Lessons from Jack Dorsey, the billionaire CEO who can't concentrate for more than 4 hours

Jack Dorsey, the co-founder of Twitter, is not your conventional executive. One of his peculiarities is his ability to concentrate for short periods of time, among others.

Dorsey has been primarily innovating in the world of technology for the past 20 years. He started along with shipping software program him in 1999, and even back then he was already doing 10 issues at the same time. In fact, he first outlined the concept that would become Twitter in 2000. Here's what it looked like:

Jack shelved the concept for years, until in 2006 he was able to get help from his friend Florian Weber and a colleague at Odeo (a podcast company Jack worked at) named Noah Glass.

«Everyone has an idea. However, it's really about executing the concept and bringing in different people who can help you work on the concept.”

Jack Dorsey

In 2007, Dorsey became the CEO of Twitter. 12 months later, he was fired from his personal company because the distinguished members of the board of directors deemed him unsuitable for the job, unable to resolve essential technical points. Additionally, they didn't like his tendency to leave work early to go to the sauna or meditate for hours.

After this mishap, Dorsey discovered one more option to resurface. He creates Sq. 2 years after leaving Twitter, in 2009. Sq. helps anyone with a smartphone and a small business clear funds from bank cards. In 2011, he returned to Twitter as CEO. This time, he was even busier than before, and not simply with yoga.

One way or another he managed to convince everyone involved that this was not a problem, and he began to divide his time between the two tasks. In 2013, Twitter went public and Dorsey became a billionaire. 2 years later, Sq. entered the stock market with a valuation of $2.9 billion.

Being relentless and all the time juggling between tasks and concepts should not essentially be the right option to get matters executed. Many people don't really thrive on multitasking like Dorsey does. However, what is certain is this: for all his time innovating, searching for new concepts, and with little attachment to the established order, Dorsey was in a position to not only be extraordinarily productive, but also redefine 2 of the most important industries: social media and monetary companies.

«All my days are themed. Monday is the administration. In Sq. we have a management meeting, in Twitter we have our work committee meeting. Tuesday is product, engineering and design. Wednesday is advertising and marketing, development and communications. Thursday is association and builders. Friday is corporate and tradition. It really works in 24 hour blocks. On days that start with T, I start on Twitter in the morning and then go to Square in the afternoon. Sundays are for technique, and I do numerous job interviews. Saturdays are for rest.

Theming of the day is a time management method beloved among Silicon Valley's top CEOs. Steve Jobs was also recognized for using this technique. Mondays were dedicated to government staff conferences, Wednesdays to promotion and advertising and marketing. Most afternoons were spent designing with Jony Ive.

Theming the day works well when you have a mess of things to do and little time to allocate to each of those things, which is strictly the scenario many CEOs find themselves in. You are at the crossroads between time blocking and batch organization.

This method can also be very environmentally friendly, as it helps the groups you work with routinely align with you. When everyone is aware of what the current topic is, it is much easier to know what to do, what stories to organize, what information to consult. In many companies, everyone is assigned random tasks that can't really be linked to each other when it comes to the bigger picture. Theming of the day ensures a minimum of consistency in everyone's workload and work topic.

Daytime theming takes care of the day's tasks, but what about before and after work? To help set the muse for an eco-friendly time management framework, a great morning and evening routine are paramount.

Dorsey wakes up around 6 a.m. and begins his day with an hour of meditation. He is a big proponent of the Vipassana method of meditation and has been on several silent retreats. In a 2019 podcast interview with Ben Greenfield, Dorsey mentioned that the first most impactful choice he made around his psychological well-being and stress management has been meditation.

After his meditation, Dorsey does a 7-minute exercise, after which he goes into the sauna for about 20 minutes. On the days she goes to work she walks (takes about 1h15 for 8 miles), and she works remotely on Tuesdays and Thursdays.

At night, Dorsey goes to bed around 11:00 p.m. Before that, she does another hour of meditation and eats. In fact, he is known for consuming only one meal a day.

«For two years, I have only had dinner. I usually eat around 6:30, and I eat until 8:30 or 9:00 in the morning. And then I drink some wine, usually rosé.

Jack Dorsey was listed as one of the worst CEOs in the United States 2 years in a row, in 2016 and 2017. He has been criticized on many occasions for prioritizing his private life and his hobbies over the growth of the companies he helped create. Many traders haven't seen the return they expected from funding him on Twitter, typically blaming Dorsey more than before.

Stakeholders at Square and Twitter have been unhappy with Dorsey dividing his time between the two corporations. From their point of view, this dissipates power. However, is it an honest judgment?

The main complaint from advertisers is that advertising on Twitter has not been very profitable. However, can you blame the CEO's routine? The stock market basically reacts in 1,000,000 different ways to 1,000,000 different factors, most of which are outside of everyone's control.

Dorsey is aware of this, and that's why he's been fighting to keep his place on every Twitter and Square. Here's an excerpt from the book “Deep Work” by Cal Newport. In it, the author explains why Dorsey's work cannot be considered superficial:

«Dorsey says that he ends the average day with thirty or forty units of assembly notes that he evaluates and filters at night. In the small areas between all these conferences, he believes in serendipitous availability. “I do a lot of work at standing tables, where anyone can come,” Dorsey said. “I get to hear a lot of conversations throughout the company.” This type of work should not be deep (…) he darts from one assembly to another, letting people freely interrupt him in the transitory interludes between them. But we cannot say that Dorsey's work is superficial, (…) it is of low value and simply replicable, while what Jack Dorsey does is extremely valuable and extremely rewarded in our financial system.

Dorsey might not have the ability to sit idly and pay attention to one thing for several hours. She might go on silent retreats, travel an excessive amount for the merchants' style, and spend an excessive amount of time inside the sauna.

But over the past 10 years, he's helped create 2 of arguably Silicon Valley's most profitable corporations, so he must be doing something right. On April 7, 2020, it further committed to revalue $1 billion of its Sq. shares to fund Covid-19 relief efforts, common core income, women's well-being assistance and the education.

He wouldn't have ended up in that place if he had let the critics crush his imagination and hunch.