May 27, 2026

What if the things you loved most as a kid still hold clues about the life you want now?

I still remember Yankees games crackling through a transistor radio tucked under my pillow long past bedtime. For Ben Orlando, it was realizing those moments were never really about baseball.

I’m talking with psychotherapist, writer, and Midnight Library of Baseball host Ben Orlando about masculinity, nostalgia, and what happens when men lose the thread back to themselves.

We explore why the hobbies we dismiss as “not serious” often point to something much deeper, and why reconnecting with joy and authenticity matters even more as we get older.

You’ll hear about:

• Why certain childhood memories stay with us for life
• How men lose themselves in careers and responsibilities
• The importance of reconnecting with joy and nostalgia
• Why hobbies and passions matter more than we think
• The emotional power of shared memories
• What older men regret most at the end of life
• Why it’s never too late to reconnect with yourself

 

Resources:
Podcast: Midnight Library of Baseball
Website: midnightlibraryofbaseball.com
Instagram: @midnightlibraryofbaseball
Website: benorlando.com

About Ben:
Ben Orlando is a psychotherapist in Arlington, VA, and the producer of Midnight Library of Baseball, a documentary-style baseball history podcast for listeners who want something deeper, quieter, and more reflective than the typical sports show. His novel, Throwing a Butterfly, about a female knuckleball pitcher trying to make it to the majors, will be published in June, 2027.