Meet Jack Dorsey. Surrealist CEO of the Year.

"When I believe in something, I fight like hell for it." ~ Steve McQueen describes Jack Dorsey's life according to Jack Dorsey

Jack Dorsey never wanted to be a chief executive officer. When he was a little boy he wanted to be a sailor, a tailor or a surrealist painter. As CEO of  Twitter —the social media platform with the brand awareness of Coke ("but", Dorsey adds, "unlike Coke it stands for something") — and Square, the payment processing company that's starting to look like a bank, Jack Dorsey is changing our perception of the CEO. 

As John Abell put it in a recent update...

A corporation would never consider sharing a C-Suite exec with another company. Except for the chief executive. ~ John Abell

In 2015, no one played the role of polyamorous CEO quite like Jack Dorsey. He's the CEO most likely to appear on Grey's Anatomy as Dr Dreamy McDorsey, the celebrity physician who visits Grey-Sloan Memorial with the artificial heart/mind reader that he developed in two weeks while riding the bus to work. Watch him perform open-heart surgery while Snow Patrol sings...

I don't quite know / How to say / How I feel

At Square it's important to know how you feel because it's one of the questions the company asks of its employees each week. The other question is, "What are we not talking about?".

Jack Dorsey is the only CEO in history who has designed a pencil skirt, trained 1,000 hours as a massage therapist and hacked into a company to get a job. He has a tattoo on his forearm shaped like an integral/sound hole/clavicle. Dorsey describes his tattoo as: 1. the integration of opinions distilled to one; 2. a reflection of his love of music especially punk music where the artist learns an instrument by enduring the ridicule of playing in public; and 3. the graceful, powerful bone connecting the sternum to the shoulder blade that's the first to form and the last to ossify.

Dorsey delights in denim, describing jeans as a journal that you wear, the fabric telling the story of how you live, how you move and what you do with your life. He loves his mother, Virginia Woolf and the Golden Gate Bridge, but Jack Dorsey especially loves artists.

I learned so much from artists. You can see the world in a completely different way and you can make up how the world could look, then you can share it with others and inspire them to move, to think in the world in a very very different way. ~Jack Dorsey

It is his tendency to work outside the typical frame of the CEO in the way he looks, talks and behaves that makes some think that he is like a work of art made of fluorescent light, impressive at first glance, but lacking in density. 

It doesn't help that in 2013 Jack was #11 on Business Insiders' Sexiest CEOs Alive list, then jumped to #3 in 2014. In 2015 Jack responded to the objectification of CEOs by growing the longest beard this side of Duck Dynasty. Other Silicon Valley CEOs followed suit. It wasn't pretty.

I spent the weekend listening to Jack Dorsey, soaking up his wisdom, carrying him around with me in the back pocket of my jeans. His voice left an imprint. Whereas CEOs like Elon Musk are busy exploring space, what really interests Dorsey is exploring the depths of human consciousness.

Here are five things I learned from Jack's consciousness:

1. Ask WHY. The easiest question to ask and the hardest to answer, truly great companies and people are question addicts who ask why and respond with the product or service that says, "Why not?".

2. FOCUS. It's not just what we do in the world, it's what we don't do. Jack Dorsey gave Columbia University students the following exercise. He told them to write "Daily" on the top of a page, then DO skip two lines and DON'T. Then he said:

It's up to you to figure out what goes in the do's and don'ts.

Jack's do's are: be vulnerable, drink only lemon water and red wine and get 7 hours of sleep. His don'ts are: don't avoid eye contact, don't be late and don't set expectations that you don't meet. He looks at his list three times a day. 

3. THEME your days. Nobody embodies Flaubert's "be regular and orderly in your life, so that you may be violent and original in your work" like Jack Dorsey. The only way he can run two companies is by structuring his days. He wakes up at 5:30, meditates for 20-30 minutes then launches into a 7 minute workout repeated three times. Then he has coffee and eggs and heads out the door to work. Each day has a theme. Monday is "management", Tuesday is "product", Wednesday is "marketing, communications and growth", Thursday is "developers and partnerships", Friday is "company culture", Saturday is "hiking" and Sunday is "reflection". 

 4. Hiring for TEAM DYNAMICS is as important as hiring for an individual's skills. The only way you can run two companies is to surround yourself with a team you can trust so that you can focus on the most meaningful tasks to advance your company's purpose. Jack trusts Square's leadership (54% of which is female, by the way) to do the right thing, be transparent and get along with each other. He is migrating the transparency practices that worked at Square, such as sharing notes from every meeting with everyone, to Twitter.

The future has already arrived. It's just not evenly distributed yet. ~ One of Jack Dorsey's favourite quotes from William Gibson 

5. LOVE THE WORK, not just the end product. Twitter is communication and Square is commerce, both activities are essential to humanity. Dorsey's goal is to create tools people love that are so intuitive and so successful that they disappear, allowing the user to be the artist, to change their world.

Disruption is just moving things around. No values, no leadership. This is not what I want to do in the world. I want something with purpose, with direction. I want something with thoughtfulness. I want REVOLUTION. ~Jack Dorsey

Wow. Spending hours with Jack left me euphoric and disoriented, like the first time I looked into a telescope, saw a paramecium under a microscope or smoked up with my coworkers. Jack Dorsey gets my vote for CEO of the Year. Does he get yours?

Next up: Elon Musk December 11, Marissa Mayer December 15, Steve Easterbrook December 18 and Mark Zuckerberg December 21. Who would you pick as CEO of 2015? Cast your vote in the comment section along with your rationale and you'll be entered in a draw to win the best CEO book of 2015, Ashlee Vance's Elon Musk: Tesla, Space-X and the Quest for a Fantastic Future. Why? Because we're here on LinkedIn to connect, learn and have fun.

Cover art: Jack Dorsey inside the work of Robert Irwin, one of his favourite artists who said, "Seeing is forgetting the name of the thing one sees…".