The Gen Mess with Tess

In Episode 50 of The Gen Mess with Tess, Tess explores a dynamic that quietly derails high performers at every level: the moment work starts to feel like a test.

When every meeting feels evaluative and every decision feels like it determines your worth, anxiety rises, and performance often drops. Tess unpacks why this happens and why the solution isn’t caring less, but redefining what actually belongs to you.

Drawing from her clinical work with emerging leaders, she breaks down:

• Why over-focusing on outcomes increases anxiety and self-consciousness
• The psychological difference between effort and approval
• How new managers get stuck trying to predict reactions
• Why Gen Z struggles uniquely in a metrics-driven culture
• The mindset shift that restores confidence, clarity, and flow
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From a first-time manager learning to lead without control, to unexpected lessons from Olympic figure skating and competitive design, Tess illustrates one central truth:

Your job is the effort. The outcome was never yours to manage.

For HR leaders and executives, this episode is also a leadership lens. When organizations unintentionally create constant evaluation environments, employees tighten up — and innovation suffers. If you’re navigating pressure, perfectionism, or performance anxiety — this episode will help you rethink control and reconnect with your best work.

00:00 – Welcome: When Work Starts to Feel Like a Test

02:00 – Why Anxiety Increases When Outcomes Feel Personal

04:30 – What “Letting Go of the Outcome” Actually Means

06:00 – Effort vs. Approval: The Critical Distinction

07:30 – Case Study: Brittany’s Transition to Management

11:00 – The Office Hours Experiment

13:30 – Changing Your Relationship to Response

15:30 – Performance Pressure & Young Professionals

18:00 – The Gen Z Metrics Trap

21:00 – Why Measured Lives Create Outcome Attachment

23:30 – Flow State & Releasing Control

26:00 – Care Deeply About What’s Yours

28:30 – Final Reflection: Own the Effort, Release the Rest

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.

Tess sits down with Trent Cotton - self-described “non-HR HR executive,” author of Sprint Recruiting and High Performance Recruiting, and Head of Talent Insights at iCIMS. Discussing the nuanced conversation about what the data tells us about AI, generational skepticism from Gen Z to Boomers, and what leaders are getting wrong about the future of work, including:

• Why leaders often hide behind data instead of using it to deepen human conversations
• What current workforce data actually says about AI adoption across generations
• Why Gen Z may be more skeptical of AI than expected
• The risk of eliminating entry-level roles too quickly
• The emerging power skills of “agency” and “orchestration”
• How AI can both enhance human potential and erode connection if misused

This is not a hype conversation about AI. It’s a grounded discussion about leadership responsibility, workforce redesign, emotional regulation, and the long-term talent implications organizations must prepare for now.

If you’re an HR leader, executive, or people strategist navigating uncertainty around automation, layoffs, bias, and generational tension — this episode offers clarity without panic.

Because the future of work isn’t just technological. It’s psychological.

00:00 – Welcome + Meet Trent Cotton

The “non-HR HR executive” and why business fluency matters in people strategy.

04:20 – Data vs. Humanity: Where Leaders Get It Wrong

Why hiding behind numbers erodes trust — and how to use data to deepen conversations.

11:20 – AI Anxiety: Survival Instinct or Rational Fear?

Why resistance to AI may be more about control than job loss.

14:50 – The Early Career Crisis No One Is Talking About

The danger of automating entry-level roles too quickly.

21:00 – Is AI Replacing Human Connection?

Attachment to tech, loss of discomfort, and emotional consequences.

29:00 – How to Actually Use AI Without Losing Your Voice

Practical examples of human-AI collaboration.

38:45 – What the Data Says About Generations & AI

Why Gen Z may be more skeptical than you think.

43:05 – The New Power Skills: Agency & Orchestration

What leaders should be developing now.

48:05 – AI, Disability & Expanding Human Capability

Where technology can increase access and 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.

In Episode 49 of The Gen Mess with Tess, Tess tackles a reality many professionals experience but rarely have language for: what to do when your manager does not create psychological safety and you cannot simply walk away.

Drawing on the research of Harvard Business School professor Amy Edmondson, who coined the term psychological safety, Tess breaks down the difference between discomfort and harm, high standards and humiliation, resilience and self-abandonment.

This episode explores:

• Why unpredictable leadership activates the nervous system
• How generational conditioning shapes our response to toxic management
• The hidden cost of “enduring” unsafe environments
• Five strategic tools to protect your identity and regulate anxiety
• How to decide whether to adapt, escalate, or exit intentionally

For HR leaders and executives, this episode is also a mirror. Psychological safety is not about lowering performance expectations, it is about creating conditions where people can meet high standards without fear. Whether you are managing up, supporting emerging professionals, or building healthier leadership pipelines, Tess offers practical insight into how psychological safety shapes retention, burnout, and long-term performance.

00:00 – Opening: Living in the Mess

01:00 – The Reality of Unsafe Managers

02:24 – “Paying Your Dues” and Toxic Normalization

04:45 – Defining Psychological Safety

07:07 – What Psychological Safety Is (and Isn’t)

09:28 – Your Nervous System at Work

11:52 – Generational Patterns: Gen Z, Millennials, Gen X

14:18 – Strategy #1: Containment (Observe, Don’t Absorb)

16:05 – Strategy #2: Clarity in Writing

17:45 – Strategy #3: Borrow Safety Elsewhere

19:03 – Strategy #4: Emotional Boundaries

20:30 – Strategy #5: Identity Protection & Your “Reality File”

21:23 – Discomfort vs. Harm

23:00 – Adapt, Escalate, or Exit?

24:45 – Psychological Safety Is Not Entitlement

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.

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

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.

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-whisperer

00:01 – Welcome to The Gen Mess with Tess

00:52 – Jenny Calcoen’s story: success, identity, and the first “inner earthquake”

01:32 – When illness becomes a wake-up call

02:38 – Rebuilding life… while unknowingly repeating old patterns

04:30 – Burnout as an identity crisis, not a performance issue

06:45 – Why high achievers ignore early warning signs

09:10 – The danger of living by expectations instead of values

11:40 – What leaders misunderstand about burnout and resilience

14:20 – How HR and managers can spot “quiet breaking points”

17:10 – Supporting transitions without pathologizing employees

20:00 – Redefining success in leadership and work

22:40 – Final reflections: listening before the earthquake hits

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.

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.

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.

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.

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.

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.

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 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 family
• Generational patterns and how each age group defines asking for help and resilience
• Why anticipatory grief and caretaking are acts of love—and also sources of silent pain
• Lessons Tess Brigham is carrying forward, and the generational beliefs she's choosing to leave behind
• A vulnerable reminder that "hanging tough" means allowing yourself to soften, seek support, and be human

This 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 lens

00:31 – Tess Brigham addresses why sharing her own story matters

03:02 – Navigating simultaneous personal crises: parental loss, caregiving, and self-identity

06:33 – The unique grief of losing a parent's mind versus a parent's body

08:40 – Generational patterns: independence, vulnerability, and the cost of stoicism

11:32 – Tess Brigham on what Millennials and Gen Z are teaching the rest of us

13:05 – The realities of “functioning” through grief and anticipatory loss

17:17 – Each generation’s wisdom, and what Tess Brigham plans to carry—and leave behind

20:35 – A gentle call to "hang tough" in a way that honors both strength and softness

Ready to feel seen and understood in the messiest moments of life? Hit play and join the conversation.

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 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:

• The shocking length of the modern job search—and why it’s no longer a "three-month process"
• How technology and AI have totally transformed the hiring landscape (for better and worse)
• Actionable strategies for networking that actually work, whether you’re an introvert, a new grad, or making a mid-career pivot
• The key differences in how Gen Z, Millennials, and Gen X approach work, fulfillment, and branding themselves
• Why keeping your own “brag book” is essential for beating imposter syndrome and keeping your confidence alive amid career changes
• How AI isn’t taking jobs, but people who know AI are—and how you can upskill right now

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:

• [00:00:01] Introduction: Bridging generational gaps at work
• [00:01:16] Meet Liz Helton: From PR to guiding career transformations
• [00:06:44] The evolving job search: Why it takes so much longer now
• [00:08:47] Why everyone feels like they’re “shouting into a void”
• [00:13:13] How to beat interview anxiety and imposter syndrome
• [00:17:44] Building resilience: The emotional side of job hunting
• [00:19:38] Essential networking tips for introverts and extroverts alike
• [00:27:40] AI in the job hunt: What you need to know now
• [00:36:42] How Gen Z, Millennials, and Gen X view work differently
• [00:43:01] Liz Helton’s #1 piece of advice for anyone feeling stuck
• [00:46:49] Where to find Liz Helton and free career resources

Tune in to discover why you’re not alone in your career mess—and how you can thrive in it.

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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