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.

Timestamped Overview

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

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