Why Am I Stuck? episode artwork

EPISODE · Jun 15, 2026 · 11 MIN

Why Am I Stuck?

from Career Blindspot · host Juan Kingsbury

Smart + Kind But Stuck: The Missing Ingredient Is Experimentation   In this episode, Juan explores why smart, kind people still feel stuck, arguing it often comes from avoiding risk and clinging to perceived safety, security, and responsibility. He notes that loud voices frame empathy as weakness, but for people trying to live well and care for others, empathy is an advantage; the real problem is not experimenting beyond what's familiar. Drawing on personal ruts despite past leaps (entrepreneurship, podcasting, writing), the speaker reframes risk as playful experimentation, like solving puzzles in Zelda, and suggests that misery signals there's more to learn about oneself. They cite pandemic-driven innovation such as telemedicine—possible before but adopted when forced—as evidence people can change without crisis. The call to action is to get curious and try small new experiments in work, health, or daily routines.   00:00 Why You Feel Stuck 01:03 Smart Kind But Safe 03:19 Experiment Over Risk 05:29 Miserable Means Learning 06:20 Opportunity In Uncertainty 07:05 Small Risks Daily 08:43 Pandemic Innovation Lesson 10:27 Whats Up Danger 10:41 Your Call To Experiment  

Episode metadata supplied by the publisher feed · Published Jun 15, 2026

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Why Am I Stuck?

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This episode was published on June 15, 2026.

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Smart + Kind But Stuck: The Missing Ingredient Is Experimentation   In this episode, Juan explores why smart, kind people still feel stuck, arguing it often comes from avoiding risk and clinging to perceived safety, security, and responsibility. He...

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