Silicon Valley executives are hiring philosophers to teach them to question everything

Silicon Valley is obsessed with happiness. The pursuit of a mythical good life, achievement blending perfectly with fulfillment, has given rise to the quantified self movement, polyphasic sleeping, and stashes of off-label pharmaceuticals in developers’ desks.

Yet Andrew Taggart thinks most of this is nonsense. A PhD in philosophy, Taggart practices the art of gadfly-for-hire. He disabuses founders, executives, and others in Silicon Valley of the notion that life is a problem to be solved, and happiness awaits those who do it. Indeed, Taggart argues that optimizing one’s life and business is actually a formula for misery.

“I call it “the problematization of the world,” he said. “Once you start looking for this relatively new way of thinking—problem, challenge, solution, repeat—you see it nearly everywhere.” Instead of asking, How can I be more successful, he says, “It’s far more important to ask, ‘Why be successful?’”

 Instead of asking, How can I be more successful, “It’s far more important to ask, ‘Why be successful?’” 

Taggart is among a small band of “practical philosophers” entering the world of business. Serving as a kind of Chief Philosophy Officer, they summon ancient thinkers to probe eternal questions like, “How does one live a good life?” but also more practical ones like “What should my startup build?” This strand of philosophical inquiry, aided by books, blogs, and advisors, is gaining a small but intensely loyal following.

“The business community in Silicon Valley can really use philosophy,” said Joseph Walla, founder of HelloSign, who hosts other founders in his own reading group on the ancient Greek philosophy of Stoicism. “The most important thing for founders to manage is their own psychology,” he said citing a popular saying in the Valley. “The moments where [philosophy] is most helpful are during the biggest swings” in managing a startup.

A “practical” philosophy for Silicon Valley

Many in Silicon Valley have never hidden their derision for philosophy. Paul Graham, a computer scientist and co-founder of the startup fund Y Combinator, studied philosophy as an undergraduate at Cornell University because “it was an impressively impractical thing to do…like slashing holes in your clothes or putting a safety pin through your ear,” he wrote in 2007. “Most philosophers up to the present have been wasting their time,” he argued, calling for a more “useful” philosophy to help people actually trying to improve the world.

This plea for practicality would probably be Silicon Valley’s philosophical creed if it had one. And its institutional home would probably be Stanford University’s Symbolic Systems program. Conceived in 1986 by faculty seeking to educate the next generation of technology leaders, it examines how computers and humans communicate. “SymSys” fuses neuroscience, logic, psychology, artificial intelligence, computer science, and contemporary philosophy into studies that Stanford philosopher professor Kenneth Taylor calls “a 21st-century version of a liberal arts education.” (Noticeably absent are Plato and Aristotle.) Silicon Valley’s biggest names have graduated from the program—Peter Thiel, Yahoo’s Marissa Mayer, LinkedIn founder Reid Hoffman, Instagram founder Mike Krieger, among others.

 This plea for practicality would probably be Silicon Valley’s philosophical creed if it had one. 

But Stanford’s expansive vision for the philosophy has yet to reach most of the technology community, let alone the business world. A preference for lessons easily grasped during a flight from San Francisco to New York produces titles like “If Aristotle Ran General Motors: The New Soul of Business” and “life-hack” essays on Stoicism.

Still, practical philosophers like Taggart insist philosophical inquiry is the essence of an executive’s job. Philosophy, unlike other fields, offers no assumptions, just relentless inquiry. By subjecting every belief to critical reflection, Taggart’s clients start down a path of inquiry that can lead to genuine understanding, better business decisions, and, eventually, happiness. But that only happens after a painful period of reflection, which will often involve abandoning the deceptive stories we tell ourselves.

“Philosophers arrive on the scene at the moment when bullshit can no longer be tolerated,” says Taggart. “We articulate that bullshit and stop it from happening. And there’s just a whole lot of bullshit in business today.” He cites the rise of growth hackers, programming “ninjas,” and thought leaders whose job identities are invented or incoherent.

Taggart started his practice in 2010, and now works with more than 40 clients over Skype in the US, Europe, Central America, and Canada. Practitioners can charge $100 per hour, rates comparable to clinical psychologists, but Taggart lets his clients pay however much they can for sessions that can last for hours.

He asks clients to deeply examine their own beliefs, often for the first time. While psychologists aim for a therapeutic approach, philosophical counselors (who do not treat those with mental illness) focus on identifying and dispelling illusions about one’s life through logic and reason (although the line is admittedly blurry). Taggart says his clients have changed jobs, careers, and even sexual orientation. Jerrold McGrath, who founded his own consulting firm after working with Taggart, said his questions were “unrelentingly annoying” but forced him to confront the lies he was telling himself. He ultimately quit his job, prioritized his role as a father, and started a new consulting career. The process “allowed us to cut through the bullshit and see what was really going on,” said McGrath.

 “If you put Socrates in a room during a pitch session, I think he’d be dismayed at so many young people investing their time in ways that do not make the world any better. 

Philosophy remains rather unpopular among the general public. It ranks 89th on a list of the most popular college majors, and rarely appears on bestseller lists or mass media. Philosophical counseling is no different. Despite being around since the early 1990s, there are only a few hundred members, say the field’s two credentialing bodies. No government agency certifies the practice, and it is not yet reimbursed by insurance, so only a handful of people like Taggart are making a full-time living at it, admits the American Philosophical Practitioners Association.

Even in Silicon Valley, philosophy remains a largely behind-the-scenes pursuit. Stoicism, perhaps the most popular school of thought for startup founders, has only a handful of public adherents. Ryan Holiday, a former marketer for American Apparel, authored three books on Stoicism (which some scholars have slammed as “bad pop psychology….for arrogant successniks”). A second book, A Guide to the Good Life: The Ancient Art of Stoic Joy by Wright State University philosophy professor Bill Irvine, is passed among entrepreneurs in San Francisco who call it a guide for dealing with the challenges of startup life.

Irvine understands the appeal. “Stoicism was invented to be useful to ordinary people,” he says. “It’s a philosophy about defining what counts as a good life.” Silicon Valley likes to see itself on a similar mission. Google was public in leading the way here. It offers all its employees free classes through the “Search Inside Yourself” initiative, now an independent foundation devoted to encouraging focus, self-awareness, and resilience to “create a better world for themselves and others.”

But Scott Berkun, a former Microsoft manager and philosophy major who has written multiple business books on the subject, says philosophy’s lessons are lost on most in Silicon Valley. Many focus on aggrandizing the self, rather than pursuing a well-examined purpose. “If you put Socrates in a room during a pitch session, I think he’d be dismayed at so many young people investing their time in ways that do not make the world or themselves any better,” he said.

Silicon Valley’s strivers might find happiness by rethinking their definition of “success.” Stoics had something to say about this. Far from being emotionless scolds as the name suggest today, says Irvine, Stoics were early psychologists who sought to rid us of illusions that bring misery. By refocusing on what truly matters, people can find joy and purpose in their daily lives. As Irvine puts it, why “spend your life in an affluent form of misery when it’s possible to have a much simpler life that would be much more rewarding?”

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