Lessons on careers, achievement and life from the tech legends

One piece of old advice that is increasingly shared today is that nobody on their death bed remembers their time at work or wishes they had worked more. But tech journalist Kara Swisher, known for her tart, trenchant and often counter-the-crowd comments, dismissed that advice after suffering a stroke.

“The lesson I learned from my stroke is that I didn’t want to slow down and that I enjoyed what I do and that I did not want to smell any flowers,” she writes in her memoir, Burn Book.

She has had some fantastic times at work. She has a passion for it. She covered the legendary tech entrepreneurs of the past 30 years, including Apple founder Steve Jobs, who she noted had his most productive years after he was initially diagnosed for cancer. He created the iPhone and the iPad and was working on reinventing television when he died.

“Jobs never talked about not doing. He never said relax. He never said slow down. He pushed himself very hard until the end,” she writes. “The stroke crystallized that I wanted to be one of those people who did not die before they had lived.”

But how do you live? It starts by knowing yourself. For her, seeking money is not the answer. She turned down huge offers from both news organizations and internet companies. She has a taste for entrepreneurship – even calling herself a “reportrepreneur.” But she thinks her hesitancy was because she didn’t want to work for someone to whom she would be beholden. “It was impossible for me not to say what I thought, which made me a bad employee,” she says.

Many of the people she covered are billionaires. But she does not believe they have lived fully productive lives despite the heights of fame and power they have achieved. Indeed, they have endangered society.

“I love tech. I breathe tech. And I believe in tech. And for tech to fulfill its promise, founders and executives who ran their creations needed to put more safety tools in place. They needed to anticipate consequences more. Or at all,” she writes.

Instead, she feels they were careless, even childish, when embracing the notion that the key to success was moving fast and breaking things – after all, it’s children who like to break things. They spawned the online rage that is extending into the real world in what she feels are scary ways.

She calls tech a “mirrortocracy,” full of people who like their reflection so much they only see value in those who look the same. Over the years, their work has “curdled their souls” she says. “I have never seen a more powerful and rich group of people who saw themselves as the victim so intensely.”

She cherishes a quote by philosopher Paul Virilio: “When you invent the ship, you also invent the shipwreck; when you invent the plane you also invent the plane crash; and when you invent electricity, you invent electrocution … Every technology carries its own negativity, which is invented at the same time as technical progress.”

She calls Mark Zuckerberg, founder and chief executive officer of Facebook and Meta, “the most dangerous man in the world” because of his carelessness about consequences. “While Zuckerberg was not evil, not malevolent, not cruel, what he was, and continued to be was extraordinarily naive about the forces he had unleashed,” she says.

She initially liked Elon Musk, founder of Tesla – “sometimes testy, often funny, and always accessible,” engaging with her in “a semi-human way.” But over time and Twitter (now called X), the worst parts of his personality have taken hold, and he is deeply damaging others. “If Mark Zuckerberg is the most damaging man in tech to me, Musk was the most disappointing,” she writes.

There are people in tech to admire. She cites serial entrepreneur Mark Cuban and Salesforce chief executive Marc Benioff as tech leaders who learn from their mistakes rather than wear those as badges of honour. She likes Alphabet chief executive Sundar Pichai, Microsoft chief executive Satya Nadella, Netflix co-founder Reed Hastings, and OpenAI chief executive Sam Altman. Long-time entrepreneur Dave Goldberg’s early death hit her hard – in a eulogy she called the husband of better-known tech executive Sheryl Sandberg a Mensch, a person of integrity, a rock of humanity.

So on your death bed, will you be happy with your work?

Quick hits

  • Professional was the most misspelled word in a study by QR code generator QRFY, the second “s” missing. Other words commonly spelled wrong: Environment (the “n” missed), management (mangled into mangment), receive (remember “i” before “e,” except after “c”), independent (an “a” used instead of the last “e”), knowledge (the ‘g” missed”) and separate (there’s “a rat” in separate).
  • Gloria Mark, author of Attention Span and a professor at the University of California, has been working with Microsoft Research on a prototype of an artificial-intelligence-based agent that will nudge you toward better focus. It would learn about your behaviour; ask questions at the start of the day about mood, how you want to feel at the end of the day, how many breaks you want to take; and advise you when you are unreasonably giving in to distraction.
  • Bioethicist Elizabeth Yuko recommends the “FORD” method for small talk, based on an acronym for asking about family, occupation, recreation and dreams.
  • “You don’t need more time; you need more focus,” says Ottawa blogger and thought-leader Shane Parrish.

Harvey Schachter is a Kingston-based writer specializing in management issues. He, along with Sheelagh Whittaker, former CEO of both EDS Canada and Cancom, are the authors of When Harvey Didn’t Meet Sheelagh: Emails on Leadership.

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