This work is a thorough and probing look into the ancient book of Ecclesiastes, comparing the contemporary and existential issues of postmodern man (meaning, purpose, significance, lifestyle, death, eternity) to the struggles of Solomon’s era. Indeed, Solomon greatly struggled with his existence on this earth—he was shockingly pessimistic and cynical. Fortunately, he deeply struggled out-loud through his writing of Ecclesiastes and boldly surfaced the dilemmas in the human experience (e.g., “evils under the sun”). His struggle is not unlike our struggle and that of almost every human being. If a person doesn’t go after a thrilling relationship with the Creator, there is only one thing left—the creation, and thus, by default, an individual pursues the creation through pleasure, materialism, achievement, intellectualism, and even false religion (it seems quite apparent that man cannot live without some kind of spirituality). Solomon pursued all of these things (like most people) and he came back feeling “empty” (like most people), and declared it is all a “meaningless” experience. This work assesses Solomon’s pessimistic experience through his own words in the text of Ecclesiastes but in juxtaposition offers an optimistic alternative. It gives a balanced understanding to having pleasure, achieving in life, accumulating things/materialism, pursuing education/intellectualism, and what is the difference between true and false religion. In addition: wisdom versus foolishness is delineated, the true path to the enjoyment of life is offered, how to work with the inevitable experience of death, and a cogent case for an afterlife/eternity is all laid out in this book. This is a substantive and yet delightful read for anyone considering the issues of the human experience.