Fortune 500 leaders reveal their habits. Discipline and courage are the key to success

In 2025, I interviewed approximately 80 managers, including over 30 leaders of Fortune 500 companies and approximately 20 CEOs or founders. They included the heads of consumer-demanded brands such as Whoop and Olipop, the CEO of CorePower Yoga, and senior leaders of large technology companies such as Google, Microsoft and Amazon.

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After talking to leaders from various industries and companies of various sizes, I cannot say that I have discovered a universal recipe for success. However, I noticed recurring themes and patterns that appeared in our conversations.

Here are the three most important conclusions:

Many of them took unconventional paths

A straight path to top positions was the exception, not the rule, among the managers I talked to.

Even those who started out with degrees from prestigious universities experienced twists and turns or setbacks along the way. For example, Glenn Fogel, CEO of Booking Holdings, told Business Insider that after losing his investment banking job, he was unemployed for two years, during which time he wrote a novel.

Other leaders started out in completely “normal” jobs. The CEO of Brooks Running, a billion-dollar company, began his career as a high school teacher. Colleen Aubrey from AWS said that early in her career she worked as a receptionist for the Australian government. Autodesk's president admitted that at one point he dropped out of high school and was on probation as a teenager.

Others, like Google Cloud's Yasmeen Ahmad, also found their roles in a roundabout way. Ahmad began her career in genomics and life sciences after earning her Ph.D. She said her biggest challenge was accepting uncertainty while transitioning from academia to business. Although it was difficult, working in sales and finance before joining Google gave her a broader perspective.

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They are disciplined

Most managers I spoke to demonstrated a high level of discipline and curiosity that went beyond working after hours.

For Oliver Jenkyn, CEO of Visa Group, that means spending four uninterrupted hours a week learning something new. For John Stecher, Blackstone's CTO, it's about using his 35-minute subway ride to and from work to read technology news from other industries.

This discipline extends beyond their professional lives and influences their diet, exercise routines and lifestyle.

Ben Goodwin, president of Olipop, starts his mornings with a shower, in which he alternates between hot and cold water to build resistance to discomfort. He also regularly uses cold baths and saunas, spending five minutes or more in water at a temperature of around 4°C.

For Niki Leondakis, president of CorePower Yoga, discipline manifests itself in the ability to set boundaries at work. As an introvert, she emphasizes that regeneration is crucial for her. Her assistant blocks 30 minutes on her calendar before each important speech so she can calm down and do breathing exercises.

Others, like VC founder Harry Stebbings, have mandatory daily and weekly goals — e.g. steps a day and walking a marathon with my mother every weekend. Stebbings also holds off on her first meal — always sushi — until about 8:30 p.m. each day.

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They don't avoid risk

Many managers described a pattern of making bold decisions throughout their careers — and some, like AT&T's Jennifer Van Buskirk, are looking for candidates with a similar mindset.

This courage can manifest itself in a variety of ways – from starting a company in college, as Will Ahmed, CEO of Whoop, did, to speaking out publicly about AI-enabled fraud, as the founder of Cluely did.

Others, like Sameer Samat, head of Android at Google, were bold by making the first move. In 1999, in the middle of the night, he sent the so-called cold e-mail (a personalized message sent to a potential customer with whom there has been no previous contact, in order to establish a relationship and interest him in the offer)) to Sergey Brin, asking for advice on a conflict with the co-founders of his start-up. The exchange of messages led to a visit to the Google office, which resulted in a job offer – although Samat then turned it down.

For AWS's Sarah Cooper, taking risks means writing detailed proposals for new ideas she wants to implement. This strategy allowed her to create her own positions. But it also sometimes backfired — Cooper said that at one company, a poorly received proposal led to her being fired.

Although risk does not always pay off, the most important lesson I learned from conversations with leaders is this: failure is inevitable, and they prefer to act rather than stand still.

The above text is a translation from American edition of Business Insider