We sat down with
—award-winning author, licensed psychologist, and founder of The Less Triggered Tribe for a conversation that went straight to the heart of what it means to build a business that doesn’t just succeed, but transforms you in the process.Kelly’s story isn’t your typical “I had a plan and executed it” narrative. His path has been one of following breadcrumbs, listening to intuition even when it didn’t make logical sense, and learning that the moments we get most triggered are actually our greatest invitations to grow. After a partnership dissolved, COVID hit, and a bike accident left him with a broken collarbone, Kelly made a New Year’s resolution that changed everything: to notice when his heart was closing and practice opening it back up.
What emerged from that practice became his life’s work: a nine-step process for navigating triggered moments that don’t create conflict, but instead lead to deeper connection. This is the work that his upcoming book, The Road Less Triggered, is built on.
Show Notes
[00:00] - From Academic to Practitioner
Kelly’s turning point in his PhD program: “I just want to work with clients all day, every day”
The realization that hit him like awareness “happening to him” rather than being calculated
Why research wasn’t his path, even though it looked good on paper
[04:15] - The Breadcrumb Trail of Building a Business
How a 15% insurance rate cut forced Kelly to diversify his income
Starting a blog with six readers—and one person who asked “what are you writing next week?”
The viral moment that led to The Today Show and changed everything
“Nothing I’ve planned has worked out. It’s worked out better because I didn’t stay tethered to the plan”
[12:07] - The New Year’s Eve That Changed His Life
Rock bottom at the end of 2020: business partnership dissolving, COVID stress, broken collarbone
The Michael Singer quote that became his turning point: “Don’t let anything in life be important enough that you’re willing to close your heart over it”
Making the resolution to notice his heart closing and open it back up—moment to moment
The voice in the driveway that said “let it die” when he finally opened his heart to the truth about his practice
[23:00] - Understanding the Difference Between Fear and Resistance
Why your survival instinct is healthy and necessary (don’t step off the cliff!)
How resistance masquerades as fear—and why it actually points you toward your growth
Steven Pressfield’s wisdom: “The more important a call to action is to our soul’s evolution, the more resistance we will feel”
The nervous system activation test: “Am I being confronted by a tiger, or did my wife just ask where the bananas are?”
[27:00] - The Peaceful Pivot Process
Part one: Learning to get calm and regulate your nervous system first
Why trying to connect with someone else to calm yourself down has “worked zero times in human history”
The powerful pause: seeing what you want to do defensively—and choosing not to do it
“Open-heartedness doesn’t make you weaker, it makes you wiser”
[32:00] - Pattern Problems, Not Business Problems
Why most entrepreneurs don’t have dozens of different situations to solve—just one or two pain points underneath everything
How triggered moments in business, relationships, and parenting are often rooted in the same core wound
The liberation of discovering your pattern: “This is something I can actually affect”
Moving from “everyone else is the problem” to taking personal ownership
[38:00] - Building Authentic Connection Online
Why consistency is king—but not in the way you think
Treating your audience like relationships: “If you only showed up sporadically to your kid’s soccer game, they’d emotionally wall off”
The practice of pausing for 10-15 seconds when someone subscribes to honor the reality of that human connection
“Remember the one”—every person is working their ass off to make their life better and choosing to spend time with you
[42:00] - The Fraud and the Imposter
Why Kelly will say “I’m in imposter syndrome today” from stage—and how it instantly breaks the spell
The competitive advantage of intimacy when you’re just getting started
“Don’t let that be the thing that gets in. Don’t feel like you can’t start this thing till 40 people show up in the room”
“We all have that. We all worry. Be the fraud. I’m a fraud. I’m an imposter. Exactly.”
Key Quotes
“Nothing I’ve planned has worked out. It’s worked out better because I didn’t stay sort of tethered to the plan.” - Dr. Kelly Flanagan
“Don’t let anything in life be important enough that you’re willing to close your heart over it.” - Michael Singer (quote that transformed Kelly’s life)
“Open-heartedness doesn’t make you weaker, it makes you wiser.” - Dr. Kelly Flanagan
“There’s no relationship problems. There’s only individual problems that get worked out in relationships. There’s not a business problem. There’s a pattern problem that’s getting worked out in the business.” - Dr. Kelly Flanagan
“The more important a call or action is to our soul’s evolution, the more resistance we will feel toward pursuing it.” - Steven Pressfield, The War of Art
Resources Mentioned
Book: The Road Less Triggered by Dr. Kelly Flanagan (releases March 3, 2026)
Book: The War of Art by Steven Pressfield
Book: Lovable: Embracing What is Truest About You by Dr. Kelly Flanagan
Teacher: Michael Singer and his work on open-heartedness
Community: Front Row Dads (mentioned as connection point for Kelly,
, and )
Where to Find Dr. Kelly Flanagan
Substack: drkellyflanagan.substack.com - The Less Triggered Tribe community
Website: drkellyflanagan.com
Upcoming Book Pre-Order Bonuses: Join his Substack by December 2025 to receive $350 worth of free bonuses when you pre-order The Road Less Triggered
Your Business Isn’t Separate from Your Growth—It’s the Container for It
If Kelly’s story resonates with you, there’s a reason.
The triggered moments in your business—when a client pushes back, when you resist raising your prices, when you feel paralyzed about showing up online—those aren’t distractions from your work. They’re the work itself.
Your business challenges aren’t business problems. They’re pattern problems. And just like Kelly discovered that one New Year’s Eve, when you learn to notice your heart closing and practice opening it back up, everything shifts. Your relationships transform. Your business grows. Your energy changes.
This is exactly what we help entrepreneurs understand through the Sacred Business Harmony Map.
Our assessment measures the 9 fundamental frequencies that create the foundation of a sustainable, soul-aligned business: Connection, Growth, Vitality, Discipline, Service, Simplicity, Faith, Love, and Bliss.
Your lowest frequency—the one seeking the most balance right now—isn’t a weakness to hide. It’s your doorway to liberation. It’s where your trapped energy is waiting to be freed. And when you transform that pattern, you don’t just improve your business metrics. You literally free the life force energy that’s been locked in old survival patterns.
Take the Harmony Map Assessment and discover your unique energetic blueprint for business growth. You’ll receive your personalized results showing exactly which frequencies are in balance and which ones are calling for your attention.
Then, if you’re ready to go deeper, we’ll invite you to a free Harmony Map Integration Call where we’ll:
Create space for you to share what’s really happening in your business (not what you think you should say)
Explore what your specific frequency patterns mean for your unique situation
Discover what kind of support would feel most helpful for where you actually are
See if there’s alignment for us to work together
This isn’t a high-pressure sales call. It’s an open conversation where you can share what’s true for you with people who deeply understand the inner patterns that affect business success.
Take the Harmony Map Assessment →
Thank You
Thank you to everyone who tuned in live and to those listening on the replay. Your presence in this community matters. If this conversation sparked something in you, share it with someone who needs to hear it.
And thank you, Kelly, for your vulnerability, wisdom, and willingness to share your transformation with us. We’re grateful.
P.S. If you missed previous episodes of Sacred Business Stories, you can find them all here. Each conversation explores how entrepreneurs are building businesses that serve their evolution, not just their bank accounts.
What’s Next: Subscribe to our Substack to receive weekly insights on building your sacred business, invitations to our live calls, and first access to new offerings.
New here? Welcome. Sacred Business is about refusing to fragment anymore—bringing your whole self to your work, integrating your spiritual growth with your business growth, and building something that serves both profit and purpose. If that resonates, you’re in the right place.
Ready to discover your unique energetic blueprint for business growth? Take the Harmony Map Assessment and receive your personalized results today.
