Ep 04 | Why Does It Feel So Wrong to Ask for Help?

Season 2, Episode 4: Why Does It Feel So Wrong to Ask for Help at Work?

 

Episode Description

Is asking for help a sign of weakness—or is it the key to doing great work and being fully human?

In this heartfelt episode of Why Does It Feel So Wrong to Be Human at Work?, hosts Pinaki Kathiari and Chris Lee explore why asking for help often feels like failure in today’s work culture—and why that couldn’t be further from the truth.

Sparked by a powerful story about Pinaki’s late grandmother (“When you're in trouble, don't sit by yourself”), this conversation dives into the subtle social rules, psychological biases, and cultural expectations that prevent people—especially men, leaders, and high performers—from speaking up when they need support.

Together, they unpack:

• Why asking for help is tied to power dynamics, imposter syndrome, and fear of judgment
• How leaders can make it safer for people to admit they don’t know something
• The link between help-seeking and collaboration, innovation, and growth
• How AI tools are triggering even more “help guilt” in the modern workplace
• The risk of helping too much and enabling dependency
• How to know when to step in—and when to let people grow through struggle

This one is personal, practical, and packed with real-world stories, from fixing dryers to managing emotional labor. Plus, the team closes with their latest segment, Wisdom That Feels So Right, with book, video, and therapy recs that meet you where you are.

 

Timestamps

• 00:00 – Story: Ronnie’s advice from age 96—“Ask for help.”
• 02:00 – Dryer repair, YouTube, and the myth of male competence
• 05:00 – Workplace fears: Looking incompetent, affecting your brand
• 08:00 – Why people hesitate to ask for help (even when they want to)
• 10:00 – Tips for managers: Reframing help as collaboration
• 12:00 – Pressure, workload, and the cost of silence
• 15:00 – Creating psychological safety in 1:1s
• 18:00 – The switch: When “asking for help” suddenly feels weak
• 21:00 – The risk of helping too much—and how it stunts growth
• 24:00 – Leading without stepping on others’ autonomy
• 25:00 – Designing conversations that invite honesty and vulnerability

 

Wisdom That Feels So Right

• The Botany of Desire by Michael Pollan
• Daring Greatly and other works by Brené Brown
• Help: The Original Human Dilemma by Garret Keizer
• Therapy and support lines — because real help starts with reaching out
• SBX Productions for help creating your own podcast

 

Mic-Drop Moments

“Individually we’re limited—but together, we’re unlimited.”

“Help isn’t a detour—it’s the road to stronger work.”

“Sometimes people need to struggle. And sometimes they need to know they’re not alone in it.”

 

Connect with Us

Pinaki Kathiari – LinkedIn | Local Wisdom

Chris Lee – LinkedIn | Gallagher Communication

 

Special Thanks

Thank you to Local Wisdom for funding and fostering the conversations that bring more heart to the workplace. Shoutout to Brielle Saracini (producer), and the incredible team at SBX Productions—Vince, Taylor, and Bill—for helping us sound as good as we feel.

 

Share the Help

If something in this episode moved you, reminded you, or gave you courage—don’t keep it to yourself. Rate, review, share with a friend, or forward to someone who needs a nudge to raise their hand and say, “Hey, I could use a little help.”

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

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