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New Yorker staff writer and author Evan Osnos spent decades chronicling the social, economic, and political changes in China and currently writes about American politics. To understand the second election of President Trump, though, he realized he needed to understand the vast inequality in American society. According to 2024 data from the Federal Reserve, more than two-thirds of the countrys wealth is held by the top 10% of U.S. households. And the top 1% of U.S. households hold more than one-third of the country’s wealth. Osnos’s new collection of essays, The Haves and Have Yachts: Dispatches on the Ultrarich, explores the world of the 1%, from their tax-dodging and yacht-buying techniques to their propensity for building luxury bunkers and employing pop stars to perform at private events. Osnos came on the Most Innovative Companies podcast to talk about his book, whats behind the rising inequality in America, and the danger that inequality poses to democracy. Why did you want to write about the ultrarich? In 2016 when Donald Trump was elected president, I realized that the normal tools of political analysisthe way that I usually write about what’s happening in the worldwere not going to suffice. I couldn’t understand how a guy who declared himself the enemy of the elites could somehow inhabit that role while being the billionaire son of a real estate family in New York. I needed to understand. The answer to that lay, ultimately, in trying to understand the mechanics of the big money world. That was the origins of this. You begin the book by talking about how ubiquitous the ultra wealthy are in the administration and you write that inequality has led to the undoing of many societies. Do you think that is happening in America? We are at a very tenuous moment, and I don’t think I’m unique in that impression. All of us, no matter where we sit on the political spectrum, we look at it and say, this feels really fragile and it feels volatile. The question of course is, why? From my perspective, you can’t understand this period without recognizing that we’re living at a time of really historic, arguably unprecedented inequality in this country. That’s not an abstraction. The richest people in America have a larger share of the nation’s wealth than their predecessors did in the Gilded Age. If you want to really have an honest conversation about what it will take to hold this country together, we have to be honest about the facts. Let’s remind ourselves [that] we’ve been through these moments before and we’ve found our way back to a more stable, productive, democratic future. The first essay is a piece about yachts. What attracted you to the topic, which also provides the title for your collection? The super yacht is the super symbol of our era. There used to be 10 of the largest yachts [available] a generation ago, and now there are 170. They occupy this kind of strange place in our culture. They’re both visible and invisible. I mean, you see them in the New York Post or in the Daily Mail. They’re designed to stay out of reach, but they are the most conspicuous machines that anybody could possibly own. [Osnos photo by Pete Marovich] The yachts are a symbol of a world in which capital is more mobile and more fluid and in which borders are liquified. I had this really interesting interview with a guy who has been in the yachting world for decades. He watched it turn into this ginormous industry with huge amounts of money on the line. And he said every decade or two [the yacht buyers are coming from] a new industry. First it was the Greek shipping fortunes. And so you saw Aristotle Onassis competing against another shipping magnate [for the most ostentatious yacht]. [Then] it was the oil money. All of a sudden, it was people from Saudi Arabia and the Emirates, and they had different needs. They were sailing their yachts around the Arabian Peninsula and they were inside all the time. They needed good air-conditioning. But what’s really interesting about [yacht buying] is that it tells you something about the global economy. Where is the center of gravity at any moment in our time? You could chart the history of American economics over the last 60 years by looking at the high seas. They also depreciate in value immediately. I remember the Financial Times wrote a great piece that described them as about as financially prudent as buying 10 Van Goghs and then holding them above your head while you’re treading water. [Yachts are] essentially something for people who have limitless resources. You write about how it’s almost easier for a billionaire to live on a luxurious yacht than on land. It might seem uncouth to show how rich you are on land; on water, it’s a different story. A Silicon Valley CEO said to me that the honest fact is that you can’t live in a $500 million house because the optics are weird. Your employees will be enraged at you. But a half billion dollar boat is pretty nice. This same CEO said to me that the yacht is the best place to, as he put it, absorb excess capital. A certain number of businesses have generated so much [money] because of the ownership structure for their founders and for key investors that [these people] are quite literally encountering this problem of having excess capital and having to figure out ways to park it in places that won’t cause blowback socially and culturally and ultimately in business terms. One of the themes that I noticed across this world was that, in a way, this is the natural result of an unthinking cult of scale. t’s not that long ago that we thought scale was an unambiguous good. When I wrote a profile of Mark Zuckerberg a few years ago [for The New Yorker], I was talking to him and to his employees about this period when essentially connecting people was a euphemism for growing. And growing was a self-justifying, self-fulfilling idea. It was an end in itself. The yachts are the symbolic representation of that concept. You grew up in Greenwich, Connecticut, and decided to write about the towns turn towards Trump. Why did you want to write about it? It’s always been a prosperous place. It was an amazing place to grow up as a kid. It has the only public high school that I know of that has an electron microscope. There was also a point at which I became aware that Greenwich told us something important about what was happening in Republican politics. Greenwich had been traditionally the birthplace of the country club Republican. The Bush family was from there. Prescott Bush, who was the father of George H.W. Bush, was quite literally the country club golf champion in town. He was the senator from Connecticut, and he was an old-school moderate Republicanwhat they used to call a Rockefeller Republican. But in 2016, the Republican Town Committee in Greenwich was led by somebody who came out and said they were not going to vote for Jeb Bush. They were going to vote for Donald Trump. That became a revealing indicator: Republican strongholds that we might’ve thought of being more inclined towards moderate Republicans were lining up with Trump. Part of the explanation is that there had been a decision along the way that we can no longer afford to do the kind of moderate Republican thing that gives a little here and takes a little here, but ultimately believes in working with Democrats. There was an argument to be made that there was a similar thing going on in the Democratic side, in terms of getting more and more extreme. But it was when you had the birthplace of Country Club Republicanism begin to line up with Donald Trump, I said, I’ve got to understand how that happened. And this essay tells that story. What did you learn about how American elites paved the way for Trump’s election? There is a lot of blame to go around for creating the myth of Donald Trump that continued for so long. Around New York City, Donald Trump was a permanent piece of media furniture. He was in the papers all the time, partly because he was pretending to be his own publicist and planting stories. To see him, through The Apprentice, become something else in the eyes of Americans more broadly was a turning point. All of a sudden he [became] known, through the power of this invented persona, as the icon of a big city, successful capitalist. Part of the reason why I think why the word elite has become so fraught is that Trump used his own position in communities of power to say to the American public, Because I am an elite, I can help you pick the lock. I will help you understand why [the government] is corrupt, how it works, and therefore I, dear voter, will give you a piece of the action. After a half a century of him selling the illusion of access to power and fortune, he and his family have now realized that in 2025 the thing people will pay most exorbitantly for is access to the highest reaches of the United States government. His son has created a club called Executive Branch with an initiation fee of up to $500,000. Its funny because at the same time, he hired a lot of elites to his cabinet. He named 13 billionaires to the highest ranks of his administration. You can imagine a scenario in which you say, look, these are people who have succeeded. They understand the market; they understand economics. What becomes a problem is when the administration is so secluded from the experience of regular life that it has a very hard time expressing and enacting the public will. It was quite telling when Howard Lutnick, Secretary of Commerce, said that his mother-in-law wouldn’t notice if her social security check didn’t show up. I think there’s a lot of Americans that probably would notice if their social security check didn’t show up. I think this is part of what Elon Musk ran into, when he started talking about empathy as a weakness of Western civilization or social security as a Ponzi scheme. It was a revealing indicator of how much his life had become divorced from the experience of ordinary people. Youve written about elites deriding other elites and saying, I’m different because I understand the common man. Why do you think that is so resonant with voters? Americans at their core want to get rich. We always have and we always will. That is baked into the American idea. Whats happening now is that people in larger numbers are beginning to realize that there are impediments to that process. Part of the reason why Donald Trump was able to win again was that he is able to say to people, even in an unspoken way, that he wants them to prosper and succeed. Part of the process of getting people to understand [our level of inequality] is getting [them to] visualize some of the fault lines in our economy that are making it harder for people to prosper. The key is not saying to people they should give up on the goal of getting rich. The key is giving people the information to understand why they’re not. When you’re talking about the sort of elites who have yachts, are they completely divorced from understanding the common person? I think that the experience of entering into that world is actually farther away from regular life than outsiders imagine. There was a yacht owner who said on a documentary that if the public ever knew what it’s really like on these yachts, they’d bring back the guillotine. It sounds like a joke except that part of what’s happening is that [elites] are aware. There was a really prophetic comment a century ago from [Supreme Court justice] Louis Brandeis. He said, you can either have democracy or you can have money concentrated in the hands of a small number of people, but you can’t have both. That was one of the observations that led to the New Deal and to an effort to try to shift the balance from a concentration of resources into the hands of too few, into a more equitable distribution. [That] led to what was ultimately a period of rising standards of living for more people. That period came to an end in the late 1970s. I think there is a recognition on the part of some in politics that we need to figure out a way to get back to that. What was your favorite essay to write in the book? The piece about pop stars performing at private parties. I embedded with Flo Rida for a bar mitzvah. It was an experience that as you’re doing it, you say to yourself, I think I will be able to die happy when I’ve done this. The reason I got interested in it was [wondering], what are the economics of that? What makes a pop star who could be performing in front of 40,000 screaming fans say, Actually I’m going to go to a sweet 16 in Teaneck. In the end, it’s not that complicated what motivates them to go. The reason why this is an artifact of our time, why it’s like a new thing, is the simple fact that, until recently, people couldn’t afford to have the Foo Fighters in their backyard on a Thursday, and now they can. I sometimes feel like I’m like a historian writing in real time about a world that we need to describe while it exists. In 2015, Uber famously offered Beyoncé $6 million to perform at one of teir corporate events. Instead, she requested an equity stake in the company and ultimately made $300 million from it. If you step back, what’s fascinating about that is that right there is a transaction between billionaire and billionaire. When you can get on board a certain kind of opportunity and experience, then the curve goes vertical, and you get access to all kinds of other things. It can be quite dangerous for a country because it means that those people are then getting further and further from the experience of everybody else. I think it’s perilous for those individuals because they run the risk of suddenly encountering a kind of backlash and realizing they’ve lost touch with the people they were supposed to be in touch with. I quoted Ramsay MacMullen, the great scholar of Rome, in the book. He was once asked if he could summarize the epic history of the fall of Rome as concisely as possible. He said that it took 500 years but it can be distilled into three words: fewer had more.
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In 2014, I left a secure job at Goldman Sachs to start a nonprofit. On paper, it looked like a reckless move: no funding, no team, barely any experience. But it was the best decision I ever made because it taught me that adaptability matters more than certainty. While you cant control President Trumps second term, you can control how you respond to it by learning to work with uncertainty. As his policies rock supply chains, jobs, and lives, the best career plan is the one that can bend and flex. Transformation But lets be clear: Its not just Trump driving this uncertainty. AI and automation are transforming entire industries. Generational shifts are changing how people work and what they value in their careers. No matter whos in the White House, uncertainty is constant. The message couldnt be more explicit: Nothing is guaranteed except the importance of adaptability. This is what I call Trump-proofing your career, and its not about being anti-Trump. Whether you support him or not, his leadership brings unpredictability, and your career plan cant hinge on any one leader or policy. It must be built to flex and shift with the world around you. The old idea of climbing a single career ladder no longer holds up. In today’s job market, staying in the same role for too long can hold you back. According to HRreview, workers who change jobs regularly earn, on average, 31% more than those who stick around in the same job for years. The best plan isnt a perfect five-year road map. Its about treating your career like an ongoing experiment, in which trying new roles, taking smart risks, and building transferable skills is more important than following a linear path. This mindset keeps you adaptable and engaged in a world thats changing faster than any one job can keep up with. The ripple effects of this new reality are already apparent. More than 120,000 U.S. federal workers have lost their jobs or been targeted for layoffs in 2025, a stark reminder that even government work, once considered the gold standard for stability, isnt immune to sudden change. THE PLANNING FALLACY According to psychologists, the planning fallacy is how we fool ourselves into thinking the future will follow our plans. Ive seen this firsthand. At 22, I thought I wanted to work in finance. I had spent years pursuing that path, convinced it was the surest way to build a successful career. But once I got there, I realized that the skills I wanted to develop and the goals I cared about didnt match what I was doing. The daily work didnt challenge me in the ways I needed, and it didnt lead me in a meaningful direction. I realized that sticking with a path that didnt fit was actually riskier than stepping into the unknown. So I did it. I moved back to Canada to build something that felt real and important, which pushed me to grow in the right ways. This led me to founding my nonprofit, Venture for Canada, which raised $80 million and empowered more than 10,000 young professionals to launch their careers. Most people thought I was out of my mind. But I learned that real progress in your career and life happens when youre willing to adapt your skills and goals to match what you and the world at large need most. Not everyone can walk away from a steady paycheck. My story is just one example. But adaptability isnt about giant leaps. Its about small experiments that keep you aligned with what matters most. FOCUS ON OBJECTIVES AND KEY RESULTS One tool thats made a real difference for me is using objectives and key results. OKRs are a great way to break down overwhelming goals into small, measurable steps. Instead of mapping out the next 10 years, focus on the next three months. Pick one meaningful short-term objective, like exploring mission-driven work or building skills in a new sector. Then set two or three key resultssmall, specific actions you can track. At the end of three months, look back. What worked? What didnt? Where do you need to pivot? Heres how I explain this in my upcoming book, The Uncertainty Advantage: First, identify your top three personal values. For example, if youre in marketing, your values might be creativity, collaboration, and growth, which inspire you when the world is unpredictable. Second, set one short-term objective that aligns with those values. Dont worry about the next decade. Focus on what you can start todaysomething specific and achievable, like launching a new marketing campaign that pushes your creative skills and brings your team together. Third, define two or three key results to measure your progress. In this marketing example, your key results might be testing three campaign concepts, meeting with two colleagues to brainstorm fresh ideas, and sharing early results with your manager within the month. Theyre small steps that build momentum, keep you learning, and help you stay adaptable. TREAT YOUR CAREER LIKE AN EXPERIMENT For some, adaptability might mean staying the course in a stable job. For others, it might mean pivoting into something entirely new. The key is to treat your career like an experiment. If you treat your next move as a chance to test what you care about and what you can build, you can shift from panic to purpose. I think of a friend who shifted from teaching to technical program management and now wants to work in AI. He didnt have a 10-year plan. He focused on what sparked his curiosity and where he wanted to grow. It wasnt about having all the answers. It was about testing, learning, and staying true to his values. So heres my challenge to you: Treat your career like the most crucial experiment of your life. Stay curious. Stay connected to what matters. Keep testing new ideas. Because in a world that can shift overnightand it willthe only plan that keeps working is the one youre willing to adapt.
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For centuries, weve believed that the act of thinking defines us. In what is widely considered a major philosophical turning point, marking the beginning of modern philosophy, secular humanism, and the epistemological shift from divine to human authority, the French philosopher and mathematician René Descartes (15961650) famously concluded that everything is questionable except the fact that we think, Cogito, ergo sum(I think, therefore I am). Fast-forward a few hundred years, however, and in an age where generative AI can produce emails, vacation plans, mathematical theorems, business strategies, and software code on demand, at a level that is generally undistinguishable from or superior to most human output, perhaps its time for an update of the Cartesian mantra: I dont think . . . but I still am. Indeed, the more intelligent our machines become, the less we are required to think. Not in the tedious, bureaucratic sense of checking boxes and memorizing facts, but in the meaningful, creative, cognitively demanding way that once separated us from the rest of the animal kingdom. The irony, of course, is that only humans could have been smart enough to build a machine capable of eliminating the need to think, which is perhaps not a very clever thing. Thinking as Optional Large segments of the workforce, especially knowledge workers who were once paid to think, now spend their days delegating that very function to AI. In theory, this is the triumph of augmentation. In practice, its the outsourcing of cognition. And it raises an uncomfortable question: if we no longer need to think in order to work, relate to others, and carry out so-called knowledge work, what is the value we actually provide, and will we forget how to think? We already know that humans aren’t particularly good at rationality. Nobel laureates Daniel Kahneman and Amos Tversky showed that we mostly operate on heuristics (fast, automatic, and error-prone judgments). This is our default System 1 mode: intuitive, unconscious, lazy. Occasionally, we summon the energy for System 2(slow, effortful, logical, proper reasoning). But it’s rare. Thinking is metabolically expensive. The brain consumes 20% of our energy, and like most animals, we try to conserve it. In that sense, as neuroscientist Lisa Feldman Barrett noted, the brain is not for thinking; its for making economic, fast, and cheap predictions about the world, to guide our actions in autopilot or low energy consumption mode. So what happens when we create, courtesy of our analytical and rather brilliant System 2, a machine that allows us to never use our brain again? A technology designed not just to think better than us, but instead of us? Its like designing a treadmill so advanced you never need to walk again. Or like hiring a stunt double to do the hard parts of life, until one day, theyre doing all of it, and no one notices youve left the set. The Hunter-Gatherer Brain in a High-Tech World Consider a parallel in physical evolution: our ancestors didnt need personal trainers, diet fads, or intermittent fasting protocols. Life was a workout. Food was scarce. Movement was survival. The bodies (and brains) weve inherited are optimized to hoard calories, avoid unnecessary exertion, and repeat familiar patterns. Our operating model and software is made for hungry cavemen chasing a mammoth, not digital nomads editing their PowerPoint slides. Enter modernity: the land of abundance. As Yuval Noah Harari notes, more people today die from overeating than from starvation. So we invented Ozempic to mimic a lack of appetite and Pilates to simulate the movement we no longer require. AI poses a similar threat to our minds. In my last book I, Human, I called generative AI the intellectual equivalent of fast food. It’s immediate, hyper-palatable, low effort, and designed for mass consumption. Tools like ChatGPT function as the microwave of ideas: convenient, quick, and dangerously satisfying, even when they lack depth or nutrition. Indeed, just like you wouldnt choose to impress your dinner guests by telling them that it took you just two minutes to cook that microwaved lasagna, you shouldnt send your boss a deck with your three-year strategy or competitor analysis if you created with genAI in two minutes. So dont be surprised when future professionals sign up for thinking retreats: cognitive Pilates sessions for their flabby minds. After all, if our daily lives no longer require us to think, deliberate thought might soon become an elective activity. Like chess. Or poetry. The Productivity Paradox: Augment Me Until Im Obsolete Theres another wrinkle: a recent study on the productivity paradox of AI shows that while the more we use AI, the more productive we are, the flip side is equally true: the more we use it, the more we risk automating ourselves out of relevance. This isnt augmentation versus automation. Its a spectrum where extreme augmentation becomes automation. The assistant becomes the agent; the agent becomes the actor; and the human is reduced to a bystander . . . or worse, an API. Note for the two decades preceding the recent launch of contemporary large language models and gen AI, most of us knowledge workers spent most of their time training AI on how to predict us better: like the microworkers who teach AI sensors to code objects as trees or traffic lights, r the hired drivers that teach autonomous vehicles how to drive around the city, much of what we call knowledge work involves coding, labelling, and teaching AI how to predict us to the point that we are not needed. To be sure, the best case for using AI is that other people use it, so we are at a disadvantage if we dont. This produces the typical paradox we have seen with other, more basic technologies: they make our decisions and actions smarter, but generate a dependency that erodes our adaptational capabilities to the point that if we are detached from our tech our incompetence is exposed. Ever had to spend an entire day without your smartphone? Not sure what you could do. Other than talk to people (but they are probably on their smartphones). Weve seen this before. GPS has eroded our spatial memory. Calculators have hollowed out basic math. Wi-Fi has made knowledge omnipresent and effort irrelevant. AI will do the same to reasoning, synthesis, and yes, actual thinking. Are We Doomed? Only If We Stop Trying Its worth noting that no invention in human history was designed to make us work harder. Not the wheel, not fire, not the microwave, and certainly not the dishwasher. Technology exists to make life easier, not to improve us. Self-improvement is our job. So, when we invent something that makes us mentally idle, the onus is on us to resist that temptation. Because heres the philosophical horror: AI can explain everything without understanding anything. It can summarize Foucault or Freud without knowing (let alone feeling) pain or repression. It can write love letters without love, and write code without ever being bored. In that sense, its the perfect mirror for a culture that increasingly confuses confidence with competence: something that, as Ive argued elsewhere, never seems to stop certain men from rising to the top. What Can We Do? If we want to avoid becoming cognitively obsolete in a world that flatters our laziness and rewards our dependence on machines, well need to treat thinking as a discipline. Not an obligation, but a choice. Not a means to an end, but a form of resistance. Here are a few ideas: Be deliberately cognitively inefficientRead long-form essays. Write by hand. Make outlines from scratch. Let your brain feel the friction of thought. Interrupt the autopilotAsk yourself whether what youre doing needs AI, or whether its simply easier with it. If its the latter, try doing it the hard way once in a while. Reclaim randomnessAI is great at predicting what comes next. But true creativity often comes from stumbling, wandering, and not knowing. Protect your mental serendipity. Use genAI to know what not to do, since its mostly aggregating or crowdsourcing the wisdom of the crowds, which is generally quite different from actual wisdom (by definition, most people cannot be creative or original). Teach thinking, not just promptingPrompt engineering may be useful, but critical reasoning, logic, and philosophical depth matter more. Otherwise, were just clever parrots. Remember what it feels like to not knowCuriosity starts with confusion. Embrace it. Lean into uncertainty instead of filling the gap with autocomplete. As Tom Peters noted, if you are not confused, you are not paying attention. Thinking Is Not Yet Extinct, But It May Be Endangered AI won’t kill thinking. But it might convince us to stop doing it. And that would be far worse. Because while machines can mimic intelligence, only humans can choose to be curious. Only we can cultivate understanding. And only we can decide that, in an age of mindless efficiency, the act of thinking is still worth the effort, even when it’s messy, slow, and gloriously inefficient. After all, I think, therefore I am was never meant as a productivity hack. It was a reminder that being human starts in the mind, even if it doesnt actually end there.
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