The saying goes, there’s no elevator to success. But when you consider the “typical” career path of a CEO, you might think it’s pretty linear: First, earn an MBA, then, through a combination of sweat equity and savvy networking, rise up through one or more companies’ ranks, securing managerial, senior managerial, and then finally executive-level positions.
But in today’s environment of unpredictable change, the CEO’s role is evolving quickly. The job no longer comes with a standard template to follow, and many of the most impactful CEOs have forged unorthodox paths to success—paths that are now recognized more as strengths than weaknesses.
This shift can partly be attributed to what some call the “Succession Effect.” Due to the rise in popularity of series like HBO’s Succession, which details the dysfunctional Roy family’s battle for control over the Waystar RoyCo media empire, more interest—and more scrutiny—has been applied to what goes on in the corner office.
In fact, a 2024 study by Harvard Law School tracking top managers found that 28% of S&P 500 company CEOs had vacated their positions last year—often due to the heightened attention. “The increased emphasis on the CEO role and the accompanying celebrity status has ramped up the pressure, and we’re seeing more CEOs who only want to do the job once,” said RRA Managing Director Stephen Langton.
The rise of activist investors has further fueled leadership shifts. According to Forbes, corporate stakeholders are increasingly advocating for changes in top management, forcing out three times more CEOs in 2024 than in 2020, for example.
Economic and geopolitical forces certainly play roles, too. As chaos mounts in 2025, the job of CEO has extended beyond meeting quarterly expectations. Today’s CEOs must lead companies through unpredictable situations and navigate “left-field encounters”—those events and relationships that simply defy expectations.
Many of the most successful CEOs now carry the scars of career pivots, failures, and big risks taken—but they should wear them like a badge of honor, a symbol that they not only survived an era of extreme change; they also found a way to prevail.
There is no single path to executive success anymore, and there probably never will be, either, which proves the importance of flexibility and adaptability. Here are four CEOs who show how second acts and creative beginnings truly can forge visionary leadership.
Arianna Huffington faced plenty of rejection as a young political writer before eventually finding success in online news.
Arianna Huffington’s story is about success, but it’s also one of remarkable reinvention. Born in Athens, Greece, in 1950, she moved to England at age 16 to study at Cambridge University. After graduating, Huffington immigrated to the US and began her early career as a political commentator for CNN and Fox News, initially espousing conservative ideologies before later shifting to liberal views.
But Huffington was nowhere near an overnight success. In fact, she received 37 rejections for her manuscript, After Reason, before it was finally published in 1978. In the meantime, the broke 30-something had to take out a bank loan just to make ends meet.
Even The Huffington Post, her most defining career move, was slow to get off the ground.
Huffington recognized the growing power of the Internet long before anyone else, launching her online news and blogging platform in 2005.
But it took six years for people to “get” the combination of traditional reporting inside a new, digital format. By 2010, the site had received over a billion views. Soon, HuffPost became one of the most popular outlets in the country, and one that challenged “traditional” print media. AOL acquired The Huffington Post for $315 million in 2011; as of 2025, Huffington’s net worth is estimated to be around $100 million, according to Celebrity Net Worth.
In 2016, Huffington founded her second major enterprise: Thrive Global, a company focused on wellness and mental health. Its genesis stemmed from its founder’s own collapse from exhaustion in 2007. Thrive Global was valued at $700 million by Bloomberg in 2021; today, Huffington remains a hugely influential figure in both digital journalism and the wellness sphere.
Tony Xu took life lessons from his time washing dishes.
Tony Xu’s story is the quintessential American Dream: Born in Nanjing, China, in 1985, he immigrated to the U.S. with his parents when he was five years old. However, despite his mother being a doctor and his father a professor, they had to work as restaurant servers in their new country to support their family.
Before founding DoorDash, Xu held internships at eBay and McKinsey, and also worked as a dishwasher in a restaurant, a job he now credits with teaching him humility and resilience. His experience as “chief, cook, and bottle washer” afforded him a unique perspective on how technology could empower local entrepreneurs—rather than replace them.
While studying for his MBA, Xu noticed how small restaurants did not have the same infrastructure that allowed larger businesses to afford delivery services. And so, in 2013, Xu and a group of classmates built DoorDash to help these businesses reach more customers.
Company growth exploded during the pandemic. What began as a side project became Xu’s bread and butter, and since its IPO in 2020, DoorDash has grown to be valued at $116 billion. According to Forbes, Tony Xu has an estimated net worth of $3.3 billion as of 2025.
Brian Chesky’s creativity spawned a billion-dollar business.Kimberly White/Getty Images
As a child, Brian Chesky grew up with a love for two things: Playing hockey and design. So, he went to college at the Rhode Island School of Design (RISD), where he captained the school’s hockey team and honed his creative thinking.
After graduating in 2007, he and his friend, Joe Gebbia, moved to San Francisco. Struggling to pay rent, they came up with a bold idea: What if they rented out air mattresses in their apartment to conference attendees? They called it “AirBed & Breakfast,” literally laying the foundation for the company that would become known as Airbnb.
At first, they were met with skepticism. Chesky and Gebbia, along with another friend, Nathan Blecharczyk, faced countless rejections from investors. In order to keep their idea afloat as well as help to build buzz for it, they created and sold political-themed cereal boxes during the 2008 presidential election: “Obama O’s” and “Cap’n McCain’s.” (The quick sell-out of the Obama-themed boxes would correctly prove the race’s outcome.)
The friends’ big break came after they were accepted into the famed Y Combinator startup accelerator in 2009, a tech incubator that provided seed funding to other Millennial success stories, like Dropbox and Stripe. There, they learned how to scale their business.
Under Chesky’s leadership, Airbnb simply revolutionized the hospitality industry by transforming homes into 5-star destinations. In December 2020, Airbnb went public with one of the most successful IPOs of the decade, debuting at $68 per share before soaring to $144 that day alone; today, it’s valued at around $75 billion.
Chesky himself has seen his valuation rise; he has an estimated net worth of $8.5 billion in 2025, according to Forbes. His journey from struggling graduate to tech leader illustrates how outside-the-box thinking can grow a global empire.
Microsoft’s modest chief executive, Satya Nadella, leads with empathy.Image source: Ben Kriemann/Getty Images
Satya Nadella’s ascent to Microsoft’s C-Suite was not fueled by ambition or starpower, like so many other tech leaders, but rather by a lifelong passion for learning and empathy.
He studied electrical engineering in India before moving to the U.S. to obtain a Master’s degree in computer science from the University of Wisconsin and an MBA from the Chicago Booth School of Business. He also became a U.S. citizen in the process.
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Nadella’s career began as a software engineer at Sun Microsystems, but Microsoft’s top brass noticed his talents, and he was recruited in 1992. Nadella was assigned to the Windows NT software team, where he worked on the company’s primary business operating system.
Nadella was considered to be a surprise choice when he was named CEO of Microsoft on February 4, 2014. The modest manager had big shoes to fill, following in the footsteps of Bill Gates and Steve Ballmer, as well as some hefty messes to clean up, notably the Windows 8 debacle and the decline in popularity of Microsoft Windows, which at the time was the company’s core business.
However, his leadership style was shaped less by MBA theory and more by his personal experiences, particularly being a parent to a child with special needs, which taught him the value of thinking “big picture” as well as practicing empathy.
Nadella was responsible for blazing new paths in artificial intelligence, cloud computing, and the gaming industry for Microsoft, and the company’s share price grew by more than 969% since he took over—and his own net worth has soared to $1.1 billion in 2025, according to Forbes, which is no small feat for a quiet engineer.
