Rituals of a 4:30 a.m. CEO: Discipline over balance, decade after decade

Khozema Shipchandler, the chief executive officer of Twilio Inc. , has attributed his rapid rise in the corporate world to a rigorous daily schedule that he has followed since college. Starting his day at 4:30 a.m., Shipchandler dedicates long hours to work, maintaining a disciplined routine that includes early morning reviews of emails and Slack messages, followed by breakfast, exercise, and a formal workday that often extends until 9 p.m. This lifestyle, which he has maintained for decades, enabled him to become CFO of a multi-billion-dollar company by the age of 31 and now leads one of the most valuable tech firms with a market value of $16 billion [1].

Shipchandler, 51, emphasizes the importance of hard work and the sacrifices it entails. While younger generations are increasingly prioritizing work-life balance and flexibility, he argues that such a path is unlikely to lead to executive-level success. “Every one of us has to make certain work-life choices,” he told Fortune, noting that his own sacrifices included missing out on family events like his son’s tennis matches. However, he also acknowledges that there is no one-size-fits-all approach, stating that if someone is content with a traditional eight-to-five schedule and personal time, that is a valid choice—though he claims it is rare among his peers [1].

Despite his long hours, Shipchandler insists on maximizing productivity through smart work habits. His daily schedule is meticulously structured, with short, focused meetings and intentional movement breaks between tasks. For instance, he runs laps around his house in between meetings to clear his mind and maintain physical energy. He also avoids social media to reduce distractions and stays on the treadmill for 10 minutes after lunch to avoid an afternoon slump [1].

On weekends, Shipchandler’s routine is slightly more relaxed, but he still works most Sundays. He allows himself only six to eight hours of time off on Saturdays—often the only period when he is not thinking about work. This schedule reflects his belief that high performance is sustained through consistent, intentional habits. “When you have a set of habits, it allows you to kind of move through the work in a way in which is very intentional and you don’t let a lot of distractions creep in,” he explained [1].

Shipchandler’s approach contrasts with current trends in the workforce, particularly among Gen Z and millennial employees, who are pushing for more flexibility and boundaries between work and personal life. While some companies are experimenting with four-day workweeks and remote work models to enhance employee well-being and productivity, Shipchandler remains skeptical that such changes are compatible with reaching the top of a major corporation. His career trajectory suggests that, at least for him, long hours and a laser-focused routine have been critical to his success.