The Gen Mess with Tess

The Gen Mess with Tess
Podcast Description
Are generational divides in the workplace and in life driving you crazy?The Gen Mess with Tess is here to help! Hosted by Tess Brigham—certified coach, licensed therapist, TEDx speaker, author, and mom to a Gen Zer—this podcast tackles the challenges and complexities of navigating life and work across multiple generations. From the unique struggles of Gen Z to the evolving perspectives of Millennials, Gen X, and Baby Boomers, Tess brings her expertise to the table, offering practical advice, expert insights, and real conversations to bridge the generational gap. Whether you're trying to communicate better with colleagues, understand your kids, or just get a clearer perspective on the "mess" of it all, The Gen Mess with Tess is your go-to resource for understanding how different generations think, work, and live. Hosted on Acast. See acast.com/privacy for more information.
Podcast Insights
Content Themes
The podcast delves into themes such as generational divides, burnout, and workplace communication. Examples include episodes discussing the unique challenges faced by Millennials and Gen Z regarding burnout, and practical strategies for improving generational communication in the workplace. The show also highlights societal expectations and personal perspectives, aiming to bridge the gap among Baby Boomers, Gen X, Millennials, and Gen Z.

Are generational divides in the workplace and in life driving you crazy?
The Gen Mess with Tess is here to help! Hosted by Tess Brigham—certified coach, licensed therapist, TEDx speaker, author, and mom to a Gen Zer—this podcast tackles the challenges and complexities of navigating life and work across multiple generations. From the unique struggles of Gen Z to the evolving perspectives of Millennials, Gen X, and Baby Boomers, Tess brings her expertise to the table, offering practical advice, expert insights, and real conversations to bridge the generational gap. Whether you’re trying to communicate better with colleagues, understand your kids, or just get a clearer perspective on the “mess” of it all, The Gen Mess with Tess is your go-to resource for understanding how different generations think, work, and live.
Hosted on Acast. See acast.com/privacy for more information.
What if your company’s employee benefits plan could be the secret weapon that keeps your top talent loyal—and even attracts new superstars through the door?
In this enlightening episode of Gen Mess with Tess, host Tess Brigham sits down with powerhouse employee benefits strategist, Sirena Dimas, to pull back the curtain on what really makes benefits matter in today’s rapidly changing workplace.
Key Highlights:
- Why company benefits aren’t just an expense—they’re an underused asset that could drive business growth and retention (and how to shift your mindset).
- Sirena’s unique journey from young mom to industry leader, and the “listening” skill that launched her success.
- The generational evolution of benefits: what companies (and employees!) wanted 20 years ago versus today, including a powerful look at the rise of mental health support and financial wellness benefits.
- Candid stories on multigenerational workplaces and families—like what happens when a Gen X, an elder Millennial, Gen Z, and Alphas all live together (hint: mediation skills come in VERY handy!).
- Practical tips for boosting benefit engagement—open enrollment meetings, digital resources, FAQs, and why communication must match each generation’s style.
Whether you lead a business, manage a team, or just want to understand how work culture is evolving across generations, this episode is packed with the wisdom (and real-world stories) you need to start fixing the Gen Mess—one conversation at a time.
Loved this episode?
- Share it with a manager or HR pro who wants to rethink their benefits strategy!
- Try a new way of communicating with your colleagues this week—see what clarity and connection you can create.
- Stay tuned and subscribe for more insights on navigating generational dynamics at work and at home.
Remember: Your benefits package and your people are your company’s greatest assets. Make sure everyone knows how to use them!
Timestamped Overview
00:00 “Gen Mess Podcast with Tess”
03:27 Insurance: A Personal Journey
07:25 Consumer Mindset: Expense to Asset
11:19 Employee Financial Literacy Gaps
13:47 Navigating Employee Health Benefits
19:54 Children Witness Work Stress
22:39 Graduating in the ’90s vs. ’00s
25:28 Supportive Client Relationships
29:05 Hands-On Learning Beats Tech
31:20 Printer and Battery Misunderstandings
34:18 Parenting Approaches Across Generations
37:18 “First Speaker Buys the Product”
Hosted on Acast. See acast.com/privacy for more information.

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