Crossing the Threshold: Rites of Passage and Raising Good Men with Luke Entrup
In this conversation, Shaun Dawson and Luke Entrup explore what it really means to guide boys into manhood in a culture that has lost its rites of passage. Luke shares how fathers can reclaim the ancient practice of initiation to raise sons of character, courage, and conviction. Together, they discuss how emotional intelligence, mentorship, and time in nature can help boys develop “heart-connected power” — strength balanced with compassion.
Key Takeaways
Key Takeaways
- Rites of passage matter. When boys lack meaningful thresholds into adulthood, they seek belonging in unhealthy or toxic ways.
- Healthy masculinity is heart-connected power. Strength and sensitivity can coexist; empowerment means “power with,” not “power over.”
- Mentorship is missing. Fathers and communities must step up to guide boys intentionally into manhood.
- Growth requires discomfort. Modern initiations should challenge boys safely but meaningfully.
- Connection before correction. Daily “special time” strengthens the bond that supports discipline and trust.
- Digital disconnection. Real growth happens offline — in nature, in silence, and through shared experiences.
“If we don’t provide a healthy framework for initiation, a toxic one will take its place.” - Luke Entrup
“Power over is an expression of weakness; empowerment is an expression of strength.” - Luke Entrup
“Silence is noble — it helps me listen better, parent better, and see more clearly what needs to happen next.” - Luke Entrup
“Recognizing where we’ve fallen short as fathers isn’t failure — it’s the only way we grow.” - Shaun Dawson
Timestamps / Chapter Markers
- 00:00 — Welcome + who is Luke Entrup
- 02:14 — What a rite of passage actually is
- 03:48 — Why thresholds matter (and what we lost)
- 05:41 — Two key transitions: childhood→adolescence, adolescence→manhood
- 08:56 — Belonging first, then independence
- 10:59 — Emotional intelligence as real power
- 13:56 — Adapting ancient rites for modern life
- 15:29 — Discomfort over danger: designing challenge well
- 16:29 — When boys miss initiation (mentorship gap)
- 18:39 — Screens hijack belonging
- 20:22 — Two ails: phone culture + loss of free-range mobility
- 22:02 — What healthy masculinity looks like
- 25:52 — Reframing “toxic” vs healthy masculinity
- 27:01 — How to build thresholds at home
- 27:43 — Father-Son Connection Experience (Luke’s program)
- 28:59 — Annual “hard thing together” in nature
- 31:17 — Daily “special time” (15-minute ritual)
- 32:43 — Closing the gap between the parent you are and hoped to be
- 34:50 — The power of repair: “I’m sorry”
- 37:13 — What Luke thinks he’s done well (awe + the natural world)
- 39:15 — What he’d change (rigidity → flexibility)
- 41:07 — Anti-fragility over brittleness
- 42:08 — One principle: “Silence is noble”
- 45:58 — The 3-step challenge for parents
- 47:20 — The 4th step: “What do you need from me this year?”
- 49:38 — Closing + credits
Supporting Content
- The Anxious Generation by Jonathan Haidt – on technology’s impact on youth.
- Bill Plotkin – Nature and the Human Soul – developmental stages and human initiation.
- Father–Son Connection Experience – Luke Entrup’s program for fathers and sons.
- Hand in Hand Parenting – source of the “special time” practice.
- Buddhist concept: “One eye in, one eye out” — awareness of both inner and outer landscapes.
The Father’s Challenge by Luke Entrup
Simple but powerful four-step challenge for fathers:
- Daily Special Time – 15 minutes of uninterrupted, child-led play.
- Join a Community – find or create a group of fathers committed to rites of passage.
- An Annual Adventure – one outdoor challenge shared with your son each year.
- Ask the Question – “What’s one thing you need from me this year to feel connected to me?”