of it all, The Gen Mess with Tess is your go-to resource for understanding how different generations think, work, and live.
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What if finding your dream job actually takes a year—or even longer?
In this eye-opening episode of "Gen Mess with Tess," host Tess Brigham sits down with career strategist Liz Helton to pull back the curtain on the realities of job searching and career transformation in today's ever-evolving workforce. If you've ever wondered why sending off hundreds of applications can feel like shouting into a void, this episode will reveal why—and most importantly, what you can do about it.
Together, Tess Brigham and Liz Helton dig into:
You’ll learn practical tips for standing out in a crowded applicant pool, making LinkedIn work for you, and reframing both rejection and uncertainty as essential steps toward meaningful work. Plus, Liz Helton shares her own journey from PR exec to career consultant, and why sometimes your superpower is that thing that feels as natural as breathing.
If you feel stuck, overwhelmed, or unsure about your next step—no matter your age—this heartfelt, actionable episode is for you.
Episode Overview with Timestamps:
Tune in to discover why you’re not alone in your career mess—and how you can thrive in it.
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What if the brutal truth is that your corporate job is more likely to slowly kill you with stress than set you up for a dream retirement?
In this episode of Gen Mess with Tess, host Tess Brigham sits down with powerhouse business mentor, international speaker, and award-winning author Katrena Friel for a candid and eye-opening conversation about breaking free from the golden handcuffs—and finding your true value.
Katrena Friel pulls back the curtain on her own journey, from teenage jobs and personal heartbreak to a devastating $30,000 scam—a turning point that sparked her to build her own thriving training and mentoring practice. Together, she and Tess Brigham dissect why so many Gen Xers are “quietly quitting” or burning out, how younger generations are refusing to repeat the cycle of debt and overwork, and why we need to rethink the way we approach careers, money, and even family living.
Key highlights include:
Loaded with tangible advice, real talk, and a bit of industry myth-busting, this episode will make you rethink everything you thought you knew about career success, purpose, and what it takes to build a legacy—on your terms.
Episode Overview by Timestamp:
Tune in for an episode packed with hard truths, practical strategies, and inspiration to reinvent work and life—no matter your generation!
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What if the secret to building a thriving law firm wasn’t about grinding out endless billable hours—but about rethinking the entire way attorneys work and lead?
In this eye-opening episode of Gen Mess With Tess, host Tess Brigham welcomes law firm growth expert Alay Yajnik for a candid conversation that shakes up everything you thought you knew about legal hustle and business success.
Discover how Alay Yajnik pivoted from running multimillion-dollar Silicon Valley companies to coaching attorneys—and why most lawyers stumble when it comes to building a lasting, profitable business. You’ll learn why working harder doesn’t always mean earning more, and how breaking out of traditional law firm mindsets—from hourly billing to team management and rate setting—is the real game-changer.
Key episode highlights:
Whether you lead a law firm, run a small business, or just want to understand how generational perspectives are upending the way we work, this episode is loaded with actionable insights and relatable stories.
Episode Overview:
Tune in for an episode that’s more than just law—it’s about building the future of work, one honest conversation at a time.
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What if the only way you could escape your toxic work environment was being hit by a bus—not to die, but just to get a break?
Shocking as it sounds, that’s the level of desperation bestselling author and executive coach Diana Lowe once felt, and she’s not alone. In this riveting episode of "Jen Mess with Tess," Tess Brigham pulls back the curtain on the hidden emotional toll of modern workplaces and the true meaning behind being “hard to handle.”
Join Tess Brigham as she sits down with Diana Lowe—author of "Hard to Handle"—for a raw, honest conversation about surviving abusive bosses, how ‘difficult’ is just a matter of perspective, and why clinical depression became a turning point for radical career reinvention. Together, they untangle how we can learn to live in the mess of work (and life) and find purpose where others might only see crisis.
Key highlights include:
If you’ve ever felt misunderstood at work, frustrated with your boss, or questioned your place in the corporate ladder—this episode will not only validate your experience but give you practical wisdom on how to lead (and live) with more awareness and empathy.
Episode Overview
Don’t miss this episode’s honest, no-fluff take on surviving—and thriving—in the workplace chaos.
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What if everything we thought was “wrong” with Gen Z was actually the outcome of generations striving to do better for their children?
In this solo episode of Gen Mess with Tess, host Tess Brigham turns the tables on common complaints about today’s youth and boldly reveals how every “mess” in the workplace and at home is really generational evolution in real time—and a sign of remarkable progress.
Drawing deeply from her own life as a Gen Xer, therapist, and parent to a Gen Z son, Tess Brigham unpacks the hidden links between generational values, shifting parenting philosophies, and the transformation of work and life. She discusses the evolution from silent survivalists, boomers’ pursuit of success, to Gen X’s badge of independence—and how each generation has tried to heal the wounds of the last, often by swinging the pendulum in new directions.
Key highlights from this episode:
By the end of the episode, you’ll see generational “mess” through a new lens—one of ongoing evolution, empathy, and hope.
Timestamped Episode Overview:
Ready to witness how generational messiness is actually a story of hope and healing? Press play.
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What if you could overcome a lifelong fear—like a spider phobia—in under ten minutes?
In this episode of "Gen Mess with Tess," host Tess Brigham sits down with Viki Johnston, founder of Accelerate and master practitioner of NLP (neuro linguistic programming), for a fascinating deep-dive into the secrets of learning, growth mindset, and generational shifts in the workplace.
Viki reveals how she conquered her extreme fear of spiders on stage using powerful NLP techniques, sparking a new obsession with the method that now impacts her work coaching managers and teams for light bulb moments of transformation. Together, Tess Brigham and Viki Johnston break down why learning should be fun (not serious!), the dramatic differences NLP can make versus traditional therapy, and how “aha” moments propel people to lasting change.
The episode unpacks what separates good managers from great leaders—hint: it’s more than delegation—and explores the unique challenges (and superpowers) that new Gen Z and millennial managers are bringing to today's workplace. From using AI and ChatGPT for instant answers to balancing remote work and real-life teamwork,
Viki Johnston shares practical strategies for thriving across generations and cleaning up the “Gen Mess.”
Tune in for relatable stories, actionable insights, and a fresh perspective on why letting go of old habits (and sometimes, just saying "I don't know") can be a game-changer for growth—at any stage of your career.
Episode Highlights & Overview:
Whether you’re a new manager, parent, or lifelong learner, this episode will help you see challenges in a whole new way—and maybe even tackle that fear you thought would last forever.
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What if every time you judged a younger generation for having it "easy," you were really just grieving your own unmet dreams?
In this revealing solo episode of Gen Mess with Tess, host Tess Brigham turns the generational blame game upside down, making a powerful case that beneath every eye-roll and stereotype—Boomers are out of touch, Gen Z is fragile, Millennials are entitled—there’s a shared experience of grief. From nostalgic bitterness to deep-seated anxieties, Tess explores how each generation clings to the belief that their struggles had meaning, while often resenting the freedoms and boundaries claimed by those coming after.
Drawing on pop culture examples, workplace trends, and even the existential challenge of AI, Tess dissects why the world feels so tense, how each generation is coping with constant uncertainty, and what it truly means to evolve—not just as a society, but as individuals learning to let go. In a candid reflection on her own journey and those of her clients, Tess challenges listeners to see generational progress as an invitation to heal and redefine purpose, rather than a competition over who "had it worst."
Tune in for thoughtful insights, practical strategies, and an honest invitation to make peace with change—because maybe the real legacy isn’t just the pain we survived, but the wisdom we share.
Episode Overview & Timestamps:
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What if the secret to surviving career chaos isn’t more hustle—but smarter engineering?
In this eye-opening episode of Gen Mess with Tess, host Tess Brigham sits down with systems architect and organizational consultant Belle Walker, who reveals why most companies—and leaders—are fighting the wrong fires, and how “engineering thinking” can fundamentally change how we navigate the messiest parts of work and life.
Belle shares her unusual journey from a family of engineers to stage management and humanities, and ultimately, to designing scalable, human-centered organizational systems. She explains how her approach blends classic problem-solving with deep empathy—translating abstract chaos into actionable clarity. Belle and Tess dig into why the real friction in organizations isn’t just between people, but between the functions and systems behind them, and how leaders often overlook the root causes of workplace tension.
Key highlights include:
Tune in to uncover actionable strategies for bridging generational gaps, managing energy, and architecting workplace solutions that really work—plus, hear Belle’s take on parenting, the myth of innate genius, and her foolproof method for separating noise from necessity.
Episode Overview:
00:00 – Podcast intro & meet Belle Walker: organizational chaos vs. blueprints
00:04 – Belle’s origin story: engineering family, humanities leanings, Google, and finding the love of “building systems”
00:10 – What is engineering thinking? Problem setup vs. pure math
00:15 – Real-life chaos: Maps, autonomous vehicles, and the importance of communication
00:20 – Managing today’s workplace noise & energy budgets—satellites, commutes, and training
00:28 – Generational perspectives: Gen Z, Millennials ask for what they want, impacts on work culture
00:34 – AI’s impact on organizational jobs—pitfalls and policy mistakes
00:40 – Why leaders miss functional friction (security vs. usability, quick fixes vs. lasting change)
00:44 – Change takes time—why it always feels faster in hindsight
00:46 – Elder Millennials, COVID parenting, work-life transformations
00:52 – How to actually “clean up” the generational mess: leverage strengths, address gaps, solve the right problems
00:56 – Belle’s plug for her Friction to Function newsletter
00:57 – Tess wraps up: the power of problem-solving, empathy, and learning to live in the “mess”
Ready to see your workplace (and maybe your whole life) through a new lens? Hit play and join Tess and Belle as they engineer the way out of the Gen Mess!
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What if the real badge of honor isn’t how hard you work, but how well you rest?
In this eye-opening solo episode of Gen Mess with Tess, host Tess Brigham pulls back the curtain on the cultural obsession with burnout—and exposes how every generation has unwittingly contributed to making exhaustion seem like a symbol of strength. Tess traces the roots of hustle culture from Gen X’s independent “latchkey kid” mentality, through Millennials’ overachievement during the Girl Boss era, and lands on Gen Z’s radical redefinition of ambition and mental health.
You’ll learn why each generation internalized burnout a little differently, why Millennials became the “burnout generation”, and how Gen Z’s refusal to conflate self-worth with overwork is shaking up workplaces everywhere. Plus, Tess opens up about her own journey to unlearn burnout and offers clarity on how we can collectively move toward a more sustainable, joyful way of living and working.
Key Highlights:
Ready to question everything you’ve believed about ambition, success, and rest? Tune in and discover why taking off the burnout badge might be the most rebellious—and freeing—move you’ll ever make.
Episode Overview with Timestamps:
00:00:01 – Podcast introduction and the generational divide
00:01:09 – How burnout became a badge of honor and generational differences
00:02:40 – Gen X’s origin story and attitude toward burnout
00:04:11 – Millennials, hustle culture, and the Girl Boss era
00:08:21 – Gen Z’s boundary-setting and work-life philosophy
00:11:10 – Tess’s approach to cleaning up “Gen mess” at organizations
00:12:56 – The grief and resentment beneath generational tension
00:14:19 – Gen Z’s impact on workplace culture
00:15:16 – Why exhaustion became a measure of excellence
00:16:20 – How workplaces promote burnout and reward dysfunction
00:18:55 – Steps to unlearning burnout and redefining success
00:20:58 – Closing thoughts and embracing grace over grit
00:22:19 – How to connect with Tess Brigham and continue the conversation
Subscribe to Gen Mess with Tess for more insights and strategies on bridging generational gaps and building workplaces where everyone thrives!
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What if your quest for love is actually a quest for safety?
In this eye-opening solo episode of "Gen Mess with Tess," host Tess Brigham dives deep into the messy reality behind the hit TV show Love is Blind—and reveals the uncomfortable truth: the show isn’t just a high-drama dating experiment, it's a mirror reflecting how we all perform, protect, and hide in our own relationships.
Tess explores why so many of us crave genuine connection but run from vulnerability, and how the performative world of swiping, texting, and social media shapes our fears of rejection and being truly seen. She breaks down unforgettable examples from Love is Blind—from avoiding tough conversations to sabotaging intimacy—and connects these moments to universal patterns we all share.
Key highlights include:
If you’ve ever caught yourself performing instead of connecting, or wondered why intimacy can feel so terrifying, Tess’s honest reflections and actionable tips will help you see your own patterns, and maybe, just maybe, get braver.
Timestamped Overview:
Ready to turn the spotlight back on yourself? Hit play and start making sense of your own emotional mess!
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What if the secret to unlocking true leadership isn’t about knowing all the answers, but about learning to ask the right questions—especially across generations?
In this eye-opening episode of the “Gen Mess with Tess,” host Tess Brigham sits down with powerhouse executive coach Kristi Royse, founder of KLR Consulting, to uncover the real challenges—and unexpected opportunities—leaders face in today’s rapidly shifting workplace. You might be surprised to learn that the biggest workplace problem isn’t generational conflict, but something much sneakier: ignorance and a reluctance to adapt.
Tess and Kristi pull back the curtain on why leadership has changed so drastically since Kristi’s early Boston Market days—from command-and-control to flexible, empathic management. Together, they slice through stereotypes about “lazy” young workers and stubborn older bosses, revealing why every generation falls into the trap of judging the next—and how that holds companies back from monumental growth and innovation.
Key highlights from this episode include:
Whether you’re a CEO, manager, or early-career professional, this episode will challenge your assumptions and equip you with practical tips to create a healthier, more connected, and future-ready workplace. Get ready to make sense of the generational “mess”... and maybe even learn to thrive in it.
Timestamped Episode Overview:
00:01 – Tess introduces Kristi Royse and her extensive leadership background
01:13 – Kristi shares her origin story: from Boston Market COO to leadership consultant
02:25 – Night-and-day differences in leadership then and now
03:34 – The complex realities of leading five generations at once
06:01 – Tess and Kristi discuss fear, assumptions, and resistance to change among leaders
08:25 – Generational stereotypes: Why every young cohort gets accused of being “lazy”
09:48 – Coaching leaders to communicate and collaborate across generational divides
11:02 – The pitfalls of promoting technical stars to management without support
12:54 – Case study: Transforming engineers at Strava into people leaders
14:09 – Gen Z and the new meaning of work-life blend
15:26 – Building trust: How real conversations and vulnerability build stronger teams
18:00 – Younger vs. older generations: What key assumptions are holding us back?
20:17 – How to invest in employees—even if you fear they might leave
22:03 – Simple, actionable ways managers can support every direct report
23:27 – Overcoming resistance: Why the “it’s too much work” excuse falls flat
26:28 – Kristi on the greatest workplace struggle: ignorance and culture clashes
29:30 – Coaching, courage, and patience: The real keys to personal and company growth
40:02 – Doing meaningful work: When passion and purpose trump the paycheck
43:52 – Kristi’s positive spin: The generational “mess” is actually the best opportunity of our time
47:49 – Where to find Kristi’s work & resources for leaders ready to do better
Listen in and discover how you can turn generational tension into your organization’s biggest asset!
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What if the greatest barrier to your success isn’t the world outside—but the silent story you keep telling yourself inside your own head?
In this compelling episode of Gen Mess with Tess, host Tess Brigham sits down with Dr. Ashok Bhattacharya, psychiatrist and founder of The Empathy Clinic, to explore why empathy isn’t just a “soft skill”—it’s the invisible glue shaping our relationships, workplaces, and personal growth. Dr. Bhattacharya reveals how early life experiences and powerful moments (sometimes as tiny as a single comment from a grade school teacher) can shape the narratives that define—and sometimes limit—us for decades.
Together, Tess and Dr. Bhattacharya dig deep into how we can unravel unhelpful stories, challenge survival-mode thinking, and truly transform how we connect with ourselves and each other. They break down the real difference between empathy, compassion, and kindness, and explain why even a little bit of genuine empathy can make or break a relationship, a workplace, or even your own self-worth.
Key highlights you’ll discover in this episode:
If you’re curious about how to actually practice empathy (not just talk about it), handle disagreement gracefully, or help your team, family, or yourself thrive in a messy, ever-changing world, this episode is packed with actionable wisdom and heartfelt stories.
Timestamps Overview:
00:00 – Intro: The generational “mess” & Tess’s mission
00:31 – Dr. Ashok Bhattacharya’s origin story & why empathy matters
04:40 – How the stories we tell ourselves can cripple us
07:04 – Why falling down (in skating…or life) is harder to process than you think
10:16 – The amplified pressures of today’s tech-driven world for the younger generation
12:39 – Practice, failure, and shame: Why young people get “stuck”
14:40 – What empathy, compassion, and kindness actually are
16:28 – The real challenge of empathy and “getting out of your head”
19:46 – Can you be empathic with people you disagree with?
23:03 – Tess’s therapy work: The invisible ripple effect of empathy
26:57 – “Soft skills” and how small moments shape lives
31:16 – The privilege of being “with” someone as a therapist
32:37 – Why bridging generational divides requires empathy
34:59 – How generations value and practice empathy differently
39:08 – Practical steps for leaders and teams to actively use empathy
42:07 – Why “a little empathy goes a long way” in the workplace
44:08 – Empathy as a proactive force for productivity and trust
45:54 – Where to find Dr. Bhattacharya + his books on empathy and burnout
48:33 – The secret power of reciprocal empathy in couples
49:13 – Outro: Embracing the mess and learning to live in it
Listen in—and discover how empathy isn’t a luxury. It’s your greatest tool for navigating the messiness of modern life.
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What if the American Dream your parents promised you was nothing but a myth? What if the payoff for all your hard work simply… never arrives?
In this eye-opening episode of the Gen Mess with Tess, host Tess Brigham sits down with writer, podcaster, and former writing professor Amye Archer to pull back the curtain on generational work myths, shifting values, and what’s really happening as Gen Xers raise Gen Z kids in a world that looks nothing like the one they inherited.
Key Highlights:
Whether you’re wondering how to deal with your Gen Z coworkers, trying to understand your kids, or facing your own career pivot, this episode is a must-listen for anyone ready to finally make sense of the generational mess—and maybe even be inspired by it.
Episode Overview:
00:00 – Introductions & Pop Culture Blindspots: Gen X vs Gen Z
01:16 – Work, Creativity & Gen X Disillusionment
04:09 – Gen Z’s Bargaining Power at Work
06:06 – Parenting Styles Then and Now
10:56 – Mental Health, Communication & Anxiety in Kids
11:20 – Building a Podcast Career Outside the Traditional Path
12:52 – How Writing, Creativity, & Therapy Fuel Podcasting
15:00 – Why Amye Started Little Miss Recap & Murder She Watched
16:13 – Leaving Academia and Lessons from Career Pivots
18:27 – Working With a Spouse in the Podcasting World
19:33 – Surprises in Raising Gen Z Daughters
23:42 – Gen Z, World Issues & Climate Anxiety
25:23 – Gen Z and Money, Work-Life Balance, and Defining Success
26:58 – Gen X, Boomers, and the Vanishing American Dream
29:14 – Advice Gaps: Why “Old” Solutions Don’t Fit New Problems
31:09 – Why Professors (and Managers) Are Burned Out
33:27 – What Gen Z Has Taught Gen X About Self-Respect and Boundaries
35:25 – Parental Concerns: Coddling vs. Independence
38:39 – The Importance of Modeling and Letting Kids Fail
40:13 – Advice for Managing Gen Z at Work
41:58 – Why Work Should Focus on Output, Not Hours
43:11 – The Need for Personal Connection in the Modern Workplace
45:14 – Wrapping Up & Amye’s Podcast Plugs
Press play to discover how to stop fixing the mess—and start living in it.
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What if the secret to skyrocketing your company’s profits isn’t better tech, but happier employees?
In this episode of Gen Mess With Tess, host Tess Brigham sits down with powerhouse people & culture leader Jessica Holst (SpaceX, CAA, Mattel, Verve) to pull back the curtain on why traditional HR practices—and even today’s obsession with AI—are missing the real leverage point for business success: the emotional well-being and engagement of your team.
Jessica reveals why most companies are completely underestimating how much empowering employees (instead of controlling them) transforms productivity, innovation, and the bottom line. Through compelling stories from Hollywood’s notorious agency world to surprising data on what actually drives performance, Jessica and Tess dive into:
If you’re a business owner, manager, future leader, or anyone struggling with workplace “mess”—don’t miss this deep, frank, and refreshingly actionable conversation. You’ll walk away with new strategies (and maybe a few hard truths) for bridging generational divides, unlocking creativity, and making your company a magnet for talent.
Episode Overview
Tune in for an episode that just might change the way you think about work—and how to make it work better, for everyone.
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What if the biggest problem with your writing isn’t your grammar or structure—but the way you think?
In this eye-opening episode of Gen Mess with Tess, host Tess Brigham sits down with her personal writing coach, Brian Morgan, founder of Think Deeply, Write Clearly, to reveal the transformative link between writing, thinking, and the human condition. Get ready to reconsider everything you thought you knew about creativity, communication, and the very process of making sense of the world.
Brian shares his unconventional journey from struggling actor to billion-dollar report editor, ultimately landing as a leading expert in sense-making through writing. Together, Tess and Brian dive into:
Whether you’re a business leader, educator, or someone wanting to bridge the generational communication gap, this episode is packed with vulnerable stories, tough truths, and actionable takeaways for thriving in the modern world—mess and all.
Timestamped Overview:
00:00 – Tess introduces the Gen Mess with Tess and welcomes Brian Morgan
00:01 – Brian’s background: From acting to editing billion-dollar contracts to writing coaching
00:07 – Are artists really after creative mastery or just fame?
00:14 – What acting teaches about observation, sense-making, and writing
00:17 – Why most writing “problems” are actually thinking problems
00:22 – The danger of conclusions without sense-making frameworks; politics and business examples
00:29 – Is it our individual job to make sense of the world? Stories of self-reflection, failure, and growth
00:43 – The crisis in education: Why today’s students struggle with thinking and writing (COVID-19’s impact and beyond)
00:50 – Rapid fire: Brian’s top writing/communication tip you can use right now
00:53 – Free resource: How to join Brian’s 90-day prolific writing program
Listen, reflect, and discover how you can clean up your own “gen mess”—one clear thought at a time.
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What if the American Dream was never really meant for everyone? And what if today’s younger generations are reinventing it into something healthier and more meaningful?
In this thought-provoking solo episode, Tess Brigham dives headfirst into the messy legacy of the American Dream—exposing who it really served, how it shaped generations, and why Gen Z and Millennials are outgrowing the old rules. Tess peels back the glossy myth of "work hard and you’ll have it all," uncovering the hidden realities of racial, gender, and economic exclusion. Through personal anecdotes, cultural observations (from Bake Sale Betty to Barbie to Mad Men), and data-driven insights, Tess reveals how younger generations are rewriting the dream: prioritizing enough over excess, values over grind, and happiness over hustle.
Tune in to discover:
If you’ve ever wondered why “kids these days” have different aspirations—or if you’re struggling with your own feelings about work and self-worth—this episode will help you see the American Dream in a whole new light.
Timestamps:
Subscribe for more real talk with Tess Brigham, or visit tessbrigham.com to learn how Tess can help your organization thrive across generations!
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What if the secret to true influence is saying “no” more often than saying “yes”?
In this eye-opening episode of Gen Mess with Tess, host Tess Brigham sits down with Brad Hoos—CEO of The Outloud Group and founder of Musk Ox—to unravel the myths and realities behind the influencer industry, generational shifts at work, and what it really takes to lead with authenticity.
Brad didn’t set out to become an influencer marketing expert—in fact, he’s a self-described “recovering engineer” and ex-management consultant. But after an unlikely twist in his career, Brad now leads an agency representing top creators on YouTube, TikTok, and beyond. Together, Tess and Brad dig deep into:
Plus, Tess and Brad open up about parenting across generations, living in the chaotic mess of life, and what today’s rising leaders are getting right (and wrong) about carving their own paths.
This episode is a must-listen whether you’re an aspiring influencer, people leader, or simply navigating the generational dynamics at work and home.
Timestamped Episode Overview:
00:00 – Tess introduces Brad Hoos and the evolving generational “mess”
01:09 – Brad’s unexpected journey from engineering to influencer marketing
03:50 – Why consulting shaped his approach to data-driven, people-first campaigns
05:46 – The Super Bowl, Kendrick Lamar, and the myth of “faking” influence
06:48 – How trust and authenticity drive true influence online
09:06 – The power of creators saying “no” and the perils of commercial oversaturation
12:02 – Brad’s daily routines and mental health as a CEO
15:09 – Productivity hacks that actually work (and those that don’t)
18:42 – Why subtraction is the real path to sanity for leaders
21:58 – Outloud’s unique definition of success and growth-focused culture
25:37 – Building a company around emotional intelligence and radical candor
28:05 – Brad’s pivotal moment learning to stop carrying leadership’s emotional weight
32:37 – Parenting, presence, and finding joy in living fully “in the moment”
36:53 – How millennials and Gen Z have redefined influence, fame, and advocacy
44:27 – Why Gen Z’s drive for purpose and connection is changing everything
50:41 – Is the influencer dream a search for real community?
Don’t forget to subscribe, and if you’re ready to bridge your own generational gaps, check out Tess’s work at tessbrigham.com or connect with Brad and his team at outloudgroup.com!
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What if your favorite ‘90s sitcom is actually an aspirational fantasy—and today’s TV is a brutally honest mirror?
In this unexpected solo episode, Tess Brigham dives into the wild evolution of 20-something life on TV, revealing what Friends got right (and wrong) about young adulthood, and why the new FX series Adults hits closer to home for Gen Z.
Tess shares her own Hollywood background before she became a therapist and coach, unpacking how pop culture doesn’t just entertain us—it reflects our deepest worries, hopes, and the messy realities of growing up. Using Friends and Adults as cultural bookends, Tess explores how economic stability, rent prices, college debt, technology, social media, and discussions around identity and mental health have radically reshaped what it means to "grow up" over just 30 years.
Key highlights include:
Whether you grew up wishing you could hang out at Central Perk or you’re hustling in your parents' house in Queens, this episode asks: What does adulthood really mean—and how do we redefine it together?
Timestamped Episode Overview:
00:00:01 – Intro & show mission; Tess shares her Hollywood background
00:01:33 – Why pop culture is a “mirror” for our lives
00:02:02 – Comparing FX’s Adults and Friends: then vs. now
00:03:38 – Economic realities for young adults in the ‘90s
00:04:51 – Tech, social media, and how comparison has changed
00:05:31 – How Adults depicts modern realities: housing, healthcare, and job insecurity
00:07:59 – (Ad break) Tess discusses her work with organizations
00:08:45 – Diversity, privilege, identity: from invisible to center stage
00:09:31 – Universal truths of young adulthood that never change
00:10:59 – Today’s heightened pressures: rent, debt, and fragile economy
00:12:11 – Technology amplifies awareness—and anxiety
00:13:18 – Why comparing the two shows matters for every generation
00:14:16 – What each generation can learn from Friends and Adults
00:14:58 – The enduring importance of friendship and connection
00:16:25 – Closing thoughts & where to find more from Tess
Don’t miss this episode if you’ve ever felt caught between nostalgia and reality—or want to understand how every generation tries (and struggles) to make sense of this “gen mess.”
Hosted on Acast. See acast.com/privacy for more information.
What if the secret to manifesting the life you want isn’t just about thinking positive thoughts—what if it’s about understanding how your mind, heart, and healing all work together?
In this episode of Gen Mess with Tess, host Tess Brigham sits down with transformational speaker and life coach Billy Giannouloudis (aka Billy G), and the conversation is full of surprising wisdom, down-to-earth insights, and a fresh, spiritual take on both coaching and therapy.
Billy shares the profound turning point in his life when everything seemed to fall apart—family, relationships, career plans—only to realize that this mess was exactly what led him to his true calling. He opens up about his coaching journey, including his training with Tony Robbins, and reveals how real transformation happens when we blend action-based coaching with deeper therapeutic healing.
Key highlights include:
Whether you’re curious about what really works in life coaching, trying to rewrite your own mental script, or just looking to finally “get” manifestation without the hype, this episode brings the real talk and actionable steps you need.
Episode Overview (Timestamps):
Listen in for a truly fresh conversation that blends the pragmatic, the spiritual, and the real challenges we all face living in the “mess” of modern life.
Hosted on Acast. See acast.com/privacy for more information.
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What if your job was just a hobby—and not your entire reason for existence?
On this episode of “Gen Mess with Tess,” host Tess Brigham sits down with Katie O’Brien, a Gen Z professional working abroad at a multinational company, who’s redefining what it means to build a career in a world overflowing with choices, expectations, and the ever-present pressure of comparison.
Together, Tess and Katie dive into the most surprising realities of starting out in today’s workforce—not just the freedom to pivot and explore multiple paths, but also the unexpected paralysis that comes from “too many options.” Katie opens up about the struggles of decision making in an age of social media highlight reels, the burden of being compared to previous generations, and her candid take on why Gen Z refuses to let work define their entire lives.
Other key highlights include:
Whether you’re trying to figure out your next move, manage Gen Z employees, or just want to know how today’s young professionals are navigating their own “gen mess,” this episode will give you insight, practical advice, and maybe even a little relief knowing everyone’s just figuring it out as they go.
Episode Overview:
Listen in for an authentic, cross-generational conversation about what it really means to make sense of the mess today.
Hosted on Acast. See acast.com/privacy for more information.