Why Men Struggle to Ask for What They Want After Retirement

Dec 17, 2025

Why is it often easier to know what we don’t want than to ask for what we do?

 

In this episode, I’m joined by Paul Quinn, author of The Big Ask: Unlock the Possibilities in Your Work Life and Dreams with Courageous Requests. Paul began his career as an actor before moving into corporate training and writing, where he became fascinated by the moments that spark real change.

 

Today, we explore how identity, fear, and unspoken rules shape the choices we make. Paul also shares stories that show how a single, well-timed question can open doors we didn’t know were there.

 

You’ll hear about:

• How asking the right questions can help you reconnect with what you actually want
  
  
• Why redefining identity after work can feel so disorienting
  
  
• The trap of focusing on what we don’t want (instead of naming what we do)
  
  
• How fear and perfectionism can limit what you’re willing to try
  
  
• A simple question that can shift how we imagine what comes next

 

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Resources:

 

Visit Paul's Website

The Big Ask: Unlock the Possibilities in Your Work Life and Dreams with Courageous Requests

Follow Paul on Facebook