In My Early Life, Churchill describes his education and his experience in four wars on three continents as a young officer and newspaper correspondent, including his cavalry charge against the Dervishes at Omdurman in the Sudan and his capture and escape from a Boer prisoner of war camp in South Africa. He explains how he wrote his first five books and launched his political career before taking his seat in the House of Commons at twenty-six. By the time he wrote this book, the First World War had ushered in many changes, not all of them good, and Churchill perceived a low spirit in his countrymen. He thinks a time may come when young Britons will need more love of "adventure, and adventure for adventure's sake," which his early life exemplifies, and he offers "the new generation" his own "story of youthful endeavour" to encourage and rekindle the spirited part of their souls. Giving an account of his own life is a summons to young people who are drifting in an eddy of mass effects to surmount their fear of death, aiming to stir up unselfish endeavor in them. Lest anyone mistake his intention in writing the book, he dedicates it "TO A NEW GENERATION."

This edition of My Early Life includes "The Dream." This short story was first mooted at a family meal at Churchill's country house at Chartwell in late November 1947, in the company of Winston and Clementine Churchill's children, Diana and Randolph. Diana asked her father, if he could conjure up anyone, who would fill an empty chair in the dining room. He replied that he would choose to dine with his own father, Lord Randolph Churchill, who had died more than fifty years earlier. He went on to describe a story he meant to write, based on a dream in which Lord Randolph returned to his son's painting studio to inquire what had occurred in the intervening half-century. Encouraged by his family's enthusiasm, Churchill wrote the story soon afterwards but, after revising it, set it aside to be published later. This "Private Article," as he styled it, first appeared a year after his death in the Sunday Telegraph, January 30, 1966, which described it as "his last story-locked away in a box for years-now published for the first time." By permission of Churchill College, it is reprinted, with explanatory editorial notes, as a fitting epilogue to Churchill's autobiography.