Could your drive to succeed actually be the thing keeping you stuck?

Phil sits down with clinical psychologist and author Dr. Kelly Flanagan, whose work has resonated most with an unexpected audience: high-achieving entrepreneurial men.

Dr. Flanagan breaks down the difference between guilt and shame, and how shame quietly hijacks careers, marriages, and parenting. He explains why achievement does not resolve the original wound of “something is wrong with me,” and how success can actually intensify it.

He also shares the pivotal question he and his wife asked themselves before walking away from prestigious paths to build a different kind of life…one shaped by worthiness instead of proving.

You’ll hear them unpack:

• The question that reveals whether your next move is driven by freedom or the need to prove
  

• Why success often strengthens shame instead of resolving it
  

• Why passion always involves suffering, and why that is not a signal to quit
  

• The three stage cycle of worthiness, belonging, and purpose
  

• How to build relationships where you feel less pressure to perform and more freedom to be yourself

If achievement hasn’t quieted the voice that says you’re not enough, this conversation explains why.

0:00 Intro

02:21 Who Lovable Was Written For

06:59 Shame as the Original Wound

10:16 Guilt vs. Shame

13:22 Parenting Triggers and Self Grace

19:05 Meeting His Wife

23:22 The Freedom Question That Changed Everything

29:19 The Cycle of Worthiness, Belonging, Purpose

32:04 Why Relationships Come First

39:22 How Passion, Pain, and Purpose Connect

42:21 Why Resistance Is Not a Sign to Quit

44:28 The Road Less Triggered

Dr. Kelly Flanagan’s books:

📚 Lovable

📚 The Unhiding of Elijah Campbell

📚 The Road Less Triggered Available now for pre-order with bonuses: https://lesstriggered.com

➡️ Download the Purpose Matrix tool for FREE:https://www.thepurposematrix.com/

Follow @PhilOnPurpose

https://www.instagram.com/philonpurpose

https://www.facebook.com/philonpurpose

Most of us don’t feel stuck because we’re failing. We feel stuck because we were trained to be.Trained to stay busy. To do it alone. To worry about how it LOOKS instead of who we’re becoming.That realization led to one word that kept resurfacing: broken.Not as a flaw to hide, but as a starting point that we all have in common.In this episode, Phil reflects on the ways society shapes our habits, our fears, and our definition of success…and how those patterns can slowly pull us off course without us even noticing.Key moments:• Why feeling “stuck” is often learned, not earned• The difference between being broken and being hopeless• How busyness and ego quietly block purpose• Why reframing regret can unlock growth• The role the right people play in moving forwardThis isn’t about “fixing yourself.” It’s about seeing clearly, asking for help, and choosing a different way forward.0:00 Intro1:02 The word that changed everything5:43 The 5 hidden obstacles in our way7:05 How busyness steals your peace9:27 Regret as your greatest teacher15:44 The real thing holding you back20:42 Brokenness means we need help21:19 How to find your Iron Few➡️ Download the Purpose Matrix tool for FREE:https://www.thepurposematrix.com/Follow @PhilOnPurposehttps://www.instagram.com/philonpurpose https://www.facebook.com/philonpupose

Dreamers don’t fail because they lack ideas. They fail because they don’t have a Driver owning execution.

Today, Phil talks with Stephanie Brackett, COO of Gobundance and a lifelong operations leader who has spent decades turning vision into finished work.

From her early years at Home Depot to scaling real estate teams and executive partnerships, Stephanie has thrived in the second-in-command seat.

The discussion centers on the “dreamer and driver” relationship, why hiring leverage too late quietly taxes growth, and how execution breaks down when founders refuse to give up control.

Stephanie lays out her personal operating system for getting things done (including inbox discipline, task capture, and decision filters) while also naming the emotional and relational realities that make operations work or fail.

A few practical takeaways:

• Why the “dreamer and driver” relationship matters more than org charts or titles

• How waiting to hire operations costs more than the salary itself

• The C-CORE framework for capturing and executing work without mental overload

• Why inbox zero is about decision making, not email management

• How to tell whether a task deserves attention now, later, or never

• The difference between being busy and being dollar productive

• Why great operators are wired to serve, not dominate

If you’re carrying the vision and feeling buried by execution, this episode gives language to what’s missing and how to fix it.

…and if you’re an operator, this conversation will fire you up!

0:00 Intro

0:40 Stephanie’s career path

2:57 Differentiator for success and traits to hire

7:27 Why the Dreamer & Driver relationship matters

9:29 When a small business should hire an operations leader

15:41 Getting things done using C-CORE

19:19 Prioritizing tasks

25:00 Inbox zero

29:56 Calendar categories

33:27 Who her book is for

38:40 The secret sauce: desire to serve

43:04 Zones and matching work to energy

46:49 Bringing operations to the forefront

Resources Mentioned:

📚 Getting Things Done by David Allen

https://gettingthingsdone.com

📚 The One Thing by Gary Keller

https://www.the1thing.com

📚 At Your Best by Carey Nieuwhof

https://careynieuwhof.com/atyourbest

📚 Rocket Fuel by Gino Wickman and Mark C. Winters

https://www.eosworldwide.com/rocket-fuel-book

Todoist

https://todoist.com

WHY.os Assessment

https://whyinstitute.com/

Second In Command Club

https://secondincommandclub.com

GoBundance

https://gobundance.com

Follow @PhilOnPurpose

https://www.instagram.com/philonpurpose

https://www.facebook.com/philonpupose