Airbnb CEO Brian Chesky has achieved many things in his 43 years of life. To name a few: launching a $100 billion brand, graduating with a fine arts degree in industrial design, befriending a former U.S. president, and becoming a body builder.
Work-life balance, however, is a bit tricky.
“There's many things that I claim to know a lot about, and work-life balance is not one of them,” Chesky tells Fortune. “I'm 43 and single, so the best people to answer this question are people with families.”
The millennial founder says that while he’s achieved “an excellent work-life balance for a single person,” he doesn’t believe his current lifestyle is conducive to family life. However, he is the father of a lively 3-year-old golden retriever named Sophie Supernova, who, according to Chesky, “unleashes more energy than an exploding star.”
“I've been able to have the luxury of being able to automate things,” Chesky explains, freeing him up for exercise, traveling, reading, and connecting with friends.
“My parents, growing up, would mow the lawn, clean their house, do the dishes,” he says. “I've tried to automate as much as I can, so the time I spend is spent doing either work or true leisure activities and as few logistics as possible.”
Chesky emphasizes it is a “privilege” that he can automate his chores, but “sometimes I will go to a grocery store just to not lose my mind, just live in the world,” he says. “I will only do that periodically because I’m working so much.”
However, Chesky does have a hack for managing the hectic day-to-day of a $100 billion Fortune 500 brand: journaling.
“I keep a daily journal and a digital note app, like Apple Notes, and every day I write notes to myself,” he says; however, they’re often not complete sentences. “The pros are more like bullet points, and it's anything that comes [to] mind.”
Among other leadership advice—including encouraging CEOs to choose favorites—Chesky gave Fortune an exclusive look at his daily routine, which he admits kicks off “pretty late” for an entrepreneur.
Inside the Airbnb CEO’s daily routine
8:30 a.m.: Most entrepreneurs champion an early start to the day to squeeze in personal time before running to the office. For Chesky, his daily routine “starts pretty late, because I go to bed pretty late.”
Even with a later start, the chief executive’s first tasks are still focused on productivity, beginning with a bit of cardio like the StairMaster or a walk with his dog. Chesky, a former competitive body builder, notes that his morning fitness routine starts with an empty stomach “when I have low glucose level.”
“There's a lot of hills where I live, so I try to do that for like 20 minutes in the morning,” he says. “Then I'll begin my day.”
9 a.m.: While Mondays are often spent working from home, for the remainder of the week, Chesky will shower and eat a light breakfast before heading into Airbnb’s headquarters in San Francisco. A coffee drinker, Chesky may enjoy one to two cups of black coffee without any milk or sugar.
10 a.m.: Chesky’s meetings begin, but he emphasizes his preference for an “unstructured” workday.
“I generally don't like to have back-to-back meetings,” he says. “I like to have some free time to roam around and to be able to do some head-down work.”
Chesky also abhors one-on-one meetings with direct reports, instead preferring meetings with multiple participants.
“The one-on-one model is flawed. It’s a recurring one-hour one-on-one meeting where the employee owns the agenda,” he says. “What happens is that they often don’t talk about the things you want to talk about, and you become like their therapist.”
12 p.m.: Chesky eats five meals throughout the day beginning at 9 a.m., breaking for lunch at 12 p.m., enjoying a snack at 3 p.m., dinner at 6 p.m., and ending with another snack at 9:30 p.m.
“The only caveat is I do a little bit of intermittent fasting too,” he says. “I’ve found that's kind of helpful.”
3 p.m.: Chesky enjoys his third meal of the day, and may take a break by traversing through Airbnb’s large office space to say hello to colleagues.
Recently, the chief executive has also implemented transcendental meditation—the practice of pausing for up to 20 minutes twice per day—into his routine to help with stress or overwhelm.
“But I don't actually do it for 20 minutes, twice a day,” he says. “I'm lucky if I do it like a handful of times a week.”
6 p.m.: Chesky’s schedule of meetings tends to wind down after 6 p.m., but his workday seldom ends at the close of business, and he rarely stops communicating with his colleagues. However, Chesky says he almost never sends emails. Instead, emails are reserved only for serious or nuanced topics, and he replies “with as few words as possible.”
“The way to communicate with me is almost entirely by text message,” he says.
7:30 p.m.: Chesky's second workout of the day starts around 7:30 p.m. with a personal trainer. The CEO trains with weights four times per week, and ends with half an hour of cardio before heading home.
9:30 p.m.: Chesky spends half of his weeknights with a mix of personal activities like catching up with friends, reading, drawing, or watching TV. The other half of the week may be spent concentrating on head-down work.
“Sometimes I'll call employees that are available at night to check in, or I'll do really head-down work, and I could be writing from like 10 a.m. to 1 a.m.,” he says. “I'm not doing it every night, but if I really want to do some deep work, I'll do that.”
1:30 a.m.: Chesky, along with Melinda French Gates, who recently deemed the phenomenon as “so dumb,” rejects the notion that CEOs should forgo proper sleep in favor of productivity.
“[A] non-negotiable is I want to try to get at least seven hours of sleep,” he says. “I know there are people that go off four, five, even six hours of sleep, but the extra hour you save by not sleeping probably makes every hour the next day a little less productive.”
More CEO daily routines:
- Inside the new Starbucks CEO’s daily routine while he was running Fortune 500 giant Chipotle
- The CEO of Crunch Fitness thinks there’s no such a thing as work-life balance: 'That’s for somebody who's not fully committed'
- Build-A-Bear’s CEO spends her Fridays penning old-fashioned ‘thank-you’ notes to bolster her $486 million toy empire
- Inside the routine of Red Lobster’s 35-year-old CEO from when he ran P.F. Chang’s
- The 38-year-old co-founder of $200 million Olipop is a college-dropout-turned DJ. Here’s his daily routine
