The Gen Mess with Tess

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

Follow for weekly episodes, and be sure to visit tessbrigham.com to learn more about Tess's work as a licensed therapist and certified coach.

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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"

Follow for weekly episodes, and be sure to visit tessbrigham.com to learn more about Tess's work as a licensed therapist and certified coach.

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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

Follow for weekly episodes, and be sure to visit tessbrigham.com to learn more about Tess's work as a licensed therapist and certified coach.

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What if the biggest reason you hate your job isn’t YOUR fault—but a 150-year-old management system designed to treat you like a cog, not a human being?

That’s exactly what gets uncovered in this episode of Gen Mess with Tess, where Tess Brigham sits down with workplace revolutionary Jason Lauritsen. Jason shares his compelling journey from Iowa farm kid to corporate HR leader and bestselling author on a mission to fix—yes, FIX—the way we treat people at work.

Key Highlights You’ll Hear:

• Jason’s eye-opening origin story: How witnessing his father’s battle for integrity at work ignited Jason’s lifelong drive to repair “broken” workplaces.
• The ugly truth about how industrial-age management STILL rules today—and what needs to change so people can actually thrive.
• Why generational “workplace drama” is often just a lack of clarity and relationship skills, not a battle between ages.
• The simple, genius “Check-In Method” for managers and coworkers—a four-step, 5-minute approach that will transform the way you communicate, build trust, and solve problems at work.
• Debunking resistance: Why leaders fear real conversations (and how to move through your fear of not having all the answers).
• Ways generational trauma shows up at work—and the critical shift needed to break the cycle, no matter your age or role.

For more on Jason’s management strategies and the Check-In Method, connect with him at jasonlauritsen.com, check out his podcast Check in with Jason Lauritsen, or find him on LinkedIn.

Ready to stop letting the “gen mess” mess with YOU? Listen in, stay curious, and let’s start cleaning up the workplace—one real conversation at a time.

00:00 Understanding My Origin Story

06:07 Headhunting: Navigating Workplace Dysfunction

09:07 Choosing People-Centric Workplaces

10:05 "Outdated Work Systems"

14:14 Desire for Individuality at Work

18:21 Hollywood's Hierarchical Hazing Culture

22:34 "The Check-In Method's Simplicity"

23:47 Essential Management: The Check-In Method

29:21 "Transformative Leadership Through Better Questions"

31:17 Listening to Younger Employees

34:13 Supporting, Not Fixing Relationships

38:26 Avoid Generational Stereotypes

42:50 Managing Expectations and Clarity

45:02 Align Expectations with Employees

47:26 "Find Jason at JasonLauritsen.com

Follow for weekly episodes, and be sure to visit tessbrigham.com to learn more about Tess's work as a licensed therapist and certified coach.

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What if the generational "mess" at work isn't just about age—it's about culture, communication, and what no one ever tells you on your first day?

In this revealing episode of Gen Mess with Tess, host Tess Brigham sits down with Tracy Ward, award-winning HR executive and corporate culture strategist, to unpack the real dynamics that shape our workplaces. Together, they dive deep into Tracy's unique journey from aspiring bioengineer to HR leader, and share eye-opening insights on why so many new employees feel lost—not because they're unprepared, but because companies forget to teach the "unwritten rules" that create true belonging at work.

Key Highlights:

• The hidden pitfalls of workplace culture that trip up new hires—and how to fix them before burnout sets in.
• Generational patterns at work: How Gen Z's desire for purpose, Gen X's "work first" mentality, and evolving attitudes toward boundaries and self-care are changing the way leaders need to engage and retain talent.
• Actionable ways to make your onboarding process more intentional, including assigning buddies, demystifying strange company jargon, and leveraging peer support.
• The critical importance of communication around employee benefits, and why reminding your team about available resources is an act of genuine care.
• Why relationships at work—not just salary or perks—are the #1 reason people stick around (or leave).
• Balancing business goals with creating sustainable, people-first workplaces—and the business case for happiness and trust.

Ready to clean up the gen mess at your own workplace? Tune in and discover practical strategies to create a place where every generation—and every individual—can thrive.

Resources: Find Tracy Ward and learn more about Forward Talent Strategies at www.forwardtalentstrategies.com, or connect with her on LinkedIn. And don’t forget: the path to a healthier, more vibrant work culture starts with one intentional conversation—maybe yours!

00:00 "Passion for HR Leadership Journey"

06:05 Onboarding: Organizational Responsibility Debate

08:53 Generational Shifts in Workplace Values

10:25 Empowered Employee Communication

15:45 Enhancing Employee Benefits Communication

18:45 Promoting Resources Through Accessibility

22:50 Workplace Bonds and Purpose

24:51 "Impact of Employee Turnover"

27:13 Leadership Change and Influence Struggles

33:03 Importance of Third-Party Trust

34:34 Balancing People and Profits

Follow for weekly episodes, and be sure to visit tessbrigham.com to learn more about Tess's work as a licensed therapist and certified coach.

Hosted on Acast. See acast.com/privacy for more information.

What if your company’s employee benefits plan could be the secret weapon that keeps your top talent loyal—and even attracts new superstars through the door?

In this enlightening episode of Gen Mess with Tess, host Tess Brigham sits down with powerhouse employee benefits strategist, Sirena Dimas, to pull back the curtain on what really makes benefits matter in today’s rapidly changing workplace.

Key Highlights:

• Why company benefits aren’t just an expense—they’re an underused asset that could drive business growth and retention (and how to shift your mindset).
• Sirena’s unique journey from young mom to industry leader, and the “listening” skill that launched her success.
• The generational evolution of benefits: what companies (and employees!) wanted 20 years ago versus today, including a powerful look at the rise of mental health support and financial wellness benefits.
• Candid stories on multigenerational workplaces and families—like what happens when a Gen X, an elder Millennial, Gen Z, and Alphas all live together (hint: mediation skills come in VERY handy!).
• Practical tips for boosting benefit engagement—open enrollment meetings, digital resources, FAQs, and why communication must match each generation’s style.

Whether you lead a business, manage a team, or just want to understand how work culture is evolving across generations, this episode is packed with the wisdom (and real-world stories) you need to start fixing the Gen Mess—one conversation at a time.

Loved this episode?

• Share it with a manager or HR pro who wants to rethink their benefits strategy!
• Try a new way of communicating with your colleagues this week—see what clarity and connection you can create.
• Stay tuned and subscribe for more insights on navigating generational dynamics at work and at home.

Remember: Your benefits package and your people are your company’s greatest assets. Make sure everyone knows how to use them!

00:00 "Gen Mess Podcast with Tess"

03:27 Insurance: A Personal Journey

07:25 Consumer Mindset: Expense to Asset

11:19 Employee Financial Literacy Gaps

13:47 Navigating Employee Health Benefits

19:54 Children Witness Work Stress

22:39 Graduating in the '90s vs. '00s

25:28 Supportive Client Relationships

29:05 Hands-On Learning Beats Tech

31:20 Printer and Battery Misunderstandings

34:18 Parenting Approaches Across Generations

37:18 "First Speaker Buys the Product"

Follow for weekly episodes, and be sure to visit tessbrigham.com to learn more about Tess's work as a licensed therapist and certified coach.

Hosted on Acast. See acast.com/privacy for more information.

What if your “common sense” approach at work is actually causing a generational divide you don’t even see?

In this thought-provoking episode of Gen Mess with Tess, host Tess Brigham sits down with leadership coach and author Rachel Burr for a refreshingly honest and practical look at why generational misunderstandings are so rampant in the workplace—and how leaders (and employees!) can finally start cleaning up the “gen mess.”

Key Highlights:

• The Circuitous Path to Great Leadership: Rachel shares her real, non-linear journey from clinical psychology into executive coaching—and how detours are often where true growth happens.
• The Emperor’s New Clothes in the C-Suite: Discover why senior leaders often stop hearing the truth from their people, and why intentional listening is the most overlooked tool for powerful leadership.
• Inside-Out Leadership: We explore what it means to show up as an authentic leader (regardless of personality type), and why “cookie-cutter” solutions always fall short.
• Generational Blind Spots: Dive into the biggest misunderstandings between Boomers, Gen X, Millennials, and Gen Z. You’ll learn how “common sense” is built on common experience—and why neither side is right or wrong.
• What Gen Z Really Wants (and Needs): Rachel shares what young professionals are seeking from their leaders—context, purpose, and the why behind what they do—and how these are human essentials, not generational demands.
• The Hard Truth About Transformation: Rachel’s new book, Butterfly Goo, challenges the Instagram myth that growth is glamorous. Real transformation is messy, uncomfortable, and never happens overnight.

Want to go deeper? Check out Rachel’s book, Butterfly Goo: The Down and Dirty Truth of Transformation, for raw, real stories and practical strategies for authentic growth.

Curious to break your own generational cycle at work? Start by sharing this episode with your team, and open up a real dialogue. Because cleaning up the gen mess starts with one honest conversation at a time.

00:00 "Humorous Memoir on Nonlinear Journeys"

06:18 Leadership Disconnection Challenges

08:40 Promotion Challenges Within a Team

11:35 Core Values and Leadership Identity

15:50 "Leaders Seeking Context and Purpose"

18:02 "Generational Experiences and Challenges"

23:00 Generational Perspectives on Change

24:38 Internalize Less, Respect More

28:36 The Challenge of Common Knowledge

32:14 Rethinking Success: Sink or Swim

34:33 "Emotional Intelligence and Management"

38:09 Shaming: Ineffective Leadership Strategy?

42:12 Bridging Generational Understanding

46:51 "Choose Your Own Transformation Adventure"

50:07 "Comfort Zones Limit Growth"

51:11 "Conscious Choice and Growth"

Follow for weekly episodes, and be sure to visit tessbrigham.com to learn more about Tess's work as a licensed therapist and certified coach.

Hosted on Acast. See acast.com/privacy for more information.

What if fear isn't your enemy, but actually your greatest secret weapon?

In this powerful episode of Gen Mess with Tess, host Tess Brigham sits down with the dynamic Jacqueline Wales—TEDx speaker, author, coach, and all-around powerhouse—to unpack how fear runs (and often, ruins) our lives, across every generation. Jacqueline, whose inspiring journey includes overcoming childhood trauma, financial devastation, and a life rebuilt from scratch, reveals why “being fearless” is a myth—and why courage is really about making your next bold move in the face of fear, not its absence.

Key Highlights:

• Fear Exposed: Hear why Jacqueline calls fear a “strategic advantage”—and how to use it as fuel for your own growth.
• The Science of Fear: Gain crucial insight into the biology and stories your mind fabricates, including how fear operates on a subconscious and cellular level, and why most of our fears are based on imagined threats.
• Generational Mess: Explore why Gen Z is more risk-averse and anxious than previous generations, and what boomers get wrong (and right) about the next wave of leaders.
• Deceitful Thinking: Discover how “deceitful thinking” tricks us into believing self-doubt, procrastination, and perfectionism are facts—not just stories we’ve internalized over time.
• Real-Life Tools: From simply saying “thank you” to a compliment, to breaking through resistance and perfectionism, get actionable steps to flip the fear narrative in your daily life.

Ready to clean up your gen mess by turning fear into your fiercest ally? Listen in, challenge your old beliefs, and take bold steps toward the life you want. And don’t forget—stay curious, stay courageous, and stop letting fear run the show.

Connect with Jacqueline Wales:

• Website
• LinkedIn (search Jacqueline Wales)
• Email for the free 30-Day Fear Busting Challenge: [email protected]

Let us know how you’re using these lessons—share your breakthroughs and questions with us, and keep the conversation going. Until next time, own your power and don’t let the gen mess mess with you!

00:00 "Gen Mess Podcast: Fear as Advantage"

05:32 Confronting Fear and Self-Limitation

06:50 Struggles with Self-Worth

13:20 "Deceitful Thinking Explored"

16:28 "Growing Up in Unsettled Times"

17:57 "Personal Growth and Social Impact"

22:49 Fostering Understanding and Curiosity

26:41 "Embrace Self-Worth Over Validation"

27:51 Healing Emotions at Cellular Level

30:49 Reclaim Your Personal Power

34:38 "Horror Curiosity and Women's Voice"

37:16 Generational Workplace Expectations Clash

40:42 "30-Day Fear-Busting Challenge"

Follow for weekly episodes, and be sure to visit tessbrigham.com to learn more about Tess's work as a licensed therapist and certified coach.

Hosted on Acast. See acast.com/privacy for more information.

What if your career achievements are actually the least memorable thing about you at work?

In this captivating episode of "Gen Mess with Tess," host Tess Brigham sits down with John Garrett, a former Big Four CPA turned stand-up comedian and award-winning keynote speaker, to dig deep into the messy world of generational workplace dynamics—and why bringing your whole self to work is your biggest asset.

Episode Highlights:

• The Surprising Power of Your “And”: John reveals how your outside interests—not just your job title—define who you are at work and are what people actually remember years later.
• From CPA to Comedian: Hear how John’s journey from cubicles to comedy clubs (and back again as a corporate culture guru) taught him lessons every leader should know about authenticity, connection, and communication.
• Authenticity vs. Professionalism: Why embracing your passions and quirks doesn’t mean sacrificing professionalism—and how leaders can balance both for a thriving workplace.
• Generational Differences, Demystified: Tess and John dive into whether Gen Z, Millennials, and Boomers really want such different things—or if we’re all just seeking belonging in our own way.
• Actionable Connection: The show unpacks research, real stories, and simple strategies to build rapport across generational divides and foster a workplace where people want to stick around.
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Continue the Conversation: Want practical tools, leadership trainings, or just a dose of fun inspiration? Check out John Garrett’s book and resources at whatsyourand.com and tune in for more real-talk every week here on "Gen Mess with Tess."

Remember: The Gen Mess gets cleaned up one authentic conversation at a time. So what’s your “And”—and how will you share it this week?

00:00 First Comedy Paycheck Surprise

04:46 Midwest Comedy Opportunities

07:26 "Comedy and Identity Merge"

10:07 Technical Skills Aren't Enough Anymore

16:10 "The Power of Speaking Out Loud"

17:29 Conversational Language and Comedy Confidence

21:28 Ego and Miscommunication Issues

23:40 Reevaluating Work-Life Balance

27:48 Redefining Success Across Generations

30:09 "Balancing Work and Personal Identity"

32:55 COVID's Impact on Mutual Understanding

38:39 "Workplace that Values Whole Self"

41:19 "Embracing Imperfection in the Workplace"

44:17 Intentional Time Between Work Hours

48:26 Vetting by Conversation

49:25 "Pug Passionate Conversations Thrive"

Follow for weekly episodes, and be sure to visit tessbrigham.com to learn more about Tess's work as a licensed therapist and certified coach.

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What if the real reason your team is struggling isn’t just about generational clashes—but about whether your employees feel seen, heard, and valued at work?

On this eye-opening episode of Gen Mess with Tess, host Tess Brigham sits down with Dr. Ryan Warner, award-winning consulting psychologist, military leader, and Fortune 500 organizational strategist. Together, they dig beneath the surface of generational dynamics to reveal the hidden causes of workplace stress and conflict—and show you what truly builds inclusive, high-performing teams.

Key Highlights:

• Dr. Warner’s riveting journey from college athlete to military psychologist, and how his passion for health and wellness led to a global consulting career.
• Behind-the-scenes in the military: the surprising generational dynamics and why communication, not just hierarchy, drives team success.
• The truth about DEI (Diversity, Equity, Inclusion) in 2024: Why performative checkbox initiatives fail and how truly embedding inclusion into daily practice can transform organizations—regardless of what the headlines say.
• How real inclusion boosts productivity, mental well-being, and innovation—plus why addressing bias and building psychological safety are essential.
• Actionable advice for leaders who feel overwhelmed: Where to start, how to create more inclusive systems without piling on more work, and why even small changes (like feedback loops and cross-generational mentoring) can make a massive impact.

Connect with the Show: Visit TessBrigham.com or find Dr. Ryan Warner at rcwarnerconsulting.com to learn more about their work and upcoming opportunities.

Don’t let generational misunderstanding or outdated workplace practices hold your team back. Dive into this episode for real strategies—and start cleaning up your “gen mess” today!

00:00 Passion for Health and Education

05:06 Military Leadership and Entrepreneurial Journey

07:56 "Internship Insights and Career Paths"

10:35 "DEI Changes Spark Reflection"

14:24 "Addressing Workplace Generational Challenges"

19:13 Generational Bias in Organizations

23:26 Inclusion's Impact on Workplace Productivity

25:35 Balancing Work Culture and Leadership

27:50 "Mindful Leadership & Inclusion"

Follow for weekly episodes, and be sure to visit tessbrigham.com to learn more about Tess's work as a licensed therapist and certified coach.

Hosted on Acast. See acast.com/privacy for more information.