The idea that entrepreneurs need to pull all-nighters working and never take a day off to be successful is outdated, according to Jack Dorsey. In fact, that attitude often leads to burnout, the Twitter and Square CEO and co-founder said on a recent episode of "The Boardroom: Out of Office Podcast."
"I would rather optimize for making every hour meaningful — or every minute meaningful — than I would maximizing the number of hours or minutes I'm working on a thing," Dorsey told Rich Kleiman on the podcast, which aired on Aug. 12. "Because I just found that the maximization of time takes away from the quality within the time I do have."
The 43-year-old billionaire explained that when people are "too rigid about having to work all hours," it's harder to be self-aware and pay attention to what's happening in the world around you. Self-awareness is one personal trait that he attributes to his massive success, he said.
Many people are under the assumption that "success means I work 20 hours a day and I sleep four — because that's what I read that Elon Musk does," Dorsey said. But Dorsey said that is "bulls---." (The Tesla CEO has said that he sometimes works 80 to 90 hours a week, and has admitted working up to around 120 hours a week at times, which he called "nutty.")
Dorsey has found ways to schedule self-reflection into his day so he can make the most of the time he spends working.
Before Twitter and Square employees began working from home due to Covid-19, a typical day for Dorsey would start at 5 am with meditating, he said on the podcast. He practices "vipassana meditation" or "insight meditation," a technique that focuses on observing and understanding thought patterns. (Dorsey has been criticized for going on a 10-day vipassana meditation in Myanmar on his birthday in 2018, which some called tone-deaf amid the military attacks on Rohingya Muslim people.)
Dorsey would then drink coffee and walk five miles to work, which took an hour and 20 minutes. He says he would usually listen to podcasts or audiobooks on the walk, "so that I learn," he said.
"The most important thing about that morning is, I meditated, which means I calmed my head, I did some physical exercise, [and] I learned in just a short, effectively three-hour window before my meeting started," Dorsey said.
The routine also gives Dorsey a confidence boost: "I already won the day," he said. "The day could be a terrible day, and I feel like I already did so much for myself and I felt like I had another day entirely."
Once the workday begins, Dorsey said that he tries to get rid of all distractions. "I just get so much more done and time really slows down, so the hour feels like three hours," he said. "You can make this time so fungible and flexible if you really understand how to kind of focus on it."
In the past, Dorsey has said that he eats only dinner seven days a week, so that he's not interrupted by breakfast or lunch.
"I just found that I got so much more done during those fasting periods because I was so focused and it just felt like I had much more time to really think and to work in that moment," Dorsey said on Ben Greenfield Fitness: Diet, Fat Loss and Performance podcast in April 2019. (While some studies on mice suggest that fasting can improve cognition and potentially protect the brain against neurodegenerative diseases, more research needs to be done to show that it's safe for humans. Furthermore, feeling hungry during fasting periods can mess with your ability to make decisions, think and concentrate.)
Dorsey splits his day to devote time to both of his companies: Twitter in the morning, Square in the afternoon and evening, he told Kleiman. At the end of a typical day, Dorsey would go home, make dinner and wind down, he said.
While some details of Dorsey's habits are far-fetched for the average person, at the end of the day he comes back to one relatable question, which he often journals about. "What did I learn today?"
Dorsey said he's been keeping a journal since he was 14, but the same prompt still applies to his life as a billionaire and entrepreneur: "What is the world trying to teach me about what I need to do personally to maintain this level, or to extend, or go beyond the level?"