Ep.183 I Deciding to Take Initiative: What Happens When Men Step Up with Ryan Michler

Is it possible to become the man you never had as a role model?

Ryan Michler didn’t grow up with a blueprint for manhood—but that didn’t stop him from building one. He and Sanger talk about why so many men feel aimless and how stepping up—not faking it—is the way out. They talk about the appeal of distractions like sports and alcohol, the discomfort of starting from zero, and the kind of fulfillment that comes from actually doing hard things.

 

KEY TOPICS

• Why men substitute purpose with stats, screens, and manufactured intimacy.
• What happens when young men admire risk—and older men discourage it.
• How men get mocked both for not knowing—and for trying to learn.
• Why it’s better to take a first step than wait for certainty.

 

CHAPTERS

00:00 – Intro: Defeating Bad Decisions in Life & Business

00:50 – Learning by Failing on a Ski Trip

03:18 – Meet Ryan Michler: Founder of Order of Man

04:20 – Growing Up Without a Present Dad

06:48 – Can You Still Learn Manhood as an Adult?

08:27 – Why Men Hide What They Don’t Know

09:14 – The Catch-22 of Men Asking for Help

10:51 – Why Not Knowing Feels Like a Threat

11:38 – How Ego Blocks Growth

13:43 – Finding Mentors & Letting Go of Pride

16:08 – Why Ryan Walked Away from His Firm

18:26 – Taking the Leap Toward Autonomy

20:53 – Rebuilding on Your Own Terms

23:09 – Why Advice Often Reflects Regret

25:33 – Vested Interests & Biased Guidance

27:46 – Seeking Deeper Purpose in Friendships

29:49 – Choosing Relationships Intentionally

31:03 – Escaping Into Sports When Life Lacks Purpose

34:42 – False Meaning in Porn, Alcohol, & Ego

37:02 – What Are You Escaping From?

39:22 – Balance Is a Constant Act

41:45 – Why Fulfillment Beats Happiness

44:09 – You Don’t Find Purpose—You Build It

46:25 – Podcasting & the Birth of Order of Man

48:50 – Try What Interests You (Without Attachments)

51:11 – Ryan’s Battle Plan: 4 Areas of Purpose

53:13 – Decision Tip: Find Someone Who’s Done It

53:21 – Where to Connect with Ryan Michler

54:15 – Key Takeaways

54:50 – Message from the Producer

 

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Thank you to Shelby Peterson of Transcend Media for editingand post-production of the Decidedly podcast.

 

SANGER’S BOOK: ⁠A Life Rich with Significance: Transforming Your Wealth to Meaningful Impact⁠

 

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