Description

What if every time you judged a younger generation for having it "easy," you were really just grieving your own unmet dreams?

In this revealing solo episode of Gen Mess with Tess, host Tess Brigham turns the generational blame game upside down, making a powerful case that beneath every eye-roll and stereotype—Boomers are out of touch, Gen Z is fragile, Millennials are entitled—there’s a shared experience of grief. From nostalgic bitterness to deep-seated anxieties, Tess explores how each generation clings to the belief that their struggles had meaning, while often resenting the freedoms and boundaries claimed by those coming after.

Drawing on pop culture examples, workplace trends, and even the existential challenge of AI, Tess dissects why the world feels so tense, how each generation is coping with constant uncertainty, and what it truly means to evolve—not just as a society, but as individuals learning to let go. In a candid reflection on her own journey and those of her clients, Tess challenges listeners to see generational progress as an invitation to heal and redefine purpose, rather than a competition over who "had it worst."

Tune in for thoughtful insights, practical strategies, and an honest invitation to make peace with change—because maybe the real legacy isn’t just the pain we survived, but the wisdom we share.

Episode Overview & Timestamps:

• 00:00:01 - 00:00:31 –Intro Announcer kicks off the show, teasing generational divides and introducing Tess.
• 00:00:32 - 00:03:41 – Tess Brigham opens on the theme: every generation resents the next, touching on grief and why struggles “need to mean something.”
• 00:03:41 - 00:06:09 – Generational stereotypes in headlines and pop culture, from Boomers to Gen Z, and the underlying grief of unmet expectations.
• 00:06:09 - 00:09:31 – How generational pain shapes identity and workplace norms, especially around boundaries and mental health.
• 00:09:31 - 00:11:19 – Why Gen Z’s approach isn’t laziness, but boundary literacy—and Tess explains her work helping organizations bridge generational gaps.
• 00:11:20 - 00:14:37 – The paradox of technology, AI, and accelerating change; generational exhaustion and instability as the new normal.
• 00:14:37 - 00:16:07 – Collective grief: safety lost, predictability gone, and the urge to “defend our pain.”
• 00:16:07 - 00:19:39 – Tess reframes the purpose of pain: not to compete, but to transform and work together for positive change.
• 00:19:40 - 00:21:01 – Practical advice on reconciling your own grief and embracing evolution in how you view work, mental health, and generational progress.
• 00:21:05 - 00:21:26 –Outro Voiceover wraps up with a message to subscribe, follow Tess, and learn more.

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