238: The Hidden Cost of Leading Without Laughter | Greg Kettner

Update: 2025-11-01

Description

Get ready for a powerful, laughter-filled deep dive into workplace happiness and mental health. In this episode of the Learn-It-All™ podcast, host Damon Lembi sits down with keynote speaker, sales expert, and Work Happy founder Greg Kettner, who shares how his experiences as a comedian (including a transformative encounter with Robin Williams) shaped his mission to make mental health an everyday leadership conversation. They unpack why burnout and loneliness quietly hurt even at the top, how humor unlocks trust and retention, and why leaders must prioritize empathy without losing their edge. Greg shows that creating a workplace where people really want to show up isn’t just about perks or pay—it’s about connection, authenticity, and small acts of kindness.

You’ll walk away with actionable tools to spark more joy at work, lead with vulnerability, and help your team not just chase happiness, but create it. Whether you’re a CEO, manager, or individual contributor, this episode offers hard-hitting advice and inspiring stories for anyone ready to build more engaging, human-first organizations.

In this episode, you’ll learn:

Why empathy and vulnerability are leadership superpowers in today’s culture
How humor—with or without a joke-telling skill—creates trust and retention
The difference between chasing happiness vs. making space for “happier”
Concrete ways leaders can destigmatize mental health and foster psychological safety
Surprising ROI of prioritizing employee wellbeing (including retention and performance!)
The quickest way to turn around a bad day—and why serving others works
The untold dangers of loneliness for CEOs and founders—and how to build your support system
How to use time-blocking and positive rituals for daily mental health boosts
Why small moments of kindness change teams—and change lives

Timestamps:

00:00 – The CEO’s role in creating a fun, engaging culture

00:23 – Meet Gregg Kettner: comedian turned workplace happiness expert

01:32 – Robin Williams’ advice—make people laugh, it's magical

02:09 – Greg’s transformative story with Robin Williams

07:52 – What would work look like if we were happier?

10:20 – When the grass isn’t greener: reflecting before leaving a job

12:28 – Why the goal is “happier,” not happiness—and how to get there

13:53 – “Put your mask on first”: Why leaders need their own support

16:50 – Serving others: the fastest way to boost your own mood

18:05 – How to create psychological safety for mental health at work

22:07 – Empathy, boundaries, and HR: how leaders walk the line

25:42 – Greg’s top happiness-building tools (and why to stop chasing “happy”)

27:52 – Meditation for leaders: starting small, practicing daily

29:52 – Time-blocking—and how to engineer “happy breaks” at work

31:18 – Stress is rising: how leaders can help teams cope

32:57 – Workshops, keynotes, and fun training for happier culture

35:58 – Ask your staff—what perks actually help make work joyful?

40:55 – Greg’s most rewarding mental health impact story

44:14 – Comedy and compassion: making a difference in tough moments

45:41 – Kindness, connection, and what leaders must do now

47:17 – 40,000+ strong: The Humor Lab community

About Greg Kettner

Greg Kettner is an acclaimed keynote speaker, workplace happiness advocate, podcast host, and the founder of Work Happy, an organization dedicated to helping leaders build mentally healthy and engaging workplaces. Leveraging his career as a professional comedian (opening for the likes of Robin Williams and Norm Macdonald), Greg now blends humor, stories, and research-backed tools to tackle loneliness, burnout, and disengagement—especially among leaders and their teams. His mission: making mental health a non-negotiable part of every workplace conversation.

Resources & Mentions:

Podcast Contact Information:

Website: www.learnit.com

Email: podcast@learnit.com