WASHINGTON—J.D. Salinger, the author of “The Catcher in the Rye,” the great novel about adolescent alienation, died the same day that Steve Jobs launched the iPad, a manifesto on the treasures that America offers its youth.

I first read “The Catcher in the Rye” in boarding school, when I was 14. As was the case with many kids of my generation, it fell into my hands at a time of personal crisis when a particular experience filled me with anger toward the world of adults. A fellow student had been sexually assaulted by someone who had sneaked into our dorm and quietly dragged him to the bathroom at knifepoint. The classmate woke the rest of us up two hours later to tell what had happened. The story of Holden Caulfield, who spends three days in New York after his expulsion from school despising the “phony” adult society, had a strangely comforting quality.

Holden’s meeting in New York with his 10-year-old sister Phoebe, the only living person for whom he has profound affection and whose hope to run away with him he turns down, movingly conveyed his protective nature toward innocent beings.

Years later, I reread the book on an airplane bound for Hong Kong. I became captivated once again, but this time I found Caulfield to be a self-centered phony himself. His meeting with Phoebe no longer revealed a protective soul but the opposite: a cowardly rejection of responsibility. It disproved the claim that he wanted to be a “catcher in the rye” and rescue children before they fell off a cliff.

The third time I read the book, I was on my way to speaking engagements in Europe. I still considered it to be a masterpiece, but by then I had difficulty reacting to Caulfield either admiringly or with enmity. He struck me as the kind of dysfunctional being that free countries produce from time to time for reasons that have little to do with society’s evils and much to do with an individual’s own demons. The 1950s, the decade whose sense of alienation “The Catcher in the Rye” supposedly symbolized, was one of extraordinary achievement in the United States. The postwar economy took off, 10 million households gained access to television, the first credit card (Diners Club) found its way to people’s wallets, life was so busy that fast-food chains sprang into action and families moved to the suburbs, and couples were so optimistic that the era was known for its baby boom.

Yes, rebellion was in the air. Rock ‘n’ roll and the celluloid anti-heroes and anti-heroines—James Dean, Marlon Brando, Ava Gardner, Kim Novak—were early harbingers of the nonconformism that the 1960s would turn into a religion. But all of that was creative; instead, Salinger’s fictional character, though perceptive, is sterile. The rebellious youth who began to emerge in the 1950s replaced traditional values with new ones, legitimate or not. Caulfield is not interested in replacing “phony” society with anything.

Which brings me to Steve Jobs. He was also an outcast—a college dropout. But he turned his disconnect with the conventions of adulthood into an epic poem that started when he and Steve Wozniak virtually invented the personal computer. They launched the Apple saga with no more than $1,300; last year the company had $43 billion in sales. Along the way, Jobs revolutionized personal computers, mobile communications, portable music and video, and has now integrated those functions into a fantastic new tool of personal freedom.

Jobs’ tale is the story of youth overpowering “phony” adults. And so are plenty more tales of entrepreneurial and innovative defiance. Thousands of small companies continually displace larger ones in the United States. In the 1960s, it would take 20 years for one-third of the Fortune 500 list to change. Now, it takes four years. Some of the greatest names in American capitalism—Microsoft, Gap, Hewlett-Packard, Polaroid, Burger King—were started by youthful nonconformists in the midst of recession.

Alienation is by no means a monopoly of free societies—a reason why alcoholism reached astronomical proportions in the Soviet Union. But free societies place at one’s disposal all sorts of possibilities to turn what feels alien into something more intimate or meaningful. How ironic that you will soon be able to read masterpieces on adolescent alienation such as “The Catcher in the Rye” on an iPad tablet, a monument to youthful liberation.