Insights from Top Executives after Talking to 80 Leaders in 2025

After engaging with nearly 80 business leaders this year, my understanding of what sets high-achievers apart has deepened, though there's no definitive recipe for success.

My interactions included more than 30 executives from Fortune 500 firms and 20 CEOs or founders from diverse and consumer-loved brands such as Whoop, Olipop, and leading tech entities like Google, Microsoft, and Amazon.

Through these discussions, consistent themes emerged, painting a picture of common traits among the successful.

Unorthodox Career Paths

Many executives I met veered away from traditional career trajectories en route to the C-suite.

For instance, Glenn Fogel of Booking Holdings shared how, following his layoff from investment banking, he faced a two-year employment gap and turned to novel writing.

Others embarked on entirely different initial careers — the Brooks Running CEO once taught high school, and an AWS executive, Colleen Aubrey, began as a receptionist for the Australian government.

Similarly, Yasmeen Ahmad from Google Cloud transitioned from life sciences to the tech industry after obtaining a PhD, navigating unfamiliar territory to eventually broaden her professional viewpoint.

A Persistent Commitment to Discipline

The leaders I spoke to demonstrate incredible discipline and curiosity, which extend beyond merely clocking in extra hours.

For instance, Visa's Oliver Jenkyn dedicates four uninterrupted learning hours weekly, while John Stecher of Blackstone uses his commute to absorb industry news.

This discipline permeates their lives, influencing everything from dietary choices to exercise regimes.

Ben Goodwin of Olipop starts his day with alternating temperature showers to cultivate discomfort tolerance, and Niki Leondakis of CorePower Yoga maintains a boundary-setting regiment to ensure peak focus and energy management.

Others, like VC founder Harry Stebbings, adhere to daily and weekly routines such as a daily step count and regular marathon-length walks with family.

The Embrace of Risk

Another commonality is a penchant for boldness and embracing uncertainty, which shapes their professional journey.

This can take diverse forms—whether it's launching a startup during university like Will Ahmed of Whoop or tackling controversial issues publicly akin to the Cluely founder.

An example of proactive risk-taking comes from Sameer Samat of Google, who took the initiative to contact Google co-founder Sergey Brin via email, leading to an unused job opportunity later.

Sarah Cooper from AWS shows her courage by proposing innovative ideas, which sometimes paid off with role creations, though also resulted in career setbacks.

While risks don't always guarantee success, the overarching message is that leaders would rather engage actively, preferring mistakes over indecision.