Even as a child, Jobs exhibited a defiant streak. He was a prankster who challenged authority, both at home and at school. His early pranks, often involving electronics, foreshadowed his later knack for bending technology to his will.
"I had a good friend named Rick Ferrentino, and we'd get into all sorts of trouble," Jobs recalled. Their antics included disrupting school with fake "Bring Your Pet to School Day" posters and switching bike locks so that no one could get their bikes. As he got older, his pranks became more elaborate, involving wiring his house with speakers so he could listen in on conversations.
Jobs came of age during a time of cultural ferment. The Vietnam War, the civil rights movement, and the rise of the counterculture all shaped his worldview. He was drawn to Eastern spirituality, Zen Buddhism, and the quest for enlightenment.
Jobs famously dropped out of Reed College, not out of a lack of academic aptitude, but out of a yearning to explore alternative paths to knowledge and self-discovery. "The minute I dropped out I could stop taking the required classes that didn't interest me, and begin dropping in on the ones that looked interesting," he said. This included a calligraphy class that would later inspire the elegant typography of the Macintosh.
He immersed himself in books on Zen, Hinduism, and meditation, embracing a philosophy of intuition and experiential wisdom. His pilgrimage to India in 1974 further deepened his spiritual quest, and he later said, “Intuition is a very powerful thing, more powerful than intellect, in my opinion. That’s had a big impact on my work."
Jobs’s embrace of both technology and counterculture values was not a contradiction; it was a defining aspect of his genius. He saw technology not as a cold, impersonal force, but as a tool for personal empowerment and creative expression.
He was drawn to Stewart Brand’s Whole Earth Catalog, which celebrated the idea that technology could be a force for good. "Our consciousness was raised by Zen, and also by LSD," Jobs reflected later. “Taking LSD was a profound experience, one of the most important things in my life. LSD shows you that there’s another side to the coin, and you can’t remember it when it wears off, but you know it. It reinforced my sense of what was important—creating great things instead of making money, putting things back into the stream of history and of human consciousness as much as I could.”
Jobs’s rebellious spirit was most evident in his collaboration with Steve Wozniak on the infamous Blue Box, a device that allowed users to make free long-distance calls by hacking into the AT&T phone network.
"If it hadn't been for the Blue Boxes, there wouldn't have been an Apple," Jobs later reflected. “Woz and I learned how to work together, and we gained the confidence that we could solve technical problems and actually put something into production.” The Blue Box was a testament to their shared ingenuity, audacity, and willingness to defy authority.
Jobs infused Apple with his rebellious spirit. He wanted it to be a company that challenged the status quo, embraced creativity, and put a dent in the universe. His “Think Different” ad campaign, featuring iconic rebels such as Albert Einstein, Bob Dylan, and Martin Luther King, Jr., was a celebration of this ethos.
Even as Apple became a corporate behemoth, Jobs remained fiercely independent and dismissive of conventional business practices. He famously parked in handicapped spaces, eschewed market research, and ran the company with an autocratic style that could be both inspiring and infuriating.