Why Does It Feel So Wrong To Be Human At Work?

Ep 10 | Why Does It Feel So Wrong to Be Entitled?

Episode Summary

Entitlement at work gets a bad rap, but is it always a bad thing? In this season’s season finale, Chris and Pinaki unpack how expectations shape what we think we deserve, how entitlement shows up across generations, and what happens when organizations and employees aren't aligned. From working remotely to self-advocacy, we explore the tension between earned rights and perceived demands – and how empathy can bridge the gap.

Episode Notes

Season 2, Episode 10: Why Does It Feel So Wrong to Feel Entitled at Work?

Episode Description

Is feeling entitled at work… actually a bad thing?

In the Season 2 finale of Why Does It Feel So Wrong to Be Human at Work?, hosts Pinaki Kathiari and Chris Lee challenge the stigma around workplace entitlement. They explore what happens when expectations don’t match reality when it comes to salary assumptions and generational values to promotions, office return mandates, and even who gets to speak up.

Together, they unpack:

• What “entitlement” really means—and why it’s become a dirty word
• Why everyone feels entitled to something (yes, including employers)
• The difference between healthy self-worth and toxic expectations
• Generational gaps in defining success, fairness, and work ethic
• How social media, corporate culture, and experience gaps shape what people think they deserve
• What to do when you feel undervalued, overworked, or overlooked
• And why the employer-employee relationship should be a mutual exchange, not a power imbalance
• It’s a vulnerable, witty, and wise closer to a season full of deep dives into the human experience at work.

Timestamps

• 00:00 – Do some generations feel more entitled than others?
• 02:00 – What is entitlement, really? A mismatch between cause and effect
• 04:30 – Remote work expectations and the post-pandemic “entitlement bubble”
• 07:00 – Why confidence isn’t the same as readiness (but both show up at work)
• 09:00 – What are we universally entitled to—and where things get murky
• 11:00 – Gen Z’s idea of financial success vs. other generations
• 13:00 – Culture clashes: Structure vs. flexibility, loyalty vs. opportunity
• 15:00 – Employer entitlement: What companies think they deserve
• 17:00 – The history of employer-employee power dynamics
• 20:00 – What happens when people don’t speak up
• 23:00 – Why confidence + lack of experience ≠ arrogance
• 25:00 – Letting go, letting them fail, and learning from new ways of doing things
• 28:00 – Entitlement ≠ laziness: Grit, effort, and advocating for yourself
• 32:00 – Wisdom That Feels So Right: Books, tools, and reflections

Wisdom That Feels So Right

The Let Them Theory by Mel Robbins (and TED Talk)

Strong, Calm, Confident You by Kelsey Buckholz

How Money Works YouTube channel by Darin Soat

The Confidence Code by Katty Kay and Claire Shipman (for adults and teens)

Local Wisdom – Your digital comms partner (like silly putty for your team)

Mic-Drop Moments

“Entitlement is a byproduct of belief—belief that your effort deserves a return.”

“The problem isn’t entitlement. The problem is when our expectations don’t match someone else’s reality.”

“We stay human at work by not letting work dehumanize us.”

Connect with Us

Pinaki Kathiari – LinkedIn | Local Wisdom

Chris Lee – LinkedIn | Gallagher Communication

Special Thanks

To the people and teams who made Season 2 possible: Brielle Saracini, SBX Productions, and everyone at Local Wisdom. Thank you for helping us stay human while keeping it real. 

And to our listeners: thank you for letting us in.

Stay Human, Stay Curious

What’s something you feel entitled to—and why? Did this episode make you reflect, nod, or even cringe a little? We’d love to hear your thoughts. Share it, tag us, rate us, and visit whydoesitfeelsowrong.com to learn how we’re bringing these conversations to teams and stages.