Ep 05 | Why Does It Feel So Wrong to Be An A**hole?

Season 2, Episode 5: Why Does It Feel So Wrong to Be an A**hole at Work?

 

Episode Description

We said what we said. In this bold and uncensored episode of Why Does It Feel So Wrong to Be Human at Work?, hosts Pinaki Kathiari and Chris Lee are joined by internal comms legend Chuck Gose to take on the big question that no one talks about—but everyone experiences:

Why does it feel so wrong (yet so common) to act like an a**hole at work?

Together, they dive into:

• How to define “a**holery” (yes, it’s a spectrum)
• Why even good people act badly under pressure
• How work culture breeds incivility, and how to stop it
• The difference between bluntness and toxic behavior
• Cultural, psychological, and power dynamics behind a**hole behavior
• Why empathy, self-awareness, and reflection are your best antidotes

From office politics and passive-aggressive emails to visionary leaders who bulldoze their teams, this episode is part hilarious storytelling, part therapy session—and part HR intervention.

 

Timestamps:

• 00:00 – What makes someone “an a**hole” anyway?
• 03:00 – The cultural toxicity equation: it’s about the mix, not just the person
• 06:30 – Driving, Jersey slang, and workplace metaphors
• 09:00 – Level 1 vs. Level 5 a**holery (passive-aggression and beyond)
• 13:00 – Are visionaries more prone to bad behavior?
• 16:00 – Cultural and geographic friction in work styles
• 20:00 – What to do when someone’s a jerk at work (and it might be you)
• 25:00 – Pain, pressure, and psychopathy in leadership
• 30:00 – Relationships, reactions, and road rage: how to catch yourself before lashing out
• 33:00 – A**holes are contagious: are you hiring and breeding them?
• 36:00 – How corporate culture rewards toxic traits
• 40:00 – Parenting, kindness, and learning from Cobra Kai
• 43:00 – Final thoughts: no one is born an ahole, but we can all become one

 

Wisdom That Feels So Right

• Frequency podcast by Chuck Gose and Jenni Field
• How to Be a Gentleman by John Bridges
• Strong, Calm, Confident You by Kelsey Buckholtz
• Spaceballs (not really appropriate for work, but maybe)
• The Psychopaths Who Lead Us (Forbes article)
• Wonderwell – Kindness toy for kids

 

Mic-Drop Moments:

“One person’s visionary is another person’s jerk.”

“If you’re surrounded by a**holes… maybe it’s hiring. Or maybe it’s you.”

“Individually, we might slip. But when the system rewards bad behavior? That’s a culture problem.”

 

Connect with Us:

Pinaki Kathiari – LinkedIn | Local Wisdom

Chris Lee – LinkedIn | Gallagher Communication

Chuck Gose – LinkedIn | ICology | Frequency Podcast

 

Special Thanks:

Huge shoutout to Local Wisdom for making this show possible, and to our incredible team behind the scenes: Brielle Saracini and SBX Productions. You make us sound smooth—even when the topic is rough.

 

Keep the Conversation Going:

Whether you’ve encountered one, been one, or managed one—this topic hits home. Share your thoughts, leave a review, tag us on LinkedIn, or email us your story (names changed to protect the guilty, of course). Visit whydoesitfeelsowrong.com to bring these conversations into your workplace.

Special thanks to digital communication agency Local Wisdom (www.localwisdom.com) for really believing in our mission and