The Night Owl CEO Lifestyle: Inside Brian Chesky’s Unconventional Routine and the Changing Face of Executive Work

 The fascination with CEO lifestyles has long been a subject of business journalism, corporate culture, and even mainstream curiosity. For decades, the archetype of the successful executive was built on the image of an early riser, a leader who greeted the dawn with discipline and rigor, answering emails before most of the world was awake, and finding power in the silence of the early morning hours. Tim Cook of Apple is known for starting his day before 4 a.m., Howard Schultz once spoke of his 4:30 a.m. coffee routines, and Richard Branson’s mornings on his private island became a symbol of entrepreneurial freedom and self-discipline. Yet as the culture of work evolves and technology reshapes the way companies are led, a new archetype is emerging: the night owl CEO. Among those redefining the CEO lifestyle is Brian Chesky, the cofounder and CEO of Airbnb, who has shared in recent interviews that his most productive and creative hours happen not at sunrise but deep into the night, often stretching until 2:30 in the morning.

For Chesky, who at 43 remains one of the most closely watched leaders in Silicon Valley, the late-night hours provide an uninterrupted sanctuary for creativity, reflection, and strategic thinking. Unlike the rigid schedules of CEOs who pride themselves on early alarms, Chesky has crafted a lifestyle around his own rhythm of productivity. He told The Wall Street Journal that his creativity peaks around 10 p.m., and from there he often enters long stretches of “heads-down” work, drawing, sketching ideas, or refining detailed company plans. Over Thanksgiving weekend, while many executives might have taken the opportunity to unplug, Chesky immersed himself in drafting a 10,000-word plan to expand Airbnb beyond stays and into booking services and experiences, later revising it into a concise 1,500-word roadmap. That kind of obsessive attention to detail, combined with his unusual working hours, paints a picture of a CEO lifestyle that is not about conformity to an external ideal but rather about designing a daily rhythm that matches one’s own cognitive and emotional strengths.

When Chesky describes his evenings, the portrait is of a man who treats nighttime not as downtime but as the beginning of his creative shift. At 8 p.m., while many leaders are winding down, Chesky is ramping up with 90 minutes of exercise, preparing his body and mind for the mental sprint that will follow. Afterward, his time splits between personal pursuits—drawing, watching television, or spending time with his dog—and professional focus. He relies less on emails, which he has confessed to disliking, and more on texts and phone calls, often reaching out to team members who are also awake and engaged in work. By 10 p.m., Chesky is in his flow state, and his productivity extends well into the early hours, often ending only when he finally heads to bed at 2:30 a.m.

This stands in contrast to the lifestyles of CEOs like Tim Cook or Evan Spiegel, who have publicly shared their preference for morning routines. For Cook, the morning is a sacred time to review customer feedback, exercise, and prepare for the day ahead. Spiegel similarly uses mornings for strategic clarity and decision-making. Chesky, however, demonstrates that success at the highest levels of business leadership is not confined to one template but rather is a matter of aligning personal rhythms with professional demands. His choice not to schedule any meetings before 10 a.m.—nearly two hours after he wakes up at 8:30—further highlights how the CEO lifestyle can be reshaped to maximize personal well-being and performance. As he told The Journal, “When you’re CEO, you can decide when the first meeting of the day is,” an understated acknowledgment that leadership comes with the freedom to design one’s own time.

This approach connects Chesky with a lineage of leaders who have rejected the cult of the morning in favor of late-night focus. Aaron Levie, the CEO of Box, has admitted to working until 3 a.m., and in a 2023 interview, Bill Gates reflected on his younger years believing that “sleep is laziness,” often pushing himself to work into the night. While Gates has since acknowledged the importance of rest as he grew older, his story underscores a recurring truth about CEO lifestyles: they are not static but evolve alongside personal growth, company maturity, and changing cultural attitudes toward health and productivity.

Part of the fascination with Chesky’s nightly routine lies in what it says about modern CEO culture more broadly. The relentless early riser image has long been celebrated in business literature, often linked to values of discipline, sacrifice, and control. Yet the glorification of 4 a.m. wake-ups has also been critiqued as unsustainable, unrealistic, and even exclusionary, promoting a narrow vision of success that may not fit the natural rhythms of most people. Chesky’s unapologetic embrace of late nights and later mornings challenges that stereotype and opens the door to a broader understanding of how executive lifestyles can be optimized for different types of people. In fact, neuroscience and psychology increasingly suggest that cognitive performance varies across chronotypes, with some individuals naturally performing better at night. For Chesky, leaning into his night owl tendencies rather than forcing himself into an early bird mold may be a form of authenticity that benefits not only his personal productivity but also his leadership.

There is also a symbolic dimension to Chesky’s routine that resonates with the story of Airbnb itself. The company was founded on challenging conventions—turning strangers’ homes into trusted stays and reshaping travel through community and creativity. Chesky’s leadership style mirrors this ethos: rejecting convention, carving out unique approaches, and relying on creativity as a core strength. His late-night hours are not just about getting work done; they represent a philosophy of design-driven leadership, where ideas are nurtured in moments of quiet reflection, far removed from the noisy demands of daytime meetings and back-to-back calls. In a world where CEOs are often portrayed as machines optimizing for efficiency, Chesky’s narrative adds a human and artistic layer to the role.

The broader trend of CEOs personalizing their lifestyles also reflects shifting generational attitudes. Younger executives, many of whom grew up in the era of flexible work, are more inclined to resist rigid schedules and embrace routines that align with their natural rhythms. The pandemic further accelerated this shift, as remote work blurred the boundaries of traditional office hours and normalized more diverse schedules. Chesky’s choice to rely on texts and calls instead of emails since 2020 is emblematic of this evolution, highlighting how technology is reshaping not only communication but also the very texture of daily leadership.

At the same time, Chesky’s lifestyle is not without trade-offs. The late-night focus can mean fewer traditional social engagements or a different rhythm from peers and colleagues. He acknowledges that being single and living with his dog affords him the flexibility to commit deeply to his work. This raises questions about how CEO lifestyles intersect with personal lives, relationships, and broader definitions of balance. For some leaders, the demands of running a multibillion-dollar company may make work-life balance elusive; for others, the ability to design a schedule that suits their preferences may be the very definition of balance.

Comparing Chesky’s lifestyle to Warren Buffett’s underscores how varied CEO routines can be while still supporting extraordinary success. Buffett, who has often said he sees no need to wake up at 4 a.m. and prefers a more leisurely start to his day, represents yet another model of leadership that works on its own terms. He has long emphasized that his value lies not in the volume of hours worked but in the quality of decisions made, and he prioritizes rest with a full eight hours of sleep each night. This juxtaposition—Buffett starting later, Cook starting earlier, Chesky staying up late—illustrates that there is no single formula for a successful CEO lifestyle. Instead, the modern lesson is that high-level leadership is about designing routines that maximize personal strengths while aligning with the demands of the company and the expectations of stakeholders.

The cultural intrigue surrounding CEO lifestyles also speaks to a deeper collective desire to understand the secrets of success. Articles, podcasts, and books devoted to “morning routines of billionaires” or “habits of successful CEOs” proliferate because they suggest a formula that others might replicate. Yet the reality, as Chesky demonstrates, is more nuanced. Success at the executive level does not arise from waking up at a particular hour but from aligning one’s time, energy, and focus with one’s creative and strategic strengths. The CEO lifestyle is less about emulating others and more about designing a system that works for the individual leader, their company, and their stage of life.

For blog readers, entrepreneurs, and professionals fascinated by the world of CEO lifestyles, Chesky’s story is both inspiring and liberating. It disrupts the myth that success requires conforming to rigid patterns and instead emphasizes authenticity, creativity, and personalization. His late-night routine, complete with exercise, drawing, and long hours of solitary work, reveals that leadership can be as much an art as a science. It shows that in an era of constant connectivity and shifting cultural norms, there is space for multiple versions of success, and the “ideal” executive routine is not a single blueprint but a spectrum.

Ultimately, the trend toward more personalized CEO lifestyles mirrors broader societal changes around work and well-being. Just as companies are embracing flexible work arrangements for employees, CEOs are modeling flexibility in their own lives, rejecting the notion that leadership must follow one rigid timetable. In Chesky’s case, the willingness to embrace his natural night owl tendencies may not only fuel his own creativity but also send a signal to others that success does not have to mean sacrifice in the form of conformity. Instead, it can mean designing a life that harmonizes with one’s own rhythms, values, and aspirations.

The allure of CEO lifestyles will no doubt continue to capture attention, as society looks to business leaders for inspiration, discipline, and sometimes even spectacle. But as the example of Brian Chesky illustrates, the story is shifting. No longer is the successful CEO simply the person waking up earliest; it may just as well be the one going to bed latest, immersed in thought, creating plans, and shaping the future of a company long after the rest of the world has gone to sleep.