Jocko Podcast – Underground #194: Obsessing Over Your Spouses Past

Date: December 29, 2025
Hosts: Jocko Willink & Echo Charles

Overview

In this special episode of Jocko Underground, Jocko Willink and Echo Charles address an intense listener question about dealing with obsessive compulsions regarding a partner’s past relationships, especially under high-stress life circumstances. Their conversation centers on discipline, self-leadership, and developing a mindset focused on confidence, the present, and building strong relationships rather than fixating on what cannot be changed.

Key Discussion Points & Insights

1. Living in the Present, Not the Past

• Jocko stresses the importance of not dwelling on your partner’s history.
  • “You do not want to be living in the past, bro. You can’t change what happened in the past. It doesn’t really matter what happened in the past. It’s like, where are you now? That’s what matters.” (01:27)
  • He underscores that what matters is “where your partner is now and where you are now” and that focusing on today is key for growth as a parent, partner, employee, or individual.

2. Seeking Control in a Stressful Environment

• Jocko acknowledges the listener feels a lack of control due to external stresses (like custody battles or finances).
  • “So there seems like there’s things that seem more out of control to you right now... So you’re probably, like, searching for things that are in your world that you can control ... but in fact, the past is controlling you.” (02:55–03:44)
• He explains that obsessing over the past is an unhealthy coping mechanism stemming from these out-of-control circumstances.

3. The Dangers of Insecurity

• Obsessing over your partner’s past stems from insecurity and can damage the relationship.
  • “You can make it pertinent by freaking out about it and concentrating on it. And by the way, you know what that is? That’s super insecure. And it looks insecure and desperate. It looks weird and it looks jealous and it looks weak, bro. It looks weak. Don’t look weak.” (04:27–04:53)
• Jocko demonstrates the alternative: be confident, accepting, and unphased.
  • “A confident man’s like, ‘Oh, cool. Oh, that’s your ex boyfriend over there? Oh, cool. Nice to meet you, man. ... No factor.’” (05:12)

4. Practical Advice: Fake It Until You Make It

• Even if you don't feel confident, act as if you are.
  • “I’m telling you, do not act insecure and, like, worried about this stuff in the past ... Fake it. Fake it. Pretend if you have to that you’re like, ‘Oh, cool. Used to date other guys. I don't really care because you’re with me now.’” (06:21–06:45)
• Jocko highlights the value of focusing on your blended family and the positive things you’re building.
  • “We’re kind of like putting our own little system together. Got a little fam going. That’s what I’m concerned about. Be that guy.” (06:48)

5. Echo Charles on Emotional Discipline

• Echo emphasizes self-regulation—what you feel versus how you behave.
  • “I get it, bro. You have internal feelings like everybody else. ... But, brad, you gotta develop that barrier, bro, that filter of, like, I understand you’re gonna feel, but the difference between what you feel and how you behave, right? You gotta make some, you know, put up...some boundaries right there.” (07:27)
• He also introduces a process-driven mindset: decide the outcome you want and act in accordance with it.
  • “You gotta decide what outcome do you want?... and then behave towards that outcome.” (07:51)

6. Building a Strong Self-Identity

• Echo further advises:
  • “If you want the outcome to be positive and strong and secure...you’re not gonna be busting out these, ‘Who are you with? How many guys were you with before me?’ All this stuff, you just won’t do that. ... You just sort of become the person who is like that.” (08:44–08:58)

Notable Quotes & Memorable Moments

• Jocko (on the futility of obsessing):

  • “Dwelling in the past doesn’t get it. Doesn’t give you anything. It gives you nothing. Well, I can’t really say it gives you nothing because what it does give you is like heartache, paranoia, and stress.” (02:10)

• Jocko:

  • “Don’t be that guy. Don’t be insecure about it. You got her now. She’s your girl, right? You guys are in a relationship now? Awesome. Be stoked on that. Be like, yeah, cool.” (05:03)

• Echo:

  • “You have internal feelings like everybody else...you gotta develop that barrier...the difference between what you feel and how you behave, right?” (07:27)

Timestamps for Key Segments

• Question read and background: 00:29–01:27
• Jocko on letting go of the past: 01:27–03:44
• The illusion of control and insecurity: 03:44–05:54
• Practical advice—faking confidence, focusing on the present: 05:54–07:22
• Echo on behavioral boundaries and desired outcomes: 07:22–08:58

Conclusion & Takeaways

• Obsessing over a partner’s past is unhelpful and rooted in insecurity.
• Focus instead on the present and future—what you’re building together.
• Confidence is key. Even if it takes pretending at first, act confident and positive.
• Understand the difference between your emotions and your outward actions. Build barriers and make conscious choices towards your desired outcome in the relationship.
• Ultimately, be the strong, calm partner who builds a secure blended family, regardless of challenging external circumstances.

For more advice and content on discipline and leadership in challenging situations, the hosts recommend subscribing to Jocko Underground.