The Mindful Midlife Crisis

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

Billy Lahr

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.

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