Ep. 85 - What Regret Taught Me About Love, Leadership, and Legacy

In this solo episode, Keith L. Callaway opens up about the power of regret—not as a weight, but as a teacher. Drawing from personal experiences in marriage, business, and fatherhood, Keith challenges the modern mindset of "no regrets" and invites listeners to view past mistakes as essential ingredients in their growth journey.

Key Points:

  • The emotional toll of regret during high-pressure seasons (like summer)
  • Why "no regrets" isn’t always a healthy mantra
  • Real-life stories of youthful mistakes in marriage and their lasting impact
  • Business missteps and the lessons they seeded
  • The danger of getting stuck in resentment, comparison, or worry
  • The “bushes” metaphor: how emotional traps keep us in the dark
  • How God’s light and intentional coaching can guide us out of regret
  • Final encouragement to see past experiences as seeds of greatness

Referenced Insights:

  • Inspiration from a “country philosopher” with a beard (Instagram/YouTube)
  • Mike Rowe's podcast analogy about emotions pulling us into hiding