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Yet the loss of leadership capability and potential that results from unresolved grief, as well as the human suffering and pain, can seem beyond measure.

A major part of managing Big Data projects, he says, is asking the right questions: How do you define the problem? What data do you need? Where does it come from? What are the assumptions behind the model that the data is fed into? How is the model different from reality?

Society might be well served if the model makers pondered the ethical dimensions of their work as well as studying the math, according to Rachel Schutt, a senior statistician at Google Research. “Models do not just predict, but they can make things happen,” says Ms. Schutt, who taught a data science course this year at Columbia. “That’s not discussed generally in our field.”

the increasing use of software that microscopically tracks and monitors online behavior has raised privacy worries. Will Big Data usher in a digital surveillance state, mainly serving corporate interests?

my bigger concern is that the algorithms that are shaping my digital world are too simple-minded, rather than too smart. That was a theme of a book by Eli Pariser, titled “The Filter Bubble: What the Internet Is Hiding From You.”

“Educational investment will not be attractive to those without unique skills,” she said. Graduates, she noted, need to earn a return on their investment in training: “But instead they will lose jobs, replaced by information simulation. They will stay uneducated.” In such a scenario, high-salary jobs would remain for those equipped with problem-solving skills, she predicted. But many common tasks now done by college graduates might vanish.

Over the next 10 to 20 years, “10 percent to 20 percent pushed out of work by A.I. will be a catastrophe,” she says. “I can’t begin to think what 50 percent would mean — way beyond a catastrophe and such numbers can’t be ruled out if A.I. performs well in the future.”

A recent study published by the Program on the Impacts of Future Technology, at Oxford University’s Oxford Martin School, predicted that nearly half of all jobs in the United States could be replaced by computers over the next two decades.

Smart machines will give companies “the opportunity to automate many tasks, redesign jobs, and do things never before possible even with the best human work forces,” according to a report this year by the business consulting firm McKinsey.

Advances in speech recognition, translation and pattern recognition threaten employment in the service sectors — call centers, marketing and sales — precisely the sectors that provide most jobs in developed economies.

Gartner’s 2013 chief executive survey, published in April, found that 60 percent of executives surveyed dismissed as “‘futurist fantasy” the possibility that smart machines could displace many white-collar employees within 15 years.

Kenneth Brant, research director at Gartner, told a conference in October: “Job destruction will happen at a faster pace, with machine-driven job elimination overwhelming the market’s ability to create valuable new ones.”

Optimists say this could lead to the ultimate elimination of work — an “Athens without the slaves” — and a possible boom for less vocational-style education. Mr. Brant’s hope is that such disruption might lead to a system where individuals are paid a citizen stipend and be free for education and self-realization. “This optimistic scenario I call Homo Ludens, or ‘Man, the Player,’ because maybe we will not be the smartest thing on the planet after all,” he said. “Maybe our destiny is to create the smartest thing on the planet and use it to follow a course of self-actualization.”

But that is exactly what Mr. Grinda did. He moved out of the Bedford house in December 2012, ditched the city apartment and got rid of the McLaren. He donated clothes, sports equipment and kitchen utensils to the Church of St. Francis Xavier in Lower Manhattan. He gave his furniture to Housing Works and he packed a Tumi carry-on suitcase with 50 items, including two pairs of jeans, a bathing suit and 10 pairs of socks.

Once he realized his days as a roving houseguest were numbered, Mr. Grinda decided to shift his approach: He kept traveling, but now he was renting apartments on Airbnb or staying in luxury hotels.

Born in suburban Paris in 1974, Mr. Grinda graduated from Princeton in 1996 with a degree in economics. He worked as a consultant at McKinsey & Company for two years before moving back to France to found an online auction start-up funded by the business magnate Bernard Arnault, which Mr. Grinda sold in 2000.He returned to the United States, where he co-founded Zingy, a mobile phone ringtone and game maker, which fetched $80 million in a 2004 sale. After that, he was a founder of OLX, a Craigslist-like service that has become one of the largest global classified websites.Now he is an entrepreneur and angel investor, with more than 200 investments to date, who visits start-ups in Berlin, Paris, New York, San Francisco and other cities.

He looks (and acts) something like Sheldon Cooper, the oddball science geek played by Jim Parsons on “The Big Bang Theory,” an observation Mr. Grinda himself has made.“Friends, who knew me in my late teens and early twenties, would tell you I had exactly the same delusional sense of self-worth and condescending and arrogant self-centered worldview,” he wrote in a blog post that noted his similarities to the sitcom character.

In all, Mr. Grinda said, he stayed with about 15 friends and family members in the first months of 2013. “Everyone was, like, ‘It’s a great idea. Come over,’ ” Mr. Grinda said. “The problem is, the idea of ‘Great, come over’ and me there 24 hours a day, seven days a week, is very different. Especially when their lives are not in sync with mine.”

“When I looked back at the things that mattered the most to me,” he said, “they were experiences, friendships and family — none of which I had invested much in, partly because I was too busy, and partly because I felt anchored by my possessions.”

He hatched a new plan: His friends and family members would come to him.“Rather than me going to them and disrupting their routine,” he said, “getting everyone together in a setting of vacation makes more sense.”

He invited his parents, his friends, their partners, children and nannies for a two-week stay in Anguilla, an island east of Puerto Rico, where he rented two conjoining houses, at a cost of $240,000, with chefs and full house service (and a total of 19 bedrooms).

Mr. Grinda forgot to consider that not everyone lives as he does.For one thing, he had scheduled the Anguilla vacation during the school year, which meant friends with children couldn’t make it. The island’s remoteness, furthermore, meant some guests were forced to endure a tangle of flight connections, leaving some of them exhausted by the time they arrived.And many of the people he invited, who had jobs and other obligations, could stay only for a long weekend.

Mr. Grinda said he has learned a lot from his very big downgrade. He reconnected with old friends, even if it meant annoying them a little, and he rekindled his relationship with his father.“We spent time talking about his life,” he said. And he is no longer against the idea of having a fixed address; he said he is now in negotiations to buy a two-bedroom apartment on the Lower East Side, which he plans to rent out when he is not in town.

Still, the experiment has taken its toll. “The philosophy is interesting,” he said. “But how do you put it into practice? How do you make it real?”

He recently split up with Otilia Aionesei, a former model who works at technology start-up, whom he had been dating, off and on, for two years. The sticking point was their lack of a shared home.“If you want to be his girlfriend, this is the life you have to lead,” Ms. Aionesei said. “I like simple things, to watch movies on the same couch.”Mr. Grinda had a different view. “We went to the Galápagos,” he said. “We went to Tulum. To St. Barts. We have these wonderful experiences and memories together.”

“My home is where I am,” he said. “And it doesn’t matter if it is a friend’s place or a couch or the middle of the jungle or a hotel room on the Lower East Side. But I realize that most of humanity, especially women, don’t see it that way.”