Ep 12: Laughing Off the Job Title: Identity, Irony and The Art of the &
The Gen Mess with TessMay 07, 2025
12
00:54:49

Ep 12: Laughing Off the Job Title: Identity, Irony and The Art of the &

What if your career achievements are actually the least memorable thing about you at work?


In this captivating episode of "Gen Mess with Tess," host Tess Brigham sits down with John Garrett, a former Big Four CPA turned stand-up comedian and award-winning keynote speaker, to dig deep into the messy world of generational workplace dynamics—and why bringing your whole self to work is your biggest asset.


Episode Highlights:

  • The Surprising Power of Your “And”: John reveals how your outside interests—not just your job title—define who you are at work and are what people actually remember years later.
  • From CPA to Comedian: Hear how John’s journey from cubicles to comedy clubs (and back again as a corporate culture guru) taught him lessons every leader should know about authenticity, connection, and communication.
  • Authenticity vs. Professionalism: Why embracing your passions and quirks doesn’t mean sacrificing professionalism—and how leaders can balance both for a thriving workplace.
  • Generational Differences, Demystified: Tess and John dive into whether Gen Z, Millennials, and Boomers really want such different things—or if we’re all just seeking belonging in our own way.
  • Actionable Connection: The show unpacks research, real stories, and simple strategies to build rapport across generational divides and foster a workplace where people want to stick around.

Continue the Conversation: Want practical tools, leadership trainings, or just a dose of fun inspiration? Check out John Garrett’s book and resources at whatsyourand.com and tune in for more real-talk every week here on "Gen Mess with Tess."

Remember: The Gen Mess gets cleaned up one authentic conversation at a time. So what’s your “And”—and how will you share it this week?


Timestamped Overview

00:00 First Comedy Paycheck Surprise

04:46 Midwest Comedy Opportunities

07:26 "Comedy and Identity Merge"

10:07 Technical Skills Aren't Enough Anymore

16:10 "The Power of Speaking Out Loud"

17:29 Conversational Language and Comedy Confidence

21:28 Ego and Miscommunication Issues

23:40 Reevaluating Work-Life Balance

27:48 Redefining Success Across Generations

30:09 "Balancing Work and Personal Identity"

32:55 COVID's Impact on Mutual Understanding

38:39 "Workplace that Values Whole Self"

41:19 "Embracing Imperfection in the Workplace"

44:17 Intentional Time Between Work Hours

48:26 Vetting by Conversation

49:25 "Pug Passionate Conversations Thrive"

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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