I recently received updates from two authors on the same day. One breathes the exhausted fumes of disillusionment after a long career of solid sales. The other exudes the enthusiasm of unanticipated action as he publishes his first book. In them, I see bookends of the expectations of every aspirant, in writing and life.

The new author—let’s call him Bob—presents a ticklish dilemma. Not because it is a delicate matter, but for the laughter I could hear in his vo...