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January 15th, 2025

Episode 182–Should You Go All In or Play It Safe?

  1. Episode 182--Should You Go All In or Play It Safe? Billy Lahr 45:23

Text your questions, comments, & topic suggestions here! You can also email billy@mindfulmidlifecrisis.com.

In this episode, I unpack one of life’s most relatable dilemmas: whether to go all in on a dream or play it safe. Drawing inspiration from Robert Frost’s “The Road Not Taken,” I explore my recent decision to either go all in as a digital nomad coach or honor a teaching contract in Seoul. Along the way, I reflect on social perfectionism, fear of failure, and impostor syndrome while sharing practical steps to navigate uncertainty and make aligned, confident decisions.

Key Talking Points:

  • Living at a Crossroads: Reflecting on my recent life decision to choose financial stability over pursuing a high-risk dream.
  • Social Perfectionism and Anxiety: How the pressure to be perfect influences decision-making and how mindfulness can help ease that burden.
  • Courage vs. Confidence: Why leading with courage, rather than waiting for confidence, is the key to making bold decisions.
  • Balancing Risk and Stability: How to weigh the thrill of chasing a dream against the value of a safety net.
  • Logic Meets Intuition: The importance of integrating practical considerations with gut instincts to make well-rounded decisions.

All of our episodes are available at www.mindfulmidlifecrisis.com.
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Billy Lahr The Mindful Midlife Crisis Podcast

Billy Lahr is currently the host of The Mindful Midlife Crisis, a podcast for people navigating the complexities and possibilities of life’s second half. Billy spent 21 years as an educator but became disenfranchised the last half due to budding mental health concerns and lack of job satisfaction. In 2021, Billy left his job as dean of students in order to travel the world in search of more meaningful life experiences. Since then, Billy has been focused on helping others navigate their own midlife crisis more mindfully through practical and intentional daily routines that focus on consistency, discipline, and mindful awareness.

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