Sadly, there’s no secret formula for success — but after speaking with dozens of leaders this year, I have a few ideas about what makes people at the top stand out.
In 2025, I interviewed around 80 executives, including more than 30 leaders at Fortune 500 companies, and roughly 20 CEOs or founders. They ranged from the heads of consumer-coveted brands like Whoop and Olipop, to the CEO behind CorePower Yoga, and senior leaders at major tech companies like Google, Microsoft, and Amazon.
After speaking with leaders across various industries and company sizes, I can’t say I discovered the blueprint for success. However, I did notice similar themes and patterns that kept popping up in our conversations.
These are the three takeaways I observed:
Many took non-traditional paths
A straight path to the C-suite was the exception, not the rule, among the executives I spoke with.
Even those who started with Ivy League credentials experienced some twists or setbacks along the way. Booking Holdings CEO Glenn Fogel, for example, told Business Insider that after losing his job in investment banking, he remained unemployed for two years and wrote a novel.
Other executives started on completely different paths. The CEO of Brooks Running, a billion-dollar company, began his career as a high school teacher. AWS executive Colleen Aubrey said she worked as a receptionist for the Australian government at the start of her career. The CEO of Autodesk shared that he dropped out of high school at one point and was on probation as a teenager.
Others, like Google Cloud’s Yasmeen Ahmad, also took indirect paths. Ahmad started her career in genomics and life sciences after earning a PhD. She said her biggest challenge was accepting the unknown as she transitioned from academia into the workforce. While uncomfortable at the time, she said moving through roles in sales and finance before joining Google ultimately gave her a broader perspective.
They stay disciplined
Most executives I spoke with displayed a high level of discipline and curiosity that went beyond working overtime.
For Visa Group President Oliver Jenkyn, it means setting aside four uninterrupted hours each week to learn something new. For Blackstone CTO John Stecher, it’s using his 35-minute subway rides to and from work to read up on tech news in other industries.
That discipline extends outside of their professional lives, shaping everything from their diets to their workout routines and lifestyles.
Ben Goodwin, the CEO of Olipop, for example, starts his mornings with a shower that toggles between hot water and the coldest setting to help build tolerance for discomfort. He also regularly cycles between cold plunges and sauna sessions, spending five minutes or more at a time in roughly 40-degree water.
For CorePower Yoga CEO, Niki Leondakis, that discipline shows up in the way she sets boundaries for work. As an introvert, she said recharging is crucial for her. She said her assistant blocks off 30 minutes on her calendar before any high-stakes engagement so she can ground herself and do breathwork.
Others, like VC founder Harry Stebbings, have mandatory daily and weekly milestones, like hitting 30,000 steps every day and walking a marathon with his mother every weekend. He also holds off on eating his first meal, which is exclusively sushi, until around 8:30 p.m. everyday.
They don’t shy away from risk
Many executives described a pattern of bold decision-making in their careers — and some, like AT&T exec Jennifer Van Buskirk, look to identify candidates with the same impulse.
That boldness can manifest in different ways — from founding a company in college, like Whoop CEO Will Ahmed, to publicly taking a stand on AI-assisted cheating in interviews, as the founder of Cluely did.
Others, like Google’s head of Android, Sameer Samat, displayed boldness by making the first move. In 1999, he sent a cold email to Sergey Brin in the middle of the night, asking for advice about a disagreement with his startup cofounders. The exchange led to a visit to Google’s office, which ended with a job offer, though Samat turned it down at the time.
For AWS executive Sarah Cooper, taking risks means writing detailed proposals about new ideas she wants to implement. The strategy has led her to create her own roles. However, it’s also backfired. Cooper said that at one job, a poorly received proposal resulted in her being pushed out of the company.
While risks don’t always pay off, the resounding message I gathered from leaders is that failing sometimes is inevitable, and they’d rather act than stand still.
