We loved our first conversation with Dr. Kelly Flanagan so much that we wanted to bring him back for something different.
This isn’t a regular episode of our show. It’s an Author’s Spotlight to support the launch of his new book, The Road Less Triggered, and to share his work with as many people as we can.
Kelly is a clinical psychologist, author, and coach who’s been featured on The Five Love Languages and Today Show. But what grabbed our attention wasn’t his resume. It was his core insight: connection doesn’t break down between people. It breaks down within them.
That idea is really imporant in how we think about relationships, and the way we show up when things get hard. Which is why we wanted this conversation to happen.
Show Notes
[00:00] Why We Brought Kelly Back
We don’t do this often. But when someone’s work directly applies to everything we teach about sacred business, we make exceptions. Kelly’s framework for staying open-hearted during conflict is too practical to keep to ourselves.
[03:00] The Core Problem: Wanting Connection While in Protection Mode
Most of us spend most of our time wanting to connect while simultaneously protecting ourselves. It’s a form of self-sabotage we don’t know we’re doing. Kelly calls it the grind of trying to connect when our impulse is actually to protect.
When you close off and switch into protection mode, you lose access to creativity, communication, empathy, patience, and forgiveness. All the things you need most.
[07:00] The New Year’s Resolution That Actually Stuck
End of 2020. COVID year. Kelly blew up his business partnership, damaged his closest friendship, got so triggered one afternoon he went on a frustrated bike ride and broke his arm in two places.
Then he found a quote from Michael Singer: “Do not let anything in life be important enough that you’re willing to close your heart over it.”
That hit harder than the asphalt road had. He made a resolution going into 2021: moment to moment, notice his heart closing and try to keep it open.
The word “try” was important. He knew this would be hard.
[10:00] The Peaceful Pivot Process (3 Parts, 9 Steps)
Kelly spent five years developing what Michael Singer couldn’t teach him how to do. The result is a framework for turning triggers into togetherness:
Part One: Get Calm
Sense your conflict coming using your body
Disrupt your defensiveness (watch your urges instead of wielding them)
Cultivate calmness before attempting connection
Part Two: Get Free
Get familiar with what’s hurting in that moment
Trace the story of that hurt throughout your life
Learn to feel it instead of defending it
Part Three: Get Connected
Show up and express yourself
Stay curious instead of critical
Give yourself compassion so you can express it to others
[12:00] The 80% Earlier Warning System
Here’s the research that caught our attention: your body gives you 80% earlier warning that your heart is about to close than your thoughts or behaviors do.
Kelly calls it interoception. Your sixth sense. You use it all the time without realizing it. When someone asks how badly you need to go to the bathroom, you use interoception. Your consciousness travels to an organ, does an assessment, reports back.
You can harness that same superpower to notice when your heart is closing before you’ve already closed it.
Everyone feels it differently. Some people feel it in the center of their chest. Others a little to the left, the right, down in the sternum, or in the gut. But it’s always somewhere between your waist and your temples.
No one has ever said their toes cramped when their heart started to close.
[19:00] The Mexico Story
One year after starting his open-heartedness practice, Kelly’s family came back from a chaotic Christmas trip to Mexico. Machine guns. COVID restrictions. People extorting cash just to get back into the country.
His daughter looked at him and said: “That must be why every time something went wrong, I looked at you and felt safe.”
Kelly realized the practice wasn’t just changing him. It was changing the people around him even when they weren’t doing anything.
A soothed nervous system soothes nervous systems. A calm soul calms souls. An open heart opens hearts.
[26:00] You Only Control You (And That’s the Point)
The part of us that wants to change the other person will feel deep injustice at this. But the wisest part knows we can only control ourselves.
When you’re part of a pattern and you change your part, the pattern changes. Family systems theory shows this clearly. When one part of a system changes, the other parts first resist, then adapt.
You are the environment in which your people live and move and exist. When that environment becomes calmer and safer, it influences how they show up.
[31:00] Start in the Empty Parking Lot
Kelly’s driver’s ed teacher used to say: “When I’m done with you, you’ll be able to drive on LSD.” He meant Lakeshore Drive in Chicago. But they didn’t start there. They started in an empty parking lot at the community college.
Same principle applies here. Start with the small disappointments. The weather you didn’t want. The traffic jam. The cancelled plans.
Kelly’s son tested positive for COVID on Christmas Day. They had to cancel the family gathering. Then his wife tested positive on New Year’s. More cancelled plans.
These disappointments became training ground. If you can’t keep your heart open to small frustrations, how will you handle the really big ones?
[34:00] A Book That’s Actually Fun to Read
Kelly wrote a novel within the non-fiction. At the end of each chapter, you follow two fictional characters through a coaching session where they work through the exercises.
His wife cried reading chapter six. That’s when he knew it worked.
The book is built around the three-part process with nine steps total. But instead of dry descriptions in a box at the end of each chapter, you get story.
[42:00] Building in Public
Kelly brought each chapter to his Substack community during development. Monthly calls where they told him what worked, what didn’t translate, what was too complicated.
His Substack is on its third name since 2023. That evolution reflects how much his understanding deepened as he built this in front of real people.
[45:00] His Biggest Hope
By the time someone finishes the first chapter, Kelly wants them to have a new lens they can’t take off. Just to walk around noticing: my heart closed there. And there. Opportunities for transformation are everywhere.
The ambitious version: he wants this book in as many hands as possible because our big human experiment is at a critical point. We’re going to have to take responsibility for showing up with open hearts if we want to miss the tipping point.
The longest longitudinal experiment in human history out of Harvard has shown definitively that above every other factor, our sense of togetherness with our people determines our happiness.
And here’s the kicker: how many times has being triggered resulted in more togetherness in all of human history?
Zero.
Key Quotes
“Connection doesn’t break down between people. It breaks down within people.”
“Do not let anything in life be important enough that you’re willing to close your heart over it.” — Michael Singer
“A soothed nervous system soothes nervous systems. A calm soul calms souls.”
“You are the environment in which your people live and move and exist.”
“How many times have we ended up more together as a result of being triggered in all of human history? Zero.”
Resources Mentioned
The Road Less Triggered by Dr. Kelly Flanagan (March 2025)
The Untethered Soul by Michael Singer
roadlesstriggered.com — Pre-order and get the first chapter immediately plus a 90-minute masterclass
Harvard’s longitudinal study on happiness and togetherness
Where to Find Dr. Kelly
Substack: Dr. Kelly Flanagan
Thank You
Thank you Josh Woll, Claire Machado, Jennifer O'Neill, drcharlesparker, Cecilia, and many others who joined us live and shared this conversation. Special thanks to Dr. Kelly for being generous with his time, his work, and his willingness to come back twice.
P.S. Want to explore past editions? You can check them out here.
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