I am rereading Walter Isaacson's biography of Steve Jobs. I read it the first time soon after Jobs died in October 2011, the way most of the country read it — fast, slightly stunned, looking for clues. I am reading it again now in my forties, slowly, with a pen, the way you read a book when you know the man it is about is gone, and you are trying to figure out what he would tell you if he were still here.
This is the first article in a new series on this blog. The plan is to read biographies of people I admire and write about what they teach me. Not book reviews. Reflections. Notes I want to have, in writing, for myself — and for anyone else who is reading these books, or wishes they had time to. Steve Jobs is first. Elon Musk will be next. Warren Buffett after that.
I want to be honest about one thing before I begin. I am not aiming to be Steve Jobs. No one should. But there is a kind of man Isaacson describes in this book that I find myself returning to — the focus, the unapologetic ownership of a vision, the refusal to apologize for being driven. I find myself, in my own life, still apologizing for the very things I should be standing in. That is what this essay is really about.
The Book and the Man
Walter Isaacson — the former CEO of CNN, the former editor of Time, the biographer of Benjamin Franklin and Albert Einstein — published Steve Jobs on October 24, 2011. Nineteen days after Jobs died. It became Amazon's number one bestseller of the year and has sold more than three million copies in the U.S. alone since. Six hundred and fifty-six pages. Forty-two chapters. Forty interviews with Jobs himself, over two years. More than a hundred interviews with the family, friends, adversaries, competitors, and colleagues who orbited him.
Jobs first asked Isaacson to write the book in 2004. Isaacson hesitated — Jobs was only 49, and surely there were decades of story still to come. Jobs persisted. After the cancer recurrence and the 2009 liver transplant, Isaacson said yes. Jobs told him why he wanted the book. "I wanted my kids to know me. I wasn't always there for them, and I wanted them to know why and to understand what I did." Laurene Powell, his wife, gave Isaacson one instruction. Don't whitewash it.
Isaacson did not. The book lets Jobs be great and lets Jobs be cruel, often on the same page, often in the same paragraph. That, to me, is what makes it worth reading. It does not separate the genius from the difficulty. It presents them as the same trait viewed from two sides.
The Adopted Kid
The book opens with a chapter called Childhood: Abandoned and Chosen. Jobs's biological parents — Joanne Schieble, a Wisconsin grad student, and Abdulfattah Jandali, a Syrian Muslim grad student — gave him up for adoption in 1955. Joanne's father refused to let her marry a Syrian. She gave the baby up with one condition. The adopting parents had to be college graduates.
The first prospective couple backed out at the last minute. Paul and Clara Jobs — a Coast Guard machinist and a bookkeeper, neither of them college-educated — were given the baby anyway, after they promised to fund his college education. They moved to Mountain View, then Los Altos. Paul Jobs taught Steve in a garage. He restored cars. He fixed Heathkits. He told Steve that the back of a fence should be as well-made as the front, because a man who would do good work on the part nobody sees is the kind of man who does good work, period.
Isaacson treats this as the origin of everything. The obsession with the inside of the iPod. The screws on the back of the Mac. The unrelenting demand that the parts customers would never see still be beautiful. Even the parts you can't see should be beautiful. It came from the man who raised him.
Jobs internalized two words from this story — abandoned and chosen — and built a life on the second one. He told friends, again and again, that being adopted made him special. Isaacson is careful with this. He says it both ways. Special, yes. But also marked. The kid who was given up. The kid who decided, very early, that he would never give himself up.
I think about my own childhood when I read this chapter. I grew up in Catbalogan, a small city in Samar in the Philippines. The first seven years of my life I slept beside my Lola Lupe — Guadalupe, my grandmother — who taught me how to pray. I was raised by Mama, who was not the woman who gave birth to me but who became my Mama in every way that mattered. I had a Papa too, who raised me. They are both gone now. My story is nothing like Jobs's. But I know what it is to be shaped by hands that did not have to take you in. I know what it is to feel both chosen and carried. And I know that the people who shape you most are not always the ones who made you.
The Dropout, and the Calligraphy Class
Jobs went to Reed College in Portland because his birth mother had wanted him to go to college, and his adoptive parents had promised it. He lasted one semester as an enrolled student. Then he dropped out and spent the next eighteen months sitting in on classes he was not even enrolled in, sleeping on friends' floors, returning Coke bottles for the five-cent deposits, walking seven miles across town for a free meal at the Hare Krishna temple.
One of those classes was calligraphy, taught by Robert Palladino. He learned about serifs and proportional spacing and the history of typefaces. He had no idea what he would do with any of it. Ten years later, when he and his team designed the Macintosh, the Mac shipped with multiple beautiful typefaces because Jobs had sat in that calligraphy class. He told that story at Stanford in 2005. You can't connect the dots looking forward; you can only connect them looking backwards. So you have to trust that the dots will somehow connect in your future.
This is the chapter where Robert Friedland enters Jobs's life — the man Isaacson credits with teaching Jobs what would later be called the reality distortion field. Then comes the trip to India with Daniel Kottke, looking for the guru Neem Karoli Baba (who had died before they arrived). Jobs returned with a shaved head, in robes, vegetarian, Buddhist.
I think about my own dots when I read this. I trained as a chemical engineer at the University of San Carlos in Cebu. I was on the dean's list. I was the president of the chemical engineering council. I could have walked the safe path. Engineer at a refinery. Steady paycheck. Promotion every few years. I sacrificed that career — the one real career pivot of my life — to walk into something I could not yet see. Since then I have been in finance. I have been in investments. I have consulted for businesses. Through all of it I have loved the same things — reading, writing, learning, picking up the next skill, building the next tool. Now I am in another chapter. I run the Golden Pines family of companies. I am integrating AI into the medical and caregiving work. The next concrete goal is growing into another, bigger facility. The longer goal — the one underneath everything — is thoroughly improving senior care across the United States. Sixteen years of mostly silence on the writing side has ended with this blog. Looking backward, the dots connect. Forward, they never do. You just have to keep walking.
Apple, and the Word "Focus"
Jobs and Wozniak founded Apple Computer on April Fools' Day, 1976. Their first commercial product before Apple — the Blue Box, a phone-phreaking device that let you make free long-distance calls — paid for the first machine. Jobs, on the Blue Box: If it hadn't been for the Blue Boxes, there wouldn't have been an Apple.
The Apple I was a kit for hobbyists. Jobs insisted the Apple II be a finished consumer product. Plastic case. Internal power supply. No fan, so it would be silent. Mike Markkula, a retired Intel marketing executive, invested $250,000 and became the third partner. Markkula wrote a single-page memo for the company called the Apple Marketing Philosophy — three words. Empathy. Focus. Impute. Empathy was knowing the customer better than they knew themselves. Focus was saying no to everything else. Impute was the principle that every signal a product sends — its box, its weight, its ad, its store — must convey care. Markkula's memo is, in a real sense, the operating system of Apple to this day.
The Apple II would sell six million units. On December 12, 1980 — Apple went public. Jobs was 25 years old and worth about $256 million.
Then came the Macintosh. Jef Raskin started it as a low-cost appliance computer. Jobs muscled his way onto the team, pushed Raskin out, and redirected the Mac toward what he had seen at Xerox PARC in December 1979 — the graphical user interface, the mouse, the bitmapped display. Isaacson recounts the moment Jobs walked through the PARC demo, bouncing on his heels, almost shouting at the Xerox engineers: Why aren't you doing anything with this? This is the greatest thing! This is revolutionary! Xerox failed to commercialize what its own engineers had invented. Jobs understood, in that one afternoon, that the future of computing was sitting in a Xerox conference room and Xerox did not know.
It was at the Mac that the phrase reality distortion field was coined inside Apple, by an engineer named Bud Tribble, borrowing from a Star Trek episode. The other engineer, Andy Hertzfeld, described it in the book as a mix of charm, charisma, bravado, hyperbole, marketing, appeasement and persistence — the ability to convince himself and everyone around him that the impossible was possible. The reality distortion field is the reason the Mac shipped. It is also the reason a generation of engineers describes the experience of working for Jobs as the most exhilarating and the most damaging years of their professional lives. Both true. Same field.
The Macintosh launched on January 24, 1984, preceded by Ridley Scott's 1984 Super Bowl ad — the most famous television commercial ever made, almost killed by the Apple board before Jobs forced it through. The Mac team worked under a pirate flag flying over their building. Jobs's motto for them: It's better to be a pirate than to join the navy. Their motto for themselves: Real artists ship. He made every engineer sign the inside of the case, because the inside mattered too.
Focus is the word I keep returning to in this section. Markkula put it second on the page. Jobs spent the rest of his life defending it. When he came back to Apple in 1996 and 1997, the very first thing he did was draw a two-by-two grid on a whiteboard — consumer and pro, desktop and portable — and cut the product line by seventy percent. He killed the Newton. He killed OpenDoc. He killed the printers. He killed the Pippin. He said no to a thousand things so the four products that remained could be insanely great. Focus is about saying no, he told his team — and then said no, in front of them, hundreds of times.
He was equally clear about who decided what was worth building. It's not the consumers' job to know what they want, he said, more than once, in the book. He thought market research was a way for unconfident leaders to outsource the hardest decision in any company. He thought the leader's job was to know.
I have a focus essay on this blog from earlier this year. In it I wrote that I have realized, in my forties, that I do not have time to do everything. I have to pick. Reading Isaacson again makes me see that more sharply. Focus is not a productivity trick. It is the willingness to cut. It is the willingness to disappoint a hundred people about a hundred things, so that you can do one thing well enough that it lasts.
The Ouster, and the Wilderness
The Mac under-performed commercially in its first year. Jobs's bullying became intolerable. John Sculley, the man Jobs himself had recruited from Pepsi with the line Do you want to sell sugared water for the rest of your life, or do you want to come with me and change the world? — Sculley, with the Apple board behind him, stripped Jobs of operational authority in May 1985. Jobs resigned in September 1985.
He was 30 years old. He had been fired from the company he had founded. He sold almost all his Apple stock. He said later, at Stanford in 2005, that getting fired from Apple was the best thing that could have ever happened to him. The heaviness of being successful was replaced by the lightness of being a beginner again.
What he did with that lightness was found NeXT, a beautiful and overpriced black-cube workstation that almost no one bought, and buy a small computer graphics division from George Lucas for ten million dollars and rename it Pixar. NeXT bled money for a decade. Pixar bled money for a decade. He kept funding both. He believed in something neither was yet doing.
Then, in November 1995, Pixar released Toy Story and went public a week later. Jobs, who had funded the company through years of losses, became a billionaire. Not on Apple. On Pixar.
This is the chapter I find the most quietly instructive. The world saw the iMac and the iPod and the iPhone and decided Steve Jobs was a genius who had always known the way. He did not. For over a decade he had been in the wilderness, paying out of his own pocket to keep two failing companies alive, on the strength of a conviction that turned out to be right but had no proof while he was holding it. Time is the currency. He spent ten years and his fortune on a future that was not yet visible.
This is the part of every great life that gets compressed in the retelling. There is no version of any biography where the wilderness is short.
The Return
In December 1996, Apple — now under Gil Amelio, in steep decline — bought NeXT for about $429 million to get NeXT's operating system, which would eventually become the foundation of Mac OS X and iOS. Jobs returned to Apple as an adviser. By mid-1997 he had quietly maneuvered Amelio out and become interim CEO. iCEO, he called it.
The first move was the seventy-percent cut. The second was the truce with Microsoft. In August 1997, at Macworld Boston, Jobs announced — to loud boos from the audience — that Microsoft was investing $150 million in Apple and committing to keep Office on the Mac. Then came Think Different, the Lee Clow campaign that put the company back on its feet. Then the iMac in May 1998 — Bondi blue, translucent, no floppy drive. Hello (again). Apple was saved.
Then came the years Isaacson treats as the long crescendo. Jonathan Ive became Jobs's daily creative partner — their meetings in the design studio became the engine of the company. Ive told Isaacson, simply, He treats me as if I were his spiritual partner. That was the relationship. Ron Johnson built the Apple Stores. The iPod shipped in October 2001. A thousand songs in your pocket. The iTunes Store opened in April 2003. Jobs personally negotiated with the five major labels and individually with Bono and Mick Jagger and Don Henley and Dr. Dre to sell singles at ninety-nine cents. The iPhone shipped in 2007 — three revolutionary products in one, he said at Macworld. An iPod, a phone, and an internet communicator. These are not three separate devices. This is one device. The iPad followed in 2010 — the post-PC era, he called it.
Isaacson notes the discipline that ran through all of it. At every product launch, Jobs ended with a slide showing a road sign at the corner of Liberal Arts and Technology. That intersection was his thesis. He believed Apple existed there. He believed the most beautiful products came from the people who could stand on both streets at once. His own life — calligraphy and circuits, Bach and Bauhaus, Zen and Silicon Valley — was the proof.
The Hard Parts
I want to be honest about this section because Isaacson is, and because the book would not be worth reading if he weren't.
In 1978, Jobs's on-and-off high school girlfriend Chrisann Brennan gave birth to a daughter, Lisa Nicole Brennan. Jobs denied paternity. A DNA test gave 94.4 percent certainty. Jobs's response, in court documents, was that 28 percent of American men could be the father. He paid minimal child support while Apple was going public. He named one of the early Apple computers the Lisa and publicly insisted the letters stood for Local Integrated Systems Architecture. In private, years later, he admitted to Isaacson: Obviously, it was named for my daughter.
He did eventually come around. Lisa moved in with the family as a teenager. He paid for Harvard. He took her on trips. Lisa wrote her own memoir, Small Fry, in 2018 — a literary and complicated portrait of intermittent coldness and rare warmth, more textured than Isaacson's account.
There is also the chapter on what was called inside Apple the hero/shithead rollercoaster. Jobs flipped between extremes hourly. People were geniuses or bozos. Work was insanely great or shit. He cried in meetings when he did not get his way. He took credit for ideas he had originally killed. He called engineers names in front of their teams. His test for the people around him was strict and on the record. My number one job here at Apple is to make sure that the top 100 people are A+ players, he told Isaacson. And: If you start to get B players, soon you'll have C players, and then D players. … This is called a bozo explosion. He was unforgiving on this point. He thought mediocrity was the original sin of every great company that had ever decayed.
He yelled at Tim Cook five times in thirteen years — one of those times because Cook, the same blood type, had offered him a partial liver during the cancer recurrence and Jobs refused. He cut me off at the legs, Cook said later, in Becoming Steve Jobs. Almost before the words were out of my mouth.
There is the Android section too — the most quoted few sentences Jobs ever spoke about another company. After Google released Android, Jobs told Isaacson: I'm going to destroy Android, because it's a stolen product. I'm willing to go thermonuclear war on this. I will spend my last dying breath if I need to, and I will spend every penny of Apple's $40 billion in the bank, to right this wrong. The intensity in those sentences is the intensity that made everything else. You cannot disentangle them. The man who would not let a screw on the inside of a Mac case be ugly was the same man who would burn $40 billion to settle a grudge.
And then there is the Mercedes story. Jobs leased a new silver SL55 AMG every six months to exploit a California rule that allowed new cars to be driven without plates for the first six months. He parked, regularly, in the handicapped spots on Apple's campus. He gave the impression that the rules did not quite apply to him.
Isaacson does not let any of this sit lightly. Joe Nocera wrote in the New York Times that the book "offers so many examples of his awful behavior — incorrigible bullying, belittling, and lying — that you're soon numb to them." Malcolm Gladwell, in The New Yorker, took the contrarian position that Jobs was not an inventor but a tweaker — a man whose genius was editorial, not original. Tim Cook said the biography did Jobs a tremendous disservice. Jony Ive said his regard for it couldn't be lower. Both objected to what they saw as a caricature. Brent Schlender's Becoming Steve Jobs, published in 2015, was partly written to correct the record.
I think Isaacson is right about the central thing, though. The cruelty was not separable from the greatness. They were the same trait, the same intensity, the same refusal to settle for anything less than what he saw in his head. You cannot keep one and not the other. That is the contradiction. The book refuses to resolve it.
There is one small grace note in the book that I keep coming back to. Bill Gates, who had spent thirty years arguing the opposite philosophy from Jobs — software should run everywhere, no integration, open systems — visited Jobs at home in the last months. They sat for hours. At one point Gates said, of his old rival's approach, Your way of integrating end-to-end products, that actually makes for beautiful products. The two men had fought for three decades. At the end, Gates conceded the aesthetic. Jobs, who treated almost no one with that kind of generosity, kept the follow-up letter Gates wrote him at his bedside. He could not be the man he was. He could, sometimes, recognize one.
This is also where I have to be careful in my own reading. I admire the focus. I admire the refusal to apologize for the standard. I do not admire — and I will not take from him — the cruelty, the denial of his own daughter, the readiness to humiliate people who had given him their best work. The line I draw is the line many people who have read this book have drawn. Demand greatness of yourself, first. Demand it of the goal. Be relentless. But be tender with the people who are walking the road with you. The work I do — running senior care, sitting with families in the hardest weeks of their lives — does not allow for the other path. You cannot be cruel and tender at the same time. You have to pick.
The Nine Months
In October 2003, Jobs was diagnosed with a rare, slow-growing islet-cell neuroendocrine tumor of the pancreas. The treatable kind. His doctors recommended immediate surgery. He refused. For nine months he tried a strict vegan diet, juice fasts, acupuncture, herbal remedies. He saw a psychic. He finally had the Whipple procedure in July 2004. He later told Isaacson, with what Isaacson called a hint of regret: I really didn't want them to open up my body, so I tried to see if a few other things would work.
The cancer came back. He had a liver transplant in Memphis in April 2009. He died on October 5, 2011, at home in Palo Alto, at 56 years old. His sister Mona Simpson, in her New York Times eulogy, wrote that his last words, looking past his family, were Oh wow. Oh wow. Oh wow.
I run a senior care business. I have watched families do exactly what Jobs did in those nine months. Denial is, in a strange way, its own kind of focus — focus turned the wrong way. The mind that built the iPhone, the mind that cut Apple's product line by seventy percent, the mind that demanded the inside of the case be beautiful — that same mind decided, for nine months, that a fruit juice fast would do the work that surgery should have done. The man who saw clearly in every other area of his life did not, could not, see clearly here.
I am not interested in judging him for that. I am interested in noticing how easy it is for any of us to do the same. We are all clear-eyed about the things we know and willfully blind about the things we cannot face. That is the human condition. It does not exempt anyone — not the genius, not the saint, not me, not you.
Stanford, 2005
Jobs gave one commencement address in his life. June 12, 2005. Stanford. Twenty-three minutes. Three stories. It has been viewed more than 120 million times.
The first story was about connecting the dots — the adoption, the drop-out, the calligraphy class, the Mac. You can't connect the dots looking forward; you can only connect them looking backwards.
The second was about love and loss. Apple at 20, fired at 30. The heaviness of being successful was replaced by the lightness of being a beginner again. He met Laurene during that period. He founded NeXT. He bought Pixar. He came back.
The third was about death. No one wants to die. Even people who want to go to heaven don't want to die to get there. And yet death is the destination we all share. Then the line that has stayed with me longest. Remembering that I'll be dead soon is the most important tool I've ever encountered to help me make the big choices in life.
He closed with Stay hungry. Stay foolish. He lifted it from the back cover of the final Whole Earth Catalog, 1974.
I sit with that speech a lot. I sit with it more in my forties than I did in my twenties. Time is the only currency any of us actually has. The dollars come and go. The titles come and go. The houses, the cars, the things — they pass through. Time does not come back. To have lived each day in the worthy pursuit of a worthy goal — that is the only sacrifice that makes sense to me anymore. That is the only measure of a life I can stand to hold up to my own.
What I Am Taking, and What I Am Leaving
I said at the start of this essay that I am not aiming to be Steve Jobs. I want to be more direct now.
From him I am taking the focus. The willingness to say no. The discipline of cutting the product line by seventy percent, in my own life, so that the four things that remain can be done well. I have done a lot in this life — chemical engineer, financial adviser, senior care operator, now writing again, now building local AI tools — and the temptation, with so many threads, is to do all of them poorly. The lesson is to pick the few that matter and do them like the inside of the case has to be beautiful too.
From him I am taking the drive. The refusal to apologize for being driven. I have caught myself, all my life, softening when I should be standing. Apologizing when I have nothing to apologize for. Filipino culture played a part in that. Imposter syndrome played a part. The Catholic instinct to take up less space played a part. None of it serves me anymore. Jobs would have laughed at it.
From him I am taking the ownership. The fact that he was unmistakably, unapologetically himself. He knew who he was. He did not adjust the volume for the comfort of the room. I do not need to take his volume. But I do need to take his refusal to make himself smaller for other people's ease.
From him I am not taking the cruelty. The hero/shithead rollercoaster. The two years of denying Lisa. The calling people bozos. The handicapped parking. The leaving people he loved on the wrong side of the line he had drawn that morning. None of it. The work I do at Golden Pines — sitting with families when the hardest weeks of their lives arrive — is not compatible with that mode. You can be relentless and tender. You can be demanding of the goal and gentle with the people. It is harder. It is the harder path. It is the one I am trying to walk.
From him I am also not taking the nine months of denial. I have watched, again and again, what avoidance costs. I want to be the man who calls the doctor on the first day. The man who has the hard conversation in the first hour. The man who does not bargain with what is in front of him.
The Decades Behind the Keynote
There is one image from this book I keep coming back to.
When most people think of Steve Jobs, they think of him onstage at Macworld, January 9, 2007, holding the first iPhone in the air. The black turtleneck. The blue jeans. The New Balance sneakers. The room going completely still. Today, Apple is going to reinvent the phone.
What people do not see is the decades that produced that moment. They do not see Reed College in 1972, the calligraphy class, the floor-sleeping, the Coke-bottle returns. They do not see the garage in Los Altos. They do not see the night in 1979 at Xerox PARC. They do not see ten years in the wilderness funding NeXT and Pixar with no proof that either would work. They do not see the seventy-percent cut, the boos at Macworld Boston, the iMac, the iPod, the iTunes negotiations with five record labels. They do not see thirty-five years of unrelenting work compressed into one stage and one phone held up in one hand.
I have a small version of this in my own life. There is a story I have told only a few people. I was a chemical engineering student in Cebu. The night before an exam — one of the hardest ones — I did not sleep at all. The top student in our year, ranked number one in all of engineering, was taking that exam with me. I got the highest score. He did not. No one knew I had stayed up all night. No one would ever know.
That has happened to me, in different forms, many times. The 100-hour weeks growing Golden Pines. The years of learning a senior care industry I had no formal training in. The long nights now learning AI development, building tools, writing this blog after sixteen years of mostly silence. People see the result. They never see the grinding. They never see the man alone in the office on a Saturday while his friends are out enjoying their weekend.
I do not say this to claim hardship. I say it because Isaacson's book is, in the end, a quiet argument for the same point. What you see on the keynote stage is decades old. The man holding the phone has been holding it, in some form, since he was twelve years old calling Bill Hewlett at home for parts.
My last essay on this blog was about Marianne Williamson's Our Deepest Fear — about playing small, about sitting in our own light, about the refusal of responsibility that hiding really is. I closed that piece by saying I did not think we were meant to die without giving all of ourselves and sharing our own light with the world.
This essay is the next step of that one. Williamson tells us our light is what we owe the world. Jobs is the picture of what it looks like when a person decides, very early, that they are not going to hide it. Even the difficult parts of Jobs are arguments for the same point — what you build when you stop apologizing for your own intensity is, on its best days, something the world has not seen before.
We do not need to be Steve Jobs to take the lesson. We need to be ourselves. We need to be focused. We need to be relentless about the goal and tender with the people. We need to stop apologizing for the drive that is already in us. We need to keep walking, knowing the dots will connect later, knowing the wilderness years are part of the work, knowing the keynote moment — whatever it looks like for each of us — is decades in the making.
Stay hungry. Stay foolish.
