Miracle Mentality with Tim Storey

Episode 29: How Case Kenny Mastered Mindfulness, Confidence, and Optimism | Positivity

Date: March 2, 2026
Guest: Case Kenny, host of “New Mindset, Who Dis?” and author of The Opposite of Settling

Episode Overview

This episode features a deep dive into the strategies and philosophies that have shaped Case Kenny’s approach to optimism, mindfulness, and confident living. Host Tim Storey explores Case’s journey from corporate sales to successful thought leadership, focusing on the actionable habits and mindset shifts detailed in Case’s new book, The Opposite of Settling. The conversation covers everything from reframing relationships and language, to practical steps for optimism, journaling, addressing burnout, and navigating singlehood with a growth mindset.

Key Discussion Points & Insights

1. Case Kenny’s Personal Path to Self-Discovery

Timestamp: 04:38 – 06:04

• Corporate Beginnings: Case spent 12 years in advertising and technology sales but felt disconnected from his true self.
• Aha Moment: Launching his podcast (New Mindset, Who Dis?) provided immediate clarity and became his calling—leveraging his type-A drive and communication skills for a more meaningful mission.
• Quote:

  "Everything changed for me when I just started the podcast amidst working that job… this is the thing that I’m called to."
  — Case Kenny [05:12]

2. Finding One’s Subject Matter and Focus

Timestamp: 06:04 – 07:31

• Initially uncertain, Case’s focus crystallized over time: helping himself (and others) pursue optimism through mindfulness.
• Personal Revelation: Realized a pattern of negative self-judgment and sought tools for resilience, optimism, and self-compassion.

3. The Power of Language and Mindset

Timestamp: 07:40 – 10:26

• Unique Academic Background: Studied Mandarin and Arabic at Notre Dame, driven by a passion for language structure and meaning.
• Connecting Dots: Linguistic skills underpin his approach to self-reflection.

  “Language is how you make sense of life. And how you make sense of life either makes you pessimistic or optimistic.”
  — Case Kenny [08:30]

4. The Making of The Opposite of Settling

Timestamp: 10:57 – 12:49

• Book Genesis: Challenged the culturally entrenched phrase "settle down" in relationships, preferring "settling up"—seeking a partner who amplifies your existence.
• Optimistic Reframing:

  “The purpose of a relationship above all else is, do they amplify that? ... You’re getting more out of life with a partner as opposed to less and certainly not settling down.”
  — Case Kenny [12:19]

• Connection: Language shapes expectation and experience in love and life.

5. Case’s "Hit Records" — Core Messages

Timestamp: 13:35 – 15:41

• Optimism as a Foundation: Defined as the belief that things can change.
• Emotional Vocabulary: The words you use shape how you experience emotions.

  “The words we use to describe our emotions dictate how we feel them.”
  — Case Kenny [14:35]

6. Origins of Optimism

Timestamp: 16:30 – 18:27

• Influence of Upbringing: Came from a "realistic" (often pessimistic) family background; desired to believe in growth and change.
• Mindfulness Evolution: Discovered that optimism isn’t just listening to yourself, but how you talk to yourself.

• “To be mindful isn’t just listening to yourself; that’s only half the battle. The rest is how you talk to yourself.”
  — Case Kenny [17:28]

7. Action Steps to Build Optimism

Timestamp: 20:15 – 22:50

• 1. Change Self-Talk: Replace “I am anxious” with “A part of me feels anxious.” This reframes negative emotions and avoids permanence.
• 2. Challenge Limiting Beliefs: Write down limiting beliefs, then frame the opposite: “If I’m wrong, it would mean ____.”

  “All we’re doing is just trying to open the door on these things that have been set in decision making, and we open our eyes to them.”
  — Case Kenny [21:28]

8. The Importance of Journaling

Timestamp: 22:50 – 25:47

• Brain Function: The brain retains but doesn’t process information well. Journaling helps process and move from “retention to intention.”
• Reframing Journaling: Position it as mental training (not just “for sad people”) and use specific prompts.

• “You are freezing retention, and you’re moving it to intention, and it’s the most powerful thing you could do in the world.”
  — Case Kenny [23:32]

9. Tackling Addiction & Mindfulness

Timestamp: 25:47 – 27:47

• Optimism and Clarity: Addiction often comes from distraction or ingrained unhealthy behavior. The process starts with clarity about the “why,” then movement towards change.
• Key Principle:

  “If you don’t believe that things can change, why would you try to get over your addiction?”
  — Case Kenny [27:30]

10. Burnout and Relentless Ambition

Timestamp: 27:47 – 30:17

• Personal Anecdote: Case shares never opening a celebratory champagne bottle—every goalpost just moves further.
• Warning:

  “Ambition without mindfulness leads to burnout every single time.”
  — Case Kenny [29:15]

• Solution: Pair ambition with mindful reflection and self-compassion.

11. Out-of-Town Confidence and Relationships (Book Excerpt)

Timestamp: 30:30 – 32:50

• Concept: Traveling gives people "out-of-town confidence” by shedding expectations and seeking joy first.
• Relationship Application:

  “The purpose of a relationship is to amplify the happiness, joy, success, ambition that you’ve already built on your own.”
  — Case Kenny [31:40]

12. Singlehood, Dating Mindsets, and Limiting Beliefs

Timestamp: 32:50 – 36:15

• Cultural Complaints: People complain about dating in every city—Case warns not to create negative stories or limiting beliefs.
• Advice:

  “Belief always comes before becoming. … If we start telling ourselves a limiting belief like that, the reality will very much follow.”
  — Case Kenny [34:18]

• Wisdom from Elders: No one regrets being single too long—it's usually the opposite.

13. The Podcast Title, and Case’s Core Philosophy

Timestamp: 36:34 – 37:16

• Title Origin: “New Mindset, Who Dis?” came from a playful phrase but underscores how dramatically shifting your mindset transforms your identity.
• Quote:

  “Your mindset can completely change who you are.”
  — Case Kenny [36:56]

Notable Quotes & Moments

• On reframing relationships:
  “I just wrote it [the book] to help give people a mindful and optimistic reframing of relationships to say, hey, the point of a relationship is not to check a box, not just to have a partner. It’s to have someone who amplifies your existence.” [11:25]

• On changing self-talk:
  "At bare minimum, when you feel a negative way, say a part of me feels this way. ... I’m not an anxious person. I’m not a sad person. I’m not an angry person. It’s a part of me." [20:34]

• On the mindset of singlehood and dating:
  “I have never heard someone ever say, I regret being single for too long … Sometimes we just need to celebrate that.” [35:12]

• On ambition and burnout:
  "Ambition without mindfulness leads to burnout every single time. We have to find a way to be ambitious and human." [29:15]

Timestamps for Key Segments

| Segment | Topic | Timestamp | |---------|-------|-----------| | 1 | Case’s breakthrough moment | 04:38 | | 2 | Discovering his message | 06:04 | | 3 | Language & optimism | 07:40 | | 4 | Book genesis: The Opposite of Settling | 10:57 | | 5 | Case’s key messages on optimism & language | 13:35 | | 6 | Origin of optimism focus | 16:30 | | 7 | Two steps for optimism | 20:15 | | 8 | Why journaling matters | 22:50 | | 9 | Optimism & addiction | 25:47 | | 10 | Burnout & ambition | 27:47 | | 11 | “Out-of-town confidence” (book concept) | 30:30 | | 12 | Singlehood, dating mindsets | 32:50 | | 13 | Podcast title meaning | 36:34 |

Resources & Where to Find More

• Case Kenny’s Website: casekenny.com
• Book: The Opposite of Settling (Available on Amazon)
• Instagram: @case.kenny

Final Thoughts

Tim Storey and Case Kenny offer a conversation that’s practical, insightful, and candid—covering everything from subtle shifts in language to the larger journey of finding purpose and joy. For anyone seeking to upgrade their mindset or navigate change with optimism, this episode is packed with practical wisdom and memorable discussion.