What is a Good Life? What is a Good Life? #166 - Living Your Own Version Of Success with Kaylyn Lehmann
Mar 17, 2026
Kaylyn Lehmann, executive coach and co-founder of Simplified Coach, blends neuroscience-informed leadership with character strengths. She talks about using a daily mortality prompt to guide choices. She recounts leaving roles for coherence, building a business during hardship, prioritizing family time, and why autonomy, play, and awe matter for a meaningful life.
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Mentor's Loss Sparked The 'Is Today The Day' Question
- Kaylyn's mentor's husband died of pancreatic cancer, which prompted Kaylyn to ask "Is today the day?" as a guide for living.
- That question pushed her to leave an ill-fitting VP role and return to work she loved: training adults and opening restaurants.
Autonomy Is A Fundamental Motivation Driver
- Autonomy appears repeatedly in motivation research as a core human need driving engagement and creativity.
- Kaylyn cites Daniel Pink's autonomy/mastery/purpose and David Rock's SCARF model to explain why lack of autonomy feels like a drag.
Walking Away For Coherence Over Income
- Kaylyn refused to deceive a colleague by staying quiet while their employer planned to fire that colleague during a shared car ride.
- She walked away from the relationship and income, calling it empowering coherence rather than sacrifice.
