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Fresh Remedies for Relationship Struggles with Andy Chaleff (Episode #150)

Today we talk with author Andy Chaleff about some fresh remedies for our relationship struggles. The points of friction in our relationships can feel like a broken record and have us stuck, or worse, on the brink of heartbreaking separations. But Andy’s  insights are so helpful, simple and inspiring that they will make you feel like a path is appearing. 

Episode Highlights

About Our Guest:

Andy Chaleff is a multiple award-winning author known for his ability to explore the depths of the human experience through great storytelling and humor.

In 2020, Chaleff released “The Wounded Healer”: the story of his three-month journey across the United States in the pursuit of radical self-love. 

Those lessons become a through-line, in the book we’re talking about in this episode: The Connection Playbook.

After reading it, I just had to interview Andy. 

The book and his wonderful, conversational style feel like the ultimate relationship repair kit, for anyone seeking to build healthier connections with their spouse, family members, friends, and beyond. 

This interview will give you countless ah-ha moments if: 

  • you constantly catch yourself in repetitive arguments with your partner or someone you love.
  • You or your loved one are grappling with the aftermath of some recent or long past trauma and may be bringing all that baggage into the present. 
  • struggle with parenting a difficult child.
  • endure constant criticism from a parent or partner.

I’ll be transparent, the first two are true for my husband and I, and though our marriage has lasted 42 years, things would have been a heck of a lot easier, had we understood a fraction of the insights in Andy’s book.

I’m guessing that this book hits 90% of the issues most couples, families and friends try to work through with various measures of success. 

Today, Andy and I chat today about many fronts that people struggle on, but the conversation is full of laughter and joy. 

We cover some fresh perspectives on relationship success like: managing expectations, being aware of faulty assumptions, and making peace with old wounds. 

We talk about how to shift our goals in conversations, because “the winner” almost never wins, and here we get some methods of working together on our triggers. And of course, we talk about some tips for seeing the way our media culture is cementing our “personal truths,” while positioning others as “wrong.” 

The interview has a few insights I haven’t been able to “unsee” since having this conversation: like the exercise at the end of Chapter 7, about focusing on the word in each sentence that triggers assumptions of bad intention, and the alternative words we could be using. 

If there was ever an example of a thoughtful, measured, helpful voice arriving on the scene to help us sort out the complexities in all our relationships (not just our romantic partners) then this book is it and our conversation today with Andy Chaleff will start you on a journey of repair, growth and deep connections. 

After this podcast episode, you can start mastering the ability to zoom-in, to make certain you are in a good place with the people you love, and then, zoom-out for validation that all the struggle is worth it.

And a beautiful, less friction filled future awaits us all.  

Show Notes

00:00 Intro & Welcome

03:01 The Connection Playbook

  • Andy’s new book is focused on building connections.
  • Each chapter of the book has a QR code that can be scanned to trigger the audio book.
  • Andy is trying to help people understand that they’re a part of a dynamic.
  • People don’t see that once they’re triggered, they create a dynamic that they can no longer see themselves as a part of.
  • The Connection Playbook is designed to help all types of relationships including romantic relationships.
  • Andy is doing workshops at companies such as Under Armour.
  • We often don’t realize that the intention behind questions can affect the responses.

10:11 Growing Out of Repeat Trauma

  • One of the primary conditions for overcoming trauma is to avoid defaulting to blame.
  • No one wants to share their vulnerability when they are being accused.
  • We can turn mishaps into a learning opportunity by approaching issues in a wondrous way.
  • Rather than focusing on who is accountable we can consider what we can all learn.

20:02 Break

22:23 The Sorry Opportunity

  • People often shut down their creativity and get down on themselves when faced with adverse situations.
  • Andy tries to use adverse situations as an opportunity to create what he actually wants and shift the dynamic.
  • When someone says I’m sorry too often it may be a sign of insecurity.

28:02 Forgiveness

  • Andy has a strange relationship with forgiveness.
  • Andy feels like forgiveness is shouldering a burden and acting like it’s not a problem anymore.
  • Forgiveness is focused too mich on the other person and not enough on ourselves.
  • Forgiveness can be seen as something to hold over someone who wronged us.
  • Andy’s father was bipolar and abusive.
  • Andy’s relationship with his father only changed when Andy was able to forgive himself for never seeing his father’s incapacity and chemical imbalances.
  • There are no bad people – people do bad things.
  • Love is the ability to consider other people’s suffering even when they treat you badly.

32:25 Knowing When To Disconnect

  • The last four chapters of The Connection Playbook are the warnings around connection.
  • People can use connection as a form of manipulation.
  • There are people we may need to disconnect from.
  • Labeling discussions or people as difficult can make disconnection harder than it needs to be.
  • Andy suggests that we can lead with compassion and allow the space for others to heal rather than judging.
  • Try to look for the positives and even compliment people for the things they do that trigger us rather than judging.

43:17 Turning the Mirror on Ourselves

  • We can choose not to allow others to be responsible for what I’m feeling.
  • The way we look at things determines how we will experience them.
  • What one person sees as bad or negative, another person can experience as freedom.
  • We don’t get to tell each other how we should be experiencing things.

47:14 What Do You Wish People Knew?

  • The more one gets close to their own incapacity and incapabilities, the more they can see that there really is just love underneath it all.
  • If we can love the most painful parts of ourselves we can love the most painful parts of everybody else.


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