How Jack Dorsey’s book life powered his passion

Jack Dorsey begins everyday listening to audiobooks and music through a 5.3-mile walk.

The book-lover folds his selected reading works that include a number of technological, business and philosophical works.

Most of Jack Dorsey’s top recommended books are thoughtful, scientific and introspective.

Tech whizkid

Dorsey is the technological entrepreneur and power baron that stands in the bracket of greats such as Steve Jobs and Elon Musk.

But one thing sets him apart. He runs not just one but two major companies – Square and Twitter. It has made him a billionaire with a net worth over $5.6 billion, according to Forbes.

Dorsey says,

Reading markets and minds

Jack doesn’t often flaunt his billions and reportedly takes the bus in order to feel the pulse of people and learn about their habits.

He once said: I saw the rise of Instagram … and how many more people were using Facebook versus Twitter, and its amazing. Like, look — anyone reading magazines, newspapers, books?

Early years

Being a habitual reader today, Dorsey began reading early.

He often tweets about his favourite lists and once wrote: I love the opening line of all Rushdie’s novels. Reading The Enchantress of Florence.

His aspirations and personality is disclosed too: In all epic stories (my favorite), I love the pivot moment the most. All is gloomy & insurmountable, but there is a slight spark of hope…

Self-reflection, introspection and growth

Dorsey’s success story is an outcome of self-reflection and his thought process.

He noted his favourite books in Product Hunt Q&A and in his Twitter posts, which give an insight into his internal development. As he comments on ‘Tao Te Ching’ by Lao Tzu: Among themes explored are self-mastery through humility.

Recommended books

The eclectic mix of books recommended by Jack Dorsey reflect his thought processes as well as his rumination and self-realisation.

To all employees, the first book he recommends is ‘The Checklist Manifesto’, by Atul Gawande. He comments about its stunningly simple point that checklists keep errors from spiraling into life-threatening situations.

Another interesting book in his reading recommendation is ‘The Start-up of You’, by Reid Hoffman & Ben Casnocha, which he points out is all about the Silicon Valley approach to building a life: start with an idea, and work over your entire career to turn it something remarkable…

In his office, he does not have his own cabin or room and always wanders into any corner. He told “60 Minutes” that “there’s a self-awareness that other people work here — it’s not just you.”

It is the physical and emotional wandering that has helped to fuel his growth and development. As he adds: The thing I’m most proud of Twitter for is that it has been a vehicle for historically marginalized groups to share their story.

What challenges has he faced?

Although the 41-year-old is best-known for co-founding Twitter in 2006, the social media platform did not have a smooth ride and in 2008, he was fired. But he returned as its chief seven years later and turned its fortunes again.  

However, the giant still faces a number of questions from opponents, accusing him of not being careful or monitoring enough of fake or misleading information.

But he explains the problems and challenges in an interview, “I agree, we have been bad at communication… We do care deeply… This work doesn’t happen overnight..”

Visions for the future

While Jack Dorsey has big visions, they start small.

He once noted that he wants to give all his wealth away and help the world to address its enduring challenges and problems.

The existential issues facing the world today, according to him, is climate change and economic disparity.

To address these problems, he explained in an interview: I don’t think it’s fair what I have access to. I started a foundation called Start Small Foundation, which is intending to teach people how to build businesses in places like Ferguson and stay in business, because I see a business as a fabric to an enduring community.

Expressing great admiration for Elon Musk, who wants to populate other worlds, Dorsey’s future seems to be to open new perspectives and thought revolutions.

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