Overcoming Self-Doubt, Perfectionism, and the Illusion of Success with JJ DiGeronimo
What if everything you’ve been chasing—title, salary, prestige—still leaves you feeling empty?
In this powerful episode, John and Tony sit down with three-time award-winning author and former tech executive JJ DiGeronimo to unpack the hidden costs of success and the three internal obstacles that prevent high performers from realizing meaningful fulfillment:
The Oasis of Success — why what looks like success may leave you feeling stuck
Self-Doubt — how to recognize and reframe the inner critic
Perfectionism — when high standards become a mask for fear and inaction
JJ shares her personal transformation from achievement-driven executive to purpose-centered leader, offering deeply relatable insights and grounded practices like mindfulness, reframing self-talk, and learning to “listen to the whispers.” Through storytelling, humor, and hard-won wisdom, she gives you permission to slow down and reconnect with your own inner compass.
Whether you’re facing burnout, stuck at a career plateau, or wondering if you’re chasing the right version of success—this episode is your invitation to step out of striving and into alignment.
Key Themes:
How to identify when your version of success is no longer serving you
The power of mindfulness in breaking patterns of doubt and perfectionism
Why your inner dialogue is the key to professional transformation
A simple mindset shift: “Let me see what I can do”
How to interpret intuitive nudges and whispers as guidance for your next step
What we discussed:
1:18 Discussing High-Impact Professional Obstacles
1:51 Unpacking the Oasis of Success
2:14 JJ’s Realization and Working from the Inside Out
3:29 The Power of Present Moment and Joy
3:48 JJ’s Career Shift to Mindfulness
4:50 Awakening to Inner Fulfillment
5:30 The Importance of Stillness and Self-Discovery
6:00 Self-Discovery Questions and Insights
6:58 Advice to Younger Self on Mindfulness
7:08 Mindfulness as a Tool for Self-Awareness
8:12 The Conveyor Belt of Thoughts
9:01 Stepping Out of the Oasis of Success
10:06 Self-Awareness and the Present Moment
10:35 Addressing Those Who Need External Validation
11:10 Overcoming the Oasis of Success
12:23 Defining Self-Doubt and Resistance
13:26 Stories We Tell Ourselves and Self-Doubt
14:23 Transitioning to Perfectionism as an Obstacle
15:24 Perfectionism as a Hiding Mechanism
16:30 Tools for Integrating Fears and Moving Forward
17:32 JJ’s Tools for Overcoming Self-Doubt
18:24 Perfectionism and Its Impact on Action
19:48 Using Failure as Motivation
20:23 Collecting No’s and Embracing Rejection
21:17 Incrementalism and Consistency in Achieving Goals
22:10 JJ’s Strategy for Taking Action
23:22 Listening to the Whispers and Leaning In
24:00 The Power of Simplicity in Pursuing Passions
25:28 The Test of Listening and Being Present
26:54 JJ’s Resource for Personal Growth: Audibles
27:44 How to Connect with JJ and Her Work
29:20 Final Thoughts on Living from the Inside Out
30:43 JJ’s Experience with Following Whispers
32:42 Stepping into Heart-Centered Work
33:10 JJ’s Final Advice for Listeners
Other ways to connect:
Ready to Take the Next Step in Your Growth?
Listening is the first step. Now it’s time to turn insight into action.
If today’s conversation around Overcoming Self-Doubt, Perfectionism, and the Illusion of Success with JJ DiGeronimo resonated with you, we invite you to take the next step in your development with our Leadership Emotional Intelligence Assessment.
🧠 Start with our free EI snapshot – a quick, powerful way to better understand your leadership strengths and emotional blind spots.
🔍 Looking to go deeper? Choose one of our three paid assessment and debrief options, each including a one-on-one session with a certified coach to help you build self-awareness and step more fully into your unique leadership style.
Subscribe Today!
Want thoughtfully crafted updates, tips, and strategies to help you grow personally and professionally? How about event promos? Then fill out the form below!