Life Simulator · Steve Jobs
True Story · Interactive

He dropped out of college, got fired from his own company, bought Pixar for $5 million when everyone laughed, then came back and built the iPhone. At every turning point, you make the call.

This is a life simulation. At each critical moment in Steve Jobs' real story, you face the same choice he did — before you're told what he actually did.

Steven Paul Jobs was born on February 24, 1955, in San Francisco. He was adopted as an infant by Paul and Clara Jobs — a machinist and an accountant — who moved to Mountain View, California, and raised him in the emerging suburban landscape of what would later be called Silicon Valley.

He was not an easy child. He was smart enough to test into a grade ahead, curious enough to take apart every piece of electronics in the house, and difficult enough that his parents enrolled him in a school more interested in creative students than obedient ones. By high school he was sitting in on engineering lectures at Hewlett-Packard and calling Bill Hewlett directly to ask for spare parts.

In 1972, at 17, he enrolled at Reed College in Portland, Oregon. His adoptive parents had spent their savings on the tuition. After six months, Steve Jobs dropped out.

Decision 1 · 1972 · Age 17 · Reed College, Oregon1 / 7

Jobs has enrolled at Reed College. His adoptive parents spent their savings on the tuition. After six months, he's convinced that the required courses are pointless — he's learning nothing he cares about. What does he do?

What Steve Jobs Did
He dropped out. He slept on floors in friends' dorm rooms, returned Coke bottles for food money, and attended classes he chose himself — including a calligraphy course that he called "beautiful, historical, artistically subtle."
Jobs later said the calligraphy class was directly responsible for the Mac having beautiful typography — the first personal computer to do so. "If I had never dropped in on that single course in college, the Mac would have never had multiple typefaces or proportionally spaced fonts." He also said dropping out was "one of the best decisions I ever made. The minute I dropped out I could stop taking the required classes that didn't interest me." He spent 18 months wandering campus, studying what he wanted. Then he went to India, came back, and built Apple.
1976 · Age 20 · Los Altos, California · A Garage

Steve Wozniak — "Woz" — was the most talented hardware engineer Jobs had ever met. Working at Hewlett-Packard, Woz had designed a computer circuit board so elegant and capable that engineers who saw it couldn't believe one person had built it.

Woz's plan: present the design to the Homebrew Computer Club for free. Share it. Let other hobbyists build from it.

Jobs had a different idea. He saw a business.

He proposed they start a company. Woz was skeptical — he had a good job. Jobs would need to quit his position at Atari. Their startup capital would be: Jobs' Volkswagen van and Woz's HP scientific calculator, sold for a combined $1,300.

Decision 2 · 1976 · Age 20 · The Garage2 / 7

Wozniak has designed a remarkable computer. He wants to give the design away for free to the Homebrew Computer Club. Jobs sees a business. Starting a company means quitting a real job and betting $1,300 in total capital. What does Jobs do?

What Steve Jobs Did
He founded Apple Computer on April 1, 1976, with Wozniak and Ronald Wayne. He insisted on selling finished computers, not kits — because he believed most people didn't want to assemble anything. He was right.
The first Apple I sold for $666.66. Apple II, launched in 1977, became one of the best-selling personal computers ever made. Within four years of founding the company in a garage, Apple went public. The IPO on December 12, 1980, generated more capital than any IPO since Ford in 1956 and created more millionaires overnight than any company in history at that point. Jobs was 25 years old.
1985 · Age 30 · Cupertino, California · The Firing

In 1983, Jobs had recruited John Sculley away from PepsiCo to be Apple's CEO, famously asking: "Do you want to sell sugar water for the rest of your life, or do you want to come with me and change the world?"

By 1985, it had gone wrong. The Macintosh, launched to enormous fanfare in 1984, was not selling fast enough. Jobs and Sculley had come to fundamentally disagree about Apple's direction. The board sided with Sculley. Jobs was stripped of his operational role, then resigned from the company he had co-founded.

He was 30 years old. He was publicly humiliated. He had just been fired from Apple.

He later described this period as devastating — and then as the most creatively free time of his life.

Decision 3 · 1985 · Age 30 · After the Firing3 / 7

Jobs has been fired from Apple — the company he founded. He is 30, publicly humiliated, and stripped of the work that defined him. What does he do next?

What Steve Jobs Did
He founded NeXT Computer. He also bought The Graphics Group from George Lucas for $5 million — a struggling computer graphics division that everyone said was worth far less, if anything. It became Pixar.
NeXT made expensive, elegant workstations that were ahead of their time and never sold in large numbers. But its operating system, NeXTSTEP, was so technically superior that when Apple was dying in 1997 and needed a new operating system, it acquired NeXT — bringing Jobs back with it. Pixar, meanwhile, was losing money consistently under Jobs' ownership until 1995, when Toy Story became the highest-grossing film of the year. Jobs sold Pixar to Disney in 2006 for $7.4 billion, making him Disney's largest individual shareholder. He bought it for $5 million when it was a failing division of a film company.
1997 · Age 41 · Cupertino · Apple, 90 Days from Bankruptcy

Apple acquired NeXT in December 1996 for $429 million. Jobs came with it. By September 1997, he was named interim CEO — iCEO.

Apple was 90 days from insolvency. The company was losing $1 billion a year. It had 350 different products. It had no coherent strategy. The board was dysfunctional. Morale was catastrophic.

Jobs looked at the product line and said something his team never forgot.

"What are the ten things we should be doing next?" someone asked in an early meeting. Jobs went around the room, then said: "No, no. You're wrong. The question is: what are the ten things we should NOT be doing — and then kill nine of them."

He proposed cutting Apple from 350 products to 10.

Decision 4 · 1997 · Age 41 · 350 Products → 104 / 7

Apple has 350 products, is losing $1 billion a year, and is 90 days from bankruptcy. Jobs proposes cutting to 10 products immediately — eliminating years of his team's work and laying off thousands of people. What's the right call?

What Steve Jobs Did
He cut to 10 products. He also did something no one expected: he called Microsoft's Bill Gates and negotiated a $150 million investment in Apple — including an agreement that Microsoft would continue developing Office for Mac. The two companies had been at war for a decade.
Jobs stood on stage at Macworld in August 1997 and announced the Microsoft deal. The crowd booed. Jobs said: "We have to let go of this notion that for Apple to win, Microsoft has to lose." Within a year, Apple was profitable again. The product that rescued the company: the iMac, launched in 1998 — a translucent, colored, all-in-one computer that looked like nothing else in the industry. It sold 800,000 units in its first five months. Jobs had been iCEO for less than a year.
2001 · Age 45 · Cupertino · The Music Player

Apple was back. The iMac had worked. The company was profitable and growing.

Jobs wanted to enter the music player market. The signals from the industry were universally negative. Michael Dell had publicly said Apple should just shut down and give shareholders their money back. Sony and Microsoft dominated portable music. The music industry hated digital distribution. Napster had been sued into shutdown for music piracy.

Jobs believed the music industry's problem was that no one had offered a legal, easy, well-designed way to buy digital music. The market wasn't the problem. The solution didn't exist yet.

He proposed to build not just a music player, but an entire ecosystem: iPod, iTunes software, and an online store where every major label's songs could be purchased for $0.99 each. He would need to personally negotiate deals with every major label — people who had spent years watching the internet destroy their business model.

Decision 5 · 2001 · Age 45 · iPod and iTunes5 / 7

Apple is recovering. Jobs wants to build iPod, iTunes, AND an online music store — requiring him to personally negotiate with music labels who hate digital distribution. Every analyst says don't do this. Sony and Microsoft already own this space. What does he do?

What Steve Jobs Did
He flew to New York and personally met with every major label. He convinced all five to participate. The iTunes Store launched in April 2003. In its first week, it sold one million songs.
Jobs had told the label executives that the alternative to his model was continued piracy — that people were going to get music digitally regardless, and the question was whether the labels would get paid for it or not. He was right. Within three years, iTunes was the largest music retailer in the United States. The iPod became Apple's most profitable product. More importantly, it put Apple into the pockets of hundreds of millions of people who had never owned a Mac — and prepared them for what was coming next.
2005 · Age 49 · Stanford University · A Diagnosis

In 2003, Jobs had been diagnosed with pancreatic cancer. He waited nine months before agreeing to surgery, trying alternative treatments first. By the time he had the operation, the cancer had spread. He nearly died.

In June 2005, he gave the commencement address at Stanford University. He talked about dropping out of college, about getting fired from Apple, about being diagnosed with cancer. He ended with something he said he had read every morning for 33 years — a sentence from the last issue of the Whole Earth Catalog: "Stay hungry. Stay foolish."

That same year, his team had been quietly working on something that would make everything else seem small.

Decision 6 · 2005 · Age 49 · The Phone6 / 7

Jobs wants to build a revolutionary phone — a touchscreen device that runs a full operating system, replaces the iPod, browses the real internet, and will cannibalize Apple's most profitable product. Every phone maker says this is technically impossible. His own board is nervous. The risk of failure is enormous. What does he do?

What Steve Jobs Did
He built it exactly as imagined. On January 9, 2007, Jobs stood on stage at Macworld and said: "Every once in a while, a revolutionary product comes along that changes everything." Then he showed the iPhone.
Nokia's CEO, after seeing the iPhone announcement, publicly said the device had "no chance" of significant market share. Microsoft's Steve Ballmer laughed at it. The industry consensus was that a phone without a keyboard couldn't work for business users. The iPhone launched in June 2007. By 2011, Apple was the most valuable company in the world — larger than ExxonMobil, larger than Microsoft, larger than Google. The smartphone market that Nokia and BlackBerry had built was largely gone within five years. Jobs had been told the iPhone was impossible. He had decided that "impossible" was the beginning of the specification, not the end.
2010 · Age 54 · One Last Thing

By 2010, the iPhone had transformed the technology industry. Apple was building toward another device — the iPad — that the press had already decided was a large iPhone and therefore pointless.

Jobs was also running out of time. The cancer that had been treated in 2004 had returned. He was losing weight visibly. His health had become a subject of public speculation. He took two medical leaves of absence while remaining Apple's CEO.

At an internal meeting, someone asked Jobs what he thought his legacy would be. He said he didn't think about legacy.

"I just want to build great things," he said. "And then build the next great thing."

Decision 7 · 2010 · Age 54 · The iPad7 / 7

Jobs is preparing to launch the iPad. The press has already declared it "a big iPhone" — unnecessary and overpriced. His own engineers have debated whether a third device category between phone and laptop can work. Apple's credibility is now enormous — a failure here would undo years of goodwill. What does he do?

What Steve Jobs Did
On January 27, 2010, Jobs walked on stage at the Yerba Buena Center, sat in a leather chair with a coffee table beside him, and browsed the New York Times, played music, and watched a video on the iPad. He sold one million in 28 days — faster than any Apple product in history.
Jobs resigned as CEO on August 24, 2011, saying he could no longer fulfill the duties of the role. He died on October 5, 2011, at the age of 56, from respiratory arrest caused by pancreatic cancer. At the time of his death, Apple had over $81 billion in cash reserves and was the most valuable company on earth. He had been fired from it 26 years earlier. The product that made Apple the most valuable company — the iPhone — had been announced four years before he died. Jobs later told his biographer Walter Isaacson that he was most proud not of any specific product, but of the team and the company he had built — "an organization that could outlast me."
October 5, 2011 · Palo Alto, California

Steve Jobs died on October 5, 2011. He was 56.

He had dropped out of college, slept on floors, sold his van for startup capital, been fired from his own company, bought a failing animation studio for $5 million that became Pixar, returned to a company that was 90 days from bankruptcy, and built the most valuable company in the world.

He had been difficult, demanding, and sometimes cruel. He had also been one of the clearest thinkers about what technology was for — not what it could do, but what it should feel like to use. He believed design was not decoration but function. He believed that people who said something was impossible had simply not yet been required to do it.

His last words, according to his sister Mona Simpson, were looking past the family gathered at his bedside. He said it three times.

"Oh wow. Oh wow. Oh wow."

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About this simulator

This simulator is part of ordinarymantrying.com — a blog about one ordinary person using AI to navigate investing, side hustles, and building things in public. All events are based on documented historical accounts of Steve Jobs' life.