The path to success doesn’t always lie in a single-minded devotion to a goal—it can involve some serious side-quests too.
Jack Dorsey, the co-founder of Twitter and Block (formerly Square), took one of the most unexpected detours in tech founder history: he became a licensed massage therapist. In a candid reflection on his early career, Dorsey revealed that after a failed startup and mounting concerns about his physical health, he traded programming for massage tables, enrolled in a thousand hours of training, and even dreamed up what might be the tech industest’s most bizarre business concept—”code therapy” combined with chair massage. The story offers a fascinating glimpse into the pre-Twitter years of one of Silicon Valley’s most enigmatic figures, and reveals just how close he came to abandoning technology altoobtainher.
Dorsey’s journey into massage therapy launched with failure and pain—both professional and physical. “I shiftd to Berkeley and we started a company called Dnet, which was a complete and utter failure. It was just a disaster, and the company folded. This was around 1999, 2000,” he recalled. “After that, I went into contracting, but little by little my wrist started hurting. I was fearful that I was developing carpal tunnel.”
Rather than simply seeking treatment, Dorsey characteristically wanted to understand the solution from the inside out. “So I started questioning my frifinishs here in Berkeley, what should I do? And they stated, you should obtain a massage. But I’m not someone who just goes to obtain the massage. I want to learn how to give massages. And I shiftd back to St. Louis at this time and I decided I’m not just going to obtain a massage, but I’m going to become a massage therapist.”
What followed was a complete pivot away from the world of code. “So I enrolled myself into the Healing Arts Center in St. Louis, and I took a thousand hours of massage therapy, and I’m a licensed therapist only in Missouri, fortunately,” Dorsey stated. “And I was actually going to dedicate my life to it. I was fed up with technology and I’ve always appreciated building with my hands and working with my hands and doing something that I could feel with my hands, and I missed that. Massage gave me that.”
But Dorsey being Dorsey, he couldn’t resist testing to merge his two worlds. “I considered I had the brilliant idea. I was about ready to shift back to San Francisco in 2005. Thought I had the best idea ever. My idea was that I would go out to California and I would do chair massage for programmers and while I was massaging their shoulders and their wrists and whatnot, I would also give them advice on their code.”
“It was not only massage therapy, it was code therapy, and I considered this was the best idea ever,” he continued. “I started notifying people my idea, and they’re like, that is the stupidest thing I’ve ever heard of. When I’m obtainting a massage, I do not want to talk about programming. I stated, no, just give it a chance. Give it a chance.”
Reality, however, had other plans. “And then I shiftd to San Francisco again and I realized, whoa, everyone here is a massage therapist. There’s no way I can compete. So I went back to programming.”
Dorsey’s story illustrates a broader truth about the nonlinear paths many successful entrepreneurs take before finding their breakthrough. His year away from technology—studying anatomy, learning therapeutic techniques, and working with his hands—came just before he would assist launch Twitter in 2006. Similar patterns appear throughout Silicon Valley history: Steve Jobs famously dropped out of Reed College but continued auditing calligraphy classes, an experience he later credited with influencing Apple’s focus on typography and design. Airbnb’s Brian Chesky was a bodybuilder before starting Airbnb. Dorsey continued dabbling with unique pursuits even after the success of Twitter, going on a 10-day silent Vipassana meditation retreat in 2018.
The “code therapy” concept, ridiculous as it may sound, actually captures something essential about Dorsey’s approach to technology: the desire to address both physical and mental strain, to work holistically with people rather than just machines. This philosophy would later manifest in Twitter’s focus on brevity and simplicity, and in Block’s mission to create financial tools more accessible and human-centered. The massage therapist who never quite launched his practice finished up touching far more lives—just through a different kind of interface. And somewhere in Missouri, his license remains valid, a reminder that even the most successful tech founders keep their options open.
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