This week on the Conspiracy of Goodness Podcast, I invited back one of my favorite “reframers:” someone who, often out of the blue, offers a shift in perspective that can suddenly unstick some of life’s most stubborn problems. Andy Chaleff is an author, coach, game-maker, and the rare kind of human who can talk about the tricky parts of relationships with both tenderness and a big ol’ grin. 

Andy and I go back some years; he was a guest on the podcast when his book The Connection Playbook came out, and his insights helped my husband Chuck and me interrupt a few well-worn loops in our marriage (we’re high school sweethearts from 1981, so we’ve had time to, ahem, practice our loops). 

He’s since written a new book, Dying to Live, and created a couples game called Cool It that helps people role-play the arguments they have on repeat—only this time with a few thoughtful tools on the table.

And wow, did we get into it.

The Big Idea: When You’re Triggered, Look Inward First

We started exactly where so many of us live in our relationships: “How do we stop having the same fight over and over?” 

Andy offered a line from Carl Jung that landed with a thud and an a-ha all at once:

“Until we make the unconscious conscious, it will define our lives, and we’ll call it fate.”

Translation: If the same disagreement keeps circling the runway never getting any traction, it’s usually because there’s something underneath of it that we haven’t met or addressed yet. The moment we feel that hot spark—that tight chest or rising in our voice—is the very moment to pause and turn curiosity inward: What expectation of mine just got poked? What deeper ache is this brushing up against?

I took a breath and shared something personal: one of our “repeat fights” is that Chuck interrupts me a lot right as I’m laying out an idea I think might be of help to us. Could be on anything at all—but it seems like he hears the first six words, assumes that he knows what I’m going to say, and just jumps right in. (Sound familiar?) This could come from any of our relationships: mothers, know-it-all brothers or sisters, bosses and co-workers, etc. 

When Andy playfully interrupted me mid-interview to let me feel the moment in real time so we could examine it, what rose up wasn’t just annoyance—it was the old ache of not being seen. As a woman in a male-dominated profession for decades, (I’m a dentist as well as a positive media guru!) I’ve had a lifetime of moments where people assumed I was the assistant, not the doctor. 

That tenderness rides shotgun with me, so of course it pops up in an argument about—wait for it—how to move logs on our Vermont farm.

That’s the profound invitation here: the argument is often the doorway. If we can pause, name what’s really hurting (without drama or blame), and let ourselves be seen in it, the other person often meets us there. 

And when they do? The “same old fight” turns into the moment of connection we were actually longing for.

Don’t Marry an Outcome—Marry the Process

Another gem from our conversation: never marry an outcome. The more tightly we grip what should happen (for the book cover, the dinner plan, the kid’s college major, the placement of wedding logs), the more brittle we become; joy gets squeezed out. 

Andy reminds us that when we fixate on outcomes, we contaminate the path. We stop listening; we bulldoze nuance; we miss the baby harp seal because we were promised a polar bear.

If, instead, we marry the process—staying present, listening closely, and letting wonder lead—then whatever outcome emerges is one we can feel grateful for, because we didn’t betray ourselves on the way there.

Tools for the Toolbox (and Agency for the Soul)

I’m a fan of tools. In fact, I picture adulthood as each of us carrying around an eclectic toolbox filled with coping skills we picked up from grandparents, parents, teachers, neighbors, mentors, and friends. Some are great! But some are also rusted. Life throws us problems of every shape and size; whether we look like a genius or a jerk sometimes depends on whether we happen to have the tool that fits today’s bolt.

Andy and I agree on this: we can add better tools. The Connection Playbook is full of them, and his new game Cool It creates a safe container to practice using those tools—things like pattern interrupts, role-reversals, and “facilitation cards” you pull when things get hot. (He laughed, admitting that early versions of the game could’ve been called Divorce—because stirring emotion without guidance can make a royal mess. Don’t worry—he fixed that.)

But here’s the nuance I really love from Andy: while tools matter, agency matters more. If we hand our inner authority to “the next shiny tactic,” we lose the muscle of thinking and feeling for ourselves. So yes, gather tools; and also, keep choosing to stay present with your own experience! That’s how wisdom grows.

From Tension to Tenderness (and Why ‘Fighting Fair’ Matters)

Let’s be honest: when our amygdala is firing, we say the sharpest things. (Andy calls this “drawing blood.”) And here’s the kicker—once people learn we’re capable of drawing blood, safety erodes. Even if we “don’t mean it,” those moments linger.

What helps?

• Name the impact without shaming. “When you said that, here’s what happened inside me.”
  
• Hold your thoughts lightly. You don’t have to treat every thought as a command performance.
  
• Stay with the feeling, not the story. It’s tempting to litigate. Try revealing instead.
  

This is the path from tension to tenderness. It’s not about being “nice.” It’s about honoring the real feelings underneath, without using them as weapons.

Curiosity Changes More Than Minds

Two stories brought this home for me: 

Years ago, on a subway, I was about to scold a dad whose kids were bouncing off everyone’s shins—until I learned his wife had died hours before. In an instant, my certainty melted into compassion. 

More recently, Andy’s neighbor screamed at him over an issue involving pigeons (truly), and after the dust settled he learned her husband had just passed away. Feeding birds was her last gentle tether.

We can only sit with another’s pain to the degree we’ve made room for our own. That’s the work we need to do—so that when life surprises us, curiosity gets first dibs instead of contempt.

One of my favorite moments came near the end, when Andy said he notices himself making a thousand micro-choices a day between love and fear. Do I greet the weary person in the elevator? Do I kneel to high-five the toddler (with a parent right there) or worry about how it might be perceived? Do I allow the world’s cynicism to harden me—or choose softness anyway?

I see this in the innovators I interview, too: the ones moving mountains are the ones choosing love over fear as a habit. Love for the future, for community, for possibility. Not fluffy love, but bold, courageous love.

Practice: Wonder as a Way of Life

If you want a single, portable practice from this episode, try this the next time you start to loose your cool in an argument:

1. Notice the spike. Tight chest? Hot face? That’s your cue to stop, and start this process..
   
2. Name the need. “I want to be seen.” “I want respect.” “I want safety.”
   
3. Hold it lightly. Loosen your grip on the “right” outcome—make room for other possibilities.
   
4. Reveal, don’t accuse. “Here’s what just happened inside me…” “Here’s how that made me feel…”
   
5. Ask a generous question. “How much space do you have to hear my idea?” “What were you hoping would happen here?” Ensure the person you’re speaking to has the bandwidth for the conversation—and if they don’t, leave it for another day.

…And as you go, lace the whole thing with a sense of wonder. “Isn’t it fascinating that my brain did that just now?” When we treat our inner life with curiosity, life expands—not by years, but by possibilities.

What to Do Next

• Listen to this new episode with Andy—and if you want a great prequel, check out our earlier conversation, Fresh Remedies for Relationship Struggles (Episode #150).
  
• Explore Andy’s writing and his new book Dying to Live (out this September). He’s even built a chatbot trained on his coaching voice so you can “practice with Andy” between conversations.
  
• If you’re feeling brave (and playful), try a round of Cool It with someone you love. Role-play one of your classic disagreements, then pull a facilitation card when things heat up. (Hot tip: snacks help.)
  

Most of all, remember this: you are not doomed to your loops. The next time the same old fight shows up, it may actually be knocking with a gift—an invitation to be known more fully and to know your person more deeply. That’s the conspiracy of goodness in relationships: there’s a kinder world waiting right here, inside the same conversation—if we’re only willing to pause, look inward, and meet each other with wonder.

Here’s to choosing love over fear—one messy, beautiful micro-decision at a time.

• Website: Andy Chaleff
• CoG Podcast: Fresh Remedies for Relationship Struggles (Episode #150)
• Book: The Connection Playbook
• Game: Cool It
• BOOK: Dying to Live

• 00:00 – Intro & Welcome
• 04:05  – Tools for conflict & building a “toolbox”
• 13:01 – How to stop having the same fight
• 26:00 – Triggers, expectations, and self-reflection
• 40:50 – The art of loving arguments & fighting fair
• 42:38 – Break
• 44:56 – The art of loving arguments & fighting fair (cont.)
• 58:14 – Choosing love over fear
• 1:19:15 – Living in wonder & final takeaways