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:

• Why most writing problems are actually rooted in muddled thinking—and why most schools do a terrible job of teaching this.
• The surprising truth about creative careers: Do most artists really want to be artists, or just famous?
• The dangers of trusting leaders who speak in conclusions instead of thoughtful frameworks (with spicy commentary on today’s political climate!)
• Why Gen Z and today’s college students are falling behind in critical thinking and communication—and how our current education structures are failing them
• The one daily practice that can immediately make you a clearer thinker, communicator, and human being

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:

• The untold limitations of the post-war American Dream—even at its peak
• How today’s economic realities stack the odds against traditional milestones
• Why Gen Z is rejecting burnout culture and chasing a new vision of “enoughness”
• What companies must change to attract and keep the next generation of talent
• The surprising truth about what really drives our pursuit of success

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:

• 00:00 — Show intro and the American Dream: myth vs. reality
• 02:16 — Who actually got access to the American Dream post-WWII
• 04:27 — Bake Sale Betty: Redefining business success and work-life balance
• 08:50 — The American Dream today: College debt, housing prices, and wage stagnation
• 12:20 — Gen Z’s new dream: Mental well-being and purposeful work
• 14:19 — Pop culture shifts: From Barbie to Mad Men
• 15:57 — A Dream of “enough”: What if fulfillment is the goal?
• 17:59 — Wrap up: Living with the messy, evolving American Dream

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:

• The science of influence: Can you “fake” true influence, or is it rooted in trust and authenticity? And why is it often the creators who turn down brand deals who drive the biggest results?
• Generational insights: How Gen Z and millennials are changing the digital landscape, why “YouTube famous” now simply means “famous,” and whether being an influencer is just a masked quest for connection and self-acceptance.
• The CEO’s balancing act: Brad reveals how he protects his mental health amid chaos, the productivity hacks that actually work, and the surprising lesson that changed everything about how he leads.
• Company culture that sticks: Hear how Outloud Group centers success on personal growth and emotional intelligence, and how radical direct communication keeps their workplace free of toxic gossip.
• The power of saying no: Why knowing when to walk away—from brand deals, tasks, or even outdated life advice—might be the ultimate “growth hack.”

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:

• The jaw-dropping gap between ‘90s economic realities and today’s housing and job market for young adults
• Why Friends never tackled race, sexuality, or student debt—and how Adults puts those issues front and center
• How social media has blown up the scale of comparison and anxiety for today’s 20-somethings
• Surprising universal truths: no matter the decade, everyone in their twenties feels lost, unsure, and desperate to find their people
• What both older and younger generations can learn from these shows

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.”

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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:

• The shocking way Billy found his life’s purpose when everything else collapsed.
• The “doorknob effect” in coaching, and why the biggest breakthroughs often come right at the end of a conversation.
• Billy’s core approach: mastering your thoughts, words, and beliefs—the three things everyone can control.
• Demystifying manifestation: Why most people get it wrong, and how manifesting is actually happening all the time, even when you’re asleep.
• A candid discussion about generational shifts, technology, and how Millennials (and younger generations) are rewriting the rules for personal growth, emotions, and healing.
• Tess and Billy’s practical advice for both skeptics and enthusiasts: how to make change stick, bridge the generational gap, and move from “fixing the mess” to thriving in it.

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):

• 00:00:01 – Intro and Tess welcomes Billy Giannouloudis
• 00:01:25 – Billy’s origin story: from psychology to rock bottom to life coaching
• 00:03:13 – Mixing therapy with Tony Robbins’ coaching: What stuck, what changed
• 00:05:27 – How to make borrowed wisdom your own—becoming the first you, not the next someone else
• 00:07:52 – Billy’s practical process for helping high performers and everyday clients get unstuck
• 00:11:49 – The “three things you control”: thoughts, words, and actions/beliefs
• 00:17:01 – What most people misunderstand about manifestation (and why it’s not just about repeating affirmations)
• 00:24:19 – How generational experiences—from 9/11 to tech—shape Millennials and beyond
• 00:32:43 – Answering skeptics: Can younger coaches help older clients? (Billy’s answer might surprise you)
• 00:36:36 – Where to find Billy online and wrap-up with Tess

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.

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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:

• Katie’s revelation that most people don’t just have one career anymore—and why that realization can be liberating (or terrifying)
• Why Gen Z is often misread as “not wanting to work,” when really they’re just setting boundaries and craving growth beyond the day-to-day grind
• A deep dive into the anxieties sparked by constant comparison (think: friends traveling, buying homes, or switching careers), and how Katie manages that voice in her head telling her to do it all
• The power of managers sharing their own stories—and how generational conversations at work are evolving
• Katie’s best advice for managers: every Gen Zer is different, so don’t assume what works for one will work for another
• A refreshingly honest reminder: Adulthood and working life is “hard, but not impossible”—and why we all need to be a little kinder to ourselves (and each other)

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:

• 00:00 — Introduction & Katie’s background: work isn’t what it used to be
• 03:00 — The myth of one career path and the overwhelm of too many choices
• 06:00 — Facing generational judgment at work
• 09:30 — The importance of supportive managers and generational perspectives
• 11:00 — Skills over degrees: Why backgrounds don’t always matter
• 16:00 — Taking advice with perspective & learning to filter feedback
• 19:00 — Social media’s impact on decision making and comparison
• 24:00 — The quest for life balance, happiness, and living intentionally
• 31:00 — Gen Z trends: Work as a hobby, not an identity
• 34:00 — What older managers should know about Gen Z
• 36:00 — The real talk: Adulthood is hard, and that’s okay

Listen in for an authentic, cross-generational conversation about what it really means to make sense of the mess today.

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What if everything you thought you knew about yourself—and the world around you—was just one small piece of a much bigger, messier puzzle?

In this deeply personal solo episode, host Tess Brigham pulls back the curtain on "The Gen Mess with Tess," revealing major changes to the direction of the show. Tess opens up about her journey from focusing solely on generational differences to confronting the deeper, messier questions about identity, purpose, and making sense of a confusing world. She candidly shares why she’s expanding the scope of the podcast, explains the real meaning behind the term “mess,” and how embracing life’s gray areas can bring more peace and self-acceptance.

Listeners will get an inside look at:

• The pitfalls of labeling entire generations and why Tess is stepping away from that as her only angle
• The story behind “Messy Tessy” and learning to embrace the messiness in life
• How sitting with uncertainty and discomfort is essential to personal growth
• A preview of richer, more honest topics coming up—from grief and work transitions to relationships, creativity, and everything in between

If you’ve ever felt lost, stuck, or overwhelmed by a world that doesn’t make sense, this episode offers comfort, clarity, and an invitation to explore life’s uncertainties together.

Episode Overview & Timestamps:

• [00:00:01] Tess introduces the episode and shares her original purpose for the podcast
• [00:01:23] Criticisms facing young generations and the generational narrative in the media
• [00:03:21] Realizing the need for a new direction and what Tess wants from her own listening experience
• [00:04:37] The desire to make sense of the world, and the importance of embracing uncertainty
• [00:05:12] Expanding beyond generations—introducing wider topics and personal stories
• [00:08:30] The meaning of “The Gen Mess” title and Tess’s journey embracing her own “messiness”
• [00:09:50] Accepting that life is messy and finding peace in the gray areas
• [00:10:20] What’s changing in the show’s format and the invitation for listener feedback
• [00:11:28] Tess closes with gratitude and excitement for what’s next

Tune in and get ready to find comfort—and maybe even answers—in the messiness of being human.

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Ever wondered why your business feels stuck in chaos—no matter how innovative your big idea is? Here’s the shocker: The real bottleneck might be you.

In this eye-opening episode of Gen Mess with Tess, host Tess Brigham sits down with Jhana Li, operations expert and founder of Spyglass Ops, who shares how even the most visionary entrepreneurs can unintentionally hold their businesses back. Jhana reveals why the skills that get you started—wearing all the hats, holding the reins tight—are the same habits that keep your company from reaching the next level of growth.

Key Highlights:

• Jhana’s candid journey from failed startup employee to 22-year-old COO and coach—plus what she learned about leadership and operations along the way
• The surprisingly simple difference between visionary founders and world-class operators
• Why trying to “do it all” is a growth killer, and the power of delegation and trust in building successful teams
• Confronting the mirror: The radical role of self-awareness, emotional work, and personal growth in business success
• How Jhana leverages her unique position as a young woman in a male-dominated space to create a competitive advantage
• The truth about Gen Z and Millennial work habits—debunking the “entitled/lazy” myth with real stories from small, successful remote teams
• Leadership hacks: Why focusing on outcomes (not hours worked) and genuinely caring about team members’ goals creates high-performing, motivated workplaces

Want to go deeper? Connect with Jhana Li at Spyglass Ops or follow her on LinkedIn and Instagram @jhanali. For more generational insights and practical strategies, subscribe to Gen Mess with Tess, and visit tessbrigham.com for coaching, courses, and more!

Remember: Cleaning up the “gen mess” in your business starts with one real, honest conversation—and that starts with you.

00:00 From Failure to Entrepreneurial Success

06:21 Balancing Leadership: Vision vs. Details

08:59 Founders Struggle to Delegate

11:38 Generational Shift in Communication Styles

14:26 "Standing Out as a Competitive Advantage"

17:29 Finding Growth in Challenges

22:44 Shifting Confidence Sources

23:48 Navigating Quarter-Life Crisis

27:33 "Focus on Individual Needs"

34:08 Quarter-Life Crisis and Mental Health

37:26 "Seeking Growth-Oriented Collaborators"

39:39 People-Centric Leadership Focus

42:43 "Human Connection is Challenging"

46:05 Scaling Teams for Digital Founders

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What if everything you thought you knew about “American culture” was invisible—to you, but glaringly obvious to everyone else?

In this revealing episode of Gen Mess with Tess, host Tess Brigham sits down with Lanie Denslow, renowned cultural translator and author, to break down the unspoken rules and quiet revolutions shaping generational and cross-cultural dynamics in the modern workplace. Together, they explore the evolving global landscape—where today’s youth, from Tokyo to Paris to California, are shaking up tradition in the name of mental health, work-life balance, and redefining success.

Key Highlights:

• Culture is More Than Food & Fashion: Lanie unpacks culture as “the software of the mind”—the unwritten scripts that guide everything from workplace etiquette to how we form friendships, often so ingrained we don’t see them until challenged by someone who does things differently.
• Generations vs. Geography: How Gen Z’s workplace “rebellions”— prioritizing mental health, rejecting burnout, and seeking meaningful experiences—are unfolding around the globe, but not always in the same ways as in the U.S.
• Peaches and Coconuts: Discover why Americans are “peaches”—friendly on the surface but private at the core—while most of the world are “coconuts,” reserved at first but deeply loyal once you break through.
• Why We All Need Cultural Training: Lanie makes the compelling case for company-wide cultural awareness—not just for executives, but for every team member—so that everyone, from new hires to seasoned leaders, learns to ask: “Could something cultural be happening here?”
• Cleaning Up the Gen Mess: Tess and Lanie offer concrete strategies for bridging generational and cultural divides, including the importance of curiosity, empathy, and open communication between all ages and backgrounds.

For more insights from Lanie Denslow, check out her books like Working with Americans and connect with her at worldwiseonline.net. Follow Tess at tessbrigham.com for resources on bridging the generational gap in your workplace and life.

Let’s get curious, get connected, and clean up the Gen Mess—one conversation at a time!

00:00 "Understanding Cultural Differences in Business"

05:00 "Cultural Perception and Interaction"

09:47 Shifting Traditions in Japan

13:03 "Cultural Diversity Among Youth"

17:19 Youth Travel Fueled by Internet

21:02 Living in the Moment: Gen Z

21:44 Embracing Failure: A Unique American Culture

26:46 "American Social Dynamics: Peaches Analogy"

28:55 Navigating International Friendships

34:29 "Close-Knit Social Circles"

39:00 Cross-Cultural Training for Global Leaders

41:36 Cultural Awareness in the Workplace

46:19 Generational Work Attitude Shift

48:25 "Training for Evolving Work Culture"

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What if the biggest obstacle to workplace harmony isn’t lazy young workers or out-of-touch bosses—but a silent, generational “stalemate” that’s sabotaging both sides?

In this solo episode of Gen Mess with Tess, host Tess Brigham takes you behind the scenes of a revealing conversation with a group of seasoned law firm owners—mostly Gen Xers—who are struggling not with legal cases, but with the rapidly shifting expectations of their Gen Z associates. Tess ditches the slideshow for honest dialogue, tackling the real questions on everyone's mind: Who’s really responsible for bridging the generational gap at work? Are younger workers asking for too much, or is it the system that’s failing them? And why are definitions of success so different—and so contentious—across age groups?

Key Highlights:

• The Heart of the Struggle: Tess shares candid moments from her talk with law firm leaders who feel overwhelmed by the need to offer more support and flexibility, while also adjusting their management styles for a new generation of workers.
• Work Ethic vs. Well-being: Hear how the expectation to “hustle” is colliding with Gen Z’s unapologetic focus on mental health, work-life balance, and redefining success.
• Systemic Traps: Tess exposes the financial pressures facing young associates, from sky-high rents to crushing student loans, and how these realities shape the modern workplace.
• The Fairness Divide: Explore how older and younger employees see “fairness” in radically different ways, and why mutual suspicion only worsens the gen mess.
• Practical Insights: From boundary-setting and honest communication to rethinking what it means to be successful, Tess offers clear, actionable advice for workers and leaders at every level.

Questions or stories to share? Tess invites you to send in your experiences—whether you’re running a law firm, working your way up, or just trying to survive the generational mess.

Don’t let the Gen Mess mess with you. Tune in, rethink what it means to thrive at work, and help fix the generation gap—one conversation at a time.

00:00 Workforce Tensions Between Generations

04:22 Empowerment Through Self-Control

07:19 Generational Work Ethic Clash

10:13 Housing Costs Outpace Wage Growth

12:42 Redefining Success and Fairness

17:45 Redefining Success Across Generations

20:07 Embrace Uncomfortable Change

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