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A Practical Guide to Deepening Every Relationship in Your Life

A Practical Guide to Deepening Every Relationship in Your Life

By Stacey Lindsay
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Andy Chaleff wants to have real conversations. This may seem like an obvious statement given that he's the author of The Connection Playbook, his most recent book about building more meaningful relationships. Also, Chaleff's other two books, as well as his work center, on the deeper spiritual themes of catharsis, truth, and self-acceptance. Still, just a few minutes on a Zoom with the author reveals that he genuinely walks the talk. There's no attempt at chit-chat to fill space. He offers only raw anecdotes and insight, peppered with laughter.

In our conversation, we dive into how we can connect more deeply, especially when the world feels so divisive and heated. Chaleff covers vast ground, touching on the loss of his mother when he was 18 and how he cultivated a skill set to help navigate growing up with a father who would explode. Getting real—with ourselves and each other—is the anchor through all of it. That, and honoring the humor. "It's really about loving the absurdity of life," says Chaleff. "And that can be hard today for many people because we feel like we're going to be judged if we don't say the right thing in the right way. That's the sad part about where we are, sometimes, in society."


Let's start at the beginning, when you were young. It was then that you began to build skills around how to read other people. How did you start to build on this awareness?

My mom and dad got divorced when I was 10. Dad was bipolar and highly dysfunctional, and mom was very loving and nurturing. I got to kind of live in the polarity of these two energies. When I was with my father, I was more sensitive. He'd get triggered and explode, and for self-preservation, I became acutely aware of anything that might set him off. I know that of other highly sensitive people when I see them scanning the room and then moderating their behavior in alignment with what's going on around them. It's a survival mechanism. It's a way for us to learn how to get through the world and not create too much damage or have too much damage done to us.

I saw through that experience that there was a skill set I didn't even know I was developing, which was the humor. Of course, your limbic system is getting charged all the time, so you have to learn how to slow that down so you're not looking at life through the lens of anxiety. But once you slow that process down, you begin to feel into what's happening around you. I would navigate this with humor as a child. My mom called me her little 'shit-stirrer' because I always say things that were really going on but no one was discussing. That was my outlet. It wasn't intended to be naughty, it was just my way of making the world make sense for me at that time.

But as I got older, I thought, I'm feeling many things and I don't see people talking about it. And if I'm going to slowly navigate the world, I've got to learn how to utilize this understanding that I apparently have. It was clear to me that there was a sensitivity that I was channeling, and I had the opportunity to utilize that.

So many of us are craving deeper connections with people in our lives. You believe all fulfilling relationships require heart connections. What do you mean by this?

There's a great exercise in the book where you say the same sentence but with five different intentions. The more vulnerable and more showing who you are, the less likely it is that another person will either misinterpret you or hold anything against you because they see that your intentions were pure, loving, and caring. If I listen to someone, I can tell if they went down two levels, or if they're not even close to the depth of where you can let someone see you. This is the difference between saying, 'How are you?' with a detached comfort, or saying 'Hey... how are you?' You know immediately that those same exact words shared with a very different intention will elicit a completely different response.

You write that one of the essential conditions for connection is our relationship to ourselves.

I was talking to a friend the other day, and the friend said to me, 'I want to have one healthy relationship with another before I die.' And I responded, 'Yes, the relationship with yourself!'

How did they respond?

They chuckled and laughed because they understood the point. And then they said, 'Yes, but it would be nice to have somebody else as well, right?'

The point being that I see that everything that's unresolved in myself bleeds into any relationship. There is a personal responsibility that we can take. I would love it if more of us did realize, Oh my god, I get to define what a relationship looks like. And if it's unhealthy, then I'm part of the thing I'm judging as unhealthy. So I can't blame the other person for that. There's a vulnerability and a personal responsibility and a rawness to that that just makes life so much more beautiful.

Taking that personal responsibility can be hard, though.

Oh, it's so hard. Because imagine if someone shoved a mirror in front of your face every single moment of every day! So, here's the humor: If someone reacts angry to me, angry or frustrated, I never assume they don't have a right to be angry or frustrated, never. They might even shout at me and I see it as the most loving act, because that's them in their most vulnerable state at that moment. So, one can respond, 'Oh, I've got to defend myself!' Or one can respond, 'Wow, that's really heavy. What's going on there?' And now you're just holding space for another to process whatever they need to process.

This leads to the topic of triggers. You write that it's so important for us to know what triggers us because that can lead to further disconnection. This is a tough one because it seems like so many of us are always getting triggered. Why is this so important and how can we start to dig into what triggers us?

I always have three books on the go, and this is one, because those triggers are so meaty! In general, we're blind to the trigger. But we're not blind to the reaction. As beings, we just do stuff. We're in the world, and we're interacting. The trigger kicks off, and then the reaction happens, and we lose that higher consciousness or that higher understanding, but what we don't lose is that feeling like oh shit, something's off. I don't know what just happened. We can make a conscious decision whether to slow down and check in or just keep moving with the trigger. That's where personal responsibility comes in. We don't decide if we get triggered, it just happens. We don't have the luxury of transcending our emotions; our emotions are just there. But we do have that single moment of Okay, I'm not going to do what I always do. That's our moment to decide.

It's those moments when I'll work with a person, and I'll give them some time to vent and to get triggered, but it's almost like a leash that I keep pulling tighter and tighter. I let the person react to that, but now they can't react to it as much. Now we have to see what's going on behind that reaction. I'll spend the first six months, maybe a year [working on this with] my clients with love and a lot of consciousness to know what triggers them. They get the chance to reflect on the trigger and the reaction. It always resolves itself in something very deep with tears. Because behind that trigger, maybe there's a father who wasn't listening to them, or a mother who wasn't there for them. There's always something behind it.

What is a tool for staying centered during those moments of getting triggered?

There's a tool that I've always used, which is to embrace the thing you resist. Because, again, you can't control the emotion. If you react and yell, that might let the emotion out of you but you might cause 20 other problems in getting it out of your system. My tool is just very simple. The term for the tool is projection reclamation. You say the thing that's hardest to say, and you follow up with "and it's okay." So, you would say, "My father and mother never loved me… and it's okay." It's never stepping away from the fact that it hurts, and it's not a mantra that you look in the mirror and then say 20 times and it changes anything. This is a deep feeling where underneath you can see it actually is okay. I would then take it on to the next level and at some point, you give it even more spaciousness and you say "…and it's fucking great." So you could say, "My father never loved me, and it's fucking great. He never really understood me. And it's fucking great."

There's a way in which by fully embracing the thing that you've been pushing down, you give it no more space in your consciousness to be suppressed and therefore impact you every day. The only way out is through, in this case. Our system may protest. It may say, 'No, it's not okay! No, this can't be!' But it's the deeper knowing within all of us knows that actually, all of this is okay. It's allowing that spaciousness that's not always easy, but that's where we're more centered. And if we're more centered, everything is easier to move through.

And when we're more centered, can we better connect with each other?

Yes! The weirdest thing for me is seeing all the people who are uncentered interacting in the world. And you'll see this and think, Do you realize the problems you are causing? It is painful seeing the suffering of others because people aren't able to find the center within themselves.

Is it because people don't know that they have another option?

I think it's because they're in a pattern, and patterns are just things that seem normal to people until there's an abrupt break in the pattern. If anything, what I'm doing is breaking patterns. In my work, I won't let somebody continue to do the thing that's not serving them without them being conscious of it. Meaning, I won't tell people to change their behavior, but I will tell them that these are the consequences of their behavior.

You refer to trust and respect as "salt and pepper" in your book. What do you want people to know about trust and respect and why they're so critical in our relationships?

Those two are so beautiful, because with those two alone you'll understand the health and well-being of a relationship in a matter of minutes.

I created a game around these two polarities and play-tested it with 10 couples, and each couple started to fight. I was confused at first, but then I realized that the intention was for each individual to reflect on their behavior to their partner, but they were using it as a tool to judge their partner. So, if I've lost trust or respect with you, I'll exhibit behaviors towards you. If I've lost trust, I'll be less likely to speak freely. If I've lost respect, I'll be less likely to appreciate what you say. Now imagine that I am being that way to you. I have two choices: I can say, 'Wow, I actually see I'm not treating you with trust and respect.' Or I can say, 'You are behaving in a way, which forces me not to treat you with trust and respect.' So, I can either blame the person or I can be self-aware.

That's a decision that one makes. How do I want to deal with the situation if I'm not treating my partner with trust and respect? Do I want to shift that behavior? Again, this is the personal responsibility to consider. However someone you're interacting with is treating you is a reflection of how you're treating them.

Andy, how do you stay hopeful in this work?

You know, this might sound sad: I'm not hopeful. I could cry saying it. But I'm not going to let that stop me from being the loving, caring person that I would love others to be more of. It's not the hope that keeps me alive or going, it's the desire that I'm not going to succumb to everything else. It's not easy. I don't watch TV. I keep my influences very tight. If I'm around people with strong belief systems, I acknowledge them and appreciate them, but I don't defend or convince. I don't blame. So, in answering your question, I'm sadly not hopeful and yet, I don't let that stop me from being everything I want to be.

What is one practice that you do to rise above all the noise?

Going back to the beginning, there is a practice embedded in my life. My mom was killed by a drunk driver when I was 18. I wrote her letter when I was [taking a] sociology of death class, not knowing I would lose her a few hours later. So, I wrote a letter to her, she got it, and then she was killed by a drunk driver. That moment has been so defining for me in so many ways. If I'm leaving a conversation or interacting with someone, I never assume that I'll see them again. I never treat it as a casual goodbye or without gratitude for whatever it is they brought me in my life—to the degree that my wife thinks I'm crazy at times because there might be someone who did me a favor in high school and I'll feel that I've never done enough to repay that favor. But I don't feel the burden of it. I feel the joy of it. And I think that practices a deep guiding intuition with a big spoonful of gratitude.

Andy Chaleff is an award-winning author known for his ability to explore the depths of the human experience through captivating storytelling. His three books include The Last Letter, The Wounded Healer, and The Connection Playbook. Learn more

Stacey Lindsay

Stacey Lindsay is a journalist and Senior Editor at The Sunday Paper. A former news anchor and reporter, Stacey is passionate about covering women's issues. Learn more at:

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