Book Review: Steve Jobs by Walter Issacson

[Note to reader: If the word asshole offends you, stop reading now. Also, this post is about three-times longer than my typical post and only slightly shorter than the book I’m reviewing.]

Open Walter Issacson’s book, Steve Jobs, to any page and, well, okay, I’ll close my eyes and here, let me open the book up to a random page: Here I am on page 265 and here’s a typical sentence: “After they broke up, (former girlfriend Tina) Redse…read in a psychiatric manual about Narcissistic Personality Disorder and decided that Jobs perfectly met the criteria.”

And that was a random page. Just imagine what I could have quoted if I had actually been looking for an example of the pathologically cruel way that Jobs treated many of the people with whom he worked. It’s hard to read more than three-pages straight without running across example after example of Jobs’, uh, narcissistic personality disorder.

Reading the book made me think of how TV dramas and sitcoms all seem to have a character with some type of personality disorder (Asperger’s seems to be the cliche condition for TV writers, these days). The characters serve in the jester role, saying what everyone thinks and knows, but no one else is willing or able to utter. House, Bones, The Office (Dwight Schrute), Glee (Sue Sylvester), 30 Rock (Jack Donahey) I could go on, but you get the idea.

Each of these characters have some quirky over-the-top personality disorder that is so over-the-top, we are entertained — even enamored — by their candor. It helps that they also have the ability to engage in extraordinarily witty repartee, thanks to having their repartee scripted by Emmy-award winning comedy writer. Because of their mysterious condition, they can serve (as I’ve noted) in the role of the dramatic jester, cutting through any BS the audience may need help understanding. But they don’t have to worry about the ramifications of their blunt force because they are just like that, bless their heart. Their boundless assholery, we learn over time, is not actually mean-spirited, but rather some screwed up wiring in that part of their brain that serves for the rest of us as a governor on our assholeometers.

We love to hate (or hate to love) them because we all fantasize about the day we’ll get to say exactly what we feel and let the chips fall where they may. But real-life responsibilities (like mortgages and tuition) and the fact that our assholeometer actually has a working-governor, keep us from doing anything more than enjoying, vicariously, these fictional proxies for our own, inner assholeness.

Unless you count the made-for-TV movie, Pirates of Silicon Valley, Steve Jobs was not a character on a TV comedy. He was a real-live person who, if you learn one thing and one thing only from Issacson’s book, you’ll learn this, was a world-class asshole. Oh sure, in the book, you’ll also learn how he changed the world and created technology that enabled people like me to do so much of what we do. And in the book, we do pick up tidbits related to his charm and charisma and about some of the sweet and loving things he did that were kind and gentle and warm. (However, you’ll get a better sense of that aspect of his being in Mona Simpson’s 2,000-word eulogy of her brother than in Issacson’s 700-pages.)

But it is the steady drumbeat of Jobs’ lack of moral-center and his outrageous displays of cruelness to those around him that provide the percussional beat to Issacson’s book. It is nearly impossible to read Steve Jobs, the book — indeed it has been a mystery to his competitors and devotees alike for the past three decades to read Steve Jobs, the man — and not wonder, how anyone can succeed in business to the degree Jobs did, yet still be such an asshole.

Several years ago on this blog, I pointed to a post by author and Stanford Business School professor (and great blogger) Bob Sutton, whose book, The No Asshole Rule: Building a Civilized Workplace and Surviving One That Isn’t, I had just read. On his blog, he explained that while doing research during the writing of the book, Steve Jobs’ name came up so many times from Sutton’s Silicon Valley friends, that he included a chapter in that book that serves as a form of exceptio probat regulam in casibus non exceptis (“the exception confirms the rule in cases not excepted”).

Quote from Sutton’s book:

(The chapter titled “The Virtues of Assholes”) starts out with the curious case of Steve Jobs, and goes onto make an empirical case for the upsides of assholes. BUT I also make clear that I still don’t want to work with assholes — there are plenty of other successful companies that aren’t led by assholes. Jobs is famous for saying the “the journey is the reward,” and for my tastes, even if the journey ends well, it still sucks when you have to travel with an asshole, or worse yet, a pack of them. If you are successful asshole, you are still an asshole and I don’t want to be around you.

If you have read this far into this post, you may be wondering why, if I seem to be so troubled by the reality of Steve Jobs’ behavior, or the way in which Issacson depends on it to move his narrative along, why am I even bothering to review it? Why did I keep reading it?

At times, I wondered that myself. At times, I felt like I was reading the biography of someone who was going to end up being a serial killer or leader of some militia in rural Washington state. This troubled, yet charismatic guy I was reading about, seemed headed for mixing up a large barrel of Koolade during the early chapters of the book.

And then, during the portion of the book in which Issacson is recounting Jobs ouster from Apple in 1985, I read this:

If Jobs was prepping for conciliation, it didn’t show in the choice of movie he wanted to see…that night. He picked Patton, the epic of the never-surrender general. But he had lent his copy of tape to his father, who had once ferried troops for the general….(A few days later), Jobs finally got hold of a tape of Patton, which he watched Wednesday evening, but (early Macintosh marketing director Mike Murray) prevented him from getting stoked up for another battle.

As the movie Patton is on my short list of favorite movies of all time (and you can stream it via Netflix), I re-watched it after reading the Issacson book. I suggest you do the same. It’s eerie, but if one starts thinking about Jobs growing up hearing stories about Patton from his father and then, in about the 10th grade, first seeing this movie. And then, reading that he watched the movie as some form of ritual to get stoked up for battle. And then, considering the story arc of Patton’s WWII experience compared to the story arc of Jobs’ Apple one. And then, noting the detail each placed on the theatrics of presentations and the sense of destiny they shared.

Well, one can start spinning out all sorts of theories.

But it won’t be me.

I chose not to believe it was Patton that Jobs had been channeling. I chose, rather, to believe — as did those who seemed loyal to him — that Jobs is like one of those TV sitcom characters: I’m thinking: Jack Donaghy meets Gregory House.

I also kept plowing through it because the book does a great job of providing, at a high altitude, a timeline of so many things that I’ve experienced as an informed and, most of the time, passionate user of Apple products. In addition to having Apple products serve as the factory equipment of the companies I’ve run since 1985, the first article I ever had published in a national magazine was in a 1985 issue of Macworld. The journey of Apple products are very connected to my life’s journey and I have been an extremely engaged observer, including attendance at a few events where Jobs displayed his rockstar product announcement skills, including the the biggest one ever.

So reading the book, and learning what was taking place on the other side of those products was extremely fascinating.

Perhaps the most compelling reason I stuck with the book, in addition to (or in spite of) Issacson’s skill at dismantling the myth of Jobs was the role of the book as a 700-page obituary, rather than as a traditional biography. And while the context of the book (Steve Jobs recruiting Issacson to write it, without any editorial control) may have seemed like it, I’m obviously not talking about one of those obituaries that survivors purchase and have published in the daily newspaper. Rather, I’m referring to the kind of obituary that appears in the New York Times written, often years beforehand, by a skilled journalist who spends some time actually doing reporting.

The hurried release of the book, so tied in its marketing to the death of Jobs, sets it up to be labeled as such a longform obituary. And the non-stop TV interviews Issacson has participated in — timed so strategically to serve as follow-up any “official” mourning period (I first wrote “to draft in Steve’s wake” but the water skiing metaphor seemed inappropriate) —  turned him into a talking-head “obituariest” more than an author on a book tour. Such marketing seemed intended to position the book as some form of  literary coda to Jobs’ life, timed, like any great product, to be released right before the holiday gift-buying season.

As a biography, I believe Steve Jobs falls flat when compared to the two Issacson books I’ve previously read, biographies of Benjamin Franklin and Albert Einstein.


When Issacson’s Franklin biography was first published, I enjoyed reading every page. Perhaps that’s because, before reading it, I knew little about Franklin other than the coloring-book outline of his life most of us retain from American History review courses. Even though I’ve read a good-deal from or about the colonial and early-American period, I had never taken a deep-dive into Franklin’s life and legacy until Issacson’s book. In hindsight, I think I may also have enjoyed it because because Issacson had two and a half centuries of history through which to peer when judging the true measure of Franklin’s legacy.

Or perhaps it’s because Franklin provided Issacson with much more source material with which to work than did Jobs. While a lot has been written about Issacson having the opportunity to conduct 40 interviews with Jobs, along with having Job’s blessing to interview family and friends (including Jobs’ 15-year-old daughter, former girlfriends and former colleagues who provided rather candid assessments), Franklin chronicled nearly every day of his adult life in journals, letters and published works. And lots of people around him chronicled their encounters with him. So stuck with the prolificacy of Franklin was I that, back in 2004, I included Issacson’s book in a library of accidental books about bloggers, in which I wrote, “If ever there was a blogger ahead of his time, it was Benjamin Franklin. He even wrote under multiple psuedonyms so that he could debate himself (and, as some of his persona were female, herself).

I found it somewhat surprising that Issacson didn’t mention the man, Benjamin Franklin, in the Steve Jobs book. (He does make a passing reference to the Franklin book in the introduction.) Henry Kissinger and Albert Einstein, both subjects of Issacson biographies, make cameo appearances in the book, Steve Jobs. But Franklin, who arguably is the American figure who most fulfills an ideal of Jobs that recurs though out the book: that Apple (and, therefore Jobs) is special because the company (he) resided at the intersection of technology and liberal arts — a place where where “creativity met tools for living.”

Franklin was America’s first globally-celebrated resident of such an intersection of technology and liberal arts — one of the few colonialists who, before the Revolution, was widely known in Europe. Before he was that 70-year-old man we remember from the history of the founding fathers and the hundred-dollar bill, he was a scientist and inventor and publisher whose discoveries were so significant that he was honored by European universities. For example, 15 years before the Revolutionary War, at about the age of Jobs when he died, Benjamin Franklin received an honorary degree of Doctor of Laws from the University of St Andrews.

Frankly, when first writing this post, I was going to point out several ways in which I found it extremely odd that Issacson, who obviously spent untold hours pondering both of these men, did not connect, compare or contrast their similarities as unique American polymaths, a term I’d never use except it is so precise in describing the unique quality that makes both Jobs and Franklin special: that their expertise and contributions can span across so many, and completely different areas. If you think of all the different types of inventions and ideas that Franklin conceived, discovered or made popular — and how today he can be both the patron saint of firemen and librarians and optometrists and mail carriers and electrical engineers and on and on — you start to find an American historical figure who must serve as a benchmark when we start listing how many things someone like Jobs may have revolutionized. (And then, there is a father-illegitimate-son estrangement story in both their lives.)

Upon reflection, I am guessing Issacson knows that such comparisons would invite rebukes that are better left to another day and another book. Issacson knows better than anyone that Steve Jobs was no Benjamin Franklin. I’m talking now about the men, not the books. Perhaps if Jobs had lived the additional 30 years Franklin enjoyed, Jobs could have learned to mellow out like Franklin did. Maybe he could have even learned to eat like Franklin. Maybe he could have learned to connect with others like Franklin.

In 2003, Issacson wrote about Franklin, “Throughout his life, he would occasionally make enemies…but he did so less than most men, especially men so accomplished. A secret to being more revered than resented, he learned, was to display (at least when he could muster the discipline) a self-deprecating humor, unpretentious demeanor, and unaggresive style in conversation.” (Or, for even more comparison, you may want to review Frainklin’s 13 Virtues.)

In the ways they approached life and relationships, Jobs was no Benjamin Franklin (even on Franklins worst day and Jobs’ best).

In terms of contributions and legacy, however, it will take a long time for history (and only history can, we cannot) to measure Steve Jobs. No matter what we think today, the jury is still out on Jobs. Issacson, nor any of the hundreds of individuals like me who may try, have the ability to do much more than theorize and debate what we believe Jobs’ lasting legacy will be.

We know his technology has changed our lives.

But we are limited to only guessing precisely how Jobs’ contributions will change the future. Stick around a couple of hundred years, and maybe a historian of that coming era can provide such judgement.

  • Jobs a polymath. No. You have to excel in those areas, he just dabbled.

  • As hard as I was on Jobs in the review above, I do think the book provides plenty of evidence that he was more than a dabbler. Extensive interviews of the individuals with whom he collaborated on the products and approaches he revolutionized are quite explicit in explaining in detail the roles Jobs played as a participant and collaborator and visionary. John Lasseter (Pixar) Jony Ive (iMac, iPhone, iPod, iPad) Ronald Johnson (The Apple Store) and Steve Wozniak all portray an intensely involved Jobs in the projects with which they are known — down to fighting Disney Studios on behalf of Lasseter’s vision for Toy Story. I believe participating in the creation of Toy Story and the Apple Store and the personal computer earns one the polymath label.