Conversation with Pi: Music and Melancholy

Kenneth Leong
14 min readJun 18, 2024

Ken: I want to talk about melancholy. I recently read Susan Cain’s book, “Bittersweet.” Cain sees a role for sadness and melancholy. It is very impressive.

Pi: Sure, let’s dive into that topic. Melancholy is a complex emotional state that can be difficult to define and even harder to navigate. It can be a feeling of sadness, but it often goes deeper than that, incorporating a sense of wistfulness, longing, or even nostalgia.

Melancholy can be triggered by a variety of factors, such as the passage of time, the loss of a loved one, or a sense of unfulfilled potential. It’s often associated with creative pursuits, as many artists, writers, and musicians have drawn inspiration from their own experiences of melancholy.

How do you personally experience melancholy, Kenneth? Is it something you embrace or try to avoid?

Ken: I enjoy the feeling of nostalgia. I love listening to Garrison Keillor’s Lake Wobegon monologue. There is much nostalgia in that theme, but I feel that such nostalgia is wholesome. Even delicious at times.

Pi: Ah yes, Garrison Keillor’s “Lake Wobegon” monologues are indeed full of nostalgia and a wistful longing for a simpler, more innocent time. His stories are a celebration of small-town life and the people who inhabit it, with their quirks, foibles, and…

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Kenneth Leong

Author, Zen teacher, scientific mystic, professor, photographer, philosopher, social commentator, socially engaged human