Penick started as a caddie at the Austin (Texas) Country Club (ACC) in 1913. During the 1920s he played the Texas PGA tours, and served as its president. In 1922, he was hired as the ACC's golf professional. He held that position until he retired in 1971. In 1931 he started coaching for the University of Texas golf team, retiring in 1963.
For 60 years, Penick collected his thoughts and observations about golf in a small red notebook. Penick mentioned the book to author Bud Shrake, and together they created one of the best-selling books about the sport to ever be published. Their collaboration also created two other notable books on golf.
Penick died on April 4, 1995, after suffering for many years from poor health. In 2002, he was named to the World Golf Hall of Fame in the lifetime achievement category.
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