I finally tracked down Mr. Craig Darrell — my 8th grade Religion teacher from Holy Name in Worcester, MA. We hadn't spoken since 2004. Turns out he's been living in Leavenworth, Kansas, working with special needs kids, and still remembers every single stunt I pulled in his class. Oh — and I still have the detention slip.

We talk about what it was really like teaching in the '90s vs. today, why he walked away from 22 years of teaching, playing semi-pro football for 17 seasons, working as a bouncer at Jillian's (where he caught me underage), painting ceramics to stay sane, and why the kindergartners he works with now are teaching HIM more than he ever expected.

This one got real. Mental health, family, distance from grandkids, and what it means to actually show up for people — Mr. Darrell never stopped teaching. He just changed his classroom.

⏱ CHAPTERS:
00:00 Reconnecting After Years
02:54 Choosing Holy Cross: A Journey of Discovery
06:12 Life Lessons from College Football
08:59 The Transition to Teaching
12:12 Challenges in Modern Education
15:05 The Evolution of Teaching Methods
17:59 Teaching Special Needs: A New Perspective
20:47 Life Skills and Real-World Applications
24:01 The Importance of Diverse Learning Experiences
28:00 Problem Solving and Adaptability
29:11 Exploring Career Paths and Personal Growth
30:07 The Impact of Sports on Life
31:59 Hobbies and Finding Relaxation
35:04 Mental Health and Life Challenges
37:03 The Importance of Community and Family
37:46 Navigating Technology and Childhood
39:56 Experiences as a Bouncer and Bartender
42:48 Reflections on Teaching and Mentorship
46:00 The Value of Family and Presence
48:47 Lessons from Children and Innocence
58:46 The Importance of Empathy in Education
01:01:09 Reflections on Growing Up and Community
01:06:30 Memories of Mischief and Learning
01:11:01 The Impact of Teachers on Students
01:15:11 Cherishing Memories and Life Lessons
01:21:31 Connecting Through Social Media

🎙️ 20-Year Timeout is a podcast about reconnecting with people from your past — unscripted, real, and always surprising. New episodes dropping regularly.

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Website: https://www.20yeartimeout.com

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20 Year Timeout is a podcast where I reconnect with people I have not spoken to in over twenty years to see what time has done to our stories.

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