• A series of interviews conducted in 2025 with approximately 80 executives, including more than 30 leaders at Fortune 500 companies and roughly 20 CEOs or founders, identified three recurring themes among top performers.
  • First, many executives followed non-traditional paths to leadership, with examples ranging from a CEO who began as a high school teacher to an executive who started as a receptionist.
  • Second, these leaders demonstrate high levels of discipline, often incorporating specific routines such as dedicated learning time, extreme temperature exposure, or strict step-count goals.
  • Third, a pattern of bold decision-making was observed, including founding companies in college, cold-emailing industry titans, and proposing new roles to employers.

Quick Summary

A comprehensive review of interviews conducted in 2025 with approximately 80 executives reveals three distinct patterns among high-level leaders. The interviewees included more than 30 Fortune 500 leaders and roughly 20 CEOs or founders from companies such as Booking Holdings, Brooks Running, Google, and Amazon.

The analysis highlights that a straight path to the C-suite is the exception rather than the rule. Many leaders, including those with Ivy League credentials, experienced significant twists or setbacks. Additionally, executives displayed rigorous discipline extending beyond their professional work into their personal lives, often involving specific health and wellness routines. Finally, a willingness to embrace risk was a common thread, with leaders frequently making bold moves to advance their careers or implement new ideas.

Non-Traditional Paths to the Top 🛤️

Among the executives interviewed, a linear trajectory to senior leadership was rarely observed. Even those who possessed elite educational credentials often faced unexpected detours. Booking Holdings CEO Glenn Fogel shared that after losing a job in investment banking, he remained unemployed for two years and wrote a novel before returning to the workforce.

Other leaders started their careers in completely unrelated fields. The CEO of Brooks Running, a billion-dollar company, began his professional life as a high school teacher. Colleen Aubrey, an executive at AWS, worked as a receptionist for the Australian government at the start of her career. The CEO of Autodesk noted that he dropped out of high school at one point and was on probation as a teenager.

Even those transitioning from academia faced hurdles. Google Cloud's Yasmeen Ahmad, who holds a PhD and started in genomics and life sciences, cited accepting the unknown as her biggest challenge. Moving through roles in sales and finance before joining Google provided her with a broader perspective she might not have gained otherwise.

A straight path to the C-suite was the exception, not the rule, among the executives I spoke with.
— Interview Analysis

Rigorous Discipline and Routine 📅

Discipline among these leaders often extended well beyond working overtime, manifesting as structured habits for learning and physical endurance. Visa Group President Oliver Jenkyn sets aside four uninterrupted hours each week specifically to learn something new. Blackstone CTO John Stecher utilizes his 35-minute subway commutes to read technology news from other industries.

Physical and lifestyle discipline was also prominent. Ben Goodwin, CEO of Olipop, starts his mornings with a shower that alternates between hot water and the coldest setting to build tolerance for discomfort. He also cycles between cold plunges and sauna sessions, spending five minutes or more in water at roughly 40 degrees.

For CorePower Yoga CEO Niki Leondakis, discipline involves setting strict boundaries. As an introvert, she requires recharging time. Her assistant blocks off 30 minutes on her calendar before any high-stakes engagement to allow for grounding and breathwork. VC founder Harry Stebbings maintains mandatory daily milestones, such as hitting 30,000 steps, and weekend rituals like walking a marathon with his mother. He also delays his first meal—exclusively sushi—until around 8:30 p.m. daily.

A Willingness to Take Risks 🚀

Bold decision-making was a recurring theme, with many executives describing career-defining moments where they chose action over hesitation. AT&T executive Jennifer Van Buskirk noted that she looks to identify candidates with this same impulse. The manifestation of this boldness varies; Whoop CEO Will Ahmed founded a company while in college, while the founder of Cluely publicly took a stand on AI-assisted cheating in interviews.

Others made decisive moves to secure opportunities. Google's head of Android, Sameer Samat, displayed boldness in 1999 by sending a cold email to Sergey Brin in the middle of the night. He asked for advice regarding a disagreement with his startup co-founders. This exchange led to a visit to Google's office and a subsequent job offer, which he turned down at the time.

Risk-taking can also involve proposing new ideas. AWS executive Sarah Cooper writes detailed proposals for new ideas she wishes to implement, a strategy that has allowed her to create her own roles. However, this approach has risks; Cooper mentioned that at a previous job, a poorly received proposal resulted in her being pushed out of the company. The resounding message from these leaders is that failing is inevitable, but they prefer to act rather than stand still.

Conclusion

The interviews with these 80 executives suggest that success at the highest levels is rarely defined by a perfect resume or a safe career strategy. Instead, the data points to a combination of resilience, personal rigor, and the courage to make bold moves. Whether it is pivoting from a failed investment banking career, maintaining a strict cold plunge routine, or emailing a billionaire for advice, these leaders demonstrate that standing out requires a willingness to deviate from the norm.

"While uncomfortable at the time, she said moving through roles in sales and finance before joining Google ultimately gave her a broader perspective."

— Yasmeen Ahmad, Google Cloud

"The resounding message I gathered from leaders is that failing sometimes is inevitable, and they'd rather act than stand still."

— Interview Analysis

Frequently Asked Questions

What are the common traits of successful executives?

Based on interviews with 80 leaders, successful executives often have non-traditional career paths, maintain strict personal discipline, and are willing to take bold risks.

How did the executives interviewed start their careers?

Many started in unrelated fields; examples include a CEO who was a high school teacher, an AWS executive who was a receptionist, and a Google executive who worked in genomics.