Beyond the Stereotypes: Generations at Work in 2026 with Tess Brigham
In this episode of Career Pulse DC, Margaret sits down with Tess Brigham, host of Gen Mess with Tess, to unpack how generational experiences, from Boomers to Gen Z, are shaping today’s workplace.
Drawing on over 20 years as a licensed psychotherapist and coach, Tess offers a rare, ground-level view of how technology, COVID, burnout, and shifting cultural norms are influencing how people work, lead, and define success. This conversation moves beyond stereotypes to explore curiosity, empathy, and sustainability at work — and why the future of leadership may look very different than the past.
Key Topics & Takeaways
Generational stereotypes vs. reality
Why age should be treated as context, not a conclusion.
Gen Z, AI, and the future of hiring
Why younger workers are not immune to anxiety about AI, automation, and resume filtering — and how curiosity (not fear) is the most adaptive response.
Managing across age gaps
What seasoned professionals should remember when reporting to younger managers — and why ego is often the biggest obstacle to career longevity.
Networking without the cringe
Reframing networking as generosity, curiosity, and relationship-building — not self-promotion or transactional hustle.
Why Gen X feels invisible (and exhausted)
How being a “small sandwich generation” shaped Gen X leadership styles, burnout, and difficulty delegating — and what they can learn from Gen Z.
Millennials as managers
Why millennials often equate responsiveness with value, struggle to unplug, and carry invisible pressure to optimize everything — including their own lives.
Workplace empathy ≠ therapy
How managers can validate employees’ experiences without becoming their therapist — and why simple acknowledgment goes further than people think.
About the Guest
Tess Brigham is a licensed psychotherapist, certified coach, author, and TEDx speaker based in the San Francisco Bay Area. She hosts the Gen Mess with Tess podcast, where she explores generational psychology, work, identity, and mental health in a rapidly changing world.
Career Pulse DC
Abridged Transcript: Generations at Work with Tess Brigham
Margaret:
Welcome to Career Pulse DC. I’m your host, Margaret, and today I’m joined by Tess Brigham — licensed psychotherapist, certified coach, TEDx speaker, and host of the Gen Mess with Tess podcast. Tess works closely with millennials and Gen Z clients and brings a ground-level perspective on how generational experiences are shaping today’s workplace.
How Tess Began Studying Generations
Tess:
About 12 years ago, I opened a therapy practice in San Francisco and suddenly found myself working with a wave of 20-somethings — millennials. Then Gen Z entered the workforce, and I worked with them through COVID.
I realized I had a unique lens. I wasn’t just looking at generational data — I was watching young professionals click into their first Zoom job from their childhood bedrooms. That experience changes how you view work, security, and identity. That’s what inspired my podcast.
Generational Misconceptions
Margaret:
What are the biggest misconceptions generations have about one another?
Tess:
We treat age as a conclusion instead of context.
Older workers assume they know what it’s like to be 25 today. But the world is fundamentally different. Wages, technology, cost of living — everything has shifted.
The mistake is believing, “That’s not how I was at your age.” Of course it wasn’t. It’s not the same world.
Technology, AI & Gen Z
Margaret:
How does Gen Z feel about AI in hiring and automation?
Tess:
They feel similar anxiety to everyone else. They understand AI is here and that they need to learn it. But it still feels like a big, somewhat unregulated force.
For older generations, AI feels like a huge monster. For Gen Z, maybe it’s smaller — but it’s still a monster.
Curiosity is the most adaptive response.
Older Workers Interviewing with Younger Managers
Margaret:
What should seasoned professionals remember when reporting to younger managers?
Tess:
There’s a reason that person is in that seat. Even if someone benefited from connections, they wouldn’t stay unless they were competent.
You have to get out of ego. Stay curious. Ask: What can I learn here?
If your identity is wrapped up in being “the expert,” you’ll struggle in a workplace that’s constantly shifting.
Ageism & “Sanitizing” Yourself
Margaret:
Should people sanitize resumes to hide their age?
Tess:
You can’t sustain pretending to be someone you’re not.
At some point, you’ll show up in person. You can’t dye your hair and fake being 15 years younger forever.
Relationships matter more than resume optimization. People hire people. Networking — real connection — still wins.
Networking Without the Cringe
Tess:
Reframe networking as generosity.
Instead of “What can you do for me?” ask, “How can I support you?”
Most people underestimate how much others want to help. Connection isn’t transactional — it’s relational.
Gen X: The Invisible Generation
Margaret:
Why does Gen X feel invisible?
Tess:
Gen X is numerically smaller — about half the size of boomers and millennials. We grew up self-sufficient and learned to push through.
The downside? Burnout.
Gen X managers often struggle to delegate because we were conditioned to handle everything ourselves.
But we may also be the generation most open to changing leadership norms.
Millennials as Managers
Tess:
Millennials are incredibly hardworking — often to a fault.
They entered the workforce when technology enabled 24/7 availability. So they equate responsiveness with value. Slack message at 8 p.m.? Immediate reply.
That nervous system pressure hasn’t gone away.
Many are now learning that management requires shifting from doing everything to delegating and leading.
Workplace Empathy ≠ Therapy
Margaret:
Managers today hear much more personal information than in previous generations.
Tess:
Yes — and managers worry they’re supposed to become therapists.
You’re not.
You validate. You acknowledge. You ask, “How can I support you?”
Validation doesn’t mean changing deadlines or fixing everything. It just means recognizing someone’s experience.
That alone resolves more than managers realize.
COVID’s Ongoing Impact
Margaret:
Do organizations truly understand how COVID reshaped work?
Tess:
The companies hiring consultants like me usually do. But many toxic workplaces don’t.
We’re still in transition. Leadership is evolving.
Burnout today isn’t just COVID — it’s technology. Constant access. Constant noise.
Real change requires leadership self-awareness. And that takes time.
Industry Towns & Identity
Margaret:
In places like DC or the Bay Area, work is deeply tied to identity. Any advice?
Tess:
When identity is fused with career, stress multiplies.
The healthier you are mentally, the more you can take work seriously without taking yourself too seriously.
Parting Wisdom
Margaret:
What’s one takeaway listeners should hold onto?
Tess:
Slow down. Stop listening to so much noise.
We live in an era of crowdsourced life advice. Too many opinions create paralysis.
Get a few perspectives. Then quiet the white noise.
You are the one who has to live your life. Trust your own decisions.
Where to Find Tess
Tess can be found at tessbrigham.com and on the Gen Mess with Tess podcast, available on all major platforms.