Deep Roots

Day 39: I don’t like to fail


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 Day 39 of preparing to run around Ireland, and doubt is creeping in. In this episode, Damian shares his raw and unfiltered thoughts while standing outside a shop at Inch Beach, County Kerry, amidst the rain and wind. He reflects on the mental and physical challenges of preparing for such an immense undertaking, the unexpected hurdles, and the shift in strategy that has led him to focus solely on running instead of incorporating cycling into the challenge.


Despite the setbacks, this episode is a testament to endurance—not just physical but mental and emotional. The journey ahead is uncertain, but as he reminds us, true resilience comes from pushing through doubt and continuing forward, no matter the resistance.

Topics Covered:

  • The shift from a triathlon-style challenge to a singular endurance feat
  • The mental battle of self-doubt and overcoming internal resistance
  • Physical setbacks, including Achilles issues and overall body deconditioning
  • The weight of sponsorship discussions and the fear of not making it to the start line
  • The power of endurance and pushing through uncertainty

Key Quote: “Endure further into the doubt. Endure further into the negativity. Because things have turned around in the past, and they can again.”


Support the Journey: If you’ve been inspired by this episode, consider supporting the journey by sharing the podcast, following along on social media, or getting involved in the project. Every bit of encouragement helps fuel the miles ahead.



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