Cover of The Roundabout Way by Jack O’Brien

The Roundabout Way

This is the book retirees give their children when the kids ask, “What’s it really like living in The Villages?”

A warm and often hilarious collection of short stories about fictional residents of America’s most famous retirement community, The Roundabout Way captures the humor, heartbreak, reinvention, and quiet courage that come with growing older.

For years the best-selling work of fiction by a local author in The Villages, the book explores the strange dilemma of finally having the freedom to enjoy life—just as time, health, and security begin to feel more precious.

Filled with wit, pathos, affection, and sharp observation, The Roundabout Way resonates with anyone over fifty—or anyone who hopes they someday will be.

Golf course sunset in The Villages Woman retrieving golf ball near gator Father dancing with daughter Senior couple kissing Suit floating in pool Duck beside golf ball

A visual journey through the humor, romance, absurdity, and quiet reinvention of life in The Villages.

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