Everyday Better with Leah Smart Case Kenny: How to Become an Optimist
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Sep 16, 2025 Case Kenney, mindfulness educator and author of The Opposite of Settling, teaches practices to shift self-talk and cultivate optimism. He discusses leaving corporate life for mindful work and building a creative career. Conversations explore self-talk energies, naming emotions precisely, journaling techniques, and ways to hold complexity while growing trust in yourself and others.
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From Sales To Mindfulness Creator
- Case Kenney left a 12-year ad-tech sales career after starting a short podcast to understand himself better.
- He built a business from guided journals and mindfulness content and now makes a living sharing feelings.
Secure Runway Before Quitting
- Build financial runway by side-hustling before quitting your job so you operate from leverage instead of desperation.
- Use runway to make choices for quality, not just to survive financially.
Create Confidence With Evidence
- Delusional confidence is created through accumulated evidence, not by magic.
- Create small wins that validate bold beliefs and build real confidence over time.
