Coaching By Jeannie | Episode 20: Real Life Adventures with Alan Underwood and How They Translated to His Success Today.

·1 hr 9 min·5 clips

Alan Underwood shares how losing both parents to cancer led him to consider ending his life in his truck.

Jeannie Hallam hosts episode 20 of Coaching by Jeannie, featuring guest Alan Underwood, a coach, mentor, and entrepreneur based in Arizona and San Diego. The episode begins with Jeannie reading Alan's bio, highlighting his roles as a capital strategist, founder of his coaching practice, partner at Momentum Capital Group, father of eight, licensed pilot, and Arizona wing leader for Angel Flight West. Alan reflects on his bio, noting the hard work behind his achievements. He then delves into a difficult three-year period from 2018 to 2020, during which he lost both parents to cancer and a stroke, leading to severe depression and a moment where he considered suicide in his truck. Alan explains how this rock bottom became a foundation for rebuilding, learning self-love, and developing a vision for his life. He shares that he is currently training for a bodybuilding competition, using the physical challenge to apply lessons from his past struggles. The conversation shifts to leadership, with Alan recounting a story about running out of fuel in his airplane over the Grand Canyon due to forgetting to switch tanks, which he uses as a metaphor for responsibility and awareness. He discusses how flying emerged as a lifeline after his father's death, inspired by a prayer for happiness, prosperity, and purpose, and how his wife's support allowed him to take his first lesson. Alan describes the immediate emotional lift he felt during that flight, which his wife recognized as his 'thing.' He connects this to coaching techniques like 'Mesa View,' where perspective shifts can unlock solutions. Alan then tells a story about being asked to fly a terminally ill 16-year-old girl, which shifted his focus from his own struggles to gratitude and service. He emphasizes the importance of family, suggesting listeners record conversations with aging parents to preserve wisdom. Alan details his volunteer work with Angel Flight West, explaining how the organization provides free medical flights across 13 western states, with pilots donating $10 million annually. He describes his role as Arizona wing leader, which he took on after volunteering to raise awareness. When asked about managing his many roles, Alan advises focusing on superpowers like connecting with people and strategic vision, while delegating other tasks. He shares past business examples, like giving free pizza to schoolchildren, to illustrate the power of generosity. Towards the end, Alan offers advice for those feeling stuck, introducing his 'two words' framework—'I am,' 'I choose,' 'I feel,' and 'thank you'—which he says can transform daily life and is the basis for a book he is writing. The episode concludes with contact information for both Alan and Jeannie.

As heard by us

A flight emergency turns generous interpretation into a practical coaching lesson.

Coaching By Jeannie uses Alan Underwood's account of a frightening engine problem to explore how two people can live through the same moment in very different ways.

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Why you'd press play

You get a coaching conversation where an engine problem becomes a case for giving people more grace.

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