Jocko Underground: Obsessing Over Your Spouses Past

Summary

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

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

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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.

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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)

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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)

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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

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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.

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

Transcript

[A]

This is the Jocko Underground podcast number 194, sitting here with Echo Charles. We have received some questions from the UG Troopers and we have some answers, some guidance, some recommendations on courses of action for you all. Let's get into it.

[B]

Yes.

[A]

All right. As we close out the year 2025, New Year's coming to a close.

[B]

Having courses of action is better than not having courses.

[A]

Oh yeah, definitely. Definitely. For sure. Let's get into it.

[B]

All right, first question. Chuck, welcome. Recently I've been under. Under a huge lot of financial stress and custody battle with having equal rights for my son, etc. In light of all this stress, doctors put me on meds again. The main issue is I don't know if it's a result of the stress, but I've been getting really bad OCD like compulsions. Questioning my partner about her past, Asking when, where and who she slept with. I'd need to know if I knew them. And I'm constantly digging for answers. We're a blended family. She has two kids and have one. But I fear these compulsive tendencies of mine will ruin what we have built. I feel like this is rotting my brain. Any advice on what kind of mindset or things a man slash leader you would do in my situation? Really appreciate the work you guys do. I'm a daily listener. Got my blue belt in Jiu Jitsu this year, so thanks.

[A]

Yeah, man. I. I would start off just by saying this. You do not want to be living in the past, bro. You do not want to be living the past. You can't change what happened in the past. You can't fix 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, that's what matters. And that's what matters with where you're partner is now, right? These are what's important now. And the future is what's important. And that's what you need to focus on. Focus on being an awesome man, right? That means being an awesome dad. That means being an awesome worker. Whatever your job is. That means being awesome at Jiu Jitsu, as awesome as you can possibly be. That means being an awesome person. Partner with your partner. So let's focus on being on awesome on those things today. Getting a little bit better every day at these things. Cuz dwelling in the past doesn't get it. Doesn't give you anything, doesn't do anything beneficial for you. 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. And yeah, I think probably, if I was to have to guess, and I'm not a psychologist, but as Echo Charles likes to say, it seems like some things are a little out of your control right now. Meaning you're in a custody battle, like the court. The court does what the court does. It's very hard to control it. They're going to make the decisions that they're going to make you financial. Like, you can only make so much money. So there seems like there's things that are. Seem more out of control to you right now. Again, finances, lawyers, judges, custody battles, legal decisions. Like, those things are very difficult. And you don't feel. You feel like you have limited control over those big things. So you're probably, like, searching for things that are in your world that you can control or you think you control and you think you're getting control of things by focusing on the past. But in fact, that's not happening. In fact, what I see happening here is the past is controlling you.

[B]

And.

[A]

We'Re not doing that, man. That's not a good game to play. That is not a good thing to focus on. We live in the present. We plan for the future. That's what we're doing. Right? So again, I know, I know. It's easier said than done. But listen, what is your. The girl that you're with right now, like, okay, cool. She's cool right now. Good. You're cool right now. Cool. Get cooler. Like, that's what we're doing, man. Just dwelling in the past and worried about what things she's been through and who she's been with. Well, those are questions. It doesn't. It's totally not pertinent at all to your current situation. Not pertinent at all. 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 it looks desperate. It looks weird and it looks jealous and it looks weak, bro. It looks weak. Don't look weak. Just be like, oh, yeah, cool. You used to date guys. Cool. Yeah. You got a couple. She sounds like she's got a couple kids. What? She has two kids? Yeah. Cool. That's awesome. Glad you had some good relationships in the past. Had these beautiful kids. Cool. That's what a man, a confident man does. A confident man's like, oh, cool. Oh, that's your ex boyfriend over there. Oh, cool. Nice to meet you, man. Cool. Good luck. Whatever. No factor. An insecure person is like, who is it? Why did you ha. What was that like? That's just insecurity. No one likes that. 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.

[B]

Oh, yeah.

[A]

You know, I dated some other girls in my past. It sounds like you got a couple kids too, maybe. Oh, you have one. You have one kid. Cool. What did that. Was that. Was that. Where'd that kid come from? Oh, you had a relationship with. So you're a human being, and she's a human being, and that's what it is. So let's just be ultra confident and secure that we're a good dude and doesn't really matter who she was with the past because you're the man now. How's that sound? Am I off base here? Echo Charles?

[B]

No.

[A]

Okay.

[B]

I do not believe so.

[A]

Right. Like, we don't want to show insecurity and being desperate and being freaked out about thing in the past. You should be confident and listen, if you lack confidence, don't show it. How's that? Am I being. What's the word? Duplicitous? Duplicate?

[B]

I don't know.

[A]

Am I being dubbed? Am I being too faced? Like, oh, I feel bad about it, but I'm not. I'm gonna acting a different way. Yes. I'm telling you to do that.

[B]

Yeah.

[A]

I'm telling you, do not act insecure and, like, worried about this stuff in the past. No, I'm telling you, do not act that way. I'm telling you to act to be like, oh, cool. You had relationships in the past. That's cool. Yeah, I'm glad you, you know. Glad. Glad. Whatever got you to be here. This cool chick that I'm with right now. Awesome. I like it. What do you want for dinner? You see what I'm saying? Gosh, it's. People get wrapped up in this stuff, man. Looks bad, feels bad. 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. That's the important thing. Got a couple cool kids. That's cool. I got my kid. 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. Be that guy. Move forward. Don't Dwell. Get after it. That's my. That's my assessment.

[B]

Yeah, it feels like he's the one bringing it up too. So it's like you're. You're expending more energy, like, doing the wrong thing, you know, kind of a thing. Just don't bring it up. Which. Exactly what you're saying, in my opinion, like, yeah, even. Look, I get it, bro. You have internal feelings like everybody else. I get it. But Brad, you gotta. 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. You gotta make some, you know, put up. Put up some boundaries right there.

[A]

Make some decisions about how you're gonna be.

[B]

Yeah, so that. And that was. That was. I'm gonna. I'm gonna invoke this little mantra again. What you gotta. You gotta decide what outcome do you want? You know, it's gonna have a lot to do with, like, how do you want to be perceived? How you say, like, who do you want to be? This has to be like, part of who you are now, you know, so you have to understand and why and. And identify what do you want the outcome to be? And obviously these two issues that he brought up, which is the custody and the stress part of it. So the custody, you know, the stress of xyz, what do you want the outcome to be? And then behave towards that outcome. Same thing with your partner that you obviously built something. Got a blended family. Cool. Sweet. What do you want the outcome to be? And if you can really understand that all this other stuff is going to be easy or simple, you know, you're going to know what not to do. Because if you want the outcome to be positive and strong and secure and stuff like that, basically the thing that we all want.

[A]

Want.

[B]

You want that to be the outcome, and you're conscious of it, bro. You're not gonna be busting out these.

[A]

Who are you with?

[B]

How many guys were you with before me? All this stuff, you just won't do that. See what I'm saying? And then you just sort of become the person who is like that. Yeah, just carry on, bro.

[A]

There we go.

[B]

Next question.

[A]

Hello, Joe.

[B]

I thank you and Echo for the time and the podcast. I'm a naval officer, thanks to your podcast. How do I keep my peace while also maintaining my relationship with family who cannot accept my choices? Thank you. I'm assuming his choice is to join the military.

[A]

Well, I'm assuming. I have no idea what to assume. These true There's a lot of context around a question like this that's not here, because what kind of choices is this dude making?

[B]

Right, Right, right.

[A]

It could be that his choices. So that is a little excerpt of what we are doing on the Jocko Underground podcast. So if you want to continue to listen, go to Jocko underground.com and subscribe. And we're doing this. We're doing this to mitigate our reliance on external platforms so we are not subject to their control. And we are doing this so that we can support the Jocko podcast, which will remain as is free for all as long as we can keep it that way. But we. But we are doing this so we don't have to be under the control of sponsors. And we're doing it so we can give you more control, more interaction, more direct connections, better communications with us. And to do that, we are. We're building a website right now where we'll be able to utilize to strengthen this legion of troopers that are in the game with us. So thank you. It's Jocko underground.com it costs $8.18 a month. And if you can't afford to support us, we can still support you. Just email assistancecounderground.com and we'll get you taken care of. Until then, we will see you mobilized Underground.