Expect the unexpected. And whenever possible, be the unexpected.

Jack Dorsey said that.

Before starting Twitter, Jack Dorsey created an open-source dispatch software for ambulances and taxis. It crashed and burned, forcing him to take up contract work as a freelance developer.

Pounding away at the keyboard left his wrists and hands aching so he started getting massages. This led to a fascination with massage therapy. He took a thousand hours of massage therapy, became licensed and was struck with a big idea. Dorsey wanted to give software developers massages while advising and guiding them on their code.

His friends told him it was a dogshit idea. Dorsey listened, started coding again and a year later founded Twitter. From there, things just go weirder. Dorsey was ousted from Twitter twice. He even ran it from a time remotely from Africa.

Sometime in the Twitter saga—and I don’t have an exact timeline here—one of Dorsey’s artist buddies couldn’t sell his art because he was unable to accept credit card. So, he started Square. Today, Square does something in the neighborhood of $500 million per month in transaction volume.

Dorsey is bizarre, wildly curious and—from the outside looking in—prone to making wild detours on a whim.

He has dated super models. He became a Buddhist. He sold his first Tweet for nearly $3 million and donated all the money to Africa. He walked 5 miles to and from work for a time. He enrolled in a few classes at fashion school. He gave up eating on the weekends. The peculiarities go on and on and on.

Dorsey’s path has been so out-of-the-ordinary, it’s difficult to parse fact from fiction. For some, his story is daunting. For others, liberating. Instead of looking for the “right” next step to take, it might be enough to simply take the next step that feels most interesting to you.

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