The Gen Mess with Tess

You left. You reflected. You did the work. You asked better questions, watched for red flags, and turned down offers that didn't feel right. And then six months into the new job, the same feeling came back.

This isn't bad luck. And it isn't a failure of effort. It's psychology. In Part 1 of this two-part series, licensed therapist and certified coach, Tess Brigham, breaks down the real reason so many people, especially Gen Z workers entering or re-entering the workforce, end up repeating the same patterns at work even when they're actively trying to avoid it.

The answer is uncomfortable but important: most people do a thorough post-mortem on the wrong thing. They autopsy the job. They never examine themselves.

In this episode:

• How to identify a toxic workplace
• Why leaving a toxic workplace and doing all the right things still isn't enough
• The three patterns that follow people from one difficult job to the next: avoidance, disconnection, and measuring the wrong things
• What years inside a difficult work environment does to your beliefs about yourself, and how those beliefs travel with you
• Why salary, title, and company reputation are the wrong filters for evaluating a new opportunity
• The questions that actually predict whether you'll thrive somewhere, and why no one ever taught you to ask them
• Amy Edmondson's research on psychological safety, and why it's the most important thing almost no organization measures
• Why Gen Z's willingness to say "this doesn't feel right" isn't a weakness. It's the question every generation should have been asking.

Researcher credit: Amy Edmondson, Harvard Business School, psychological safety research

00:00: Opening story: the client who did everything right and still ended up back in the same place

01:40: The hard truth: she solved the right problem the wrong way

02:00: You autopsied the job. The job isn't what repeated. You repeated.

02:25: The three patterns that follow people from one workplace to the next

02:35: Pattern 1: Avoidance and what making yourself smaller to survive actually costs you

03:30: How avoidance rewrites your beliefs about whether it's safe to speak up

04:10: Pattern 2: Disconnection and losing touch with how you actually feel at work

04:35: Pattern 3: Measuring the wrong things, salary, title, and the cold brew on tap

05:15: The questions that actually predict whether you'll thrive somewhere

05:40: Why most people were never taught those questions were valid to ask

06:00: Amy Edmondson's research on psychological safety and why organizations don't teach it

06:55: Gen Z is not the problem. They're the first ones saying what everyone should have been asking.

07:45: What to ask yourself if you've repeated the pattern

08:30: The bottom line: you were handed the wrong checklist

09:00: Preview of Episode 61: three exercises that go to the root of each pattern

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.

You did everything right. The school, the job, the hustle. You followed the path, and you're good at it! So why does it still feel like something's missing?

This week, Tess sits down with Malaika Smyth, a coach for high achievers who have checked every box and still find themselves asking a surprisingly hard question: what do I actually want for myself?

Malaika brings a rare combination of experience as a Division I athlete background, nearly eight years scaling coaching operations at BetterUp from 50 to over 3,500 coaches, and her own winding path through quarter-life crisis, identity shifts, and a gift box business detour. She helps people build success that actually feels like theirs.

This conversation goes deep on the psychology of high achievement, what Silicon Valley's performance culture does to young people, and why so many accomplished professionals have never once stopped to ask what they actually want.

In this episode:

• Why high achievers often tie their entire self-worth to how hard they work
• The Silicon Valley "duck effect" — calm on the surface, paddling furiously underneath
• What a Gen Z employee taught Malaika about a kind of career maturity she'd never seen before
• Why age doesn't automatically equal wisdom — and what actually does
• The sunk cost trap that keeps high achievers stuck on the wrong path
• What every client ultimately wants at their core (it's always the same thing)
• The 75-year-old exercise that cuts through all the noise and gets to what actually matters
• Where AI fits in the future of coaching — and where it absolutely doesn't

To connect with Malaika Smyth, visit malaikasmyth.com or find her on LinkedIn.

00:00 — Welcome & Malaika Smyth introduction

01:20 — When Malaika first questioned whether being a high achiever was actually working for her

02:43 — Where the drive came from — internal wiring or outside pressure?

04:10 — Growing up in Silicon Valley: the unspoken assumption that you had to do something "big"

07:00 — The duck metaphor: calm on the surface, paddling furiously underneath

08:40 — College as non-negotiable — and how environment sets a path without anyone saying a word

09:50 — Graduating in 2014: a Bay Area overflowing with opportunity and equity dreams

11:00 — Following her brother into product management — and realizing it wasn't right

11:40 — Quarter-life crisis at year two: the moment she knew something had to change

12:40 — Designing Your Life — the book that opened a new door

13:50 — Joining BetterUp and discovering what coaching actually was

14:55 — The question Malaika asks clients who are rewarded for hustle

16:00 — "My only value is that I work hard" — and why coaching helped her see beyond it

17:00 — The decision to leave BetterUp and what came next

18:30 — The gift box business detour — and the important lesson it taught

20:25 — The sunk cost trap: why people stay on the wrong path long after they know better

23:40 — Selling yourself vs. selling a product: the vulnerability of a coaching business

24:35 — "I don't really care if you work with me. I care that you work on yourself."

28:45 — The power of silence — and celebration — in a coaching session

32:00 — Learning to trust your instincts and why being wrong can still be useful

37:30 — What every client ultimately wants at their core

39:50 — Managing both younger and older employees at BetterUp

41:10 — The Gen Z employee who floored Malaika with an unexpected kind of maturity

43:00 — Age does not equal wisdom — a lesson that changed how Malaika leads

46:45 — "I've been talking to ChatGPT all morning and I need to talk to a human"

48:00 — Tess on AI: the real hope, the real fear, and what's actually at stake

54:15 — The first question to ask when you've done everything right and it still feels off

55:00 — The 75-year-old exercise: what do you want your life to have been about?

57:00 — How to connect with Malaika + closing thoughts

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.

You gave the feedback carefully. You were constructive. You even thought through every word. And they still shut down.

If you're a manager or HR leader wondering why feedback conversations keep going sideways, this episode is the one you've been waiting for.

Tess Brigham breaks down the neuroscience of why feedback feels like a threat, why Gen Z is particularly activated by it (hint: it makes complete psychological sense), and why the feedback models most leaders were trained on were built for a different era.

You'll walk away with a completely different understanding of what's happening in that room and three concrete shifts you can make starting with your very next conversation.

• Why the brain experiences feedback as a social threat, and what that means for your employees
• David Rock's SCARF model and the five psychological domains a single feedback conversation can trigger simultaneously
• Why Gen Z carries a higher baseline of anxiety into these conversations than any previous generation, and why that's not the same as being fragile
• The critical difference between feedback landing as information versus landing as a verdict
• Why technically correct feedback still fails when the environment isn't psychologically safe
• Three shifts to make right now: establishing safety first, separating behavior from identity, and giving space to process
• The fourth shift most managers skip, and why it changes everything

00:00 — The feedback conversation that went sideways — and the question every manager has

01:00 — "Can't they just take feedback like an adult?" — naming what nobody says out loud

01:45 — The neuroscience: why feedback is a threat, not just information

02:27 — The SCARF model: the five domains your brain monitors for safety

03:30 — What a single feedback conversation triggers simultaneously in the brain

04:45 — Why this hits Gen Z harder — and why it's not about fragility

05:30 — How social media turned their adolescence into a constant performance evaluation

06:15 — Graduating into a pandemic: what Gen Z never got from their first jobs

07:00 — When criticism lands as a verdict, not information

07:45 — A real client story: the five-minute feedback that caused four days of dread

09:00 — Why the old feedback playbook is quietly breaking down

09:28 — The broken assumptions behind the feedback sandwich and annual reviews

11:00 — Three shifts to make starting with your next conversation

11:15 — Shift 1: Establish safety before you say anything critical

13:00 — Shift 2: Separate behavior from identity — out loud, every single time

14:30 — Shift 3: Give them time and space to process before expecting a response

16:20 — Why "closing" a feedback conversation is the wrong instinct

17:30 — The fourth shift: check your own nervous system before you walk in

19:00 — Why walking in frustrated defeats the entire conversation

20:00 — The bottom line: what managers who are getting this right actually understand

21:00 — Free resources: the Gen Z Playbook + related episodes

Download Tess's free Gen Z Playbook at TessBrigham.com.

Episode 52 (Why Gen Z Keeps Asking Questions at Work)

Episode 47 (The Manager Effect | Why Your Boss Impacts Your Mental Health More Than You Think with Ashley Herd)

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.

Is AI really replacing jobs, or are we misunderstanding AI's role at work?

In this episode of The Gen Mess with Tess, Tess Brigham sits down with People Operations executive Erin Turnmeyer to break down what leaders, employees, and organizations are getting wrong about AI in the workplace.

With 15+ years of experience building talent systems, including time at the Office of the Director of National Intelligence, Erin brings a data-driven perspective on how AI, automation, and analytics are reshaping work.

💡 In this episode, we cover:

• Why AI is a force multiplier, not a replacement
• The real reason companies are making AI-related layoffs
• What tasks should (and should NOT) be automated
• How to use AI without losing the human element at work
• Why resume screening with AI can backfire
• Practical ways to start using AI without feeling overwhelmed
• How early-career professionals can stand out in an AI-driven world

If you’ve been feeling anxious, confused, or curious about AI, this conversation will help you rethink what’s actually happening—and how to adapt without fear.

Whether you’re a leader, job seeker, or just trying to keep up with the future of work, this episode will give you clarity and practical takeaways.

00:00 – Intro: “Fixing the mess vs living in it”

00:42 – Meet Erin Turnmeyer (People Ops + AI perspective)

01:05 – From chem bio weapons analyst → HR leader

03:10 – What people get wrong about AI at work

04:00 – “AI is a force multiplier, not a replacement”

05:00 – Fear-based headlines & why they’re misleading

06:00 – Why fear blocks people from learning AI

07:30 – How companies fail at AI adoption

08:15 – Real example: teaching AI internally at work

09:30 – What AI should NOT replace (human touchpoints)

10:30 – What to automate vs keep human

11:10 – Why AI resume screening is flawed

13:00 – Smart ways to use AI in recruiting (without bias)

15:00 – Removing “administrative weight” from work

16:00 – Will AI lead to layoffs—or growth?

17:00 – The real opportunity: 20% more strategic thinking

18:10 – Why companies must allow time to learn AI

19:20 – Advice for early-career professionals

20:00 – Using AI as a daily learning coach

21:30 – Don’t outsource your thinking

23:00 – Could AI finally deliver work-life balance?

24:00 – The 4-day workweek conversation

25:00 – Real-world AI use cases (healthcare, systems, etc.)

26:00 – What happens to jobs AI can fully replace?

27:00 – What actually gets someone hired today

28:00 – Why AI-generated resumes are hurting candidates

30:00 – How to use AI correctly for resumes

32:00 – Training AI to sound like you

34:00 – Spotting AI-generated applications instantly

35:00 – How young professionals can “train” AI on themselves

37:00 – Using AI as a thinking partner (not a cheerleader)

38:00 – Trust but verify: why sources matter

40:00 – First step: how to start using AI today

41:00 – Unexpected tip: use AI for shopping decisions

43:00 – Final thoughts + where to find Erin

Connect with Tess at tessbrigham.com

Subscribe to Erin's Substack, AI for Human Operators, at hrai.substack.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.

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

No one really warns you how psychologically hard early career can be.

You learn how to write a resume, interview, and get hired, but almost no one explains what it feels like once you’re inside the workplace. You're being evaluated constantly, questioning yourself, guessing the rules, and trying to build confidence without experience.

In this episode of The Gen Mess with Tess, Tess Brigham explains why the beginning of your career can feel so mentally intense, and why that experience is often misunderstood. She breaks down the psychological weight of uncertainty, self-doubt, comparison, unclear expectations, and why many young professionals incorrectly assume they are the problem when they are often responding normally to a demanding environment.

Tess also addresses something leaders need to hear clearly: being early career does not mean someone should tolerate unhealthy behavior, poor emotional regulation, or unclear leadership.

This is Part 2 of Tess’s solo series on the psychology of work and why younger employees need more clarity, not more criticism.

• 00:00 Why early career hits harder than expected
• 01:05 Learning who you are while being evaluated
• 02:20 Why young professionals internalize stress
• 03:05 High expectations, low control, constant comparison
• 04:20 Why unclear environments create self-doubt
• 04:50 What young employees should never normalize
• 05:30 Why yelling at work should not be accepted
• 06:15 Discomfort vs unhealthy environments
• 06:50 How to separate mistakes from identity
• 07:40 What leaders owe early-career employees 

Be sure to subscribe so you never miss a weekly episode. To learn more, or to Shop available resources, visit tessbrigham.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.

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

Think you're not a morning person? Think again.

This week, Tess sits down with Amy Landino, bestselling author, content creator, and founder of Vlog Boss Studios. Together, they blow up everything you think you know about morning routines, productivity, and what it actually means to start your day on your own terms.

Amy's newly expanded book, Good Morning, Good Life, isn't about waking up at 5am or turning your morning into an Instagram aesthetic. It's about reclaiming ownership of your day before the world gets a vote, and her simple three-bucket framework (Movement, Mindfulness, and Mastery) makes that possible for anyone, in any season of life.

Tess and Amy also get into the messy generational stuff: why Millennials were conditioned to believe "work harder" was always the answer, why a six-figure business might actually be the wrong goal, and the moment Amy told her dad she'd already made $90K that year and watched him go completely speechless.

In this episode:

• Why your morning routine is probably built around someone else's agenda
• The key difference between starting your day "on offense" vs. "on defense"
• Amy's three-bucket framework: Movement, Mindfulness & Mastery explained simply
• The real reason you're "not a morning person" (it's not what you think)
• Why a six-figure business might be the worst goal you're chasing right now
• The Millennial financial reality: student loans, a broken housing market, and boomer advice that no longer applies
• How self-compassion and accountability actually work together, not against each other
• 
  

Amy Landino's book Good Morning, Good Life is available now. DM Amy on Instagram @AmyLandino the word "Tess" to receive her free Extraordinary Action Framework.

00:00 — Welcome & Amy Landino introduction

01:00 — Amy's origin story: moving out at 18 and the "there's gotta be a better way" mindset

04:00 — The wedding video that started everything — and how YouTube changed her life

07:00 — What people get wrong about morning routines (hint: Instagram flex culture)

09:30 — Checking email vs. checking your goals: offense vs. defense

12:00 — Why you apologize for not replying fast enough — and why you need to stop

13:15 — Is Good Morning, Good Life the Gen Z version of Miracle Morning? Tess makes the case

16:45 — The three-bucket framework: Movement, Mindfulness & Mastery

19:20 — Tess's morning confession: sitting with her dogs, and finally giving herself permission

21:00 — "I'm not a morning person" — the #1 objection, completely reframed

24:00 — "But I have kids" — excuse #2, and Amy's surprisingly honest answer

28:45 — The Extraordinary Action Framework: DM Amy on Instagram to get it free

29:20 — Self-compassion + accountability: why they're not opposites

33:45 — Screw "realistic" — why shooting for the unrealistic actually makes sense

34:45 — Hot take: Why Amy tells clients with six-figure businesses to just go get a job

40:00 — Generational spotlight: Millennials as the internet's guinea pigs

42:30 — Student loans, the housing market, and what Millennials actually inherited

47:20 — Boomer advice vs. Millennial reality — a tension that's very, very real

48:00 — The $90K moment: Amy's dad, and why the people who love you don't always know what's possible for you

SUBSCRIBE to The Gen Mess with Tess podcast for weekly insights on workplace culture, generational challenges, and relationship advice.

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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Why does one vague comment from your boss stay in your head all day? Why does being left off a meeting invite suddenly feel personal? Why can work feel emotionally exhausting even when you’re technically “doing fine”?

In this episode of The Gen Mess with Tess, Tess Brigham explains why work is never just about tasks, productivity, or performance—it’s psychological.

From feedback and comparison to belonging, safety, and identity, Tess breaks down what’s happening beneath the surface when work stress feels bigger than the moment itself. She also explains why so many leaders misread performance issues that are actually clarity issues, communication issues, or nervous-system responses.

If you’ve ever replayed a Slack message, questioned yourself after feedback, or wondered why Gen Z seems to experience work differently, this episode explains why.

This is part 1 of a 2-part solo series on the emotional reality of work, leadership, and what younger employees are actually experiencing in today’s workplace. Part 2 will be published next week.

00:00 Why work is more psychological than most people realize

01:10 Why your brain treats work stress like threat

02:20 Why vague feedback feels personal

03:15 Work, identity, and self-worth

04:10 Why comparison intensifies workplace anxiety

04:45 What leaders misunderstand about Gen Z retention

06:00 Why Gen Z isn’t “too sensitive”

07:10 Communication problems are often anxiety problems

08:05 Why retention is a mental health issue

09:00 The key question leaders should ask instead 

visit tessbrigham.com to learn more

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 53 of The Gen Mess with Tess, Tess Brigham sits down with Amy Leneker, founder and CEO of the Center for Joyful Work, to explore why burnout keeps happening even to highly successful leaders who know better.

Amy has helped more than 100,000 leaders and teams, including Fortune 100 companies, rethink leadership, workplace stress, and employee well-being. A former public policy executive and recovering workaholic, Amy shares how burning out twice forced her to confront the internal patterns that kept driving overwork, achievement, and chronic stress.

Together, Tess and Amy unpack why burnout is not simply about workload; it is often tied to identity, workplace systems, leadership culture, and the stories people tell themselves about success.

This conversation explores:

• why high performers often confuse overworking with worth
• how burnout can repeat even after changing jobs
• what workplace stress is doing to leadership pipelines
• why younger employees are redefining ambition
• how Gen Z experiences stress differently at work
• why recognition and appreciation matter more than many leaders realize
• the three conditions that create joy at work: meaning, mattering, and momentum
• how AI may force a new era of critical thinking in leadership

Amy also shares findings from her national workforce research showing that employees increasingly need joy at work to perform well, yet many leaders still operate inside systems that reward exhaustion instead of sustainability.

For HR leaders, managers, and executives, this episode offers a practical framework for understanding employee burnout, generational tension, workplace stress, leadership development, and what healthy ambition may need to look like next.

If your organization is asking why employees are disengaged, overwhelmed, or pulling back from leadership, this conversation explains what may be underneath it.

00:00 – Why Amy Leneker Burned Out Twice

02:14 – The Stress Story High Achievers Carry

04:12 – Why Leadership Still Rewards Burnout

06:45 – Why Joy Belongs in the Future of Leadership

08:21 – Gen Z, Stress, and New Definitions of Work

11:52 – Are Younger Workers Redefining Ambition?

16:15 – The Three Conditions That Create Joy at Work

20:23 – Why Gen Z Needs Appreciation More Than Leaders Think

25:36 – The Exercise That Changed Amy’s Career

31:13 – Parenting, Leadership, and Invisible Overwork

35:01 – Why Workplace Systems Keep Breaking People

40:13 – AI, Critical Thinking, and the Future of Work

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 52 of The Gen Mess with Tess, Tess explores one of the most misunderstood workplace dynamics right now: why younger employees keep asking for transparency, and why many leaders misread that as entitlement.

While transparency is often described as a Gen Z workplace preference, Tess argues it is something much deeper: a psychological response to growing up in a world where trust has become increasingly fragile.

From financial instability and public institutional failures to social media fabrication, layoffs over Zoom, and the rise of AI, younger workers have developed a sharper need to understand what is real, what is changing, and what leaders are not saying.

In this episode, Tess explains why transparency is no longer just a communication style. and is now the foundation of trust in modern organizations.

• Why Gen Z’s questions are often about safety, not defiance
• How uncertainty activates worst-case thinking in the brain
• Why silence from leadership often increases workplace anxiety
• The difference between transparency and oversharing
• How honesty improves motivation, engagement, and retention
• Why every generation benefits when leaders communicate clearly

For HR leaders and managers, this episode offers a practical lens on why communication gaps create disengagement — and why explaining reality clearly may be one of the most powerful leadership tools available today.

Because in today’s workplace, transparency is not a bonus. It is how trust gets built.

00:00 – Why Transparency Keeps Coming Up in Every Workplace Conversation

02:20 – Why Gen Z Grew Up Distrusting Systems

04:38 – What the Brain Does When Information Is Missing

06:15 – Why Transparency Matters More Than Perfection

07:04 – A CEO’s Silence During Uncertainty

08:45 – How Honesty Calms the Nervous System

09:26 – Why Motivation Drops When Trust Is Unclear

10:45 – Transparency vs Oversharing

11:46 – Why Every Generation Needs More Clarity

13:10 – The Leadership Advantage of Honest Communication

14:04 – Final Takeaway: Transparency Rebuilds Trust

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 51 of The Gen Mess with Tess, Tess is joined by Corrine Ishio, founder of My Working Soul, to explore a challenge many fast-growing companies face but rarely talk about: scaling the business faster than the culture can keep up.

When organizations grow quickly, hiring often becomes reactive. Leaders focus on roles and results, while the human side of the company quietly gets lost. The result? Misalignment, disengagement, and teams that no longer feel connected to the mission that once energized them.

Corrine shares her perspective from years working in talent, recruiting, and HR; helping founders and leadership teams rethink how they hire, communicate, and define culture during periods of rapid growth.

In this conversation, Tess and Corrine explore:

• Why companies struggle to maintain culture as they scale
• The complicated role HR plays between employees and leadership
• How generational misunderstandings shape today’s workplace
• Why Gen Z communication patterns are confusing many managers
• The influence of social media on workplace behavior and identity
• Why purpose is becoming central to work in the AI era

They also discuss how leaders can create healthier workplaces by focusing less on rigid definitions of culture and more on communication, self-awareness, and intentional hiring. Because when companies grow quickly, it’s easy to forget the most important part of any organization: the humans building it.

00:00 – Introduction to Corrine Ishio & My Working Soul

01:05 – Corrine’s Path Into HR & Human-Centered Work

04:00 – What HR Actually Does (vs. what people think it does)

07:00 – Why HR Often Feels Stuck Between Employees & Companies

11:00 – The “Human” Lens Inside Business Operations

13:00 – The Meaning Behind “My Working Soul”

17:00 – Why Culture Breaks When Companies Grow Quickly

20:30 – What a Healthy Workplace Actually Looks Like

23:00 – Communication Differences Across Generations

29:30 – Why Younger Workers Are Often Misunderstood

34:30 – Purpose, Work, and the AI Era

38:30 – Are Younger Employees Harder to Manage?

43:00 – Millennials, Social Media, and Cultural Fragmentation

49:00 – Safety, Identity, and the Digital Workplace

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.