What if your work felt like play? What if that seemingly childish question—"What would you do if money was no object?"—actually held the key to living without regret?
Captain Frodo takes us on a profound journey through the false separation between play and work that dominates adult life. Drawing wisdom from philosophers Johann Huizinga and John Dewey alongside mystical thinker Alan Watts, this episode challenges our cultural assumptions about what constitutes "serious" pursuits.
The exploration reveals how children's play—far from frivolous—represents deep, meaningful engagement with the world. This "serious play" serves as their work, their way of understanding themselves and their place in society. Meanwhile, adults often abandon play for "work" defined by external rewards rather than intrinsic satisfaction, creating lives split between obligation and enjoyment.
Most poignantly, we confront the five most common regrets of the dying, with the top regret being failing to live authentically rather than meeting others' expectations. This reveals the potential consequences of abandoning our playful nature for socially prescribed paths.
Through evolutionary perspectives showing childhood's increasing importance in human development and philosophical insights about integrating play and work, Captain Frodo offers a compelling vision: work permeated with the play attitude becomes art—and potentially, the foundation of a life without regret.
Ready to reconsider the role of play in your life and work? This episode might change how you view what truly matters. Follow @thewayoftheshowman on Instagram and share this episode with someone searching for more meaning in their daily pursuits.

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