Cancel Culture and Jokes at Work: A Corporate Comedian’s Perspective

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Is it dangerous to joke at work? Let’s hear from a corporate comedian about the perils of using humor at work…and how you can overcome them.

Key Takeaways:

  • What sets Greg apart from other corporate entertainers?
  • Greg Schwem makes Fortune 500 Companies laugh at themselves
  • Greg Schwem is not your typical comedian
  • Greg rules as a comedian
  • The different definitions of what is funny
  • Rock, Roll and Laugh your way to the top
  • You can’t cancel laughter
  • Work, Laugh, Repeat
  • Benefits of humor in the workplace

In today’s fast-paced corporate world, stress and burnout are more common than ever. Yet, humor remains an underutilized tool for creating a positive, engaging, and resilient workplace. To explore this, I had the pleasure of speaking with Greg Schwinn, a motivational corporate comedian whose mission is to make the business world laugh at itself.

Greg has performed for Fortune 500 companies, business associations, and conferences, bringing levity to what can often be very serious environments. In this episode of the Lead with Levity podcast, we dove into how humor can transform workplace culture, why it’s vital for mental health, and how organizations can incorporate it into their daily operations.


Why Humor Matters in the Workplace

Greg believes that laughter is essential for a healthy and productive work environment. As he shared, “If you’re going to foster a good, healthy work environment, it has to include laughter. Everything else falls into place—mental health improves, people like their jobs, and they want to stay.”

His shows focus on helping teams laugh at themselves and their processes, creating a sense of camaraderie and breaking down hierarchical barriers.

Humor at Work: A Conversation with Corporate Comedian Greg Schwinn

In today’s fast-paced corporate world, stress and burnout are more common than ever. Yet, humor remains an underutilized tool for creating a positive, engaging, and resilient workplace. To explore this, I had the pleasure of speaking with Greg Schwinn, a motivational corporate comedian whose mission is to make the business world laugh at itself.

Greg has performed for Fortune 500 companies, business associations, and conferences, bringing levity to what can often be very serious environments. In this episode of the Lead with Levity podcast, we dove into how humor can transform workplace culture, why it’s vital for mental health, and how organizations can incorporate it into their daily operations.


Why Humor Matters in the Workplace

Greg believes that laughter is essential for a healthy and productive work environment. As he shared, “If you’re going to foster a good, healthy work environment, it has to include laughter. Everything else falls into place—mental health improves, people like their jobs, and they want to stay.”

His shows focus on helping teams laugh at themselves and their processes, creating a sense of camaraderie and breaking down hierarchical barriers.


The Role of the Corporate Comedian

When Greg gets a call to perform, it’s not just about cracking jokes. He works closely with clients to understand their goals:

  • Why did they hire him? Is the company doing well and wants to celebrate, or are they struggling and in need of a morale boost?
  • What do they want to laugh about? Whether it’s poking fun at internal processes or finding humor in the competition, Greg tailors his material to resonate with the audience.

He emphasizes that his role is to make light of situations, not to belittle anyone’s work. “There’s a fine line between having fun with a corporate audience and mocking them,” he says.


The Rules of Corporate Comedy

Greg’s approach offers valuable lessons for anyone trying to use humor at work:

  1. Avoid belittling. Humor should foster connection, not alienation.
  2. Know your audience. Understand what’s funny to them and what might cross a line.
  3. Collaborate. Greg involves clients in the process, sharing his presentation materials in advance to ensure accuracy and alignment with their values.

The Challenges of Post-Pandemic Comedy

The pandemic changed how we engage with humor. For two years, our primary source of entertainment was screens. Now, as we return to live events, audiences need to relearn how to laugh together.

“People are desperate to be out and laugh among others again,” Greg observes. But the shift to digital entertainment has created a culture where audiences are quick to judge, swipe, or move on. Rebuilding patience and the willingness to engage with humor is critical.


Why Laughter is Good for Business

Greg’s work highlights the tangible benefits of humor in the workplace:

  • Improved mental health: Laughter reduces stress and boosts resilience.
  • Stronger team connections: Shared humor fosters trust and collaboration.
  • Increased retention: Employees are more likely to stay in jobs where they feel happy and engaged.

As Greg puts it, “We can’t have an environment where nobody laughs for eight hours. That’s not sustainable.”


About Greg Schwem

​HuffPost calls Greg Schwem “Your boss’ favorite comedian.” The Chicago Tribune dubbed Greg “king of the hill in the world of corporate comedy. Performing live or virtually as a keynote humorist, master of ceremonies or motivational speaker exclusively for business conferences, association gatherings and other private events, Greg’s client list includes Microsoft, Cisco Systems, McDonald’s, IBM, Motorola, United Airlines and John Hancock. Greg’s various programs share one central theme: make audiences laugh at their work environments and do it while performing clean and politically correct.

Greg is also the creator and host of the TV travel show, “A Comedian Crashes Your Pad, ” now streaming on Roku and available in the Apple and Google Play stores through the Fantastic Entertainment app.

Finally, Greg writes a weekly, nationally syndicated humor column for Tribune Media Services and is the author of two books: “The Road to Success Goes Through the Salad Bar: A Pile of BS (Business Stories) From a Corporate Comedian’ and “Text Me If You’re Breathing: Observations, Frustrations and Life Lessons From a Low-Tech Dad.” Greg has appeared on numerous national television programs and been seen in concert with the likes of Celine Dion and Keith Urban.

Specialties: stand up comedy, comedy for business, customized stand up comedy, humor writing, motivational speaking, awards emcee, master of ceremonies, video host, moderator, facilitator, columnist, author