Avoid the Mid-life Drift, Conflict Avoidance, and Weak Leadership | ASK ME ANYTHING
Order of Man
Ryan Michler
4.8 • 9.1K Ratings
🗓️ 3 June 2026
⏱️ 66 minutes
🧾️ Download transcript
Summary
In this solo Ask Me Anything episode, Ryan Michler tackles some of the most common challenges men face in midlife: complacency after success, leading a family without becoming controlling, overcoming conflict avoidance, dealing with regret, and building meaningful male friendships.
Ryan shares practical frameworks for finding purpose after you've achieved your goals, developing conviction without coercion, stepping into leadership at home, and letting go of past mistakes through accountability and changed behavior. He also offers candid advice on creating deeper connections with other men and why meaningful struggles are essential for growth and fulfillment.
SHOW HIGHLIGHTS
00:12 - Introduction and Iron Council Preview Call
01:20 - Staying Sharp After Success and Comfort
07:09 - Passing Faith to a Teenage Son Without Control
12:32 - The Midlife Emptiness Many Men Experience
15:28 - Overcoming Conflict Avoidance and People-Pleasing
30:50 - Leading Your Family Without a Power Grab
44:18 - How to Deal with Real Regret and Move Forward
55:32 - Why Men Struggle to Build Deep Friendships
01:05:30 - Where to Find Strong Male Relationships
01:06:55 - Final Thoughts and Closing Remarks
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Transcript
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| 0:00.0 | The things that keep you up at night, the things that excite you, the things that are on your mind when nothing else is, the things that you're doing when time is moving the fastest. |
| 0:09.1 | What is that? And then roll into that. |
| 0:11.6 | Lean into it. Be excited about it. Be passionate about it. Try to build something. Try to create something. |
| 0:17.5 | Try to start something from nothing. But yeah, it sounds a little bit like you don't have |
| 0:23.6 | any giants that's a problem that man needs the joker god needs satan good needs either |
| 0:33.9 | all right you guys welcome back to another order of man ask me anything unfortunately this is the |
| 0:39.6 | best part of the ask me anythings is that kipp sorenson joins us but unfortunately he's not |
| 0:46.9 | going to be joining us today i believe he's actually doing an iron man in hawaii with his wife right now |
| 0:53.5 | so we'll have to check back in with him next |
| 0:55.9 | week and see how he did and see what he's up to and see how he's recovering. But we did pull up |
| 1:00.5 | some good questions for the week. And for better or worse, I'm going to answer these for you today. |
| 1:05.1 | And hopefully I'll give you some insight. I can't say that my answers are going to be unequivocally correct, but hopefully |
| 1:14.2 | they give you something to consider and chew on and think about as you improve your life. |
| 1:19.6 | If you are looking for an opportunity to ask these types of questions and more actually |
| 1:25.8 | engage in the conversation with men who are on |
| 1:28.9 | the same path as you, like-minded men, some further out ahead of you, some maybe a little |
| 1:33.6 | further behind you, then look no further than our brotherhood, the Iron Council. We're doing a |
| 1:40.3 | preview call on June 9th, Tuesday, June 9th at 8 p.m. Eastern. And I want every single man there |
| 1:47.9 | tuning in, seeing what we're all about. So if you go to the ironcounsel.com slash preview, |
| 1:56.5 | you can check it out. Theironcouncil.com slash june 9th at 8 p.m. Eastern. |
| 2:03.0 | All right, guys, let's get into this today. I've got quite a few questions here, |
| 2:07.1 | want to get these answered, and hopefully we'll give you, like I said, some things to consider |
... |
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