Casual Dating, Honesty, and Boundaries

Ryan Michler is the founder of Order of Man – an online movement that teaches men how to protect, provide, and preside using timeless principles of masculinity applied to the realities of modern life. He is the leader of the Iron Council – a men's group with over 1,000 members worldwide.

In this episode, James asks Ryan about his journey from a financial planner to a leader of men, dating after divorce as a single father of four, and practical tips on how men can be role models to young boys today.

Expect to learn:

• How to turn the goal of “being a better man/dad” into measurable actions
• The important difference between discipline vs. systems that lock healthy habits in
• What it's like to build a movement of men from scratch

• 00:00 – Finally Connecting: From the UK Countryside to Utah
• 02:00 – Father–Son Trips and the Value of Shared Experiences
• 03:45 – Choosing America and the Spirit of Individualism
• 07:15 – How Order of Man Accidentally Took Off
• 08:30 – Turning a Side Project into a Movement
• 09:40 – Building the Iron Council and Its Early Days
• 11:00 – Making “Becoming a Better Man” Tangible
• 13:00 – Asking Kids How You’re Doing as a Father
• 22:30 – Co-Parenting After Divorce and Showing Up Fully
• 27:00 – Raising Daughters, Emotional Regulation, and Triggers
• 28:30 – What It’s Really Like to Have Four Kids
• 33:30 – Why Kids Need Other Kids (Not Just Parents)
• 34:30 – How to Be a Male Role Model for Boys Who Aren’t Yours
• 41:40 – Where to Raise a Family: Rural Roots, City Trips
• 45:00 – Why Big Cities Can Drain the Soul
• 47:00 – Sophistication vs. Culture (and Why Culture Wins)
• 58:00 – Dating Again in Your 40s (and Why It’s Easier)
• 1:01:30 – Casual Dating, Boundaries, and Honesty
• 1:13:30 – The Habits Men Struggle With Most (and Why They Escape)
• 1:14:50 – Phones, Social Media, and Setting Boundaries for Kids
• 1:16:30 – Parenting with Systems: Phones Off at 10 p.m.
• 1:20:00 – What Ryan’s Son Thinks of Order of Man
• 1:22:00 – Wrapping Up: Building With Depth, Raising the Next Generation