Summary4 min read

Kreatures Of Habit Podcast: "Mastering Confrontation: The Key to Healthy Relationships"

Host: Michael Chernow
Episode: Monday Moments (May 18, 2026)

Episode Overview

In this Monday Moments episode, host Michael Chernow explores the often uncomfortable—but essential—topic of healthy confrontation in relationships. Reflecting on his own experiences and hard-won lessons, Michael shares actionable insights about approaching conflict not as a battle to win, but as a pathway to deeper communication, honesty, and stronger relationships—whether romantic, professional, or platonic.

Key Discussion Points & Insights

1. The Necessity of Confrontation in Relationships

Confrontation is not about winning:
- Michael emphasizes that confronting someone shouldn’t be about proving oneself right or winning the argument, but about expressing feelings and concerns to foster healthier relationships.
Dangers of Bottling Up:
- Suppressing grievances leads to eventual “explosions” in relationships. Open, regular communication prevents issues from festering ([02:00]).

2. The Art of Calm Communication

Stay Calm, Cool, and Collected:
- Michael advises addressing issues “in the most calm, cool and collected way, non-emotional, and then you shut up and listen" ([01:45]).
Don’t let emotions dictate the conversation:
- He strongly warns against allowing emotions like anger to take over during these difficult discussions.

“The person that ends up raising their voice is wrong. Whoever raises their voice and acts out emotionally… is wrong.”
– Michael Chernow, referring to advice from a friend ([02:45])

3. Listening is as Important as Speaking

After sharing your side, truly listen. Don’t interrupt or immediately counter-argue—the goal is to create space for honest exchange, not to “claim your stake” ([03:30]).

4. Discomfort is Inevitable—and Okay

Sit with the discomfort:
- Michael recounts a recent argument with his wife, explaining that the period after the confrontation was tense and awkward. Instead of digging deeper or reigniting the conflict, he allowed himself (and the relationship) to sit in that discomfort ([04:30]).
Resolution comes from acceptance:
- By not escalating or bringing up new grievances, the moment passed, and reconnection followed naturally as emotions settled ([06:00]).

“You can sit in this discomfort and just let it pass because the argument is already over… It’s okay to be uncomfortable.”
– Michael Chernow ([05:15])

5. The Trap of Competing to "Win"

Competition is counterproductive in communication:
- Michael admits his own competitive nature but recognizes:
  
  “If the goal is winning, it’s going to be really, really challenging” ([07:00]).
- Both parties often want to win, which stalls genuine resolution.

6. Make a Habit of Healthy Confrontation

Consistent openness builds communication “muscle”:
- Michael encourages listeners to address issues as they arise, not to sweep them under the rug, for the sake of long-term relationship health.
Avoidance brings bigger problems:
- “If you walk through life dodging hard conversations, they find you. And typically not on your terms.” ([09:30])

Notable Quotes & Memorable Moments

On raising your voice:

“The person that ends up raising their voice is wrong… You automatically put yourself in the wrong position.”
— Michael Chernow ([02:50])
On discomfort after arguments:

“It doesn’t feel good, but that’s okay. It’s okay to be uncomfortable… You do not need to continue digging and bring something else up because the argument is over.”
— Michael Chernow ([05:20])
On addressing rather than winning:

“You shouldn't have to get into an argument with somebody or confront somebody with the intention of winning. Winning doesn’t matter.”
— Michael Chernow ([07:40])
On communication habits:

“It would be amazing if, when the next time you feel uncomfortable about something… you have the confidence to say something—not to win, but just to say it.”
— Michael Chernow ([09:05])

Timestamps for Key Segments

[00:00] — Introduction of confrontation as the main topic; advice from a friend about voice-raising
[02:00] — Why bottling up is destructive; beginnings of practical advice on confrontation
[02:45] — “The person that raises their voice is wrong” — a mantra for handling conflict
[04:30] — Michael’s personal story: handling an argument with his wife
[05:15] — The importance of accepting discomfort after confrontation
[06:00] — Letting the moment pass; how reconnection naturally follows
[07:00] — Rejecting competitiveness in arguments
[09:30] — Final thoughts: don’t avoid hard conversations, embrace them for growth

Takeaways

Confrontation is necessary for healthy relationships but must be done with calmness and without the intent to “win.”
Letting yourself (and your relationship) sit with post-conflict discomfort, instead of compulsively defending or escalating, is critical.
Avoiding hard conversations invites bigger, more uncontrollable problems.
Communication is a skill developed through consistent practice—address what needs to be addressed, every time, and with the intention of honesty, not victory.

For anyone struggling with confrontation in any area of life, Michael Chernow’s reflections offer a blueprint for handling it gracefully and productively—ultimately strengthening all kinds of relationships.

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[00:00]
A
An old friend of mine told me years and years ago, and it was some of the greatest advice I ever got. The person that ends up raising their voice is wrong. You shouldn't have to get into an argument with somebody or confront somebody with the intention of winning. Winning doesn't matter. The more stuff we hold in, the more challenging these relationships become. And there's something that happens in a confrontation where you say your part and you try to say it in the most calm, cool and collected way, non emotional. And then you shut up and you listen. An entrepreneur straight out of New York City, Michael Chernow. What's cracking? What's going on, everybody? Welcome. Welcome back to the Creatures of Habit podcast. And today is another Monday moment. Monday moments. I'm beginning to love these Monday moments. It's time for me to dump some of the things that I've been thinking about throughout the week over the course of the month that I jot down, things that I want to communicate with the community, things that have inspired me. And I went through something about three, four weeks ago that stood out to me as a very important topic to discuss. Confrontation. Not everybody loves confrontation. It's really hard to navigate, but it's necessary, in my opinion, specifically in relationships. Confrontation is necessary specifically in relationships because communication is the core foundation of a healthy relationship. Whether it's a romantic relationship, whether it's a business relationship, whether it's just a friendship confrontation. When you feel something is not right. Having the courage to confront the other party in the relationship is really critical to the success of relationships. Because when we don't communicate and we bottle things up, at some point they are going to resurface. And if you bottle up enough, it not only resurfaces, it could potentially explode. So I want to encourage confrontation, not in an aggressive way, not in a abrasive way, in a productive way. And sometimes, well, a lot of the time it's just uncomfortable. It's uncomfortable to address something that makes you feel icky because you don't know necessarily how the other person is going to receive it. And in many cases, the other person may receive it in a defensive way. They want to defend themselves if you're telling them something that is bothering you about them. However, I have just learned that consistency with confrontation and practice is really critical. And there's something that happens in a confrontation where you say your part and you try to say it in the most calm, cool and collected way, non emotional, and then you shut up and you listen to what the other person has to say. You don't cut them off. You don't try to claim your stake. You don't try to make your point after, after your initial like, experience of communication with it. You literally just listen and typically it's gonna go back and forth a little bit, right? The one thing that I would just really wanna point out is do your absolute best to not allow your emotions to dictate the way you communicate. An old friend of mine told me years and years ago and it was some of the greatest advice I ever got. And he said, the person that ends up raising their voice is wrong. Whoever raises their voice and acts out emotionally in a conversation, an argument, or a confrontation is wrong. You automatically put yourself in the wrong position when you get angry and emotional and raise your voice. So when he said that to me, I really, because I was certainly not as good a communicator then as I am now. So you can have this argument, right? And then typically there is a moment in time where it gets uncomfortable and you're uncomfortable, they're uncomfortable. And there's this feeling in the air of discomfort. You have a choice. You can just experience the discomfort and be okay with it, or you can pick up the shovel and start digging again because you feel uncomfortable and you want to defend yourself, or you feel uncomfortable and you want to, you want to and you act out because of the discomfort. I had an argument with my wife about three, four weeks ago. We were arguing about something after dinner, which is totally normal and healthy, and it was totally uncomfortable after the argument. It was just, it just didn't feel good. And the two of us kind of like, we didn't really say much to each other. And my self awareness barometer was on full blast. And I had a thought, Michael, you can sit in this discomfort and just let it pass because the argument is already over. The argument is over. You do not need to continue digging. It doesn't feel good, but that's okay. It's okay to be uncomfortable. You do not need to continue digging and bring something else up because the argument is over. You both claimed, you both stated your points. And once that happens and that awkward silence surfaces, it's okay to be uncomfortable for a little while. Give it some time. And that's exactly what I did. And about an hour later, an hour and a half later, when we curled into bed, it was still a little uncomfortable. And I just rolled over and I gave my wife a hug and I told her I loved her and. And she said, I love you back. And that was that. It could have gone a very different direction. I could have not wanted to sit in the discomfort. I could have began to think about other things to throw at her, to claim my point is right and feel like I won the won the fight. And the truth is, it's just unnecessary. You shouldn't have to get into an argument with somebody or confront somebody with the intention of winning. The purpose of these confrontational, the purpose of me trying to motivate you to be to confront the people that are in your life that you have an issue with is just to get it out. It's not to win. Winning doesn't matter. The more stuff we hold in, the more challenging these relationships become. So getting it out is very different than feeling the need to win. And I'm a competitive dude. I just am. I'm a competitive dude. And in most things in my life, I really do want to win. But I've learned that in communication, if the goal is winning, it's going to be really, really challenging. And it's really, really hard because you have to understand that the person that you're confronting probably also wants to win too. And the conversation tends to not go in a great direction when there's two people that are trying to win an argument. So take the high road. Don't walk into a confrontation with the idea that you want to win. It's there so that you become a better communicator and you are able to truly release on a regular basis and not bottle up and wait for an explosion. I hope that struck a chord with some of you. I hope that made some of you think. It would be amazing if, when the next time you feel uncomfortable about something that your partner said or that your business partner said or that your friend did, that you feel the confidence to be able to just say, say something and not just like brush it under the rug, but say something without the intention of wanting to win. It's literally there so that you build the communication skill we have to have hard conversations in our lives. It's just life. And if you walk through life dodging hard conversations, They find you. They will find you. And typically not on your terms. Share the Podcast Give us a five star rating and a review. Subscribe if you're not subscribed already. I really appreciate you guys listening and tuning into the creatures that have a podcast. It means the world to me. And until the next one, y', all, peace.