The Gen Mess with Tess

In this episode of The Gen Mess with Tess, Tess is joined by Ashley Herd, founder and CEO of The Manager Method, employment attorney, former HR leader at McKinsey & Company and Yum Brands, co-host of the HR Besties podcast, and author of the newly released book The Manager Method: A Practical Framework to Lead, Support, and Get Results.Ashley brings a rare, inside view of management from every angle - frontline work, legal risk, HR leadership, and executive training - to unpack why managers have an outsized impact on employee mental health, engagement, and retention. Drawing on research showing that a manager can influence wellbeing as much as a spouse, Tess and Ashley explore how leadership behavior ripples far beyond performance metrics and into people’s lives at home.This conversation tackles the realities facing modern managers: promotion without training, identity loss when high performers become leaders, generational misunderstandings, and the crushing pressure placed on middle managers. Together, they offer practical, human-centered strategies for leading effectively without burning people out, including Ashley’s core framework: Pause, Consider, Act.This episode is essential listening for HR professionals, people managers, and executives responsible for building sustainable leadership pipelines and healthier workplace cultures in 2026 and beyond.Be sure to subscribe to The Gen Mess with Tess podcast for new episodes weekly. 00:01 – Welcome & Introducing Ashley Herd 02:02 – From employment attorney to leadership educator 03:29 – Why great individual contributors often struggle as managers 05:31 – Promotion myths and the cost of untrained leadership 07:59 – Identity loss when high performers become managers 10:06 – The “LinkedIn test” and chasing titles over fit 12:19 – Why work identity is so powerful (especially in the U.S.) 16:05 – Middle managers: too much responsibility, too little support 18:58 – Why one-on-ones still matter at every leadership level 21:33 – The data: managers impact mental health as much as spouses 24:20 – How leadership stress follows people home 27:58 – Generations at work: framework, not stereotypes 32:23 – Technology, boundaries, and modern burnout 38:22 – Overcorrection, distrust, and workplace isolation 41:16 – One shift every manager can make today: Pause, Consider, Act 44:33 – Ashley’s book, resources, and closing reflections

On this episode of The Gen Mess with Tess, Tess is joined by Jenny Calcoen, CEO and founder of Inner Earthquake LLC, former executive, and private coach to high-achieving women navigating burnout, grief, and major life transitions.Jenny shares her own “inner earthquake” - the moment when outward success no longer matched inner truth - and how a life-altering diagnosis forced her to confront the cost of living according to expectations rather than values. Together, Tess and Jenny explore what happens when achievement masks disconnection, why burnout is often an identity crisis rather than a workload problem, and how leaders can recognize the early cracks before they become breaking points.This conversation offers powerful insights for HR leaders, executives, and people managers navigating retention challenges, disengagement, and leadership fatigue. It reframes burnout not as a failure of resilience, but as a signal that both personal and organizational systems are misaligned.If you’re responsible for developing leaders, shaping culture, or supporting high performers who look “fine” on paper but feel depleted inside, this episode offers a crucial lens for understanding what’s really happening beneath the surface.Resource by Jenny Calcoen: "The Boundary Whisperer" is available as a translation tool for internal signals, or for people who know something is off but don't quite have the language yet so they can simply practice boundary literacy. Here it is - https://chatgpt.com/g/g-688fdd4aa33c8191b5503765ba20cee8-the-boundary-whisperer00:01 – Welcome to The Gen Mess with Tess00:52 – Jenny Calcoen’s story: success, identity, and the first “inner earthquake”01:32 – When illness becomes a wake-up call02:38 – Rebuilding life… while unknowingly repeating old patterns04:30 – Burnout as an identity crisis, not a performance issue06:45 – Why high achievers ignore early warning signs09:10 – The danger of living by expectations instead of values11:40 – What leaders misunderstand about burnout and resilience14:20 – How HR and managers can spot “quiet breaking points”17:10 – Supporting transitions without pathologizing employees20:00 – Redefining success in leadership and work22:40 – Final reflections: listening before the earthquake hits

In this solo episode of The Gen Mess with Tess, Tess Brigham explores a surprising social experiment that connected strangers across political divides and why it offers a powerful lesson for today’s leaders in the workplace.Drawing from her background as a therapist and her coaching work with organizations, Tess unpacks what HR leaders and managers are experiencing in 2026: burnout that isn’t driven by workload or flexibility, but by chronic psychological strain, emotional role overload, and an increasing inability to tolerate discomfort.Using the “Party Line” experiment as a metaphor, Tess examines how algorithm-driven culture has reshaped our nervous systems, intensified polarization, and made everyday workplace conversations feel high-stakes and unsafe. She breaks down how different generations experience discomfort at work, why psychological safety is often misunderstood, and how avoiding discomfort quietly erodes trust, collaboration, and culture.This episode reframes discomfort not as a failure of leadership, but as a critical skill organizations must relearn if they want healthy teams, resilient managers, and sustainable workplace cultures.00:01 — Welcome to The Gen Mess with Tess Introducing the episode and the theme of learning to live in the mess.00:58 — The “Party Line” Social Experiment Explained Two payphones, two cities, and a radical idea: conversation without algorithms.02:21 — Why Human Connection Changes the Nervous System Dopamine, cortisol, and why constant conflict keeps us dysregulated.03:42 — It’s Hard to Demonize a Human Voice What happens when stereotypes are replaced with real conversation.04:42 — What We’ve Lost Culturally Discomfort avoidance, algorithm-driven identity, and polarization.06:05 — When Beliefs Become Identity Why disagreement now feels like danger instead of difference.06:56 — Connection Requires Discomfort Why real connection—socially and at work—has always been uncomfortable.08:19 — Why Shaming Hardens People The psychological cost of humiliation, judgment, and moral certainty.08:49 — The Workplace Parallel Why the “Party Line” is a metaphor for modern workplace culture.09:16 — Generational Relationships to Discomfort Boomers, Gen X, Millennials, and Gen Z, and how each navigates stress and challenge.11:36 — Discomfort vs. Harm Why discomfort is often misinterpreted as trauma or boundary violation.12:34 — Nervous Systems, Not Moral Failures Reframing generational conflict at work.12:34 — The Leadership Skill We Avoid Curiosity, repair, and staying in the conversation.14:18 — Discomfort as Leadership Work Why these “soft skills” are actually advanced leadership competencies.14:48 — Final Reflection Discomfort as the doorway to healthier workplaces and human connection.

In this solo episode of The Gen Mess with Tess, host Tess Brigham addresses a question she hears from HR leaders, managers, and employees alike: Why does work feel so heavy right now, even when things look better on paper?Drawing from her background as a therapist and her work with organizations, Tess explains the challenges HR leaders are facing in 2026: burnout is no longer just about workload or flexibility, but about chronic psychological strain shaped by generational experiences, unclear expectations, and emotional role overload.She breaks down how burnout shows up differently for Millennials, Gen Z, and Gen X, how remote and hybrid work have changed trust, communication, and boundaries, and why managers and HR leaders are often carrying emotional responsibilities they were never trained for.This episode reframes burnout as a human, nervous-system issue - not a performance failure - and offers business leaders a clearer way to think about empathy, accountability, psychological safety, and sustainable workplace culture.

In this solo episode of The Gen Mess with Tess, Tess Brigham unpacks one of the most emotionally charged conversations happening right now: adult children going no contact with a parent.Drawing from her work as a therapist and her own lived experience, Tess challenges the oversimplified narratives dominating social media and reframes "no contact" not as a trend, punishment, or failure, but as a response to long-standing emotional disconnection and a lack of acknowledgement.This episode explores the generational divide shaping these conversations, why intent does not erase impact, and why emotional safety, accountability, and repair matter more than endurance or tradition. Tess also shares a deeply personal story about her relationship with her father, illustrating how acknowledgement - not perfection - creates the possibility for healing.For leaders, HR professionals, and parents alike, this episode offers a powerful reminder: relationships break down not because people are “too emotional,” but because discomfort is avoided instead of addressed.

What if the person giving you life advice is, behind the scenes, completely falling apart?In this deeply moving solo episode of Gen Mess with Tess, Tess Brigham pulls back the curtain, sharing the raw, unfiltered story of a year that shook the very foundations of her life. From the staggering loss of her father to the painful journey of caring for her mother as dementia set in, Tess Brigham—the certified coach and licensed therapist—describes what happens when every piece of her own identity is "activated in crisis mode."Far from the highlight reels and inspirational soundbites, this episode reveals the messy, complicated realities even therapists and coaches face. Tess Brigham explores generational differences in dealing with grief, mental health, self-reliance, and asking for help—drawing wisdom (and exposing blind spots) from Boomers, Gen X, Millennials, and Gen Z. She reflects on the exhausting duality of caring for aging parents while supporting her own child through mental health struggles, and how real-life heartbreak changed her perspective as both a professional and a human being.Key highlights include:The overlooked emotional cost of being the "strong one" in the familyGenerational patterns and how each age group defines asking for help and resilienceWhy anticipatory grief and caretaking are acts of love—and also sources of silent painLessons Tess Brigham is carrying forward, and the generational beliefs she's choosing to leave behindA vulnerable reminder that "hanging tough" means allowing yourself to soften, seek support, and be humanThis solo episode is a must-listen for anyone navigating family caregiving, loss, or simply questioning how we all handle life's hardest seasons.Episode Overview 00:00 – Intro Announcer sets up the show's generational lens00:31 – Tess Brigham addresses why sharing her own story matters03:02 – Navigating simultaneous personal crises: parental loss, caregiving, and self-identity06:33 – The unique grief of losing a parent's mind versus a parent's body08:40 – Generational patterns: independence, vulnerability, and the cost of stoicism11:32 – Tess Brigham on what Millennials and Gen Z are teaching the rest of us13:05 – The realities of “functioning” through grief and anticipatory loss17:17 – Each generation’s wisdom, and what Tess Brigham plans to carry—and leave behind20:35 – A gentle call to "hang tough" in a way that honors both strength and softnessReady to feel seen and understood in the messiest moments of life? Hit play and join the conversation.

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:The shocking downside of “more with less” workplace culture—and Australia’s new laws holding employers accountable for worker burnout and stressKatrena Friel’s $30,000 lesson in self-belief (and how that “scam” became the best investment of her life)The three inner compasses—mind, heart, and gut—and how to use them to turn self-doubt into an allyWhy so many “expert” coaches out there deliver nothing but an expensive lesson (and how to spot the real deal)Generational shifts: Why Gen Z is saying "no" to the boomer/American dream—and the case for embracing multi-generational homes and decluttering your life to gain headspaceBuilding your own brand: What it means to be the product, and how Katrena Friel helps you discover the million-dollar model inside your life experienceThe truth about online programs: Why up to 95% are never completed—and why transformation requires actual mentorship, not just another “passive income” promiseLoaded 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:[00:00:01] – Welcome and intro to Katrena Friel’s journey[00:02:11] – Early jobs and learning to be a self-starter[00:05:02] – Miscarriage, grief, and the life-changing $30,000 scam[00:08:17] – The unregulated coaching industry and lessons from mistakes[00:11:14] – The three inner compasses: Mind, gut, and heart[00:16:39] – Why it’s so hard to leave corporate: Golden handcuffs and generational differences[00:24:20] – Declutter your life: Practical steps for big change[00:27:28] – Rethinking the family home and intergenerational wealth[00:31:09] – The career marathon mindset and building your own expertise[00:34:09] – “Done for you” programs vs. the myth of the passive online business[00:42:59] – How to connect with Katrena Friel and next steps for listenersTune in for an episode packed with hard truths, practical strategies, and inspiration to reinvent work and life—no matter your generation!

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:Why technical skills don’t equal business success (and how “The E Myth Revisited” nails the problem for lawyers, therapists, and service pros)The biggest pain points holding law firm owners back—hint: it’s not just the “hours in a day”How shifting your mindset can help you work smarter, not harder—and finally create the time and income you wantNavigating generational tensions in the workplace: What attorneys get wrong about Gen Z, and why the newest workforce expects more work-life balance and financial stability than everReal talk about raising rates, burnout, hiring, and having those difficult employee conversations (plus how to screen for clients who are truly ready for change)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:[00:00:31] Tess Brigham: Welcomes Alay Yajnik; his background in law firm growth[00:01:23] Alay Yajnik: Story of switching from Silicon Valley to coaching attorneys[00:03:08] Discussion: Why attorneys make great clients and what they uniquely struggle with[00:05:15] Skills gap between technical expertise and business acumen; "The E Myth Revisited"[00:07:16] The real issue: Time, burnout, and working smarter[00:09:32] Traditional law firms vs. startup mindset; resistance to change[00:12:11] Symptom vs. cure: Time management as a lever for transforming business results[00:13:19] Raising rates, money fears, and business growth challenges[00:17:27] Navigating client readiness and coaching intake[00:18:07] Generational tensions: Gen Z’s approach to work, bonuses, and raises[00:22:05] How the cost of living, technology, and burnout are shaping new workplace expectations[00:27:04] A deeper look at employee expectations, creativity, and the evolving legal workplace[00:36:33] Final reflections: Lessons from coaching lawyers, generational stereotypes, and business owner frustrations[00:41:06] How to connect withAlay Yajnik and his resources for law firm owners[00:43:17]Intro Announcer: Show outro and next episode previewTune in for an episode that’s more than just law—it’s about building the future of work, one honest conversation at a time.