• Richie Crowley

What Mindfulness Made Jack Dorsey Do

Living a life of observation, curiosity, gratitude, and impact.

On April 7th, Jack Dorsey announced that he was moving $1B of Square stock into a philanthropic fund that when liquidated would support a combination of COVID relief, advancing girl’s and women’s health and education, and universal basic income experimentation.

He announced this via Twitter.

The $1B was 28% of his wealth.

During a recent appearance on Yang Speaks, a podcast hosted by former Democratic presidential candidate Andrew Yang, Dorsey told Yang that the donation amount value had actually increased to $1.5B.

Jack Dorsey donated $1,500,000,000.

Moving past the awe and admiration of his selflessness, I was curious to learn the practices one keeps to foster and nourish this level of humanity.

For Dorsey, decisions like these have roots in observation, telling Yang that mindfulness is the practice of honing one’s skills of observation.

“Mindfulness and meditation is a practice of honing your skills of observation, and making sure that we are present and aware of all things we are doing and we are not blindly reacting to it and falling into a hole, that we are fully aware of the what and why.
I think meditation is one of those tools that can make us aware of the decision we are making.”

He practices every morning, after a short cold shower, and before he checks his phone.

Or, his Twitter.

Yang followed up by asking if Dorsey thinks technology can make us more mindful and aware.

I was surprised to hear that most of Dorsey’s day is spent on his iPhone, explaining that he uses an iPhone instead of a computer because there is only one app open at a time.

The conviction that observation is the skill sharpened through meditation is consistent with Dorsey.

In an episode of the Rich Roll Podcast, Dorsey adds that observation is also what ignites change.

“Very active observing is what ultimately changes systems and we have the responsibility to continue observing to reflect that.”

Dorsey also credits Yuval Noah Harari’s final chapter of his book 21 Lessons for the 21st Century, which explains that a practice of meditation helps us understand why we are doing the things we are doing, why we react the way we do.

What else is it about meditation that interests Dorsey?

“I want to figure out how to unlock everything I’m born with, because I know that's all I need. All I need, is everything I’m born with.”


But, does a meditation practice alone make you want to give out all your money during your lifetime?

“I want to give out all my money in my lifetime. I want to see the impact, selfishly, in my lifetime, and I want to make sure we are helping people. I want to see that impact.”

Well, no, but meditation and principle do.

“I live by the principle that everything is connected, so if somebody is in pain, I’m in pain ultimately over time. And, I want to make sure that I am doing whatever I can in my lifetime to help that.”

Dorsey believes that part of gratitude is not just saying it, but doing it, which Yang called gratitude through action, which might lead to a new buzzphrase of actionable gratitude.

Dorsey even credits meditation with the amplification of his leadership.

“Meditation helped me by not allowing myself to be reactive to what comes in front of me. The less control that I have my wellbeing and space and mindset the less effective I am in fixing our issues.”

But, guess who else he looks to for leadership?

Jacinda Arden of New Zealand.

And, one more thing.

Jack Dorsey donated $1 Billion dollars with only an assistant and a google sheet.

You can do anything, too.

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